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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:42:55 UTC

Update Date

2022-03-07 02:52:57 UTC

HMDB ID

HMDB0031400

Secondary Accession Numbers

HMDB31400

Metabolite Identification

Common Name

Annopentocin B

Description

Annopentocin B belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. Based on a literature review a significant number of articles have been published on Annopentocin B.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 02241217582D          

 44 45  0  0  0  0            999 V2000
    0.0884   -7.6848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3241   -6.4153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5009   -6.4153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7558   -7.1999    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4703   -7.6124    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1848   -7.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8992   -7.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6137   -7.1999    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3282   -7.6124    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0426   -7.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7571   -7.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4716   -7.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1861   -7.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9005   -7.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6150   -7.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3295   -7.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0439   -7.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7584   -7.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4729   -7.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1874   -7.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9018   -7.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4703   -8.4374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6137   -6.3749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3282   -8.4374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0093   -7.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2948   -7.1999    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -4.8659   -7.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1514   -7.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4369   -7.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7224   -7.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0080   -7.1999    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2935   -7.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5790   -7.1999    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -9.0586   -7.1999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8037   -6.4153    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.9787   -6.4153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7237   -7.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3912   -8.5098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2886   -5.7479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3392   -6.6165    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 34  1  0  0  0  0
 34  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
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 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
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 20 21  1  0  0  0  0
  5 22  1  6  0  0  0
  8 23  1  6  0  0  0
  9 24  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
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 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 35  1  1  0  0  0
 26 36  1  6  0  0  0
 25 41  1  0  0  0  0
 34 33  1  6  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 37 41  1  0  0  0  0
 37 42  2  0  0  0  0
 39 43  1  1  0  0  0
  4 44  1  6  0  0  0
M  END

HMDB0031400
     RDKit          3D
Annopentocin B
107108  0  0  0  0  0  0  0  0999 V2000
  -11.0836   -1.4200   -2.3032 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1127   -2.3424   -2.9668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3606   -3.2907   -2.1730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2795   -3.0352   -1.2433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4093   -2.0852   -0.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3683   -0.6241   -0.5096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5758    0.1399    0.7842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6186    1.5886    0.7126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5418    2.4715    0.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2784    2.5438    1.0204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3151    1.4238    1.0561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6842    1.1203   -0.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8965    2.1701   -0.9113 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4456    1.7876   -2.2159 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2101   -0.0148    3.2060 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5213    0.7704    3.1240 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1834    0.1137    1.9441 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1039   -0.9551    2.5086 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8382   -1.6929    1.4212 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6516   -2.6409    1.9981 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.1126   -0.7799   -0.3913 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.1227   -0.1572    0.7592 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6219    1.0941   -1.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4979    0.2885   -2.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9185   -0.9419   -1.9254 C   0  0  0  0  0  0  0  0  0  0  0  0
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 18 75  1  0
 18 76  1  0
 19 77  1  6
 20 78  1  0
 21 79  1  1
 22 80  1  0
 22 81  1  0
 23 82  1  0
 23 83  1  0
 24 84  1  6
 25 85  1  0
 25 86  1  0
 26 87  1  6
 27 88  1  0
 28 89  1  0
 28 90  1  0
 29 91  1  0
 29 92  1  0
 30 93  1  0
 30 94  1  0
 31 95  1  0
 31 96  1  0
 32 97  1  0
 32 98  1  0
 33 99  1  1
 34100  1  0
 35101  1  0
 35102  1  0
 37103  1  0
 38104  1  6
 39105  1  0
 39106  1  0
 39107  1  0
M  END


  Mrv0541 02241217582D          

 44 45  0  0  0  0            999 V2000
    0.0884   -7.6848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3241   -6.4153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5009   -6.4153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7558   -7.1999    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4703   -7.6124    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1848   -7.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8992   -7.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6137   -7.1999    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3282   -7.6124    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0426   -7.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7571   -7.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4716   -7.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1861   -7.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9005   -7.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6150   -7.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3295   -7.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0439   -7.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7584   -7.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4729   -7.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1874   -7.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9018   -7.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4703   -8.4374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6137   -6.3749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3282   -8.4374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0093   -7.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2948   -7.1999    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5803   -7.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8659   -7.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1514   -7.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4369   -7.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7224   -7.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0080   -7.1999    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2935   -7.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5790   -7.1999    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0080   -6.3749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2948   -6.3749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3912   -7.6848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0586   -7.1999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8037   -6.4153    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.9787   -6.4153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7237   -7.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3912   -8.5098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2886   -5.7479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3392   -6.6165    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 34  1  0  0  0  0
 34  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  5 22  1  6  0  0  0
  8 23  1  6  0  0  0
  9 24  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 35  1  1  0  0  0
 26 36  1  6  0  0  0
 25 41  1  0  0  0  0
 34 33  1  6  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 37 41  1  0  0  0  0
 37 42  2  0  0  0  0
 39 43  1  1  0  0  0
  4 44  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0031400

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]1(CC[C@@H](C[C@H](O)CCCCC[C@@H](O)CC2=C[C@H](C)OC2=O)O1)[C@@H](O)CC[C@H](O)[C@@H](O)CCCCCCCCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C35H64O8/c1-3-4-5-6-7-8-9-10-11-15-18-31(38)32(39)20-21-33(40)34-22-19-30(43-34)25-29(37)17-14-12-13-16-28(36)24-27-23-26(2)42-35(27)41/h23,26,28-34,36-40H,3-22,24-25H2,1-2H3/t26-,28+,29+,30-,31-,32-,33-,34-/m0/s1

> <INCHI_KEY>
ZPRYGZNEAVBQEP-VZFMJEBSSA-N

> <FORMULA>
C35H64O8

> <MOLECULAR_WEIGHT>
612.8779

> <EXACT_MASS>
612.460119024

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
75.6627821642263

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5S)-3-[(2R,8R)-2,8-dihydroxy-9-[(2S,5S)-5-[(1S,4S,5S)-1,4,5-trihydroxyheptadecyl]oxolan-2-yl]nonyl]-5-methyl-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
5.21

> <JCHEM_LOGP>
6.246742104999999

> <ALOGPS_LOGS>
-5.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.22210087077141

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.680379402404647

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7210596544236365

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
170.9691

> <JCHEM_ROTATABLE_BOND_COUNT>
26

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.25e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S)-3-[(2R,8R)-2,8-dihydroxy-9-[(2S,5S)-5-[(1S,4S,5S)-1,4,5-trihydroxyheptadecyl]oxolan-2-yl]nonyl]-5-methyl-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0031400
     RDKit          3D
Annopentocin B
107108  0  0  0  0  0  0  0  0999 V2000
  -11.0836   -1.4200   -2.3032 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1127   -2.3424   -2.9668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3606   -3.2907   -2.1730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2795   -3.0352   -1.2433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4093   -2.0852   -0.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3683   -0.6241   -0.5096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5758    0.1399    0.7842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6186    1.5886    0.7126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5418    2.4715    0.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2784    2.5438    1.0204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3151    1.4238    1.0561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6842    1.1203   -0.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8965    2.1701   -0.9113 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4456    1.7876   -2.2159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7683    2.8579   -0.2982 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6267    4.1445   -0.9171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3583    2.8051    1.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8843    1.5234    1.6811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6269    1.0235    1.0515 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6819    0.7192   -0.2851 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0521   -0.2189    1.7491 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2101   -0.0148    3.2060 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5213    0.7704    3.1240 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1834    0.1137    1.9441 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1039   -0.9551    2.5086 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8382   -1.6929    1.4212 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6516   -2.6409    1.9981 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5417   -0.8059    0.4575 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5837    0.0884    1.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7319   -0.5740    1.6941 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5202   -1.4900    0.8019 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1126   -0.7799   -0.3913 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0441    0.3179   -0.0119 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1227   -0.1572    0.7592 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6219    1.0941   -1.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4979    0.2885   -2.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9185   -0.9419   -1.9254 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7834   -1.3128   -3.0623 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.1528   -1.6790   -2.4825 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8572   -0.1727   -3.8592 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1032    0.8126   -3.2839 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9205    1.9856   -3.7144 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2000   -0.3890    1.1590 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1466   -1.6605   -2.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9969   -1.4690   -1.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8645   -0.3822   -2.6211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3742   -1.7582   -3.6018 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6929   -2.9083   -3.7569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9343   -4.1241   -2.8938 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1557   -3.9871   -1.6550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2909   -2.8050   -1.8035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9588   -4.0397   -0.7259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6015   -2.3155    0.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3745   -2.3212    0.3984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3006   -0.4807   -0.8696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9735   -0.2619   -1.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0018   -0.2753    1.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6543   -0.1824    1.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8845    1.9342    1.7953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5816    1.9359    0.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3789    2.3598   -0.8410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9778    3.5369    0.3121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5750    2.7093    2.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7372    3.5430    0.8318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8849    0.4797    1.3131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6503    1.5741    1.8972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1724    0.1304   -0.1729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5564    0.8778   -0.9612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6607    2.9915   -1.2156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0356    1.0379   -2.5471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7869    2.3907   -0.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8173    4.7828   -0.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4345    3.4979    1.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0592    3.3461    1.7957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7543    1.6416    2.7876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6134    0.6629    1.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2110    1.7856    1.1461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1576    0.9653   -0.7847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6561   -1.1127    1.5049 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4578   -1.0111    3.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5591    0.4513    3.7973 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1034    0.6066    4.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2959    1.8371    2.9549 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7560    0.8478    1.3273 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7716   -0.5626    3.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4400   -1.6956    3.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0606   -2.2523    0.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9423   -3.3609    1.3922 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8147   -0.2086   -0.1322 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0329   -1.4755   -0.2944 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1674    0.8461    1.7435 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9986    0.7214    0.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3837    0.2171    2.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3659   -1.1593    2.5548 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9095   -2.3467    0.4624 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3606   -1.9023    1.3941 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5594   -1.5062   -1.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2934   -0.2993   -1.0060 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5176    1.0603    0.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7625   -0.4442    1.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1610    1.9790   -0.7277 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7702    1.4243   -1.7938 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7008   -1.6421   -1.0817 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3741   -2.1926   -3.6170 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2582   -1.2856   -1.4395 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3119   -2.7666   -2.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.9066   -1.1474   -3.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
 36 37  2  0
 37 38  1  0
 38 39  1  0
 38 40  1  0
 40 41  1  0
 41 42  2  0
 24 43  1  0
 43 21  1  0
 41 36  1  0
  1 44  1  0
  1 45  1  0
  1 46  1  0
  2 47  1  0
  2 48  1  0
  3 49  1  0
  3 50  1  0
  4 51  1  0
  4 52  1  0
  5 53  1  0
  5 54  1  0
  6 55  1  0
  6 56  1  0
  7 57  1  0
  7 58  1  0
  8 59  1  0
  8 60  1  0
  9 61  1  0
  9 62  1  0
 10 63  1  0
 10 64  1  0
 11 65  1  0
 11 66  1  0
 12 67  1  0
 12 68  1  0
 13 69  1  6
 14 70  1  0
 15 71  1  6
 16 72  1  0
 17 73  1  0
 17 74  1  0
 18 75  1  0
 18 76  1  0
 19 77  1  6
 20 78  1  0
 21 79  1  1
 22 80  1  0
 22 81  1  0
 23 82  1  0
 23 83  1  0
 24 84  1  6
 25 85  1  0
 25 86  1  0
 26 87  1  6
 27 88  1  0
 28 89  1  0
 28 90  1  0
 29 91  1  0
 29 92  1  0
 30 93  1  0
 30 94  1  0
 31 95  1  0
 31 96  1  0
 32 97  1  0
 32 98  1  0
 33 99  1  1
 34100  1  0
 35101  1  0
 35102  1  0
 37103  1  0
 38104  1  6
 39105  1  0
 39106  1  0
 39107  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       0.165 -14.345   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.605 -11.975   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.935 -11.975   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.411 -13.440   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.745 -14.210   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.078 -13.440   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.412 -14.210   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.746 -13.440   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.079 -14.210   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.413 -13.440   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.747 -14.210   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.080 -13.440   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.414 -14.210   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.748 -13.440   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.081 -14.210   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.415 -13.440   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      18.749 -14.210   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      20.082 -13.440   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      21.416 -14.210   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      22.750 -13.440   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      24.083 -14.210   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.745 -15.750   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       6.746 -11.900   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       8.079 -15.750   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0     -13.084 -14.210   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -11.750 -13.440   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -10.417 -14.210   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -9.083 -13.440   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -7.749 -14.210   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -6.416 -13.440   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.082 -14.210   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -3.748 -13.440   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.415 -14.210   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.081 -13.440   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -3.748 -11.900   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0     -11.750 -11.900   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0     -15.664 -14.345   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0     -16.909 -13.440   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0     -16.434 -11.975   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0     -14.894 -11.975   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0     -14.418 -13.440   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0     -15.664 -15.885   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0     -17.339 -10.729   0.000  0.00  0.00           C+0
HETATM   44  H   UNK     0       2.500 -12.351   0.000  0.00  0.00           H+0
CONECT    1   34    4                                                       
CONECT    2   34    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    1    5   44                                             
CONECT    5    4    6   22                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   23                                                  
CONECT    9    8   10   24                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22    5                                                            
CONECT   23    8                                                            
CONECT   24    9                                                            
CONECT   25   26   41                                                       
CONECT   26   25   27   36                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   35                                                  
CONECT   33   32   34                                                       
CONECT   34    1    2   33                                                  
CONECT   35   32                                                            
CONECT   36   26                                                            
CONECT   37   38   41   42                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   43                                                  
CONECT   40   39   41                                                       
CONECT   41   25   40   37                                                  
CONECT   42   37                                                            
CONECT   43   39                                                            
CONECT   44    4                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   90    0
END

COMPND    HMDB0031400
HETATM    1  C1  UNL     1     -11.084  -1.420  -2.303  1.00  0.00           C  
HETATM    2  C2  UNL     1     -10.113  -2.342  -2.967  1.00  0.00           C  
HETATM    3  C3  UNL     1      -9.361  -3.291  -2.173  1.00  0.00           C  
HETATM    4  C4  UNL     1      -8.280  -3.035  -1.243  1.00  0.00           C  
HETATM    5  C5  UNL     1      -8.409  -2.085  -0.145  1.00  0.00           C  
HETATM    6  C6  UNL     1      -8.368  -0.624  -0.510  1.00  0.00           C  
HETATM    7  C7  UNL     1      -8.576   0.140   0.784  1.00  0.00           C  
HETATM    8  C8  UNL     1      -8.619   1.589   0.713  1.00  0.00           C  
HETATM    9  C9  UNL     1      -7.542   2.471   0.279  1.00  0.00           C  
HETATM   10  C10 UNL     1      -6.278   2.544   1.020  1.00  0.00           C  
HETATM   11  C11 UNL     1      -5.315   1.424   1.056  1.00  0.00           C  
HETATM   12  C12 UNL     1      -4.684   1.120  -0.279  1.00  0.00           C  
HETATM   13  C13 UNL     1      -3.897   2.170  -0.911  1.00  0.00           C  
HETATM   14  O1  UNL     1      -3.446   1.788  -2.216  1.00  0.00           O  
HETATM   15  C14 UNL     1      -2.768   2.858  -0.298  1.00  0.00           C  
HETATM   16  O2  UNL     1      -2.627   4.144  -0.917  1.00  0.00           O  
HETATM   17  C15 UNL     1      -2.358   2.805   1.078  1.00  0.00           C  
HETATM   18  C16 UNL     1      -1.884   1.523   1.681  1.00  0.00           C  
HETATM   19  C17 UNL     1      -0.627   1.024   1.051  1.00  0.00           C  
HETATM   20  O3  UNL     1      -0.682   0.719  -0.285  1.00  0.00           O  
HETATM   21  C18 UNL     1      -0.052  -0.219   1.749  1.00  0.00           C  
HETATM   22  C19 UNL     1       0.210  -0.015   3.206  1.00  0.00           C  
HETATM   23  C20 UNL     1       1.521   0.770   3.124  1.00  0.00           C  
HETATM   24  C21 UNL     1       2.183   0.114   1.944  1.00  0.00           C  
HETATM   25  C22 UNL     1       3.104  -0.955   2.509  1.00  0.00           C  
HETATM   26  C23 UNL     1       3.838  -1.693   1.421  1.00  0.00           C  
HETATM   27  O4  UNL     1       4.652  -2.641   1.998  1.00  0.00           O  
HETATM   28  C24 UNL     1       4.542  -0.806   0.457  1.00  0.00           C  
HETATM   29  C25 UNL     1       5.584   0.088   1.023  1.00  0.00           C  
HETATM   30  C26 UNL     1       6.732  -0.574   1.694  1.00  0.00           C  
HETATM   31  C27 UNL     1       7.520  -1.490   0.802  1.00  0.00           C  
HETATM   32  C28 UNL     1       8.113  -0.780  -0.391  1.00  0.00           C  
HETATM   33  C29 UNL     1       9.044   0.318  -0.012  1.00  0.00           C  
HETATM   34  O5  UNL     1      10.123  -0.157   0.759  1.00  0.00           O  
HETATM   35  C30 UNL     1       9.622   1.094  -1.144  1.00  0.00           C  
HETATM   36  C31 UNL     1      10.498   0.289  -2.020  1.00  0.00           C  
HETATM   37  C32 UNL     1      10.918  -0.942  -1.925  1.00  0.00           C  
HETATM   38  C33 UNL     1      11.783  -1.313  -3.062  1.00  0.00           C  
HETATM   39  C34 UNL     1      13.153  -1.679  -2.482  1.00  0.00           C  
HETATM   40  O6  UNL     1      11.857  -0.173  -3.859  1.00  0.00           O  
HETATM   41  C35 UNL     1      11.103   0.813  -3.284  1.00  0.00           C  
HETATM   42  O7  UNL     1      10.920   1.986  -3.714  1.00  0.00           O  
HETATM   43  O8  UNL     1       1.200  -0.389   1.159  1.00  0.00           O  
HETATM   44  H1  UNL     1     -12.147  -1.660  -2.608  1.00  0.00           H  
HETATM   45  H2  UNL     1     -10.997  -1.469  -1.205  1.00  0.00           H  
HETATM   46  H3  UNL     1     -10.864  -0.382  -2.621  1.00  0.00           H  
HETATM   47  H4  UNL     1      -9.374  -1.758  -3.602  1.00  0.00           H  
HETATM   48  H5  UNL     1     -10.693  -2.908  -3.757  1.00  0.00           H  
HETATM   49  H6  UNL     1      -8.934  -4.124  -2.894  1.00  0.00           H  
HETATM   50  H7  UNL     1     -10.156  -3.987  -1.655  1.00  0.00           H  
HETATM   51  H8  UNL     1      -7.291  -2.805  -1.803  1.00  0.00           H  
HETATM   52  H9  UNL     1      -7.959  -4.040  -0.726  1.00  0.00           H  
HETATM   53  H10 UNL     1      -7.601  -2.316   0.611  1.00  0.00           H  
HETATM   54  H11 UNL     1      -9.375  -2.321   0.398  1.00  0.00           H  
HETATM   55  H12 UNL     1      -7.301  -0.481  -0.870  1.00  0.00           H  
HETATM   56  H13 UNL     1      -8.974  -0.262  -1.303  1.00  0.00           H  
HETATM   57  H14 UNL     1      -8.002  -0.275   1.637  1.00  0.00           H  
HETATM   58  H15 UNL     1      -9.654  -0.182   1.079  1.00  0.00           H  
HETATM   59  H16 UNL     1      -8.884   1.934   1.795  1.00  0.00           H  
HETATM   60  H17 UNL     1      -9.582   1.936   0.186  1.00  0.00           H  
HETATM   61  H18 UNL     1      -7.379   2.360  -0.841  1.00  0.00           H  
HETATM   62  H19 UNL     1      -7.978   3.537   0.312  1.00  0.00           H  
HETATM   63  H20 UNL     1      -6.575   2.709   2.120  1.00  0.00           H  
HETATM   64  H21 UNL     1      -5.737   3.543   0.832  1.00  0.00           H  
HETATM   65  H22 UNL     1      -5.885   0.480   1.313  1.00  0.00           H  
HETATM   66  H23 UNL     1      -4.650   1.574   1.897  1.00  0.00           H  
HETATM   67  H24 UNL     1      -4.172   0.130  -0.173  1.00  0.00           H  
HETATM   68  H25 UNL     1      -5.556   0.878  -0.961  1.00  0.00           H  
HETATM   69  H26 UNL     1      -4.661   2.991  -1.216  1.00  0.00           H  
HETATM   70  H27 UNL     1      -4.036   1.038  -2.547  1.00  0.00           H  
HETATM   71  H28 UNL     1      -1.787   2.391  -0.855  1.00  0.00           H  
HETATM   72  H29 UNL     1      -2.817   4.783  -0.178  1.00  0.00           H  
HETATM   73  H30 UNL     1      -1.435   3.498   1.172  1.00  0.00           H  
HETATM   74  H31 UNL     1      -3.059   3.346   1.796  1.00  0.00           H  
HETATM   75  H32 UNL     1      -1.754   1.642   2.788  1.00  0.00           H  
HETATM   76  H33 UNL     1      -2.613   0.663   1.559  1.00  0.00           H  
HETATM   77  H34 UNL     1       0.211   1.786   1.146  1.00  0.00           H  
HETATM   78  H35 UNL     1       0.158   0.965  -0.785  1.00  0.00           H  
HETATM   79  H36 UNL     1      -0.656  -1.113   1.505  1.00  0.00           H  
HETATM   80  H37 UNL     1       0.458  -1.011   3.639  1.00  0.00           H  
HETATM   81  H38 UNL     1      -0.559   0.451   3.797  1.00  0.00           H  
HETATM   82  H39 UNL     1       2.103   0.607   4.062  1.00  0.00           H  
HETATM   83  H40 UNL     1       1.296   1.837   2.955  1.00  0.00           H  
HETATM   84  H41 UNL     1       2.756   0.848   1.327  1.00  0.00           H  
HETATM   85  H42 UNL     1       3.772  -0.563   3.300  1.00  0.00           H  
HETATM   86  H43 UNL     1       2.440  -1.696   3.007  1.00  0.00           H  
HETATM   87  H44 UNL     1       3.061  -2.252   0.840  1.00  0.00           H  
HETATM   88  H45 UNL     1       4.942  -3.361   1.392  1.00  0.00           H  
HETATM   89  H46 UNL     1       3.815  -0.209  -0.132  1.00  0.00           H  
HETATM   90  H47 UNL     1       5.033  -1.476  -0.294  1.00  0.00           H  
HETATM   91  H48 UNL     1       5.167   0.846   1.744  1.00  0.00           H  
HETATM   92  H49 UNL     1       5.999   0.721   0.188  1.00  0.00           H  
HETATM   93  H50 UNL     1       7.384   0.217   2.123  1.00  0.00           H  
HETATM   94  H51 UNL     1       6.366  -1.159   2.555  1.00  0.00           H  
HETATM   95  H52 UNL     1       6.910  -2.347   0.462  1.00  0.00           H  
HETATM   96  H53 UNL     1       8.361  -1.902   1.394  1.00  0.00           H  
HETATM   97  H54 UNL     1       8.559  -1.506  -1.050  1.00  0.00           H  
HETATM   98  H55 UNL     1       7.293  -0.299  -1.006  1.00  0.00           H  
HETATM   99  H56 UNL     1       8.518   1.060   0.654  1.00  0.00           H  
HETATM  100  H57 UNL     1       9.762  -0.444   1.627  1.00  0.00           H  
HETATM  101  H58 UNL     1      10.161   1.979  -0.728  1.00  0.00           H  
HETATM  102  H59 UNL     1       8.770   1.424  -1.794  1.00  0.00           H  
HETATM  103  H60 UNL     1      10.701  -1.642  -1.082  1.00  0.00           H  
HETATM  104  H61 UNL     1      11.374  -2.193  -3.617  1.00  0.00           H  
HETATM  105  H62 UNL     1      13.258  -1.286  -1.439  1.00  0.00           H  
HETATM  106  H63 UNL     1      13.312  -2.767  -2.447  1.00  0.00           H  
HETATM  107  H64 UNL     1      13.907  -1.147  -3.085  1.00  0.00           H  
CONECT    1    2   44   45   46
CONECT    2    3   47   48
CONECT    3    4   49   50
CONECT    4    5   51   52
CONECT    5    6   53   54
CONECT    6    7   55   56
CONECT    7    8   57   58
CONECT    8    9   59   60
CONECT    9   10   61   62
CONECT   10   11   63   64
CONECT   11   12   65   66
CONECT   12   13   67   68
CONECT   13   14   15   69
CONECT   14   70
CONECT   15   16   17   71
CONECT   16   72
CONECT   17   18   73   74
CONECT   18   19   75   76
CONECT   19   20   21   77
CONECT   20   78
CONECT   21   22   43   79
CONECT   22   23   80   81
CONECT   23   24   82   83
CONECT   24   25   43   84
CONECT   25   26   85   86
CONECT   26   27   28   87
CONECT   27   88
CONECT   28   29   89   90
CONECT   29   30   91   92
CONECT   30   31   93   94
CONECT   31   32   95   96
CONECT   32   33   97   98
CONECT   33   34   35   99
CONECT   34  100
CONECT   35   36  101  102
CONECT   36   37   37   41
CONECT   37   38  103
CONECT   38   39   40  104
CONECT   39  105  106  107
CONECT   40   41
CONECT   41   42   42
END

HMDB0031400
     RDKit          3D
Annopentocin B
107108  0  0  0  0  0  0  0  0999 V2000
  -11.0836   -1.4200   -2.3032 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1127   -2.3424   -2.9668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3606   -3.2907   -2.1730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2795   -3.0352   -1.2433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4093   -2.0852   -0.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3683   -0.6241   -0.5096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5758    0.1399    0.7842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6186    1.5886    0.7126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5418    2.4715    0.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2784    2.5438    1.0204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3151    1.4238    1.0561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6842    1.1203   -0.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8965    2.1701   -0.9113 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4456    1.7876   -2.2159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7683    2.8579   -0.2982 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6267    4.1445   -0.9171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3583    2.8051    1.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8843    1.5234    1.6811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6269    1.0235    1.0515 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6819    0.7192   -0.2851 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0521   -0.2189    1.7491 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2101   -0.0148    3.2060 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5213    0.7704    3.1240 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1834    0.1137    1.9441 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1039   -0.9551    2.5086 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8382   -1.6929    1.4212 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6516   -2.6409    1.9981 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5417   -0.8059    0.4575 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5837    0.0884    1.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7319   -0.5740    1.6941 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5202   -1.4900    0.8019 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1126   -0.7799   -0.3913 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0441    0.3179   -0.0119 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1227   -0.1572    0.7592 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6219    1.0941   -1.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4979    0.2885   -2.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9185   -0.9419   -1.9254 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7834   -1.3128   -3.0623 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.1528   -1.6790   -2.4825 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8572   -0.1727   -3.8592 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1032    0.8126   -3.2839 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9205    1.9856   -3.7144 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2000   -0.3890    1.1590 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1466   -1.6605   -2.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9969   -1.4690   -1.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8645   -0.3822   -2.6211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3742   -1.7582   -3.6018 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6929   -2.9083   -3.7569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9343   -4.1241   -2.8938 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1557   -3.9871   -1.6550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2909   -2.8050   -1.8035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9588   -4.0397   -0.7259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6015   -2.3155    0.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3745   -2.3212    0.3984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3006   -0.4807   -0.8696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9735   -0.2619   -1.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0018   -0.2753    1.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6543   -0.1824    1.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8845    1.9342    1.7953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5816    1.9359    0.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3789    2.3598   -0.8410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9778    3.5369    0.3121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5750    2.7093    2.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7372    3.5430    0.8318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8849    0.4797    1.3131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6503    1.5741    1.8972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1724    0.1304   -0.1729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5564    0.8778   -0.9612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6607    2.9915   -1.2156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0356    1.0379   -2.5471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7869    2.3907   -0.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8173    4.7828   -0.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4345    3.4979    1.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0592    3.3461    1.7957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7543    1.6416    2.7876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6134    0.6629    1.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2110    1.7856    1.1461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1576    0.9653   -0.7847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6561   -1.1127    1.5049 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4578   -1.0111    3.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5591    0.4513    3.7973 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1034    0.6066    4.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2959    1.8371    2.9549 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7560    0.8478    1.3273 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7716   -0.5626    3.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4400   -1.6956    3.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0606   -2.2523    0.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9423   -3.3609    1.3922 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8147   -0.2086   -0.1322 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0329   -1.4755   -0.2944 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1674    0.8461    1.7435 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9986    0.7214    0.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3837    0.2171    2.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3659   -1.1593    2.5548 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9095   -2.3467    0.4624 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3606   -1.9023    1.3941 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5594   -1.5062   -1.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2934   -0.2993   -1.0060 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5176    1.0603    0.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7625   -0.4442    1.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1610    1.9790   -0.7277 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7702    1.4243   -1.7938 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7008   -1.6421   -1.0817 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3741   -2.1926   -3.6170 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2582   -1.2856   -1.4395 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3119   -2.7666   -2.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.9066   -1.1474   -3.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
 36 37  2  0
 37 38  1  0
 38 39  1  0
 38 40  1  0
 40 41  1  0
 41 42  2  0
 24 43  1  0
 43 21  1  0
 41 36  1  0
  1 44  1  0
  1 45  1  0
  1 46  1  0
  2 47  1  0
  2 48  1  0
  3 49  1  0
  3 50  1  0
  4 51  1  0
  4 52  1  0
  5 53  1  0
  5 54  1  0
  6 55  1  0
  6 56  1  0
  7 57  1  0
  7 58  1  0
  8 59  1  0
  8 60  1  0
  9 61  1  0
  9 62  1  0
 10 63  1  0
 10 64  1  0
 11 65  1  0
 11 66  1  0
 12 67  1  0
 12 68  1  0
 13 69  1  6
 14 70  1  0
 15 71  1  6
 16 72  1  0
 17 73  1  0
 17 74  1  0
 18 75  1  0
 18 76  1  0
 19 77  1  6
 20 78  1  0
 21 79  1  1
 22 80  1  0
 22 81  1  0
 23 82  1  0
 23 83  1  0
 24 84  1  6
 25 85  1  0
 25 86  1  0
 26 87  1  6
 27 88  1  0
 28 89  1  0
 28 90  1  0
 29 91  1  0
 29 92  1  0
 30 93  1  0
 30 94  1  0
 31 95  1  0
 31 96  1  0
 32 97  1  0
 32 98  1  0
 33 99  1  1
 34100  1  0
 35101  1  0
 35102  1  0
 37103  1  0
 38104  1  6
 39105  1  0
 39106  1  0
 39107  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₃₅H₆₄O₈

Average Molecular Weight

612.8779

Monoisotopic Molecular Weight

612.460119024

IUPAC Name

(5S)-3-[(2R,8R)-2,8-dihydroxy-9-[(2S,5S)-5-[(1S,4S,5S)-1,4,5-trihydroxyheptadecyl]oxolan-2-yl]nonyl]-5-methyl-2,5-dihydrofuran-2-one

Traditional Name

(5S)-3-[(2R,8R)-2,8-dihydroxy-9-[(2S,5S)-5-[(1S,4S,5S)-1,4,5-trihydroxyheptadecyl]oxolan-2-yl]nonyl]-5-methyl-5H-furan-2-one

CAS Registry Number

184093-45-6

SMILES

[H][C@]1(CC[C@@H](C[C@H](O)CCCCC[C@@H](O)CC2=C[C@H](C)OC2=O)O1)[C@@H](O)CC[C@H](O)[C@@H](O)CCCCCCCCCCCC

InChI Identifier

InChI=1S/C35H64O8/c1-3-4-5-6-7-8-9-10-11-15-18-31(38)32(39)20-21-33(40)34-22-19-30(43-34)25-29(37)17-14-12-13-16-28(36)24-27-23-26(2)42-35(27)41/h23,26,28-34,36-40H,3-22,24-25H2,1-2H3/t26-,28+,29+,30-,31-,32-,33-,34-/m0/s1

InChI Key

ZPRYGZNEAVBQEP-VZFMJEBSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Annonaceous acetogenins

Alternative Parents

Substituents

Annonaceae acetogenin skeleton
Long chain fatty alcohol
2-furanone
Dihydrofuran
Tetrahydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Secondary alcohol
Monocarboxylic acid or derivatives
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Polyol
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organic oxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0031400)
Cell membrane (HMDB: HMDB0031400)

Biofluid or Excreta

Urine (HMDB: HMDB0031400)

Cellular substructure

Extracellular (HMDB: HMDB0031400)
Membrane (HMDB: HMDB0031400)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031400)

Source

Endogenous

Endogenous (HMDB: HMDB0031400)

Plant

Plant (HMDB: HMDB0031400)

Animal

Animal (HMDB: HMDB0031400)

Exogenous

Food

Food (HMDB: HMDB0031400)

Fruit

Fruits (FooDB: FOOD00871)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0031400)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0031400)

Cellular process

Cell signaling (HMDB: HMDB0031400)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0031400)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0031400)

Nutrient

Nutrient (HMDB: HMDB0031400)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0031400)

Emulsifier (HMDB: HMDB0031400)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0012 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0042 g/L	ALOGPS
logP	5.21	ALOGPS
logP	6.25	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	13.68	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	26	ChemAxon
Refractivity	170.97 m³·mol⁻¹	ChemAxon
Polarizability	75.66 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	254.048	31661259
DarkChem	[M-H]-	248.431	31661259
DeepCCS	[M+H]+	258.619	30932474
DeepCCS	[M-H]-	256.795	30932474
DeepCCS	[M-2H]-	290.039	30932474
DeepCCS	[M+Na]+	264.225	30932474
AllCCS	[M+H]+	270.2	32859911
AllCCS	[M+H-H2O]+	269.1	32859911
AllCCS	[M+NH4]+	271.1	32859911
AllCCS	[M+Na]+	271.4	32859911
AllCCS	[M-H]-	240.9	32859911
AllCCS	[M+Na-2H]-	245.3	32859911
AllCCS	[M+HCOO]-	250.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Annopentocin B	[H][C@]1(CC[C@@H](C[C@H](O)CCCCC[C@@H](O)CC2=C[C@H](C)OC2=O)O1)[C@@H](O)CC[C@H](O)[C@@H](O)CCCCCCCCCCCC	5980.2	Standard polar	33892256
Annopentocin B	[H][C@]1(CC[C@@H](C[C@H](O)CCCCC[C@@H](O)CC2=C[C@H](C)OC2=O)O1)[C@@H](O)CC[C@H](O)[C@@H](O)CCCCCCCCCCCC	4505.8	Standard non polar	33892256
Annopentocin B	[H][C@]1(CC[C@@H](C[C@H](O)CCCCC[C@@H](O)CC2=C[C@H](C)OC2=O)O1)[C@@H](O)CC[C@H](O)[C@@H](O)CCCCCCCCCCCC	4934.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Annopentocin B,1TMS,isomer #1	CCCCCCCCCCCC[C@H](O)[C@@H](O)CC[C@H](O)[C@@H]1CC[C@@H](C[C@@H](CCCCC[C@@H](O)CC2=C[C@H](C)OC2=O)O[Si](C)(C)C)O1	4683.2	Semi standard non polar	33892256
Annopentocin B,1TMS,isomer #2	CCCCCCCCCCCC[C@H](O)[C@@H](O)CC[C@H](O)[C@@H]1CC[C@@H](C[C@H](O)CCCCC[C@H](CC2=C[C@H](C)OC2=O)O[Si](C)(C)C)O1	4687.9	Semi standard non polar	33892256
Annopentocin B,1TMS,isomer #3	CCCCCCCCCCCC[C@H](O)[C@@H](O)CC[C@H](O[Si](C)(C)C)[C@@H]1CC[C@@H](C[C@H](O)CCCCC[C@@H](O)CC2=C[C@H](C)OC2=O)O1	4670.6	Semi standard non polar	33892256
Annopentocin B,1TMS,isomer #4	CCCCCCCCCCCC[C@H](O)[C@H](CC[C@H](O)[C@@H]1CC[C@@H](C[C@H](O)CCCCC[C@@H](O)CC2=C[C@H](C)OC2=O)O1)O[Si](C)(C)C	4672.6	Semi standard non polar	33892256
Annopentocin B,1TMS,isomer #5	CCCCCCCCCCCC[C@H](O[Si](C)(C)C)[C@@H](O)CC[C@H](O)[C@@H]1CC[C@@H](C[C@H](O)CCCCC[C@@H](O)CC2=C[C@H](C)OC2=O)O1	4674.4	Semi standard non polar	33892256
Annopentocin B,2TMS,isomer #1	CCCCCCCCCCCC[C@H](O[Si](C)(C)C)[C@@H](O)CC[C@H](O)[C@@H]1CC[C@@H](C[C@@H](CCCCC[C@@H](O)CC2=C[C@H](C)OC2=O)O[Si](C)(C)C)O1	4629.3	Semi standard non polar	33892256
Annopentocin B,2TMS,isomer #10	CCCCCCCCCCCC[C@H](O[Si](C)(C)C)[C@H](CC[C@H](O)[C@@H]1CC[C@@H](C[C@H](O)CCCCC[C@@H](O)CC2=C[C@H](C)OC2=O)O1)O[Si](C)(C)C	4659.0	Semi standard non polar	33892256
Annopentocin B,2TMS,isomer #2	CCCCCCCCCCCC[C@H](O)[C@H](CC[C@H](O)[C@@H]1CC[C@@H](C[C@@H](CCCCC[C@@H](O)CC2=C[C@H](C)OC2=O)O[Si](C)(C)C)O1)O[Si](C)(C)C	4624.6	Semi standard non polar	33892256
Annopentocin B,2TMS,isomer #3	CCCCCCCCCCCC[C@H](O)[C@@H](O)CC[C@H](O[Si](C)(C)C)[C@@H]1CC[C@@H](C[C@@H](CCCCC[C@@H](O)CC2=C[C@H](C)OC2=O)O[Si](C)(C)C)O1	4610.3	Semi standard non polar	33892256
Annopentocin B,2TMS,isomer #4	CCCCCCCCCCCC[C@H](O)[C@@H](O)CC[C@H](O)[C@@H]1CC[C@@H](C[C@@H](CCCCC[C@H](CC2=C[C@H](C)OC2=O)O[Si](C)(C)C)O[Si](C)(C)C)O1	4619.3	Semi standard non polar	33892256
Annopentocin B,2TMS,isomer #5	CCCCCCCCCCCC[C@H](O[Si](C)(C)C)[C@@H](O)CC[C@H](O)[C@@H]1CC[C@@H](C[C@H](O)CCCCC[C@H](CC2=C[C@H](C)OC2=O)O[Si](C)(C)C)O1	4624.7	Semi standard non polar	33892256
Annopentocin B,2TMS,isomer #6	CCCCCCCCCCCC[C@H](O)[C@H](CC[C@H](O)[C@@H]1CC[C@@H](C[C@H](O)CCCCC[C@H](CC2=C[C@H](C)OC2=O)O[Si](C)(C)C)O1)O[Si](C)(C)C	4619.9	Semi standard non polar	33892256
Annopentocin B,2TMS,isomer #7	CCCCCCCCCCCC[C@H](O)[C@@H](O)CC[C@H](O[Si](C)(C)C)[C@@H]1CC[C@@H](C[C@H](O)CCCCC[C@H](CC2=C[C@H](C)OC2=O)O[Si](C)(C)C)O1	4608.4	Semi standard non polar	33892256
Annopentocin B,2TMS,isomer #8	CCCCCCCCCCCC[C@H](O[Si](C)(C)C)[C@@H](O)CC[C@H](O[Si](C)(C)C)[C@@H]1CC[C@@H](C[C@H](O)CCCCC[C@@H](O)CC2=C[C@H](C)OC2=O)O1	4610.3	Semi standard non polar	33892256
Annopentocin B,2TMS,isomer #9	CCCCCCCCCCCC[C@H](O)[C@H](CC[C@H](O[Si](C)(C)C)[C@@H]1CC[C@@H](C[C@H](O)CCCCC[C@@H](O)CC2=C[C@H](C)OC2=O)O1)O[Si](C)(C)C	4605.2	Semi standard non polar	33892256
Annopentocin B,3TMS,isomer #1	CCCCCCCCCCCC[C@H](O[Si](C)(C)C)[C@H](CC[C@H](O)[C@@H]1CC[C@@H](C[C@@H](CCCCC[C@@H](O)CC2=C[C@H](C)OC2=O)O[Si](C)(C)C)O1)O[Si](C)(C)C	4616.5	Semi standard non polar	33892256
Annopentocin B,3TMS,isomer #10	CCCCCCCCCCCC[C@H](O[Si](C)(C)C)[C@H](CC[C@H](O[Si](C)(C)C)[C@@H]1CC[C@@H](C[C@H](O)CCCCC[C@@H](O)CC2=C[C@H](C)OC2=O)O1)O[Si](C)(C)C	4576.2	Semi standard non polar	33892256
Annopentocin B,3TMS,isomer #2	CCCCCCCCCCCC[C@H](O[Si](C)(C)C)[C@@H](O)CC[C@H](O[Si](C)(C)C)[C@@H]1CC[C@@H](C[C@@H](CCCCC[C@@H](O)CC2=C[C@H](C)OC2=O)O[Si](C)(C)C)O1	4550.7	Semi standard non polar	33892256
Annopentocin B,3TMS,isomer #3	CCCCCCCCCCCC[C@H](O[Si](C)(C)C)[C@@H](O)CC[C@H](O)[C@@H]1CC[C@@H](C[C@@H](CCCCC[C@H](CC2=C[C@H](C)OC2=O)O[Si](C)(C)C)O[Si](C)(C)C)O1	4571.3	Semi standard non polar	33892256
Annopentocin B,3TMS,isomer #4	CCCCCCCCCCCC[C@H](O)[C@H](CC[C@H](O[Si](C)(C)C)[C@@H]1CC[C@@H](C[C@@H](CCCCC[C@@H](O)CC2=C[C@H](C)OC2=O)O[Si](C)(C)C)O1)O[Si](C)(C)C	4540.4	Semi standard non polar	33892256
Annopentocin B,3TMS,isomer #5	CCCCCCCCCCCC[C@H](O)[C@H](CC[C@H](O)[C@@H]1CC[C@@H](C[C@@H](CCCCC[C@H](CC2=C[C@H](C)OC2=O)O[Si](C)(C)C)O[Si](C)(C)C)O1)O[Si](C)(C)C	4566.1	Semi standard non polar	33892256
Annopentocin B,3TMS,isomer #6	CCCCCCCCCCCC[C@H](O)[C@@H](O)CC[C@H](O[Si](C)(C)C)[C@@H]1CC[C@@H](C[C@@H](CCCCC[C@H](CC2=C[C@H](C)OC2=O)O[Si](C)(C)C)O[Si](C)(C)C)O1	4539.5	Semi standard non polar	33892256
Annopentocin B,3TMS,isomer #7	CCCCCCCCCCCC[C@H](O[Si](C)(C)C)[C@H](CC[C@H](O)[C@@H]1CC[C@@H](C[C@H](O)CCCCC[C@H](CC2=C[C@H](C)OC2=O)O[Si](C)(C)C)O1)O[Si](C)(C)C	4605.1	Semi standard non polar	33892256
Annopentocin B,3TMS,isomer #8	CCCCCCCCCCCC[C@H](O[Si](C)(C)C)[C@@H](O)CC[C@H](O[Si](C)(C)C)[C@@H]1CC[C@@H](C[C@H](O)CCCCC[C@H](CC2=C[C@H](C)OC2=O)O[Si](C)(C)C)O1	4538.7	Semi standard non polar	33892256
Annopentocin B,3TMS,isomer #9	CCCCCCCCCCCC[C@H](O)[C@H](CC[C@H](O[Si](C)(C)C)[C@@H]1CC[C@@H](C[C@H](O)CCCCC[C@H](CC2=C[C@H](C)OC2=O)O[Si](C)(C)C)O1)O[Si](C)(C)C	4527.6	Semi standard non polar	33892256
Annopentocin B,1TBDMS,isomer #1	CCCCCCCCCCCC[C@H](O)[C@@H](O)CC[C@H](O)[C@@H]1CC[C@@H](C[C@@H](CCCCC[C@@H](O)CC2=C[C@H](C)OC2=O)O[Si](C)(C)C(C)(C)C)O1	4898.8	Semi standard non polar	33892256
Annopentocin B,1TBDMS,isomer #2	CCCCCCCCCCCC[C@H](O)[C@@H](O)CC[C@H](O)[C@@H]1CC[C@@H](C[C@H](O)CCCCC[C@H](CC2=C[C@H](C)OC2=O)O[Si](C)(C)C(C)(C)C)O1	4918.9	Semi standard non polar	33892256
Annopentocin B,1TBDMS,isomer #3	CCCCCCCCCCCC[C@H](O)[C@@H](O)CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1CC[C@@H](C[C@H](O)CCCCC[C@@H](O)CC2=C[C@H](C)OC2=O)O1	4892.9	Semi standard non polar	33892256
Annopentocin B,1TBDMS,isomer #4	CCCCCCCCCCCC[C@H](O)[C@H](CC[C@H](O)[C@@H]1CC[C@@H](C[C@H](O)CCCCC[C@@H](O)CC2=C[C@H](C)OC2=O)O1)O[Si](C)(C)C(C)(C)C	4895.9	Semi standard non polar	33892256
Annopentocin B,1TBDMS,isomer #5	CCCCCCCCCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)CC[C@H](O)[C@@H]1CC[C@@H](C[C@H](O)CCCCC[C@@H](O)CC2=C[C@H](C)OC2=O)O1	4893.5	Semi standard non polar	33892256
Annopentocin B,2TBDMS,isomer #1	CCCCCCCCCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)CC[C@H](O)[C@@H]1CC[C@@H](C[C@@H](CCCCC[C@@H](O)CC2=C[C@H](C)OC2=O)O[Si](C)(C)C(C)(C)C)O1	5066.2	Semi standard non polar	33892256
Annopentocin B,2TBDMS,isomer #10	CCCCCCCCCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@H](CC[C@H](O)[C@@H]1CC[C@@H](C[C@H](O)CCCCC[C@@H](O)CC2=C[C@H](C)OC2=O)O1)O[Si](C)(C)C(C)(C)C	5081.5	Semi standard non polar	33892256
Annopentocin B,2TBDMS,isomer #2	CCCCCCCCCCCC[C@H](O)[C@H](CC[C@H](O)[C@@H]1CC[C@@H](C[C@@H](CCCCC[C@@H](O)CC2=C[C@H](C)OC2=O)O[Si](C)(C)C(C)(C)C)O1)O[Si](C)(C)C(C)(C)C	5064.6	Semi standard non polar	33892256
Annopentocin B,2TBDMS,isomer #3	CCCCCCCCCCCC[C@H](O)[C@@H](O)CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1CC[C@@H](C[C@@H](CCCCC[C@@H](O)CC2=C[C@H](C)OC2=O)O[Si](C)(C)C(C)(C)C)O1	5067.6	Semi standard non polar	33892256
Annopentocin B,2TBDMS,isomer #4	CCCCCCCCCCCC[C@H](O)[C@@H](O)CC[C@H](O)[C@@H]1CC[C@@H](C[C@@H](CCCCC[C@H](CC2=C[C@H](C)OC2=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O1	5082.7	Semi standard non polar	33892256
Annopentocin B,2TBDMS,isomer #5	CCCCCCCCCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)CC[C@H](O)[C@@H]1CC[C@@H](C[C@H](O)CCCCC[C@H](CC2=C[C@H](C)OC2=O)O[Si](C)(C)C(C)(C)C)O1	5072.6	Semi standard non polar	33892256
Annopentocin B,2TBDMS,isomer #6	CCCCCCCCCCCC[C@H](O)[C@H](CC[C@H](O)[C@@H]1CC[C@@H](C[C@H](O)CCCCC[C@H](CC2=C[C@H](C)OC2=O)O[Si](C)(C)C(C)(C)C)O1)O[Si](C)(C)C(C)(C)C	5072.0	Semi standard non polar	33892256
Annopentocin B,2TBDMS,isomer #7	CCCCCCCCCCCC[C@H](O)[C@@H](O)CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1CC[C@@H](C[C@H](O)CCCCC[C@H](CC2=C[C@H](C)OC2=O)O[Si](C)(C)C(C)(C)C)O1	5081.5	Semi standard non polar	33892256
Annopentocin B,2TBDMS,isomer #8	CCCCCCCCCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1CC[C@@H](C[C@H](O)CCCCC[C@@H](O)CC2=C[C@H](C)OC2=O)O1	5064.8	Semi standard non polar	33892256
Annopentocin B,2TBDMS,isomer #9	CCCCCCCCCCCC[C@H](O)[C@H](CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1CC[C@@H](C[C@H](O)CCCCC[C@@H](O)CC2=C[C@H](C)OC2=O)O1)O[Si](C)(C)C(C)(C)C	5055.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Annopentocin B GC-MS (Non-derivatized) - 70eV, Positive	splash10-03dm-2755890000-a9d2ff72079c69cd1d6f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annopentocin B GC-MS (1 TMS) - 70eV, Positive	splash10-014j-3639728000-5309b97516c780a72d8a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annopentocin B GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annopentocin B GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annopentocin B GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annopentocin B GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annopentocin B GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annopentocin B GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annopentocin B GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annopentocin B GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annopentocin B GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annopentocin B GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annopentocin B GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annopentocin B GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annopentocin B GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annopentocin B GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annopentocin B GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annopentocin B GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annopentocin B GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annopentocin B GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annopentocin B GC-MS (TMS_3_5) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annopentocin B GC-MS (TMS_3_6) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annopentocin B GC-MS (TMS_3_7) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annopentocin B GC-MS (TMS_3_8) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annopentocin B GC-MS (TMS_3_9) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annopentocin B 10V, Positive-QTOF	splash10-002b-0001091000-00c4ac6786d414d42a97	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annopentocin B 20V, Positive-QTOF	splash10-016s-1965380000-13d50caa48b34492c93f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annopentocin B 40V, Positive-QTOF	splash10-01ba-3966060000-6e0e9b35ab1c5ec94857	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annopentocin B 10V, Negative-QTOF	splash10-03di-1111098000-d3ee181d670f8a91da52	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annopentocin B 20V, Negative-QTOF	splash10-0002-9414141000-a16b4bbf23b975b048aa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annopentocin B 40V, Negative-QTOF	splash10-054k-5389140000-3d79db55c914eccf53d1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annopentocin B 10V, Negative-QTOF	splash10-03di-2110219000-5f28a5ded4b3d84f89e0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annopentocin B 20V, Negative-QTOF	splash10-03dm-0329353000-5763d5f2c5cd49605f9e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annopentocin B 40V, Negative-QTOF	splash10-0a59-1293346000-4fb1a7c905fa19f07336	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annopentocin B 10V, Positive-QTOF	splash10-004i-1102390000-77137a0210895aeba85b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annopentocin B 20V, Positive-QTOF	splash10-004i-7001390000-2a92a93d75a68a6595fd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annopentocin B 40V, Positive-QTOF	splash10-0a4l-9021100000-0acaf5628c98493f003c	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB003472

KNApSAcK ID

C00044088

Chemspider ID

4477535

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5319163

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1826241

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Annopentocin B (HMDB0031400)

MOL for HMDB0031400 (Annopentocin B)

3D MOL for HMDB0031400 (Annopentocin B)

3D SDF for HMDB0031400 (Annopentocin B)

3D-SDF for HMDB0031400 (Annopentocin B)

PDB for HMDB0031400 (Annopentocin B)

3D PDB for HMDB0031400 (Annopentocin B)

SMILES for HMDB0031400 (Annopentocin B)

INCHI for HMDB0031400 (Annopentocin B)

Structure for HMDB0031400 (Annopentocin B)

3D Structure for HMDB0031400 (Annopentocin B)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra