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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:07:04 UTC

Update Date

2022-03-07 02:53:41 UTC

HMDB ID

HMDB0033399

Secondary Accession Numbers

HMDB33399

Metabolite Identification

Common Name

Annocherin A

Description

Annocherin A belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. Based on a literature review a small amount of articles have been published on Annocherin A.

Structure

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


  Mrv0541 05061307062D          

 29 32  0  0  0  0            999 V2000
    6.9375    2.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5597    2.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7830    2.9327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7368    0.4428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3553    0.7609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1624    0.0148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9943    0.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7316    2.6344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6225    1.5414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5458    0.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9122    2.4784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0999    1.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7383    2.0343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7865    2.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3993    2.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2152    2.6169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7496    2.4874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5599    0.6390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2706    2.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1837    1.0614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0801    2.1631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0034    1.2236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5716    1.6964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1409    1.3964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1992    3.4417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4796    3.2670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5355    0.9240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5088    2.1906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2094    1.8639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  9  5  1  0  0  0  0
 10  5  1  0  0  0  0
 11  8  1  0  0  0  0
 16  1  1  0  0  0  0
 17  2  1  0  0  0  0
 18  6  1  0  0  0  0
 18 12  1  0  0  0  0
 19  8  1  0  0  0  0
 20  7  1  0  0  0  0
 21  3  1  0  0  0  0
 21  9  1  0  0  0  0
 21 14  1  0  0  0  0
 21 19  1  0  0  0  0
 22  4  1  0  0  0  0
 22 10  1  0  0  0  0
 22 19  1  0  0  0  0
 22 20  1  0  0  0  0
 23 11  1  0  0  0  0
 23 12  1  0  0  0  0
 23 13  1  0  0  0  0
 23 20  1  0  0  0  0
 24 13  1  0  0  0  0
 24 15  1  0  0  0  0
 24 18  1  0  0  0  0
 25 16  2  0  0  0  0
 26 17  2  0  0  0  0
 27 24  1  0  0  0  0
 28 14  1  0  0  0  0
 28 16  1  0  0  0  0
 29 15  1  0  0  0  0
 29 17  1  0  0  0  0
M  END

HMDB0033399
     RDKit          3D
Annocherin A
 67 70  0  0  0  0  0  0  0  0999 V2000
   -6.0932    3.0602    0.2118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6466    1.6586    0.4225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2677    0.9872    1.2862 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5949    1.1000   -0.2917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2593   -0.2316   -0.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1184   -0.7625   -0.8185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5627   -0.6640   -2.2831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9346   -2.2088   -0.4378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3696   -2.3382    0.9342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2536   -1.4667    1.3107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1042   -0.1610    0.5966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5761    0.9337    1.5744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8132   -0.0727   -0.7093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9708   -0.5251   -1.8935 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1864   -1.4103   -1.4996 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0823   -0.6003   -0.6154 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8377    0.3582   -1.5541 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8601    0.9028   -0.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1228    1.9103    0.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6507    1.6274    0.4164 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3784    0.1270    0.4663 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2672   -0.3156    0.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2751   -0.0392    1.5796 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6297   -0.8329   -0.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5829    0.1640    0.1446 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9121   -0.0723   -0.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9747    0.9190    0.1816 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2417   -1.1769   -0.6065 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2674   -1.4123   -0.1067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0431    3.3006   -0.8891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4939    3.7757    0.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1457    3.1751    0.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1595   -0.8147   -0.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2671   -0.5101    1.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1074    0.1752   -2.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6770   -0.4768   -2.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4574   -1.6562   -2.8019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4285   -2.8115   -1.2153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9813   -2.6409   -0.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2198   -2.2136    1.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0846   -3.4258    1.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3115   -1.2946    2.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2975   -2.0669    1.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6461    1.9068    1.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5146    0.6966    2.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8188    0.8777    2.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0089    1.0277   -0.8909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5185    0.3532   -2.4354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5239   -1.0792   -2.6547 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7486   -1.5886   -2.4644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0767   -2.3940   -1.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2360    1.2073   -1.8644 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3149   -0.2193   -2.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6972    1.3469   -1.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1955    2.8929   -0.2800 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6206    2.0992    1.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0551    2.0367   -0.4249 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3537    2.1318    1.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8306   -0.2093    1.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1199    0.3870    1.7992 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6994   -1.2250   -1.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8454   -1.6888    0.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1329    1.6126   -0.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8893    0.3764    0.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6802    1.5334    1.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0455   -2.0442    0.7467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6127   -2.0116   -0.9877 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 18 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 22 29  1  0
 13  6  1  0
 21 16  1  0
 21 11  1  0
 29 16  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  5 33  1  0
  5 34  1  0
  7 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 12 44  1  0
 12 45  1  0
 12 46  1  0
 13 47  1  0
 14 48  1  0
 14 49  1  0
 15 50  1  0
 15 51  1  0
 17 52  1  0
 17 53  1  0
 18 54  1  0
 19 55  1  0
 19 56  1  0
 20 57  1  0
 20 58  1  0
 21 59  1  0
 23 60  1  0
 24 61  1  0
 24 62  1  0
 27 63  1  0
 27 64  1  0
 27 65  1  0
 29 66  1  0
 29 67  1  0
M  END


  Mrv0541 05061307062D          

 29 32  0  0  0  0            999 V2000
    6.9375    2.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5597    2.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7830    2.9327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7368    0.4428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3553    0.7609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1624    0.0148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9943    0.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7316    2.6344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6225    1.5414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5458    0.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9122    2.4784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0999    1.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7383    2.0343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7865    2.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3993    2.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2152    2.6169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7496    2.4874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5599    0.6390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2706    2.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1837    1.0614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0801    2.1631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0034    1.2236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5716    1.6964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1409    1.3964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1992    3.4417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4796    3.2670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5355    0.9240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5088    2.1906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2094    1.8639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  9  5  1  0  0  0  0
 10  5  1  0  0  0  0
 11  8  1  0  0  0  0
 16  1  1  0  0  0  0
 17  2  1  0  0  0  0
 18  6  1  0  0  0  0
 18 12  1  0  0  0  0
 19  8  1  0  0  0  0
 20  7  1  0  0  0  0
 21  3  1  0  0  0  0
 21  9  1  0  0  0  0
 21 14  1  0  0  0  0
 21 19  1  0  0  0  0
 22  4  1  0  0  0  0
 22 10  1  0  0  0  0
 22 19  1  0  0  0  0
 22 20  1  0  0  0  0
 23 11  1  0  0  0  0
 23 12  1  0  0  0  0
 23 13  1  0  0  0  0
 23 20  1  0  0  0  0
 24 13  1  0  0  0  0
 24 15  1  0  0  0  0
 24 18  1  0  0  0  0
 25 16  2  0  0  0  0
 26 17  2  0  0  0  0
 27 24  1  0  0  0  0
 28 14  1  0  0  0  0
 28 16  1  0  0  0  0
 29 15  1  0  0  0  0
 29 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033399

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)OCC1(O)CC23CC1CCC2C1(C)CCCC(C)(COC(C)=O)C1CC3

> <INCHI_IDENTIFIER>
InChI=1S/C24H38O5/c1-16(25)28-14-21(3)9-5-10-22(4)19(21)8-11-23-12-18(6-7-20(22)23)24(27,13-23)15-29-17(2)26/h18-20,27H,5-15H2,1-4H3

> <INCHI_KEY>
OQDCKOUFTOKDOD-UHFFFAOYSA-N

> <FORMULA>
C24H38O5

> <MOLECULAR_WEIGHT>
406.5555

> <EXACT_MASS>
406.271924326

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
46.288258053043684

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{5-[(acetyloxy)methyl]-14-hydroxy-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate

> <ALOGPS_LOGP>
3.54

> <JCHEM_LOGP>
3.203146448666666

> <ALOGPS_LOGS>
-5.24

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.752230216807543

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3445745031683813

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
109.17239999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.36e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{5-[(acetyloxy)methyl]-14-hydroxy-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033399
     RDKit          3D
Annocherin A
 67 70  0  0  0  0  0  0  0  0999 V2000
   -6.0932    3.0602    0.2118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6466    1.6586    0.4225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2677    0.9872    1.2862 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5949    1.1000   -0.2917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2593   -0.2316   -0.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1184   -0.7625   -0.8185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5627   -0.6640   -2.2831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9346   -2.2088   -0.4378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3696   -2.3382    0.9342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2536   -1.4667    1.3107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1042   -0.1610    0.5966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5761    0.9337    1.5744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8132   -0.0727   -0.7093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9708   -0.5251   -1.8935 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1864   -1.4103   -1.4996 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0823   -0.6003   -0.6154 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8377    0.3582   -1.5541 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8601    0.9028   -0.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1228    1.9103    0.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6507    1.6274    0.4164 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3784    0.1270    0.4663 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2672   -0.3156    0.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2751   -0.0392    1.5796 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6297   -0.8329   -0.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5829    0.1640    0.1446 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9121   -0.0723   -0.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9747    0.9190    0.1816 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2417   -1.1769   -0.6065 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2674   -1.4123   -0.1067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0431    3.3006   -0.8891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4939    3.7757    0.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1457    3.1751    0.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1595   -0.8147   -0.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2671   -0.5101    1.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1074    0.1752   -2.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6770   -0.4768   -2.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4574   -1.6562   -2.8019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4285   -2.8115   -1.2153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9813   -2.6409   -0.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2198   -2.2136    1.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0846   -3.4258    1.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3115   -1.2946    2.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2975   -2.0669    1.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6461    1.9068    1.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5146    0.6966    2.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8188    0.8777    2.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0089    1.0277   -0.8909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5185    0.3532   -2.4354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5239   -1.0792   -2.6547 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7486   -1.5886   -2.4644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0767   -2.3940   -1.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2360    1.2073   -1.8644 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3149   -0.2193   -2.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6972    1.3469   -1.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1955    2.8929   -0.2800 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6206    2.0992    1.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0551    2.0367   -0.4249 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3537    2.1318    1.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8306   -0.2093    1.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1199    0.3870    1.7992 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6994   -1.2250   -1.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8454   -1.6888    0.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1329    1.6126   -0.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8893    0.3764    0.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6802    1.5334    1.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0455   -2.0442    0.7467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6127   -2.0116   -0.9877 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 18 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 22 29  1  0
 13  6  1  0
 21 16  1  0
 21 11  1  0
 29 16  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  5 33  1  0
  5 34  1  0
  7 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 12 44  1  0
 12 45  1  0
 12 46  1  0
 13 47  1  0
 14 48  1  0
 14 49  1  0
 15 50  1  0
 15 51  1  0
 17 52  1  0
 17 53  1  0
 18 54  1  0
 19 55  1  0
 19 56  1  0
 20 57  1  0
 20 58  1  0
 21 59  1  0
 23 60  1  0
 24 61  1  0
 24 62  1  0
 27 63  1  0
 27 64  1  0
 27 65  1  0
 29 66  1  0
 29 67  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      12.950   4.141   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.778   4.352   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.062   5.474   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.109   0.827   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.130   1.420   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.170   0.028   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.723   0.398   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.099   4.918   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.629   2.877   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.619   1.124   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.569   4.626   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.053   2.140   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.378   3.797   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.935   4.833   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.745   3.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.602   4.885   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.266   4.643   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.045   1.193   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.105   3.741   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.076   1.981   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.616   4.038   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.606   2.284   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.934   3.167   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.263   2.607   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      11.572   6.425   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -2.762   6.098   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -1.000   1.725   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      10.283   4.089   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -2.258   3.479   0.000  0.00  0.00           O+0
CONECT    1   16                                                            
CONECT    2   17                                                            
CONECT    3   21                                                            
CONECT    4   22                                                            
CONECT    5    9   10                                                       
CONECT    6    7   18                                                       
CONECT    7    6   20                                                       
CONECT    8   11   19                                                       
CONECT    9    5   21                                                       
CONECT   10    5   22                                                       
CONECT   11    8   23                                                       
CONECT   12   18   23                                                       
CONECT   13   23   24                                                       
CONECT   14   21   28                                                       
CONECT   15   24   29                                                       
CONECT   16    1   25   28                                                  
CONECT   17    2   26   29                                                  
CONECT   18    6   12   24                                                  
CONECT   19    8   21   22                                                  
CONECT   20    7   22   23                                                  
CONECT   21    3    9   14   19                                             
CONECT   22    4   10   19   20                                             
CONECT   23   11   12   13   20                                             
CONECT   24   13   15   18   27                                             
CONECT   25   16                                                            
CONECT   26   17                                                            
CONECT   27   24                                                            
CONECT   28   14   16                                                       
CONECT   29   15   17                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

COMPND    HMDB0033399
HETATM    1  C1  UNL     1      -6.093   3.060   0.212  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.647   1.659   0.422  1.00  0.00           C  
HETATM    3  O1  UNL     1      -6.268   0.987   1.286  1.00  0.00           O  
HETATM    4  O2  UNL     1      -4.595   1.100  -0.292  1.00  0.00           O  
HETATM    5  C3  UNL     1      -4.259  -0.232  -0.011  1.00  0.00           C  
HETATM    6  C4  UNL     1      -3.118  -0.763  -0.818  1.00  0.00           C  
HETATM    7  C5  UNL     1      -3.563  -0.664  -2.283  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.935  -2.209  -0.438  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.370  -2.338   0.934  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.254  -1.467   1.311  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.104  -0.161   0.597  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.576   0.934   1.574  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.813  -0.073  -0.709  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.971  -0.525  -1.893  1.00  0.00           C  
HETATM   15  C13 UNL     1       0.186  -1.410  -1.500  1.00  0.00           C  
HETATM   16  C14 UNL     1       1.082  -0.600  -0.615  1.00  0.00           C  
HETATM   17  C15 UNL     1       1.838   0.358  -1.554  1.00  0.00           C  
HETATM   18  C16 UNL     1       2.860   0.903  -0.547  1.00  0.00           C  
HETATM   19  C17 UNL     1       2.123   1.910   0.274  1.00  0.00           C  
HETATM   20  C18 UNL     1       0.651   1.627   0.416  1.00  0.00           C  
HETATM   21  C19 UNL     1       0.378   0.127   0.466  1.00  0.00           C  
HETATM   22  C20 UNL     1       3.267  -0.316   0.214  1.00  0.00           C  
HETATM   23  O3  UNL     1       3.275  -0.039   1.580  1.00  0.00           O  
HETATM   24  C21 UNL     1       4.630  -0.833  -0.160  1.00  0.00           C  
HETATM   25  O4  UNL     1       5.583   0.164   0.145  1.00  0.00           O  
HETATM   26  C22 UNL     1       6.912  -0.072  -0.108  1.00  0.00           C  
HETATM   27  C23 UNL     1       7.975   0.919   0.182  1.00  0.00           C  
HETATM   28  O5  UNL     1       7.242  -1.177  -0.606  1.00  0.00           O  
HETATM   29  C24 UNL     1       2.267  -1.412  -0.107  1.00  0.00           C  
HETATM   30  H1  UNL     1      -6.043   3.301  -0.889  1.00  0.00           H  
HETATM   31  H2  UNL     1      -5.494   3.776   0.812  1.00  0.00           H  
HETATM   32  H3  UNL     1      -7.146   3.175   0.498  1.00  0.00           H  
HETATM   33  H4  UNL     1      -5.159  -0.815  -0.404  1.00  0.00           H  
HETATM   34  H5  UNL     1      -4.267  -0.510   1.054  1.00  0.00           H  
HETATM   35  H6  UNL     1      -3.107   0.175  -2.812  1.00  0.00           H  
HETATM   36  H7  UNL     1      -4.677  -0.477  -2.357  1.00  0.00           H  
HETATM   37  H8  UNL     1      -3.457  -1.656  -2.802  1.00  0.00           H  
HETATM   38  H9  UNL     1      -2.429  -2.811  -1.215  1.00  0.00           H  
HETATM   39  H10 UNL     1      -3.981  -2.641  -0.402  1.00  0.00           H  
HETATM   40  H11 UNL     1      -3.220  -2.214   1.670  1.00  0.00           H  
HETATM   41  H12 UNL     1      -2.085  -3.426   1.064  1.00  0.00           H  
HETATM   42  H13 UNL     1      -1.311  -1.295   2.430  1.00  0.00           H  
HETATM   43  H14 UNL     1      -0.298  -2.067   1.226  1.00  0.00           H  
HETATM   44  H15 UNL     1      -1.646   1.907   1.101  1.00  0.00           H  
HETATM   45  H16 UNL     1      -2.515   0.697   2.070  1.00  0.00           H  
HETATM   46  H17 UNL     1      -0.819   0.878   2.415  1.00  0.00           H  
HETATM   47  H18 UNL     1      -2.009   1.028  -0.891  1.00  0.00           H  
HETATM   48  H19 UNL     1      -0.518   0.353  -2.435  1.00  0.00           H  
HETATM   49  H20 UNL     1      -1.524  -1.079  -2.655  1.00  0.00           H  
HETATM   50  H21 UNL     1       0.749  -1.589  -2.464  1.00  0.00           H  
HETATM   51  H22 UNL     1      -0.077  -2.394  -1.133  1.00  0.00           H  
HETATM   52  H23 UNL     1       1.236   1.207  -1.864  1.00  0.00           H  
HETATM   53  H24 UNL     1       2.315  -0.219  -2.343  1.00  0.00           H  
HETATM   54  H25 UNL     1       3.697   1.347  -1.111  1.00  0.00           H  
HETATM   55  H26 UNL     1       2.195   2.893  -0.280  1.00  0.00           H  
HETATM   56  H27 UNL     1       2.621   2.099   1.247  1.00  0.00           H  
HETATM   57  H28 UNL     1       0.055   2.037  -0.425  1.00  0.00           H  
HETATM   58  H29 UNL     1       0.354   2.132   1.356  1.00  0.00           H  
HETATM   59  H30 UNL     1       0.831  -0.209   1.447  1.00  0.00           H  
HETATM   60  H31 UNL     1       4.120   0.387   1.799  1.00  0.00           H  
HETATM   61  H32 UNL     1       4.699  -1.225  -1.173  1.00  0.00           H  
HETATM   62  H33 UNL     1       4.845  -1.689   0.533  1.00  0.00           H  
HETATM   63  H34 UNL     1       8.133   1.613  -0.673  1.00  0.00           H  
HETATM   64  H35 UNL     1       8.889   0.376   0.441  1.00  0.00           H  
HETATM   65  H36 UNL     1       7.680   1.533   1.060  1.00  0.00           H  
HETATM   66  H37 UNL     1       2.045  -2.044   0.747  1.00  0.00           H  
HETATM   67  H38 UNL     1       2.613  -2.012  -0.988  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   33   34
CONECT    6    7    8   13
CONECT    7   35   36   37
CONECT    8    9   38   39
CONECT    9   10   40   41
CONECT   10   11   42   43
CONECT   11   12   13   21
CONECT   12   44   45   46
CONECT   13   14   47
CONECT   14   15   48   49
CONECT   15   16   50   51
CONECT   16   17   21   29
CONECT   17   18   52   53
CONECT   18   19   22   54
CONECT   19   20   55   56
CONECT   20   21   57   58
CONECT   21   59
CONECT   22   23   24   29
CONECT   23   60
CONECT   24   25   61   62
CONECT   25   26
CONECT   26   27   28   28
CONECT   27   63   64   65
CONECT   29   66   67
END

HMDB0033399
     RDKit          3D
Annocherin A
 67 70  0  0  0  0  0  0  0  0999 V2000
   -6.0932    3.0602    0.2118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6466    1.6586    0.4225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2677    0.9872    1.2862 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5949    1.1000   -0.2917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2593   -0.2316   -0.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1184   -0.7625   -0.8185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5627   -0.6640   -2.2831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9346   -2.2088   -0.4378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3696   -2.3382    0.9342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2536   -1.4667    1.3107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1042   -0.1610    0.5966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5761    0.9337    1.5744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8132   -0.0727   -0.7093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9708   -0.5251   -1.8935 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1864   -1.4103   -1.4996 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0823   -0.6003   -0.6154 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8377    0.3582   -1.5541 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8601    0.9028   -0.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1228    1.9103    0.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6507    1.6274    0.4164 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3784    0.1270    0.4663 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2672   -0.3156    0.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2751   -0.0392    1.5796 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6297   -0.8329   -0.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5829    0.1640    0.1446 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9121   -0.0723   -0.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9747    0.9190    0.1816 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2417   -1.1769   -0.6065 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2674   -1.4123   -0.1067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0431    3.3006   -0.8891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4939    3.7757    0.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1457    3.1751    0.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1595   -0.8147   -0.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2671   -0.5101    1.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1074    0.1752   -2.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6770   -0.4768   -2.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4574   -1.6562   -2.8019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4285   -2.8115   -1.2153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9813   -2.6409   -0.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2198   -2.2136    1.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0846   -3.4258    1.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3115   -1.2946    2.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2975   -2.0669    1.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6461    1.9068    1.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5146    0.6966    2.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8188    0.8777    2.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0089    1.0277   -0.8909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5185    0.3532   -2.4354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5239   -1.0792   -2.6547 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7486   -1.5886   -2.4644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0767   -2.3940   -1.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2360    1.2073   -1.8644 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3149   -0.2193   -2.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6972    1.3469   -1.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1955    2.8929   -0.2800 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6206    2.0992    1.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0551    2.0367   -0.4249 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3537    2.1318    1.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8306   -0.2093    1.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1199    0.3870    1.7992 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6994   -1.2250   -1.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8454   -1.6888    0.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1329    1.6126   -0.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8893    0.3764    0.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6802    1.5334    1.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0455   -2.0442    0.7467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6127   -2.0116   -0.9877 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 18 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 22 29  1  0
 13  6  1  0
 21 16  1  0
 21 11  1  0
 29 16  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  5 33  1  0
  5 34  1  0
  7 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 12 44  1  0
 12 45  1  0
 12 46  1  0
 13 47  1  0
 14 48  1  0
 14 49  1  0
 15 50  1  0
 15 51  1  0
 17 52  1  0
 17 53  1  0
 18 54  1  0
 19 55  1  0
 19 56  1  0
 20 57  1  0
 20 58  1  0
 21 59  1  0
 23 60  1  0
 24 61  1  0
 24 62  1  0
 27 63  1  0
 27 64  1  0
 27 65  1  0
 29 66  1  0
 29 67  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-[[O-6-O-[(2E)-3-(4-Hydroxy-3-methoxyphenyl)-1-oxo-2-propenyl]-beta-D-glucopyranosyl-(1->2)-O-beta-D-galactopyranosyl-(1->2)-beta-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one	HMDB
{5-[(acetyloxy)methyl]-14-hydroxy-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetic acid	HMDB

Chemical Formula

C₂₄H₃₈O₅

Average Molecular Weight

406.5555

Monoisotopic Molecular Weight

406.271924326

IUPAC Name

{5-[(acetyloxy)methyl]-14-hydroxy-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate

Traditional Name

{5-[(acetyloxy)methyl]-14-hydroxy-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate

CAS Registry Number

218281-62-0

SMILES

CC(=O)OCC1(O)CC23CC1CCC2C1(C)CCCC(C)(COC(C)=O)C1CC3

InChI Identifier

InChI=1S/C24H38O5/c1-16(25)28-14-21(3)9-5-10-22(4)19(21)8-11-23-12-18(6-7-20(22)23)24(27,13-23)15-29-17(2)26/h18-20,27H,5-15H2,1-4H3

InChI Key

OQDCKOUFTOKDOD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Kaurane diterpenoids

Alternative Parents

Substituents

Kaurane diterpenoid
Dicarboxylic acid or derivatives
Tertiary alcohol
Cyclic alcohol
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0033399)
Cell membrane (HMDB: HMDB0033399)

Cellular substructure

Extracellular (HMDB: HMDB0033399)
Membrane (HMDB: HMDB0033399)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033399)

Source

Endogenous

Endogenous (HMDB: HMDB0033399)

Plant

Plant (HMDB: HMDB0033399)

Animal

Animal (HMDB: HMDB0033399)

Exogenous

Food

Food (HMDB: HMDB0033399)

Fruit

Fruits (FooDB: FOOD00871)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0033399)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0033399)

Cellular process

Cell signaling (HMDB: HMDB0033399)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0033399)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0033399)

Nutrient

Nutrient (HMDB: HMDB0033399)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0033399)

Emulsifier (HMDB: HMDB0033399)

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0024 g/L	ALOGPS
logP	3.54	ALOGPS
logP	3.2	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	13.75	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	109.17 m³·mol⁻¹	ChemAxon
Polarizability	46.29 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	195.63	31661259
DarkChem	[M-H]-	188.017	31661259
DeepCCS	[M-2H]-	227.636	30932474
DeepCCS	[M+Na]+	202.863	30932474
AllCCS	[M+H]+	199.7	32859911
AllCCS	[M+H-H2O]+	197.7	32859911
AllCCS	[M+NH4]+	201.6	32859911
AllCCS	[M+Na]+	202.1	32859911
AllCCS	[M-H]-	197.4	32859911
AllCCS	[M+Na-2H]-	198.6	32859911
AllCCS	[M+HCOO]-	200.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Annocherin A	CC(=O)OCC1(O)CC23CC1CCC2C1(C)CCCC(C)(COC(C)=O)C1CC3	3323.8	Standard polar	33892256
Annocherin A	CC(=O)OCC1(O)CC23CC1CCC2C1(C)CCCC(C)(COC(C)=O)C1CC3	2868.9	Standard non polar	33892256
Annocherin A	CC(=O)OCC1(O)CC23CC1CCC2C1(C)CCCC(C)(COC(C)=O)C1CC3	3040.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Annocherin A,1TMS,isomer #1	CC(=O)OCC1(C)CCCC2(C)C1CCC13CC(CCC12)C(COC(C)=O)(O[Si](C)(C)C)C3	2967.5	Semi standard non polar	33892256
Annocherin A,1TBDMS,isomer #1	CC(=O)OCC1(C)CCCC2(C)C1CCC13CC(CCC12)C(COC(C)=O)(O[Si](C)(C)C(C)(C)C)C3	3240.9	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 - Annocherin A GC-MS (Non-derivatized) - 70eV, Positive	splash10-000x-3159000000-af2e9fcf16972a080c16	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annocherin A GC-MS (1 TMS) - 70eV, Positive	splash10-07dx-6014900000-a15808e923fac461291b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annocherin A GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - Annocherin A 10V, Negative-QTOF	splash10-0a4i-5005900000-2088e34c0a4a6a01ffcb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annocherin A 20V, Negative-QTOF	splash10-0a4i-9005200000-a9d06f9e7f2d3992b3b8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annocherin A 40V, Negative-QTOF	splash10-0a4i-9002000000-16111b828c744dfe0370	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annocherin A 10V, Negative-QTOF	splash10-0a4i-0028900000-b752a2f28e14dd706d78	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annocherin A 20V, Negative-QTOF	splash10-0a4i-7017900000-67a8015942d45499acd2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annocherin A 40V, Negative-QTOF	splash10-0a4i-9004000000-a1edb573892a66448b3d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annocherin A 10V, Positive-QTOF	splash10-052b-0019400000-b68bd509e3cb87e17b70	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annocherin A 20V, Positive-QTOF	splash10-0002-1039000000-7ce4f783f36f7b9b084a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annocherin A 40V, Positive-QTOF	splash10-000i-2193000000-7365c08f214addefd4d9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annocherin A 10V, Positive-QTOF	splash10-052b-0049300000-5875f88395de6247dcd9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annocherin A 20V, Positive-QTOF	splash10-0abi-1296100000-2d31e5b4ae0e119616b9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annocherin A 40V, Positive-QTOF	splash10-0kms-3942100000-79f4deb70b9c8cd5e8d7	2021-09-23	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

FDB011433

KNApSAcK ID

C00054665

Chemspider ID

35013601

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751014

PDB ID

Not Available

ChEBI ID

171902

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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 Annocherin A (HMDB0033399)

MOL for HMDB0033399 (Annocherin A)

3D MOL for HMDB0033399 (Annocherin A)

3D SDF for HMDB0033399 (Annocherin A)

3D-SDF for HMDB0033399 (Annocherin A)

PDB for HMDB0033399 (Annocherin A)

3D PDB for HMDB0033399 (Annocherin A)

SMILES for HMDB0033399 (Annocherin A)

INCHI for HMDB0033399 (Annocherin A)

Structure for HMDB0033399 (Annocherin A)

3D Structure for HMDB0033399 (Annocherin A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra