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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:18:03 UTC

Update Date

2022-03-07 02:56:42 UTC

HMDB ID

HMDB0040723

Secondary Accession Numbers

HMDB40723

Metabolite Identification

Common Name

(-)-Gossypol

Description

(-)-Gossypol belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Thus, (-)-gossypol is considered to be an isoprenoid. Based on a literature review a significant number of articles have been published on (-)-Gossypol.

Structure

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


  Mrv0541 09051417082D          

 38 41  0  0  0  0            999 V2000
   -5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 12  3  1  0  0  0  0
 12  4  1  0  0  0  0
 13  5  1  0  0  0  0
 13  7  2  0  0  0  0
 14  6  1  0  0  0  0
 14  8  2  0  0  0  0
 15  7  1  0  0  0  0
 16  8  1  0  0  0  0
 17  9  1  0  0  0  0
 18 10  1  0  0  0  0
 19 11  1  0  0  0  0
 19 15  2  0  0  0  0
 20 12  1  0  0  0  0
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 21 13  1  0  0  0  0
 22 14  1  0  0  0  0
 22 21  1  0  0  0  0
 23 15  1  0  0  0  0
 23 17  2  0  0  0  0
 24 16  1  0  0  0  0
 24 18  2  0  0  0  0
 25 17  1  0  0  0  0
 26 18  1  0  0  0  0
 27 21  2  0  0  0  0
 27 23  1  0  0  0  0
 28 22  2  0  0  0  0
 28 24  1  0  0  0  0
 29 19  1  0  0  0  0
 29 25  2  0  0  0  0
 30 20  1  0  0  0  0
 30 26  2  0  0  0  0
 31  9  2  0  0  0  0
 32 10  2  0  0  0  0
 33 25  1  0  0  0  0
 34 26  1  0  0  0  0
 35 27  1  0  0  0  0
 36 28  1  0  0  0  0
 37 29  1  0  0  0  0
 38 30  1  0  0  0  0
M  END

HMDB0040723
     RDKit          3D
(-)-Gossypol
 68 71  0  0  0  0  0  0  0  0999 V2000
   -0.1434   -2.6476   -0.1935 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9314   -1.6443   -0.4656 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4121   -0.5727   -1.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1527    0.7659   -1.5854 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1065    1.7420   -1.8288 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8534    1.1752   -1.2056 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6338    2.6050   -1.0974 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6106    3.3929   -1.3474 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8950    0.2357   -0.9607 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5970    0.6147   -0.5863 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2791    1.9287   -0.4636 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6011   -0.3273   -0.3347 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.7997    0.5032    3.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9469    0.1235    4.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4432    0.1625    5.3010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4234    0.5151    1.7009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1502    0.1400    1.3501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2253   -0.2447    2.2857 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  2  0
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  5  6  1  0
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 28 63  1  0
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 30 65  1  0
 32 66  1  0
 34 67  1  0
 38 68  1  0
M  END


  Mrv0541 09051417082D          

 38 41  0  0  0  0            999 V2000
   -5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 33 25  1  0  0  0  0
 34 26  1  0  0  0  0
 35 27  1  0  0  0  0
 36 28  1  0  0  0  0
 37 29  1  0  0  0  0
 38 30  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040723

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C1=C2C=C(C)C(=C(O)C2=C(C=O)C(O)=C1O)C1=C(O)C2=C(C=O)C(O)=C(O)C(C(C)C)=C2C=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C30H30O8/c1-11(2)19-15-7-13(5)21(27(35)23(15)17(9-31)25(33)29(19)37)22-14(6)8-16-20(12(3)4)30(38)26(34)18(10-32)24(16)28(22)36/h7-12,33-38H,1-6H3

> <INCHI_KEY>
QBKSWRVVCFFDOT-UHFFFAOYSA-N

> <FORMULA>
C30H30O8

> <MOLECULAR_WEIGHT>
518.5544

> <EXACT_MASS>
518.194067936

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
55.94711360292843

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7-[8-formyl-1,6,7-trihydroxy-3-methyl-5-(propan-2-yl)naphthalen-2-yl]-2,3,8-trihydroxy-6-methyl-4-(propan-2-yl)naphthalene-1-carbaldehyde

> <ALOGPS_LOGP>
4.49

> <JCHEM_LOGP>
8.019898530666666

> <ALOGPS_LOGS>
-5.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.29047318129364

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.799881811289805

> <JCHEM_PKA_STRONGEST_BASIC>
-6.149501497054318

> <JCHEM_POLAR_SURFACE_AREA>
155.52

> <JCHEM_REFRACTIVITY>
147.612

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.85e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-gossypol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040723
     RDKit          3D
(-)-Gossypol
 68 71  0  0  0  0  0  0  0  0999 V2000
   -0.1434   -2.6476   -0.1935 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9314   -1.6443   -0.4656 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1834   -2.0753   -0.8292 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1533   -1.1300   -1.0725 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4422   -1.5214   -1.4475 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7030   -2.9663   -1.5215 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0138   -3.2891   -2.2540 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8842   -3.5139   -0.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4121   -0.5727   -1.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6855   -0.9451   -2.0650 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1527    0.7659   -1.5854 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1065    1.7420   -1.8288 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8534    1.1752   -1.2056 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6338    2.6050   -1.0974 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6106    3.3929   -1.3474 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8950    0.2357   -0.9607 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5970    0.6147   -0.5863 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2791    1.9287   -0.4636 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6011   -0.3273   -0.3347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7248    0.1280    0.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6026    0.5014   -0.9497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1750    0.4920   -2.3634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8899    0.8828   -0.6111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3233    0.8974    0.7060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6253    1.2774    1.0089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5048    1.6672   -0.1061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9497    1.8707    0.2871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0346    3.0243   -0.6298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9861    1.2615    2.3177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2910    1.6438    2.6086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1313    0.8942    3.3085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5342    0.8900    4.6319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7997    0.5032    3.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9469    0.1235    4.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4432    0.1625    5.3010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4234    0.5151    1.7009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1502    0.1400    1.3501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2253   -0.2447    2.2857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1810   -2.9320    0.8752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1333   -2.2946   -0.4808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0860   -3.5574   -0.8065 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4044   -3.1231   -0.9293 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9385   -3.5403   -2.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9881   -4.4142   -2.4519 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8995   -3.1533   -1.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9770   -2.7557   -3.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8695   -4.0255    0.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8286   -2.6576    0.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1022   -4.2326    0.1760 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4421   -0.3317   -2.2618 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0383    1.5748   -2.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7492    3.1059   -0.8317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3508    2.2177   -0.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1943    0.0304   -2.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2543    1.5358   -2.7569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9102   -0.1173   -2.9308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6054    1.1822   -1.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4924    0.8978   -0.8746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4925    2.0055   -0.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3883    0.9637    0.7069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1508    2.8095    0.8188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0318    3.0661   -1.7382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0209    3.2620   -0.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6862    3.8486   -0.2419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7200    1.6890    3.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4513    1.1478    4.9465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9472   -0.1907    4.0957 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7523   -0.4679    2.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 13 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 25 29  2  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 31 33  2  0
 33 34  1  0
 34 35  2  0
 33 36  1  0
 36 37  2  0
 37 38  1  0
 19  2  1  0
 37 20  1  0
 16  4  1  0
 36 24  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  3 42  1  0
  6 43  1  0
  7 44  1  0
  7 45  1  0
  7 46  1  0
  8 47  1  0
  8 48  1  0
  8 49  1  0
 10 50  1  0
 12 51  1  0
 14 52  1  0
 18 53  1  0
 22 54  1  0
 22 55  1  0
 22 56  1  0
 23 57  1  0
 26 58  1  0
 27 59  1  0
 27 60  1  0
 27 61  1  0
 28 62  1  0
 28 63  1  0
 28 64  1  0
 30 65  1  0
 32 66  1  0
 34 67  1  0
 38 68  1  0
M  END

HEADER    PROTEIN                                 05-SEP-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-14         0                                  
HETATM    1  C   UNK     0      -9.336   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.002   6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -9.336   2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0     -10.669   1.540   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -5.335   0.000   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0     -10.669   4.620   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4   12                                                            
CONECT    5   13                                                            
CONECT    6   14                                                            
CONECT    7   13   15                                                       
CONECT    8   14   16                                                       
CONECT    9   17   31                                                       
CONECT   10   18   32                                                       
CONECT   11    1    2   19                                                  
CONECT   12    3    4   20                                                  
CONECT   13    5    7   21                                                  
CONECT   14    6    8   22                                                  
CONECT   15    7   19   23                                                  
CONECT   16    8   20   24                                                  
CONECT   17    9   23   25                                                  
CONECT   18   10   24   26                                                  
CONECT   19   11   15   29                                                  
CONECT   20   12   16   30                                                  
CONECT   21   13   22   27                                                  
CONECT   22   14   21   28                                                  
CONECT   23   15   17   27                                                  
CONECT   24   16   18   28                                                  
CONECT   25   17   29   33                                                  
CONECT   26   18   30   34                                                  
CONECT   27   21   23   35                                                  
CONECT   28   22   24   36                                                  
CONECT   29   19   25   37                                                  
CONECT   30   20   26   38                                                  
CONECT   31    9                                                            
CONECT   32   10                                                            
CONECT   33   25                                                            
CONECT   34   26                                                            
CONECT   35   27                                                            
CONECT   36   28                                                            
CONECT   37   29                                                            
CONECT   38   30                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

COMPND    HMDB0040723
HETATM    1  C1  UNL     1      -0.143  -2.648  -0.193  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.931  -1.644  -0.466  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.183  -2.075  -0.829  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.153  -1.130  -1.072  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.442  -1.521  -1.448  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.703  -2.966  -1.522  1.00  0.00           C  
HETATM    7  C7  UNL     1       6.014  -3.289  -2.254  1.00  0.00           C  
HETATM    8  C8  UNL     1       4.884  -3.514  -0.094  1.00  0.00           C  
HETATM    9  C9  UNL     1       5.412  -0.573  -1.696  1.00  0.00           C  
HETATM   10  O1  UNL     1       6.686  -0.945  -2.065  1.00  0.00           O  
HETATM   11  C10 UNL     1       5.153   0.766  -1.585  1.00  0.00           C  
HETATM   12  O2  UNL     1       6.107   1.742  -1.829  1.00  0.00           O  
HETATM   13  C11 UNL     1       3.853   1.175  -1.206  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.634   2.605  -1.097  1.00  0.00           C  
HETATM   15  O3  UNL     1       4.611   3.393  -1.347  1.00  0.00           O  
HETATM   16  C13 UNL     1       2.895   0.236  -0.961  1.00  0.00           C  
HETATM   17  C14 UNL     1       1.597   0.615  -0.586  1.00  0.00           C  
HETATM   18  O4  UNL     1       1.279   1.929  -0.464  1.00  0.00           O  
HETATM   19  C15 UNL     1       0.601  -0.327  -0.335  1.00  0.00           C  
HETATM   20  C16 UNL     1      -0.725   0.128   0.021  1.00  0.00           C  
HETATM   21  C17 UNL     1      -1.603   0.501  -0.950  1.00  0.00           C  
HETATM   22  C18 UNL     1      -1.175   0.492  -2.363  1.00  0.00           C  
HETATM   23  C19 UNL     1      -2.890   0.883  -0.611  1.00  0.00           C  
HETATM   24  C20 UNL     1      -3.323   0.897   0.706  1.00  0.00           C  
HETATM   25  C21 UNL     1      -4.625   1.277   1.009  1.00  0.00           C  
HETATM   26  C22 UNL     1      -5.505   1.667  -0.106  1.00  0.00           C  
HETATM   27  C23 UNL     1      -6.950   1.871   0.287  1.00  0.00           C  
HETATM   28  C24 UNL     1      -5.035   3.024  -0.630  1.00  0.00           C  
HETATM   29  C25 UNL     1      -4.986   1.261   2.318  1.00  0.00           C  
HETATM   30  O5  UNL     1      -6.291   1.644   2.609  1.00  0.00           O  
HETATM   31  C26 UNL     1      -4.131   0.894   3.308  1.00  0.00           C  
HETATM   32  O6  UNL     1      -4.534   0.890   4.632  1.00  0.00           O  
HETATM   33  C27 UNL     1      -2.800   0.503   3.021  1.00  0.00           C  
HETATM   34  C28 UNL     1      -1.947   0.123   4.122  1.00  0.00           C  
HETATM   35  O7  UNL     1      -2.443   0.163   5.301  1.00  0.00           O  
HETATM   36  C29 UNL     1      -2.423   0.515   1.701  1.00  0.00           C  
HETATM   37  C30 UNL     1      -1.150   0.140   1.350  1.00  0.00           C  
HETATM   38  O8  UNL     1      -0.225  -0.245   2.286  1.00  0.00           O  
HETATM   39  H1  UNL     1      -0.181  -2.932   0.875  1.00  0.00           H  
HETATM   40  H2  UNL     1      -1.133  -2.295  -0.481  1.00  0.00           H  
HETATM   41  H3  UNL     1       0.086  -3.557  -0.806  1.00  0.00           H  
HETATM   42  H4  UNL     1       2.404  -3.123  -0.929  1.00  0.00           H  
HETATM   43  H5  UNL     1       3.939  -3.540  -2.079  1.00  0.00           H  
HETATM   44  H6  UNL     1       5.988  -4.414  -2.452  1.00  0.00           H  
HETATM   45  H7  UNL     1       6.900  -3.153  -1.640  1.00  0.00           H  
HETATM   46  H8  UNL     1       5.977  -2.756  -3.212  1.00  0.00           H  
HETATM   47  H9  UNL     1       5.869  -4.026   0.006  1.00  0.00           H  
HETATM   48  H10 UNL     1       4.829  -2.658   0.584  1.00  0.00           H  
HETATM   49  H11 UNL     1       4.102  -4.233   0.176  1.00  0.00           H  
HETATM   50  H12 UNL     1       7.442  -0.332  -2.262  1.00  0.00           H  
HETATM   51  H13 UNL     1       7.038   1.575  -2.094  1.00  0.00           H  
HETATM   52  H14 UNL     1       2.749   3.106  -0.832  1.00  0.00           H  
HETATM   53  H15 UNL     1       0.351   2.218  -0.129  1.00  0.00           H  
HETATM   54  H16 UNL     1      -0.194   0.030  -2.516  1.00  0.00           H  
HETATM   55  H17 UNL     1      -1.254   1.536  -2.757  1.00  0.00           H  
HETATM   56  H18 UNL     1      -1.910  -0.117  -2.931  1.00  0.00           H  
HETATM   57  H19 UNL     1      -3.605   1.182  -1.368  1.00  0.00           H  
HETATM   58  H20 UNL     1      -5.492   0.898  -0.875  1.00  0.00           H  
HETATM   59  H21 UNL     1      -7.492   2.006  -0.705  1.00  0.00           H  
HETATM   60  H22 UNL     1      -7.388   0.964   0.707  1.00  0.00           H  
HETATM   61  H23 UNL     1      -7.151   2.809   0.819  1.00  0.00           H  
HETATM   62  H24 UNL     1      -5.032   3.066  -1.738  1.00  0.00           H  
HETATM   63  H25 UNL     1      -4.021   3.262  -0.280  1.00  0.00           H  
HETATM   64  H26 UNL     1      -5.686   3.849  -0.242  1.00  0.00           H  
HETATM   65  H27 UNL     1      -6.720   1.689   3.498  1.00  0.00           H  
HETATM   66  H28 UNL     1      -5.451   1.148   4.946  1.00  0.00           H  
HETATM   67  H29 UNL     1      -0.947  -0.191   4.096  1.00  0.00           H  
HETATM   68  H30 UNL     1       0.752  -0.468   2.076  1.00  0.00           H  
CONECT    1    2   39   40   41
CONECT    2    3    3   19
CONECT    3    4   42
CONECT    4    5    5   16
CONECT    5    6    9
CONECT    6    7    8   43
CONECT    7   44   45   46
CONECT    8   47   48   49
CONECT    9   10   11   11
CONECT   10   50
CONECT   11   12   13
CONECT   12   51
CONECT   13   14   16   16
CONECT   14   15   15   52
CONECT   16   17
CONECT   17   18   19   19
CONECT   18   53
CONECT   19   20
CONECT   20   21   21   37
CONECT   21   22   23
CONECT   22   54   55   56
CONECT   23   24   24   57
CONECT   24   25   36
CONECT   25   26   29   29
CONECT   26   27   28   58
CONECT   27   59   60   61
CONECT   28   62   63   64
CONECT   29   30   31
CONECT   30   65
CONECT   31   32   33   33
CONECT   32   66
CONECT   33   34   36
CONECT   34   35   35   67
CONECT   36   37   37
CONECT   37   38
CONECT   38   68
END

HMDB0040723
     RDKit          3D
(-)-Gossypol
 68 71  0  0  0  0  0  0  0  0999 V2000
   -0.1434   -2.6476   -0.1935 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9314   -1.6443   -0.4656 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1834   -2.0753   -0.8292 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1533   -1.1300   -1.0725 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4422   -1.5214   -1.4475 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7030   -2.9663   -1.5215 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0138   -3.2891   -2.2540 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8842   -3.5139   -0.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4121   -0.5727   -1.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6855   -0.9451   -2.0650 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1527    0.7659   -1.5854 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1065    1.7420   -1.8288 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8534    1.1752   -1.2056 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6338    2.6050   -1.0974 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6106    3.3929   -1.3474 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8950    0.2357   -0.9607 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5970    0.6147   -0.5863 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2791    1.9287   -0.4636 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6011   -0.3273   -0.3347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7248    0.1280    0.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6026    0.5014   -0.9497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1750    0.4920   -2.3634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8899    0.8828   -0.6111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3233    0.8974    0.7060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6253    1.2774    1.0089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5048    1.6672   -0.1061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9497    1.8707    0.2871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0346    3.0243   -0.6298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9861    1.2615    2.3177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2910    1.6438    2.6086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1313    0.8942    3.3085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5342    0.8900    4.6319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7997    0.5032    3.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9469    0.1235    4.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4432    0.1625    5.3010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4234    0.5151    1.7009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1502    0.1400    1.3501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2253   -0.2447    2.2857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1810   -2.9320    0.8752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1333   -2.2946   -0.4808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0860   -3.5574   -0.8065 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4044   -3.1231   -0.9293 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9385   -3.5403   -2.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9881   -4.4142   -2.4519 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8995   -3.1533   -1.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9770   -2.7557   -3.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8695   -4.0255    0.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8286   -2.6576    0.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1022   -4.2326    0.1760 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4421   -0.3317   -2.2618 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0383    1.5748   -2.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7492    3.1059   -0.8317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3508    2.2177   -0.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1943    0.0304   -2.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2543    1.5358   -2.7569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9102   -0.1173   -2.9308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6054    1.1822   -1.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4924    0.8978   -0.8746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4925    2.0055   -0.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3883    0.9637    0.7069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1508    2.8095    0.8188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0318    3.0661   -1.7382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0209    3.2620   -0.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6862    3.8486   -0.2419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7200    1.6890    3.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4513    1.1478    4.9465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9472   -0.1907    4.0957 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7523   -0.4679    2.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 13 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 25 29  2  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 31 33  2  0
 33 34  1  0
 34 35  2  0
 33 36  1  0
 36 37  2  0
 37 38  1  0
 19  2  1  0
 37 20  1  0
 16  4  1  0
 36 24  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  3 42  1  0
  6 43  1  0
  7 44  1  0
  7 45  1  0
  7 46  1  0
  8 47  1  0
  8 48  1  0
  8 49  1  0
 10 50  1  0
 12 51  1  0
 14 52  1  0
 18 53  1  0
 22 54  1  0
 22 55  1  0
 22 56  1  0
 23 57  1  0
 26 58  1  0
 27 59  1  0
 27 60  1  0
 27 61  1  0
 28 62  1  0
 28 63  1  0
 28 64  1  0
 30 65  1  0
 32 66  1  0
 34 67  1  0
 38 68  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-Gossypol	HMDB
(+-)-Gossypol	HMDB
(+/-)-gossypol	HMDB
(R)-(-)-Gossypol	HMDB
(R)-Gossypol	HMDB
Dipotassium salt, gossypol	HMDB, MeSH
Gossypol	HMDB
Gossypol dipotassium salt	HMDB, MeSH
Gossypol from cotton seeds	HMDB
Gossypol sodium salt	HMDB, MeSH
Gossypol, (+)-isomer	HMDB, MeSH
Gossypol, (+-)-isomer	HMDB, MeSH
Gossypol, (-)-isomer	HMDB, MeSH
Pogosin	HMDB
Racemic-gossypol	HMDB
Sodium salt, gossypol	HMDB, MeSH
Tash 1	HMDB

Chemical Formula

C₃₀H₃₀O₈

Average Molecular Weight

518.5544

Monoisotopic Molecular Weight

518.194067936

IUPAC Name

7-[8-formyl-1,6,7-trihydroxy-3-methyl-5-(propan-2-yl)naphthalen-2-yl]-2,3,8-trihydroxy-6-methyl-4-(propan-2-yl)naphthalene-1-carbaldehyde

Traditional Name

(-)-gossypol

CAS Registry Number

90141-22-3

SMILES

CC(C)C1=C2C=C(C)C(=C(O)C2=C(C=O)C(O)=C1O)C1=C(O)C2=C(C=O)C(O)=C(O)C(C(C)C)=C2C=C1C

InChI Identifier

InChI=1S/C30H30O8/c1-11(2)19-15-7-13(5)21(27(35)23(15)17(9-31)25(33)29(19)37)22-14(6)8-16-20(12(3)4)30(38)26(34)18(10-32)24(16)28(22)36/h7-12,33-38H,1-6H3

InChI Key

QBKSWRVVCFFDOT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Cadinane sesquiterpenoid
Sesquiterpenoid
2-naphthol
1-naphthol
Naphthalene
Aryl-aldehyde
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Vinylogous acid
Polyol
Organic oxygen compound
Organooxygen compound
Aldehyde
Hydrocarbon derivative
Organic oxide
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

polyphenol (CHEBI:28584 )
Cadinane sesquiterpenoids (C07667 )
Terpenoids (C07667 )
Cadinanes (C07667 )
Cadinane sesquiterpenoids (LMPR0103330002 )

Ontology

Physiological effect

Health effect

Fatigue (HMDB: None)
Paralysis (HMDB: None)
Muscle weakness (HMDB: None)

Disposition

Biological location

Cellular substructure

Membrane (HMDB: None)

Route of exposure

Parenteral

Dermal (HMDB: None)

Enteral

Ingestion (HMDB: None)

Source

Exogenous

Food

Food (HMDB: None)

Soy

Soy bean (FooDB: FOOD00085)

Herb and spice

Oilseed crop

Cottonseed (FooDB: FOOD00341)
Sunflower (FooDB: FOOD00086)

Vegetable

Other vegetable

Okra (FooDB: FOOD00420)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: None)

Biochemical process

Fatty acid metabolism (HMDB: None)

Cellular process

Cell signaling (HMDB: None)

Biochemical pathway

Lipid metabolism pathway (HMDB: None)

EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor (HMDB: None)
angiotensin converting enzyme inhibitor (HMDB: None)
EC 1.1.1.21 (aldehyde reductase) inhibitor (HMDB: None)
prostaglandin synthesis inhibitor (HMDB: None)
topoisomerase-II inhibitor (HMDB: None)

Nutrient

Nutrient (HMDB: None)

Industrial application

Manufacturing industry

Material processing agent

pesticide (HMDB: None)

Pharmaceutical industry

Antineoplastic agent

Anticancer agent (HMDB: None)

Pharmaceutical (HMDB: None)

Indirect biological role

antioxidant (HMDB: None)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	178 - 183 °C	Not Available
Boiling Point	707.89 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	1.5e-05 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	5.419 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0038 g/L	ALOGPS
logP	4.49	ALOGPS
logP	8.02	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	7.8	ChemAxon
pKa (Strongest Basic)	-6.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	155.52 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	147.61 m³·mol⁻¹	ChemAxon
Polarizability	55.95 Å³	ChemAxon
Number of Rings	4	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]+	217.563	31661259
DarkChem	[M-H]-	218.189	31661259
DeepCCS	[M+H]+	222.078	30932474
DeepCCS	[M-H]-	220.18	30932474
DeepCCS	[M-2H]-	253.42	30932474
DeepCCS	[M+Na]+	227.9	30932474
AllCCS	[M+H]+	224.6	32859911
AllCCS	[M+H-H2O]+	222.7	32859911
AllCCS	[M+NH4]+	226.3	32859911
AllCCS	[M+Na]+	226.8	32859911
AllCCS	[M-H]-	227.3	32859911
AllCCS	[M+Na-2H]-	228.5	32859911
AllCCS	[M+HCOO]-	230.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(-)-Gossypol	CC(C)C1=C2C=C(C)C(=C(O)C2=C(C=O)C(O)=C1O)C1=C(O)C2=C(C=O)C(O)=C(O)C(C(C)C)=C2C=C1C	5334.7	Standard polar	33892256
(-)-Gossypol	CC(C)C1=C2C=C(C)C(=C(O)C2=C(C=O)C(O)=C1O)C1=C(O)C2=C(C=O)C(O)=C(O)C(C(C)C)=C2C=C1C	3432.0	Standard non polar	33892256
(-)-Gossypol	CC(C)C1=C2C=C(C)C(=C(O)C2=C(C=O)C(O)=C1O)C1=C(O)C2=C(C=O)C(O)=C(O)C(C(C)C)=C2C=C1C	4402.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(-)-Gossypol,1TMS,isomer #1	CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O)=C(C=O)C2=C1O[Si](C)(C)C	4173.3	Semi standard non polar	33892256
(-)-Gossypol,1TMS,isomer #2	CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O[Si](C)(C)C)=C(C=O)C2=C1O	4168.2	Semi standard non polar	33892256
(-)-Gossypol,1TMS,isomer #3	CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C)C(O)=C(C=O)C2=C1O	4157.7	Semi standard non polar	33892256
(-)-Gossypol,2TMS,isomer #1	CC1=CC2=C(C(C)C)C(O[Si](C)(C)C)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O)=C(C=O)C2=C1O[Si](C)(C)C	4029.6	Semi standard non polar	33892256
(-)-Gossypol,2TMS,isomer #2	CC1=CC2=C(C(C)C)C(O)=C(O[Si](C)(C)C)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O)=C(C=O)C2=C1O[Si](C)(C)C	4055.3	Semi standard non polar	33892256
(-)-Gossypol,2TMS,isomer #3	CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O[Si](C)(C)C)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O)=C(C=O)C2=C1O[Si](C)(C)C	4053.6	Semi standard non polar	33892256
(-)-Gossypol,2TMS,isomer #4	CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C)C(O)=C(C=O)C2=C1O[Si](C)(C)C	4030.4	Semi standard non polar	33892256
(-)-Gossypol,2TMS,isomer #5	CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O[Si](C)(C)C)=C(C=O)C2=C1O[Si](C)(C)C	4065.6	Semi standard non polar	33892256
(-)-Gossypol,2TMS,isomer #6	CC1=CC2=C(C(C)C)C(O[Si](C)(C)C)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O[Si](C)(C)C)=C(C=O)C2=C1O	4060.4	Semi standard non polar	33892256
(-)-Gossypol,2TMS,isomer #7	CC1=CC2=C(C(C)C)C(O)=C(O[Si](C)(C)C)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O[Si](C)(C)C)=C(C=O)C2=C1O	4097.9	Semi standard non polar	33892256
(-)-Gossypol,2TMS,isomer #8	CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C=O)C2=C1O	4081.5	Semi standard non polar	33892256
(-)-Gossypol,2TMS,isomer #9	CC1=CC2=C(C(C)C)C(O[Si](C)(C)C)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C)C(O)=C(C=O)C2=C1O	4019.5	Semi standard non polar	33892256
(-)-Gossypol,3TMS,isomer #1	CC1=CC2=C(C(C)C)C(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O)=C(C=O)C2=C1O[Si](C)(C)C	4006.4	Semi standard non polar	33892256
(-)-Gossypol,3TMS,isomer #10	CC1=CC2=C(C(C)C)C(O[Si](C)(C)C)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C=O)C2=C1O	3998.9	Semi standard non polar	33892256
(-)-Gossypol,3TMS,isomer #2	CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O[Si](C)(C)C)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C)C(O)=C(C=O)C2=C1O[Si](C)(C)C	3947.7	Semi standard non polar	33892256
(-)-Gossypol,3TMS,isomer #3	CC1=CC2=C(C(C)C)C(O[Si](C)(C)C)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C)C(O)=C(C=O)C2=C1O[Si](C)(C)C	3949.2	Semi standard non polar	33892256
(-)-Gossypol,3TMS,isomer #4	CC1=CC2=C(C(C)C)C(O[Si](C)(C)C)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O[Si](C)(C)C)=C(C=O)C2=C1O[Si](C)(C)C	3988.3	Semi standard non polar	33892256
(-)-Gossypol,3TMS,isomer #5	CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O[Si](C)(C)C)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O[Si](C)(C)C)=C(C=O)C2=C1O[Si](C)(C)C	3983.2	Semi standard non polar	33892256
(-)-Gossypol,3TMS,isomer #6	CC1=CC2=C(C(C)C)C(O)=C(O[Si](C)(C)C)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C)C(O)=C(C=O)C2=C1O[Si](C)(C)C	3977.6	Semi standard non polar	33892256
(-)-Gossypol,3TMS,isomer #7	CC1=CC2=C(C(C)C)C(O)=C(O[Si](C)(C)C)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O[Si](C)(C)C)=C(C=O)C2=C1O[Si](C)(C)C	4029.7	Semi standard non polar	33892256
(-)-Gossypol,3TMS,isomer #8	CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C=O)C2=C1O[Si](C)(C)C	4019.6	Semi standard non polar	33892256
(-)-Gossypol,3TMS,isomer #9	CC1=CC2=C(C(C)C)C(O)=C(O[Si](C)(C)C)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C=O)C2=C1O	4029.2	Semi standard non polar	33892256
(-)-Gossypol,4TMS,isomer #1	CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O[Si](C)(C)C)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C=O)C2=C1O[Si](C)(C)C	3967.9	Semi standard non polar	33892256
(-)-Gossypol,4TMS,isomer #2	CC1=CC2=C(C(C)C)C(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C)C(O)=C(C=O)C2=C1O[Si](C)(C)C	3944.0	Semi standard non polar	33892256
(-)-Gossypol,4TMS,isomer #3	CC1=CC2=C(C(C)C)C(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O[Si](C)(C)C)=C(C=O)C2=C1O[Si](C)(C)C	3962.7	Semi standard non polar	33892256
(-)-Gossypol,4TMS,isomer #4	CC1=CC2=C(C(C)C)C(O[Si](C)(C)C)=C(O)C(C=O)=C2C(O[Si](C)(C)C)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C)C(O)=C(C=O)C2=C1O[Si](C)(C)C	3940.3	Semi standard non polar	33892256
(-)-Gossypol,4TMS,isomer #5	CC1=CC2=C(C(C)C)C(O[Si](C)(C)C)=C(O)C(C=O)=C2C(O[Si](C)(C)C)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O[Si](C)(C)C)=C(C=O)C2=C1O[Si](C)(C)C	3950.1	Semi standard non polar	33892256
(-)-Gossypol,4TMS,isomer #6	CC1=CC2=C(C(C)C)C(O[Si](C)(C)C)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C=O)C2=C1O[Si](C)(C)C	3949.3	Semi standard non polar	33892256
(-)-Gossypol,4TMS,isomer #7	CC1=CC2=C(C(C)C)C(O)=C(O[Si](C)(C)C)C(C=O)=C2C(O[Si](C)(C)C)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O[Si](C)(C)C)=C(C=O)C2=C1O[Si](C)(C)C	3968.8	Semi standard non polar	33892256
(-)-Gossypol,4TMS,isomer #8	CC1=CC2=C(C(C)C)C(O)=C(O[Si](C)(C)C)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C=O)C2=C1O[Si](C)(C)C	3964.0	Semi standard non polar	33892256
(-)-Gossypol,4TMS,isomer #9	CC1=CC2=C(C(C)C)C(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C=O)C2=C1O	3997.3	Semi standard non polar	33892256
(-)-Gossypol,5TMS,isomer #1	CC1=CC2=C(C(C)C)C(O[Si](C)(C)C)=C(O)C(C=O)=C2C(O[Si](C)(C)C)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C=O)C2=C1O[Si](C)(C)C	3965.0	Semi standard non polar	33892256
(-)-Gossypol,5TMS,isomer #2	CC1=CC2=C(C(C)C)C(O)=C(O[Si](C)(C)C)C(C=O)=C2C(O[Si](C)(C)C)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C=O)C2=C1O[Si](C)(C)C	3982.3	Semi standard non polar	33892256
(-)-Gossypol,5TMS,isomer #3	CC1=CC2=C(C(C)C)C(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C=O)C2=C1O[Si](C)(C)C	3977.1	Semi standard non polar	33892256
(-)-Gossypol,1TBDMS,isomer #1	CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O)=C(C=O)C2=C1O[Si](C)(C)C(C)(C)C	4419.6	Semi standard non polar	33892256
(-)-Gossypol,1TBDMS,isomer #2	CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O[Si](C)(C)C(C)(C)C)=C(C=O)C2=C1O	4384.4	Semi standard non polar	33892256
(-)-Gossypol,1TBDMS,isomer #3	CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O)=C(C=O)C2=C1O	4384.4	Semi standard non polar	33892256
(-)-Gossypol,2TBDMS,isomer #1	CC1=CC2=C(C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O)=C(C=O)C2=C1O[Si](C)(C)C(C)(C)C	4495.8	Semi standard non polar	33892256
(-)-Gossypol,2TBDMS,isomer #2	CC1=CC2=C(C(C)C)C(O)=C(O[Si](C)(C)C(C)(C)C)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O)=C(C=O)C2=C1O[Si](C)(C)C(C)(C)C	4528.0	Semi standard non polar	33892256
(-)-Gossypol,2TBDMS,isomer #3	CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O[Si](C)(C)C(C)(C)C)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O)=C(C=O)C2=C1O[Si](C)(C)C(C)(C)C	4501.7	Semi standard non polar	33892256
(-)-Gossypol,2TBDMS,isomer #4	CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O)=C(C=O)C2=C1O[Si](C)(C)C(C)(C)C	4498.9	Semi standard non polar	33892256
(-)-Gossypol,2TBDMS,isomer #5	CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O[Si](C)(C)C(C)(C)C)=C(C=O)C2=C1O[Si](C)(C)C(C)(C)C	4539.9	Semi standard non polar	33892256
(-)-Gossypol,2TBDMS,isomer #6	CC1=CC2=C(C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O[Si](C)(C)C(C)(C)C)=C(C=O)C2=C1O	4511.5	Semi standard non polar	33892256
(-)-Gossypol,2TBDMS,isomer #7	CC1=CC2=C(C(C)C)C(O)=C(O[Si](C)(C)C(C)(C)C)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O[Si](C)(C)C(C)(C)C)=C(C=O)C2=C1O	4543.1	Semi standard non polar	33892256
(-)-Gossypol,2TBDMS,isomer #8	CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C(C=O)C2=C1O	4558.7	Semi standard non polar	33892256
(-)-Gossypol,2TBDMS,isomer #9	CC1=CC2=C(C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O)=C(C=O)C2=C1O	4477.8	Semi standard non polar	33892256
(-)-Gossypol,3TBDMS,isomer #1	CC1=CC2=C(C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O)=C(C=O)C2=C1O[Si](C)(C)C(C)(C)C	4679.3	Semi standard non polar	33892256
(-)-Gossypol,3TBDMS,isomer #10	CC1=CC2=C(C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C(C=O)C2=C1O	4684.7	Semi standard non polar	33892256
(-)-Gossypol,3TBDMS,isomer #2	CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O[Si](C)(C)C(C)(C)C)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O)=C(C=O)C2=C1O[Si](C)(C)C(C)(C)C	4593.6	Semi standard non polar	33892256
(-)-Gossypol,3TBDMS,isomer #3	CC1=CC2=C(C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O)=C(C=O)C2=C1O[Si](C)(C)C(C)(C)C	4612.1	Semi standard non polar	33892256
(-)-Gossypol,3TBDMS,isomer #4	CC1=CC2=C(C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O[Si](C)(C)C(C)(C)C)=C(C=O)C2=C1O[Si](C)(C)C(C)(C)C	4651.8	Semi standard non polar	33892256
(-)-Gossypol,3TBDMS,isomer #5	CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O[Si](C)(C)C(C)(C)C)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O[Si](C)(C)C(C)(C)C)=C(C=O)C2=C1O[Si](C)(C)C(C)(C)C	4657.6	Semi standard non polar	33892256
(-)-Gossypol,3TBDMS,isomer #6	CC1=CC2=C(C(C)C)C(O)=C(O[Si](C)(C)C(C)(C)C)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O)=C(C=O)C2=C1O[Si](C)(C)C(C)(C)C	4645.2	Semi standard non polar	33892256
(-)-Gossypol,3TBDMS,isomer #7	CC1=CC2=C(C(C)C)C(O)=C(O[Si](C)(C)C(C)(C)C)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O)C(O[Si](C)(C)C(C)(C)C)=C(C=O)C2=C1O[Si](C)(C)C(C)(C)C	4684.7	Semi standard non polar	33892256
(-)-Gossypol,3TBDMS,isomer #8	CC1=CC2=C(C(C)C)C(O)=C(O)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C(C=O)C2=C1O[Si](C)(C)C(C)(C)C	4695.8	Semi standard non polar	33892256
(-)-Gossypol,3TBDMS,isomer #9	CC1=CC2=C(C(C)C)C(O)=C(O[Si](C)(C)C(C)(C)C)C(C=O)=C2C(O)=C1C1=C(C)C=C2C(C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C(C=O)C2=C1O	4724.5	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 - (-)-Gossypol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-0000690000-9df7326dd4ce60b1088c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Gossypol GC-MS (2 TMS) - 70eV, Positive	splash10-0002-0000019000-f115e0a1dfade9af2f9b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Gossypol GC-MS (TMS_4_1) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Gossypol GC-MS (TMS_5_1) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Gossypol GC-MS (TMS_5_2) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Gossypol GC-MS ("(-)-Gossypol,4TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	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 - (-)-Gossypol 10V, Positive-QTOF	splash10-014i-0000190000-afd3b7806ba77c385fc9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Gossypol 20V, Positive-QTOF	splash10-016r-1030970000-364f0989158c0f867591	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Gossypol 40V, Positive-QTOF	splash10-0pb9-5030940000-cb58d99e7632b192bd4d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Gossypol 10V, Negative-QTOF	splash10-014i-0000090000-55621847e31c93e5127f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Gossypol 20V, Negative-QTOF	splash10-066r-0070390000-dda96ff17c65a2928ec9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Gossypol 40V, Negative-QTOF	splash10-0a4u-1390300000-346fa91db1c09ffd5bec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Gossypol 10V, Negative-QTOF	splash10-014i-0000090000-fb746155c08fc8620398	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Gossypol 20V, Negative-QTOF	splash10-014r-0000950000-e97a10851934b81a7505	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Gossypol 40V, Negative-QTOF	splash10-03di-0000900000-5335728bfd7010097935	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Gossypol 10V, Positive-QTOF	splash10-014i-0000090000-4887f71c2e78af699141	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Gossypol 20V, Positive-QTOF	splash10-014i-0000390000-01a16a8a515827651a3e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Gossypol 40V, Positive-QTOF	splash10-03di-0002910000-b9dfdfbb4b3c355cb8f0	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

DB13044

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3503

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1526291

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Meng Y, Tang W, Dai Y, Wu X, Liu M, Ji Q, Ji M, Pienta K, Lawrence T, Xu L: Natural BH3 mimetic (-)-gossypol chemosensitizes human prostate cancer via Bcl-xL inhibition accompanied by increase of Puma and Noxa. Mol Cancer Ther. 2008 Jul;7(7):2192-202. doi: 10.1158/1535-7163.MCT-08-0333. [PubMed:18645028 ]
Zhang XQ, Huang XF, Mu SJ, An QX, Xia AJ, Chen R, Wu DC: Inhibition of proliferation of prostate cancer cell line, PC-3, in vitro and in vivo using (-)-gossypol. Asian J Androl. 2010 May;12(3):390-9. doi: 10.1038/aja.2009.87. Epub 2010 Jan 18. [PubMed:20081872 ]
Zhang Y, Kulp SK, Sugimoto Y, Brueggemeier RW, Lin YC: The (-)-enantiomer of gossypol inhibits proliferation of stromal cells derived from human breast adipose tissues by enhancing transforming growth factor beta1 production. Int J Oncol. 1998 Dec;13(6):1291-7. [PubMed:9824647 ]
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 (-)-Gossypol (HMDB0040723)

MOL for HMDB0040723 ((-)-Gossypol)

3D MOL for HMDB0040723 ((-)-Gossypol)

3D SDF for HMDB0040723 ((-)-Gossypol)

3D-SDF for HMDB0040723 ((-)-Gossypol)

PDB for HMDB0040723 ((-)-Gossypol)

3D PDB for HMDB0040723 ((-)-Gossypol)

SMILES for HMDB0040723 ((-)-Gossypol)

INCHI for HMDB0040723 ((-)-Gossypol)

Structure for HMDB0040723 ((-)-Gossypol)

3D Structure for HMDB0040723 ((-)-Gossypol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra