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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:51:11 UTC

Update Date

2022-03-07 02:54:17 UTC

HMDB ID

HMDB0034924

Secondary Accession Numbers

HMDB34924

Metabolite Identification

Common Name

Neoreticulatacin A

Description

Neoreticulatacin A, also known as uvariamincin-ii, 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 small amount of articles have been published on Neoreticulatacin A.

Structure

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


  Mrv0541 02241207462D          

 42 43  0  0  0  0            999 V2000
   -6.3766   -0.5451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3766   -1.3700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5929   -1.6243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1103   -0.9575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5929   -0.2935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5929    0.5313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5929   -2.4493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3079    0.9438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3079   -2.8617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8779    0.9438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1631    0.5313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4481    0.9438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7332    0.5313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0182    0.9438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3033    0.5313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5885    0.9438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1264    0.5313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8414    0.9438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5563    0.5313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2712    0.9438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9862    0.5313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7010    0.9438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4160    0.5313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1310    0.9438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9283    0.7307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3766    1.4237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8541    2.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0814    1.7660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0658    2.8617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2254   -0.0392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8793   -2.8603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1659   -2.4493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4522   -2.8603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7386   -2.4493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0252   -2.8603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3116   -2.4493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5981   -2.8603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1155   -2.4493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8290   -2.8603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5425   -2.4493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2561   -2.8603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9696   -2.4493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  8  1  0  0  0  0
  6 10  1  0  0  0  0
  7  9  1  0  0  0  0
  7 31  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
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 28  2  0  0  0  0
 25 26  1  0  0  0  0
 25 30  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  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  1  0  0  0  0
 41 42  1  0  0  0  0
M  END

HMDB0034924
     RDKit          3D
Neoreticulatacin A
110111  0  0  0  0  0  0  0  0999 V2000
   14.5142   -0.9370    0.8994 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2672   -0.6187    2.3398 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0176    0.2326    2.5363 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7946   -0.4513    2.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5738    0.3692    2.2512 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5568    1.7028    1.5907 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7043    1.7132    0.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7995    0.9314   -0.6844 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3423    1.1603   -0.7089 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5145    0.9168    0.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0768    1.2188    0.5034 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0710    0.6987   -0.4002 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0353    1.1498   -1.7928 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0627    0.9857   -2.6390 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7848    0.5877   -2.5196 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9908   -0.8838   -2.7971 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6788   -1.4932   -2.2912 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8048   -0.2877   -2.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6260   -0.3972   -1.3060 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0569   -0.7045   -0.0093 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3396   -1.4467   -1.7368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4999   -1.5258   -0.7878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2746   -0.2550   -0.7142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8170    0.1728   -2.0582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7160   -0.8155   -2.6887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9684   -1.1383   -1.9187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7956    0.1226   -1.7750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0770   -0.1582   -1.0608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8664   -0.6813    0.3204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1821   -0.9962    1.0120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9934    0.2593    1.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3655   -0.0529    1.7588 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0833    1.2479    1.7833 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4201    1.2774    2.4188 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4004    0.3512    1.8261 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.5176    0.7217    1.1688 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.2598   -0.4593    0.7097 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.6872   -0.4723    1.2591 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.6026   -1.5521    1.2781 O   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4451   -1.0936    1.9037 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5910   -1.8883    2.4511 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6546    0.6972   -1.7672 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9215   -1.8399    0.5760 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.6095   -1.1451    0.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.2282   -0.1144    0.2176 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.1492   -0.1005    2.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.0983   -1.5822    2.8858 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.1481    1.2018    1.9855 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.8871    0.4749    3.6059 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8962   -0.8252    0.9895 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6523   -1.3952    2.6419 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5220    0.5649    3.3634 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6505   -0.2265    2.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4749    2.2633    2.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7477    2.3331    1.9488 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7996    1.5609   -0.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5601    2.8206   -0.1768 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9443   -0.2093   -0.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2116    0.9547   -1.7709 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0954    2.1456   -1.1760 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0105    0.3444   -1.4913 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0166    1.3885    1.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5954   -0.2018    0.7530 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7373    0.8870    1.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9436    2.3652    0.6571 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0407    0.9649    0.0489 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0629   -0.4426   -0.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4877    1.8536   -2.9244 H   0  0  0  0  0  0  0  0  0  0  0  0
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  -16.9368   -1.4817    1.6850 H   0  0  0  0  0  0  0  0  0  0  0  0
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 36106  1  0
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 38108  1  0
 38109  1  0
 38110  1  0
M  END


  Mrv0541 02241207462D          

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  1  2  1  0  0  0  0
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  6 10  1  0  0  0  0
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  7 31  1  0  0  0  0
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M  END
> <DATABASE_ID>
HMDB0034924

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCCCCCC(O)C1CCC(O1)C(O)CCCCCCCCCCCCCCC1=CC(C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C37H68O5/c1-3-4-5-6-7-8-14-17-20-23-26-33(38)35-28-29-36(42-35)34(39)27-24-21-18-15-12-10-9-11-13-16-19-22-25-32-30-31(2)41-37(32)40/h30-31,33-36,38-39H,3-29H2,1-2H3

> <INCHI_KEY>
BDGWQMLWIGDEKO-UHFFFAOYSA-N

> <FORMULA>
C37H68O5

> <MOLECULAR_WEIGHT>
592.9328

> <EXACT_MASS>
592.506675286

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
77.98364802469423

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{15-hydroxy-15-[5-(1-hydroxytridecyl)oxolan-2-yl]pentadecyl}-5-methyl-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
9.41

> <JCHEM_LOGP>
11.368829022000002

> <ALOGPS_LOGS>
-6.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.432474809215588

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.873469726094928

> <JCHEM_PKA_STRONGEST_BASIC>
-3.148664983209411

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
175.2062

> <JCHEM_ROTATABLE_BOND_COUNT>
28

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.72e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{15-hydroxy-15-[5-(1-hydroxytridecyl)oxolan-2-yl]pentadecyl}-5-methyl-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034924
     RDKit          3D
Neoreticulatacin A
110111  0  0  0  0  0  0  0  0999 V2000
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  -11.1971    1.5748    0.6902 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7871    2.3355    2.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3341    1.0097    3.5038 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.7673    1.7866    1.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
  -15.2948   -0.5185   -0.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
  -17.4047   -0.3307    0.4166 H   0  0  0  0  0  0  0  0  0  0  0  0
  -16.7964    0.2611    2.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
  -16.9368   -1.4817    1.6850 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
 16 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
 27 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
 34 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  1  0
 37 39  1  0
 39 40  1  0
 40 41  2  0
 18 42  1  0
 42 15  1  0
 40 35  1  0
  1 43  1  0
  1 44  1  0
  1 45  1  0
  2 46  1  0
  2 47  1  0
  3 48  1  0
  3 49  1  0
  4 50  1  0
  4 51  1  0
  5 52  1  0
  5 53  1  0
  6 54  1  0
  6 55  1  0
  7 56  1  0
  7 57  1  0
  8 58  1  0
  8 59  1  0
  9 60  1  0
  9 61  1  0
 10 62  1  0
 10 63  1  0
 11 64  1  0
 11 65  1  0
 12 66  1  0
 12 67  1  0
 13 68  1  0
 14 69  1  0
 15 70  1  0
 16 71  1  0
 16 72  1  0
 17 73  1  0
 17 74  1  0
 18 75  1  0
 19 76  1  0
 20 77  1  0
 21 78  1  0
 21 79  1  0
 22 80  1  0
 22 81  1  0
 23 82  1  0
 23 83  1  0
 24 84  1  0
 24 85  1  0
 25 86  1  0
 25 87  1  0
 26 88  1  0
 26 89  1  0
 27 90  1  0
 27 91  1  0
 28 92  1  0
 28 93  1  0
 29 94  1  0
 29 95  1  0
 30 96  1  0
 30 97  1  0
 31 98  1  0
 31 99  1  0
 32100  1  0
 32101  1  0
 33102  1  0
 33103  1  0
 34104  1  0
 34105  1  0
 36106  1  0
 37107  1  0
 38108  1  0
 38109  1  0
 38110  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  C   UNK     0     -11.903  -1.018   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -11.903  -2.557   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -10.440  -3.032   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -9.539  -1.787   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0     -10.440  -0.548   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -10.440   0.992   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -10.440  -4.572   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0     -11.775   1.762   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0     -11.775  -5.342   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -9.105   1.762   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -7.771   0.992   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.436   1.762   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.102   0.992   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.767   1.762   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.433   0.992   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.098   1.762   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.236   0.992   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.571   1.762   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.905   0.992   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.240   1.762   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.574   0.992   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.909   1.762   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.243   0.992   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.578   1.762   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.066   1.364   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      11.903   2.658   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      10.928   3.853   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.485   3.296   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.323   5.342   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      11.621  -0.073   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -9.108  -5.339   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -7.776  -4.572   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -6.444  -5.339   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -5.112  -4.572   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -3.780  -5.339   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.448  -4.572   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -1.116  -5.339   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.216  -4.572   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       1.547  -5.339   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       2.879  -4.572   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       4.211  -5.339   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       5.543  -4.572   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    1    4    6                                                  
CONECT    6    5    8   10                                                  
CONECT    7    3    9   31                                                  
CONECT    8    6                                                            
CONECT    9    7                                                            
CONECT   10    6   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   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   28                                                  
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   24   27                                                       
CONECT   29   27                                                            
CONECT   30   25                                                            
CONECT   31    7   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   86    0
END

COMPND    HMDB0034924
HETATM    1  C1  UNL     1      14.514  -0.937   0.899  1.00  0.00           C  
HETATM    2  C2  UNL     1      14.267  -0.619   2.340  1.00  0.00           C  
HETATM    3  C3  UNL     1      13.018   0.233   2.536  1.00  0.00           C  
HETATM    4  C4  UNL     1      11.795  -0.451   2.034  1.00  0.00           C  
HETATM    5  C5  UNL     1      10.574   0.369   2.251  1.00  0.00           C  
HETATM    6  C6  UNL     1      10.557   1.703   1.591  1.00  0.00           C  
HETATM    7  C7  UNL     1      10.704   1.713   0.127  1.00  0.00           C  
HETATM    8  C8  UNL     1       9.800   0.931  -0.684  1.00  0.00           C  
HETATM    9  C9  UNL     1       8.342   1.160  -0.709  1.00  0.00           C  
HETATM   10  C10 UNL     1       7.514   0.917   0.467  1.00  0.00           C  
HETATM   11  C11 UNL     1       6.077   1.219   0.503  1.00  0.00           C  
HETATM   12  C12 UNL     1       5.071   0.699  -0.400  1.00  0.00           C  
HETATM   13  C13 UNL     1       5.035   1.150  -1.793  1.00  0.00           C  
HETATM   14  O1  UNL     1       6.063   0.986  -2.639  1.00  0.00           O  
HETATM   15  C14 UNL     1       3.785   0.588  -2.520  1.00  0.00           C  
HETATM   16  C15 UNL     1       3.991  -0.884  -2.797  1.00  0.00           C  
HETATM   17  C16 UNL     1       2.679  -1.493  -2.291  1.00  0.00           C  
HETATM   18  C17 UNL     1       1.805  -0.288  -2.252  1.00  0.00           C  
HETATM   19  C18 UNL     1       0.626  -0.397  -1.306  1.00  0.00           C  
HETATM   20  O2  UNL     1       1.057  -0.705  -0.009  1.00  0.00           O  
HETATM   21  C19 UNL     1      -0.340  -1.447  -1.737  1.00  0.00           C  
HETATM   22  C20 UNL     1      -1.500  -1.526  -0.788  1.00  0.00           C  
HETATM   23  C21 UNL     1      -2.275  -0.255  -0.714  1.00  0.00           C  
HETATM   24  C22 UNL     1      -2.817   0.173  -2.058  1.00  0.00           C  
HETATM   25  C23 UNL     1      -3.716  -0.816  -2.689  1.00  0.00           C  
HETATM   26  C24 UNL     1      -4.968  -1.138  -1.919  1.00  0.00           C  
HETATM   27  C25 UNL     1      -5.796   0.123  -1.775  1.00  0.00           C  
HETATM   28  C26 UNL     1      -7.077  -0.158  -1.061  1.00  0.00           C  
HETATM   29  C27 UNL     1      -6.866  -0.681   0.320  1.00  0.00           C  
HETATM   30  C28 UNL     1      -8.182  -0.996   1.012  1.00  0.00           C  
HETATM   31  C29 UNL     1      -8.993   0.259   1.082  1.00  0.00           C  
HETATM   32  C30 UNL     1     -10.366  -0.053   1.759  1.00  0.00           C  
HETATM   33  C31 UNL     1     -11.083   1.248   1.783  1.00  0.00           C  
HETATM   34  C32 UNL     1     -12.420   1.277   2.419  1.00  0.00           C  
HETATM   35  C33 UNL     1     -13.400   0.351   1.826  1.00  0.00           C  
HETATM   36  C34 UNL     1     -14.518   0.722   1.169  1.00  0.00           C  
HETATM   37  C35 UNL     1     -15.260  -0.459   0.710  1.00  0.00           C  
HETATM   38  C36 UNL     1     -16.687  -0.472   1.259  1.00  0.00           C  
HETATM   39  O3  UNL     1     -14.603  -1.552   1.278  1.00  0.00           O  
HETATM   40  C37 UNL     1     -13.445  -1.094   1.904  1.00  0.00           C  
HETATM   41  O4  UNL     1     -12.591  -1.888   2.451  1.00  0.00           O  
HETATM   42  O5  UNL     1       2.655   0.697  -1.767  1.00  0.00           O  
HETATM   43  H1  UNL     1      13.921  -1.840   0.576  1.00  0.00           H  
HETATM   44  H2  UNL     1      15.609  -1.145   0.781  1.00  0.00           H  
HETATM   45  H3  UNL     1      14.228  -0.114   0.218  1.00  0.00           H  
HETATM   46  H4  UNL     1      15.149  -0.101   2.750  1.00  0.00           H  
HETATM   47  H5  UNL     1      14.098  -1.582   2.886  1.00  0.00           H  
HETATM   48  H6  UNL     1      13.148   1.202   1.986  1.00  0.00           H  
HETATM   49  H7  UNL     1      12.887   0.475   3.606  1.00  0.00           H  
HETATM   50  H8  UNL     1      11.896  -0.825   0.989  1.00  0.00           H  
HETATM   51  H9  UNL     1      11.652  -1.395   2.642  1.00  0.00           H  
HETATM   52  H10 UNL     1      10.522   0.565   3.363  1.00  0.00           H  
HETATM   53  H11 UNL     1       9.651  -0.227   2.051  1.00  0.00           H  
HETATM   54  H12 UNL     1      11.475   2.263   2.060  1.00  0.00           H  
HETATM   55  H13 UNL     1       9.748   2.333   1.949  1.00  0.00           H  
HETATM   56  H14 UNL     1      11.800   1.561  -0.178  1.00  0.00           H  
HETATM   57  H15 UNL     1      10.560   2.821  -0.177  1.00  0.00           H  
HETATM   58  H16 UNL     1       9.944  -0.209  -0.489  1.00  0.00           H  
HETATM   59  H17 UNL     1      10.212   0.955  -1.771  1.00  0.00           H  
HETATM   60  H18 UNL     1       8.095   2.146  -1.176  1.00  0.00           H  
HETATM   61  H19 UNL     1       8.011   0.344  -1.491  1.00  0.00           H  
HETATM   62  H20 UNL     1       8.017   1.389   1.378  1.00  0.00           H  
HETATM   63  H21 UNL     1       7.595  -0.202   0.753  1.00  0.00           H  
HETATM   64  H22 UNL     1       5.737   0.887   1.571  1.00  0.00           H  
HETATM   65  H23 UNL     1       5.944   2.365   0.657  1.00  0.00           H  
HETATM   66  H24 UNL     1       4.041   0.965   0.049  1.00  0.00           H  
HETATM   67  H25 UNL     1       5.063  -0.443  -0.322  1.00  0.00           H  
HETATM   68  H26 UNL     1       4.797   2.266  -1.774  1.00  0.00           H  
HETATM   69  H27 UNL     1       6.488   1.854  -2.924  1.00  0.00           H  
HETATM   70  H28 UNL     1       3.734   1.142  -3.470  1.00  0.00           H  
HETATM   71  H29 UNL     1       4.853  -1.303  -2.279  1.00  0.00           H  
HETATM   72  H30 UNL     1       4.109  -1.056  -3.882  1.00  0.00           H  
HETATM   73  H31 UNL     1       2.826  -1.975  -1.306  1.00  0.00           H  
HETATM   74  H32 UNL     1       2.288  -2.189  -3.068  1.00  0.00           H  
HETATM   75  H33 UNL     1       1.463  -0.028  -3.276  1.00  0.00           H  
HETATM   76  H34 UNL     1       0.128   0.582  -1.280  1.00  0.00           H  
HETATM   77  H35 UNL     1       1.089  -1.692   0.107  1.00  0.00           H  
HETATM   78  H36 UNL     1       0.168  -2.460  -1.679  1.00  0.00           H  
HETATM   79  H37 UNL     1      -0.665  -1.347  -2.793  1.00  0.00           H  
HETATM   80  H38 UNL     1      -2.144  -2.419  -0.981  1.00  0.00           H  
HETATM   81  H39 UNL     1      -1.102  -1.717   0.253  1.00  0.00           H  
HETATM   82  H40 UNL     1      -3.096  -0.366   0.028  1.00  0.00           H  
HETATM   83  H41 UNL     1      -1.629   0.550  -0.336  1.00  0.00           H  
HETATM   84  H42 UNL     1      -3.359   1.125  -1.906  1.00  0.00           H  
HETATM   85  H43 UNL     1      -1.965   0.424  -2.730  1.00  0.00           H  
HETATM   86  H44 UNL     1      -4.070  -0.413  -3.686  1.00  0.00           H  
HETATM   87  H45 UNL     1      -3.239  -1.782  -2.944  1.00  0.00           H  
HETATM   88  H46 UNL     1      -4.644  -1.520  -0.913  1.00  0.00           H  
HETATM   89  H47 UNL     1      -5.524  -1.936  -2.434  1.00  0.00           H  
HETATM   90  H48 UNL     1      -5.956   0.520  -2.796  1.00  0.00           H  
HETATM   91  H49 UNL     1      -5.236   0.891  -1.205  1.00  0.00           H  
HETATM   92  H50 UNL     1      -7.631   0.829  -1.037  1.00  0.00           H  
HETATM   93  H51 UNL     1      -7.703  -0.808  -1.698  1.00  0.00           H  
HETATM   94  H52 UNL     1      -6.378   0.095   0.938  1.00  0.00           H  
HETATM   95  H53 UNL     1      -6.222  -1.578   0.358  1.00  0.00           H  
HETATM   96  H54 UNL     1      -7.912  -1.381   2.031  1.00  0.00           H  
HETATM   97  H55 UNL     1      -8.760  -1.776   0.501  1.00  0.00           H  
HETATM   98  H56 UNL     1      -9.269   0.638   0.095  1.00  0.00           H  
HETATM   99  H57 UNL     1      -8.525   1.039   1.691  1.00  0.00           H  
HETATM  100  H58 UNL     1     -10.144  -0.532   2.690  1.00  0.00           H  
HETATM  101  H59 UNL     1     -10.887  -0.705   0.989  1.00  0.00           H  
HETATM  102  H60 UNL     1     -10.394   1.993   2.268  1.00  0.00           H  
HETATM  103  H61 UNL     1     -11.197   1.575   0.690  1.00  0.00           H  
HETATM  104  H62 UNL     1     -12.787   2.336   2.391  1.00  0.00           H  
HETATM  105  H63 UNL     1     -12.334   1.010   3.504  1.00  0.00           H  
HETATM  106  H64 UNL     1     -14.767   1.787   1.036  1.00  0.00           H  
HETATM  107  H65 UNL     1     -15.295  -0.519  -0.408  1.00  0.00           H  
HETATM  108  H66 UNL     1     -17.405  -0.331   0.417  1.00  0.00           H  
HETATM  109  H67 UNL     1     -16.796   0.261   2.073  1.00  0.00           H  
HETATM  110  H68 UNL     1     -16.937  -1.482   1.685  1.00  0.00           H  
CONECT    1    2   43   44   45
CONECT    2    3   46   47
CONECT    3    4   48   49
CONECT    4    5   50   51
CONECT    5    6   52   53
CONECT    6    7   54   55
CONECT    7    8   56   57
CONECT    8    9   58   59
CONECT    9   10   60   61
CONECT   10   11   62   63
CONECT   11   12   64   65
CONECT   12   13   66   67
CONECT   13   14   15   68
CONECT   14   69
CONECT   15   16   42   70
CONECT   16   17   71   72
CONECT   17   18   73   74
CONECT   18   19   42   75
CONECT   19   20   21   76
CONECT   20   77
CONECT   21   22   78   79
CONECT   22   23   80   81
CONECT   23   24   82   83
CONECT   24   25   84   85
CONECT   25   26   86   87
CONECT   26   27   88   89
CONECT   27   28   90   91
CONECT   28   29   92   93
CONECT   29   30   94   95
CONECT   30   31   96   97
CONECT   31   32   98   99
CONECT   32   33  100  101
CONECT   33   34  102  103
CONECT   34   35  104  105
CONECT   35   36   36   40
CONECT   36   37  106
CONECT   37   38   39  107
CONECT   38  108  109  110
CONECT   39   40
CONECT   40   41   41
END

HMDB0034924
     RDKit          3D
Neoreticulatacin A
110111  0  0  0  0  0  0  0  0999 V2000
   14.5142   -0.9370    0.8994 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2672   -0.6187    2.3398 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0176    0.2326    2.5363 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7946   -0.4513    2.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5738    0.3692    2.2512 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5568    1.7028    1.5907 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7043    1.7132    0.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7995    0.9314   -0.6844 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3423    1.1603   -0.7089 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5145    0.9168    0.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0768    1.2188    0.5034 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0710    0.6987   -0.4002 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0353    1.1498   -1.7928 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0627    0.9857   -2.6390 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7848    0.5877   -2.5196 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9908   -0.8838   -2.7971 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6788   -1.4932   -2.2912 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8048   -0.2877   -2.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6260   -0.3972   -1.3060 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0569   -0.7045   -0.0093 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3396   -1.4467   -1.7368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4999   -1.5258   -0.7878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2746   -0.2550   -0.7142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8170    0.1728   -2.0582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7160   -0.8155   -2.6887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9684   -1.1383   -1.9187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7956    0.1226   -1.7750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0770   -0.1582   -1.0608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8664   -0.6813    0.3204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1821   -0.9962    1.0120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9934    0.2593    1.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3655   -0.0529    1.7588 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0833    1.2479    1.7833 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4201    1.2774    2.4188 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4004    0.3512    1.8261 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.5176    0.7217    1.1688 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.2598   -0.4593    0.7097 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.6872   -0.4723    1.2591 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.6026   -1.5521    1.2781 O   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4451   -1.0936    1.9037 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5910   -1.8883    2.4511 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6546    0.6972   -1.7672 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9215   -1.8399    0.5760 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.6095   -1.1451    0.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.2282   -0.1144    0.2176 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.1492   -0.1005    2.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.0983   -1.5822    2.8858 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.1481    1.2018    1.9855 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.8871    0.4749    3.6059 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8962   -0.8252    0.9895 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6523   -1.3952    2.6419 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5220    0.5649    3.3634 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6505   -0.2265    2.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4749    2.2633    2.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7477    2.3331    1.9488 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7996    1.5609   -0.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5601    2.8206   -0.1768 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9443   -0.2093   -0.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2116    0.9547   -1.7709 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0954    2.1456   -1.1760 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0105    0.3444   -1.4913 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0166    1.3885    1.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5954   -0.2018    0.7530 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7373    0.8870    1.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9436    2.3652    0.6571 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0407    0.9649    0.0489 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0629   -0.4426   -0.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7969    2.2665   -1.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4877    1.8536   -2.9244 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7343    1.1423   -3.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8532   -1.3029   -2.2790 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1092   -1.0558   -3.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8258   -1.9747   -1.3061 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2881   -2.1892   -3.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4628   -0.0282   -3.2756 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1282    0.5819   -1.2796 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0895   -1.6923    0.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1680   -2.4598   -1.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6651   -1.3471   -2.7928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1439   -2.4192   -0.9815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1021   -1.7166    0.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0961   -0.3656    0.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6286    0.5499   -0.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3587    1.1252   -1.9063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9653    0.4244   -2.7300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0695   -0.4131   -3.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2389   -1.7815   -2.9440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6438   -1.5200   -0.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5241   -1.9360   -2.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9558    0.5195   -2.7961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2362    0.8912   -1.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6310    0.8288   -1.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7032   -0.8082   -1.6983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3781    0.0950    0.9384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2223   -1.5776    0.3578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9118   -1.3807    2.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7596   -1.7761    0.5014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2693    0.6384    0.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5246    1.0392    1.6907 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1438   -0.5316    2.6896 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8875   -0.7053    0.9889 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3942    1.9934    2.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1971    1.5748    0.6902 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7871    2.3355    2.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3341    1.0097    3.5038 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.7673    1.7866    1.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
  -15.2948   -0.5185   -0.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
  -17.4047   -0.3307    0.4166 H   0  0  0  0  0  0  0  0  0  0  0  0
  -16.7964    0.2611    2.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
  -16.9368   -1.4817    1.6850 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
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 15 16  1  0
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 18 19  1  0
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 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
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 37 39  1  0
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 18 42  1  0
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  1 43  1  0
  1 44  1  0
  1 45  1  0
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 32100  1  0
 32101  1  0
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 38110  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Uvariamincin-II	HMDB

Chemical Formula

C₃₇H₆₈O₅

Average Molecular Weight

592.9328

Monoisotopic Molecular Weight

592.506675286

IUPAC Name

3-{15-hydroxy-15-[5-(1-hydroxytridecyl)oxolan-2-yl]pentadecyl}-5-methyl-2,5-dihydrofuran-2-one

Traditional Name

3-{15-hydroxy-15-[5-(1-hydroxytridecyl)oxolan-2-yl]pentadecyl}-5-methyl-5H-furan-2-one

CAS Registry Number

166022-35-1

SMILES

CCCCCCCCCCCCC(O)C1CCC(O1)C(O)CCCCCCCCCCCCCCC1=CC(C)OC1=O

InChI Identifier

InChI=1S/C37H68O5/c1-3-4-5-6-7-8-14-17-20-23-26-33(38)35-28-29-36(42-35)34(39)27-24-21-18-15-12-10-9-11-13-16-19-22-25-32-30-31(2)41-37(32)40/h30-31,33-36,38-39H,3-29H2,1-2H3

InChI Key

BDGWQMLWIGDEKO-UHFFFAOYSA-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
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxygen compound
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0034924)
Cell membrane (HMDB: HMDB0034924)

Biofluid or Excreta

Urine (HMDB: HMDB0034924)

Cellular substructure

Extracellular (HMDB: HMDB0034924)
Membrane (HMDB: HMDB0034924)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034924)

Source

Endogenous

Endogenous (HMDB: HMDB0034924)

Plant

Plant (HMDB: HMDB0034924)

Animal

Animal (HMDB: HMDB0034924)

Exogenous

Food

Food (HMDB: HMDB0034924)

Fruit

Fruits (FooDB: FOOD00871)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0034924)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0034924)

Cellular process

Cell signaling (HMDB: HMDB0034924)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0034924)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0034924)

Nutrient

Nutrient (HMDB: HMDB0034924)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0034924)

Emulsifier (HMDB: HMDB0034924)

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	7.7e-05 g/L	ALOGPS
logP	9.41	ALOGPS
logP	11.37	ChemAxon
logS	-6.9	ALOGPS
pKa (Strongest Acidic)	13.87	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	28	ChemAxon
Refractivity	175.21 m³·mol⁻¹	ChemAxon
Polarizability	77.98 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]+	250.782	31661259
DarkChem	[M-H]-	248.289	31661259
DeepCCS	[M+H]+	257.772	30932474
DeepCCS	[M-H]-	255.414	30932474
DeepCCS	[M-2H]-	289.582	30932474
DeepCCS	[M+Na]+	264.811	30932474
AllCCS	[M+H]+	270.6	32859911
AllCCS	[M+H-H2O]+	269.4	32859911
AllCCS	[M+NH4]+	271.6	32859911
AllCCS	[M+Na]+	271.9	32859911
AllCCS	[M-H]-	239.4	32859911
AllCCS	[M+Na-2H]-	244.0	32859911
AllCCS	[M+HCOO]-	249.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Neoreticulatacin A	CCCCCCCCCCCCC(O)C1CCC(O1)C(O)CCCCCCCCCCCCCCC1=CC(C)OC1=O	4599.9	Standard polar	33892256
Neoreticulatacin A	CCCCCCCCCCCCC(O)C1CCC(O1)C(O)CCCCCCCCCCCCCCC1=CC(C)OC1=O	4221.1	Standard non polar	33892256
Neoreticulatacin A	CCCCCCCCCCCCC(O)C1CCC(O1)C(O)CCCCCCCCCCCCCCC1=CC(C)OC1=O	4497.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Neoreticulatacin A,1TMS,isomer #1	CCCCCCCCCCCCC(O[Si](C)(C)C)C1CCC(C(O)CCCCCCCCCCCCCCC2=CC(C)OC2=O)O1	4472.4	Semi standard non polar	33892256
Neoreticulatacin A,1TMS,isomer #2	CCCCCCCCCCCCC(O)C1CCC(C(CCCCCCCCCCCCCCC2=CC(C)OC2=O)O[Si](C)(C)C)O1	4472.4	Semi standard non polar	33892256
Neoreticulatacin A,2TMS,isomer #1	CCCCCCCCCCCCC(O[Si](C)(C)C)C1CCC(C(CCCCCCCCCCCCCCC2=CC(C)OC2=O)O[Si](C)(C)C)O1	4422.2	Semi standard non polar	33892256
Neoreticulatacin A,1TBDMS,isomer #1	CCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)C1CCC(C(O)CCCCCCCCCCCCCCC2=CC(C)OC2=O)O1	4717.5	Semi standard non polar	33892256
Neoreticulatacin A,1TBDMS,isomer #2	CCCCCCCCCCCCC(O)C1CCC(C(CCCCCCCCCCCCCCC2=CC(C)OC2=O)O[Si](C)(C)C(C)(C)C)O1	4717.7	Semi standard non polar	33892256
Neoreticulatacin A,2TBDMS,isomer #1	CCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)C1CCC(C(CCCCCCCCCCCCCCC2=CC(C)OC2=O)O[Si](C)(C)C(C)(C)C)O1	4886.5	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 - Neoreticulatacin A GC-MS (Non-derivatized) - 70eV, Positive	splash10-0005-3297220000-529eba703e5b9687a6a4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Neoreticulatacin A GC-MS (1 TMS) - 70eV, Positive	splash10-006x-4019011000-c95f26718e2de573ea81	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Neoreticulatacin A GC-MS ("Neoreticulatacin A,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Neoreticulatacin A GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Neoreticulatacin A GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Neoreticulatacin A GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Neoreticulatacin A GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Neoreticulatacin A GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-10-15	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 - Neoreticulatacin A 10V, Positive-QTOF	splash10-002f-0111090000-cf0f9a9a16cf4517d529	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neoreticulatacin A 20V, Positive-QTOF	splash10-016u-2961250000-36935a53853e951a12c8	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neoreticulatacin A 40V, Positive-QTOF	splash10-014i-6952030000-bcca8811887eddc7bae3	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neoreticulatacin A 10V, Negative-QTOF	splash10-0006-0000090000-9c62aa021d7593ca4d6d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neoreticulatacin A 20V, Negative-QTOF	splash10-00kg-1353090000-001ae7d325de2218762e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neoreticulatacin A 40V, Negative-QTOF	splash10-00fv-3498020000-83223c51293ef7fc5f1b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neoreticulatacin A 10V, Positive-QTOF	splash10-056u-1001190000-dec7cf6df1efc9be1c0c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neoreticulatacin A 20V, Positive-QTOF	splash10-004j-2001090000-40363437579b6b647058	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neoreticulatacin A 40V, Positive-QTOF	splash10-0536-9002000000-f0b2e8c87fbfae0522f8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neoreticulatacin A 10V, Negative-QTOF	splash10-0006-0000090000-a71c6145c4802c665806	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neoreticulatacin A 20V, Negative-QTOF	splash10-0006-2123190000-997cee9b1b97175d3418	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neoreticulatacin A 40V, Negative-QTOF	splash10-062d-7109020000-ec839bc418bac67f07a2	2021-09-22	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

FDB013510

KNApSAcK ID

C00044292

Chemspider ID

24710089

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14759338

PDB ID

Not Available

ChEBI ID

176178

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 Neoreticulatacin A (HMDB0034924)

MOL for HMDB0034924 (Neoreticulatacin A)

3D MOL for HMDB0034924 (Neoreticulatacin A)

3D SDF for HMDB0034924 (Neoreticulatacin A)

3D-SDF for HMDB0034924 (Neoreticulatacin A)

PDB for HMDB0034924 (Neoreticulatacin A)

3D PDB for HMDB0034924 (Neoreticulatacin A)

SMILES for HMDB0034924 (Neoreticulatacin A)

INCHI for HMDB0034924 (Neoreticulatacin A)

Structure for HMDB0034924 (Neoreticulatacin A)

3D Structure for HMDB0034924 (Neoreticulatacin A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra