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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:43:01 UTC

Update Date

2022-03-07 02:53:54 UTC

HMDB ID

HMDB0033943

Secondary Accession Numbers

HMDB33943

Metabolite Identification

Common Name

Withaperuvin G

Description

Withaperuvin G belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring. Withaperuvin G is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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


  Mrv0541 02241215132D          

 36 42  0  0  0  0            999 V2000
    1.8753    1.8471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5805    2.2733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3050    1.8732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3160    1.0483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6094    0.6235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8890    1.0222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0338    0.0447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5192   -0.6235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0338   -1.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2488   -1.0359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4647   -1.4483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4647   -2.2732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1795   -2.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8931   -2.2732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6080   -2.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3229   -2.2732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3229   -1.4483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6080   -1.0359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8931   -1.4483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1795   -1.0359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1795   -0.2096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4647    0.2028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2488   -0.2096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3355    0.6097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5654    3.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0089    2.2980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8931   -0.6235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0378    0.6482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6080   -0.2096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3355   -1.8552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0338    0.8696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2365    1.0827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0338    1.6945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8312    0.2578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0378   -1.8608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8931   -3.0981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  2  0  0  0  0
  2 25  1  0  0  0  0
  3  4  1  0  0  0  0
  3 26  1  0  0  0  0
  4  5  1  0  0  0  0
  4 28  2  0  0  0  0
  5  6  1  0  0  0  0
  6 31  1  0  0  0  0
  7  8  1  0  0  0  0
  7 23  1  0  0  0  0
  7 31  1  0  0  0  0
  7 34  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
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 15 16  1  0  0  0  0
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 16 35  1  0  0  0  0
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 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
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
M  END

HMDB0033943
     RDKit          3D
Withaperuvin G
 74 80  0  0  0  0  0  0  0  0999 V2000
    5.3866   -2.0478    2.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8281   -0.8610    1.3419 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4394    2.6085    0.7794 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7260    1.2925   -0.1206 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5550   -0.0201   -0.5884 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6040   -0.2412   -1.6880 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7846   -1.6538   -2.2007 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1840    0.5510   -2.7587 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2368    0.2567   -1.7151 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3115    1.9859   -1.9628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7353    1.1260   -0.8446 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1795    1.7580   -0.8685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5102    1.0152   -0.8894 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6944   -1.2518   -1.7076 C   0  0  0  0  0  0  0  0  0  0  0  0
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 35 71  1  0
 35 72  1  0
 36 73  1  0
 36 74  1  0
M  END


  Mrv0541 02241215132D          

 36 42  0  0  0  0            999 V2000
    1.8753    1.8471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5805    2.2733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3050    1.8732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3160    1.0483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6094    0.6235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8890    1.0222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 11 12  1  0  0  0  0
 11 20  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 36  1  0  0  0  0
 14 15  1  0  0  0  0
 14 19  1  0  0  0  0
 14 36  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 35  1  0  0  0  0
 17 18  1  0  0  0  0
 17 35  1  0  0  0  0
 18 19  1  0  0  0  0
 18 29  2  0  0  0  0
 19 20  1  0  0  0  0
 19 27  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
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033943

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C(C)C(=O)OC(C1)C(C)(O)C1(O)CCC2(O)C3CC4OC44CC5OC5C(=O)C4(C)C3CCC12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H38O8/c1-13-10-18(35-22(30)14(13)2)25(5,31)28(33)9-8-26(32)16-11-19-27(36-19)12-17-20(34-17)21(29)24(27,4)15(16)6-7-23(26,28)3/h15-20,31-33H,6-12H2,1-5H3

> <INCHI_KEY>
FHBPSLRPQVOBMG-UHFFFAOYSA-N

> <FORMULA>
C28H38O8

> <MOLECULAR_WEIGHT>
502.5965

> <EXACT_MASS>
502.256668192

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
53.66089435629005

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
16-[1-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-hydroxyethyl]-13,16-dihydroxy-2,17-dimethyl-5,9-dioxahexacyclo[10.7.0.0²,⁸.0⁴,⁶.0⁸,¹⁰.0¹³,¹⁷]nonadecan-3-one

> <ALOGPS_LOGP>
1.20

> <JCHEM_LOGP>
1.8387273219999996

> <ALOGPS_LOGS>
-3.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.838546174489604

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.71733255795117

> <JCHEM_PKA_STRONGEST_BASIC>
-3.201006102074415

> <JCHEM_POLAR_SURFACE_AREA>
129.12

> <JCHEM_REFRACTIVITY>
126.61849999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.20e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-13,16-dihydroxy-2,17-dimethyl-5,9-dioxahexacyclo[10.7.0.0²,⁸.0⁴,⁶.0⁸,¹⁰.0¹³,¹⁷]nonadecan-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033943
     RDKit          3D
Withaperuvin G
 74 80  0  0  0  0  0  0  0  0999 V2000
    5.3866   -2.0478    2.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8281   -0.8610    1.3419 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3861    0.3347    1.4020 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6263    0.4238    2.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8668    1.4925    0.6747 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4394    2.6085    0.7794 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7260    1.2925   -0.1206 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5550   -0.0201   -0.5884 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6040   -0.2412   -1.6880 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7846   -1.6538   -2.2007 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1840    0.5510   -2.7587 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2368    0.2567   -1.7151 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8738   -0.0633   -3.0874 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2131    1.7997   -1.8234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3115    1.9859   -1.9628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7353    1.1260   -0.8446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3660    1.8004    0.3468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1219    0.7075   -0.6954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1795    1.7580   -0.8685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5102    1.0152   -0.8894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3481   -0.4491   -1.2197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6442   -0.0425    0.0651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0388   -0.4064    0.5153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1107   -1.8275    1.0316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0586   -2.0447    2.4111 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9113   -2.3562    1.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8189   -1.4178    1.8472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0693   -1.7631    2.7158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6226   -0.1162    1.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0469    0.9260    2.2327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2465    0.2020    0.7561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2229   -0.8584    1.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1234   -0.6279    0.4384 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1110   -0.1706   -0.9552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6944   -1.2518   -1.7076 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5504   -0.9648    0.5732 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4259   -1.8494    2.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7270   -2.2859    2.8714 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3367   -2.8904    1.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9378    1.4761    2.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4500   -0.0092    3.2281 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4254   -0.1671    1.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5848   -0.2611   -1.0566 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2770   -1.7022   -3.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4200   -2.4224   -1.5243 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8773   -1.7689   -2.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2450    0.0567   -3.5823 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2782    0.5500   -3.7122 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7045    2.1566   -2.7276 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6278    2.2906   -0.9627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5271    3.0434   -1.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6232    1.6716   -2.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2316    2.7604    0.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4481   -0.1544   -1.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2213    2.4605   -0.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0735    2.2520   -1.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3583    1.4137   -1.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7000   -0.3458   -0.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4724    0.3014    1.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8312   -2.4997    0.5291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6916   -3.4228    1.5428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2496    1.7226    2.3160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1127    0.4906    3.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9544    1.4491    1.9595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8546    1.1066    1.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0442   -0.8094    2.1709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6037   -1.9018    0.9177 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7108   -1.5485    0.6347 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6207    0.1700    1.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1042   -0.8655   -2.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1174   -1.9712   -2.0420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3453   -1.8354   -1.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4349   -2.0255    0.2732 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8077   -0.6915    1.3707 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
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 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  2  0
 27 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
  8 36  1  0
 36  2  1  0
 34 12  1  0
 34 16  1  0
 31 18  1  0
 22 20  1  0
 26 24  1  0
 29 22  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  4 40  1  0
  4 41  1  0
  4 42  1  0
  8 43  1  0
 10 44  1  0
 10 45  1  0
 10 46  1  0
 11 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 15 52  1  0
 17 53  1  0
 18 54  1  0
 19 55  1  0
 19 56  1  0
 20 57  1  0
 23 58  1  0
 23 59  1  0
 24 60  1  0
 26 61  1  0
 30 62  1  0
 30 63  1  0
 30 64  1  0
 31 65  1  0
 32 66  1  0
 32 67  1  0
 33 68  1  0
 33 69  1  0
 35 70  1  0
 35 71  1  0
 35 72  1  0
 36 73  1  0
 36 74  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       3.501   3.448   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.817   4.243   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.169   3.497   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.190   1.957   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.871   1.164   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.526   1.908   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.930   0.083   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.836  -1.164   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.930  -2.408   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.464  -1.934   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.867  -2.703   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.867  -4.243   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.202  -5.013   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.534  -4.243   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.868  -5.013   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.203  -4.243   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.203  -2.703   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.868  -1.934   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.534  -2.703   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.202  -1.934   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.202  -0.391   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.867   0.379   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.464  -0.391   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.626   1.138   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.789   5.783   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.483   4.290   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.534  -1.164   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       7.537   1.210   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -4.868  -0.391   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       0.626  -3.463   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.930   1.623   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.441   2.021   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       1.930   3.163   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       3.418   0.481   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -7.537  -3.473   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -3.534  -5.783   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   25                                                  
CONECT    3    2    4   26                                                  
CONECT    4    3    5   28                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5   31                                                  
CONECT    7    8   23   31   34                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   23   30                                             
CONECT   11   10   12   20                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   36                                                  
CONECT   14   13   15   19   36                                             
CONECT   15   14   16                                                       
CONECT   16   15   17   35                                                  
CONECT   17   16   18   35                                                  
CONECT   18   17   19   29                                                  
CONECT   19   14   18   20   27                                             
CONECT   20   11   19   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23    7   10   22   24                                             
CONECT   24   23                                                            
CONECT   25    2                                                            
CONECT   26    3                                                            
CONECT   27   19                                                            
CONECT   28    4                                                            
CONECT   29   18                                                            
CONECT   30   10                                                            
CONECT   31    6    7   32   33                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34    7                                                            
CONECT   35   16   17                                                       
CONECT   36   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   84    0
END

COMPND    HMDB0033943
HETATM    1  C1  UNL     1       5.387  -2.048   2.035  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.828  -0.861   1.342  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.386   0.335   1.402  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.626   0.424   2.225  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.867   1.493   0.675  1.00  0.00           C  
HETATM    6  O1  UNL     1       5.439   2.608   0.779  1.00  0.00           O  
HETATM    7  O2  UNL     1       3.726   1.293  -0.121  1.00  0.00           O  
HETATM    8  C6  UNL     1       3.555  -0.020  -0.588  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.604  -0.241  -1.688  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.785  -1.654  -2.201  1.00  0.00           C  
HETATM   11  O3  UNL     1       3.184   0.551  -2.759  1.00  0.00           O  
HETATM   12  C9  UNL     1       1.237   0.257  -1.715  1.00  0.00           C  
HETATM   13  O4  UNL     1       0.874  -0.063  -3.087  1.00  0.00           O  
HETATM   14  C10 UNL     1       1.213   1.800  -1.823  1.00  0.00           C  
HETATM   15  C11 UNL     1      -0.312   1.986  -1.963  1.00  0.00           C  
HETATM   16  C12 UNL     1      -0.735   1.126  -0.845  1.00  0.00           C  
HETATM   17  O5  UNL     1      -0.366   1.800   0.347  1.00  0.00           O  
HETATM   18  C13 UNL     1      -2.122   0.707  -0.695  1.00  0.00           C  
HETATM   19  C14 UNL     1      -3.180   1.758  -0.869  1.00  0.00           C  
HETATM   20  C15 UNL     1      -4.510   1.015  -0.889  1.00  0.00           C  
HETATM   21  O6  UNL     1      -4.348  -0.449  -1.220  1.00  0.00           O  
HETATM   22  C16 UNL     1      -4.644  -0.043   0.065  1.00  0.00           C  
HETATM   23  C17 UNL     1      -6.039  -0.406   0.515  1.00  0.00           C  
HETATM   24  C18 UNL     1      -6.111  -1.828   1.032  1.00  0.00           C  
HETATM   25  O7  UNL     1      -6.059  -2.045   2.411  1.00  0.00           O  
HETATM   26  C19 UNL     1      -4.911  -2.356   1.514  1.00  0.00           C  
HETATM   27  C20 UNL     1      -3.819  -1.418   1.847  1.00  0.00           C  
HETATM   28  O8  UNL     1      -3.069  -1.763   2.716  1.00  0.00           O  
HETATM   29  C21 UNL     1      -3.623  -0.116   1.175  1.00  0.00           C  
HETATM   30  C22 UNL     1      -4.047   0.926   2.233  1.00  0.00           C  
HETATM   31  C23 UNL     1      -2.246   0.202   0.756  1.00  0.00           C  
HETATM   32  C24 UNL     1      -1.223  -0.858   1.050  1.00  0.00           C  
HETATM   33  C25 UNL     1       0.123  -0.628   0.438  1.00  0.00           C  
HETATM   34  C26 UNL     1       0.111  -0.171  -0.955  1.00  0.00           C  
HETATM   35  C27 UNL     1      -0.694  -1.252  -1.708  1.00  0.00           C  
HETATM   36  C28 UNL     1       3.550  -0.965   0.573  1.00  0.00           C  
HETATM   37  H1  UNL     1       6.426  -1.849   2.333  1.00  0.00           H  
HETATM   38  H2  UNL     1       4.727  -2.286   2.871  1.00  0.00           H  
HETATM   39  H3  UNL     1       5.337  -2.890   1.305  1.00  0.00           H  
HETATM   40  H4  UNL     1       6.938   1.476   2.352  1.00  0.00           H  
HETATM   41  H5  UNL     1       6.450  -0.009   3.228  1.00  0.00           H  
HETATM   42  H6  UNL     1       7.425  -0.167   1.726  1.00  0.00           H  
HETATM   43  H7  UNL     1       4.585  -0.261  -1.057  1.00  0.00           H  
HETATM   44  H8  UNL     1       2.277  -1.702  -3.200  1.00  0.00           H  
HETATM   45  H9  UNL     1       2.420  -2.422  -1.524  1.00  0.00           H  
HETATM   46  H10 UNL     1       3.877  -1.769  -2.418  1.00  0.00           H  
HETATM   47  H11 UNL     1       3.245   0.057  -3.582  1.00  0.00           H  
HETATM   48  H12 UNL     1       1.278   0.550  -3.712  1.00  0.00           H  
HETATM   49  H13 UNL     1       1.705   2.157  -2.728  1.00  0.00           H  
HETATM   50  H14 UNL     1       1.628   2.291  -0.963  1.00  0.00           H  
HETATM   51  H15 UNL     1      -0.527   3.043  -1.732  1.00  0.00           H  
HETATM   52  H16 UNL     1      -0.623   1.672  -2.961  1.00  0.00           H  
HETATM   53  H17 UNL     1      -0.232   2.760   0.193  1.00  0.00           H  
HETATM   54  H18 UNL     1      -2.448  -0.154  -1.313  1.00  0.00           H  
HETATM   55  H19 UNL     1      -3.221   2.461  -0.009  1.00  0.00           H  
HETATM   56  H20 UNL     1      -3.073   2.252  -1.831  1.00  0.00           H  
HETATM   57  H21 UNL     1      -5.358   1.414  -1.437  1.00  0.00           H  
HETATM   58  H22 UNL     1      -6.700  -0.346  -0.375  1.00  0.00           H  
HETATM   59  H23 UNL     1      -6.472   0.301   1.252  1.00  0.00           H  
HETATM   60  H24 UNL     1      -6.831  -2.500   0.529  1.00  0.00           H  
HETATM   61  H25 UNL     1      -4.692  -3.423   1.543  1.00  0.00           H  
HETATM   62  H26 UNL     1      -3.250   1.723   2.316  1.00  0.00           H  
HETATM   63  H27 UNL     1      -4.113   0.491   3.238  1.00  0.00           H  
HETATM   64  H28 UNL     1      -4.954   1.449   1.960  1.00  0.00           H  
HETATM   65  H29 UNL     1      -1.855   1.107   1.326  1.00  0.00           H  
HETATM   66  H30 UNL     1      -1.044  -0.809   2.171  1.00  0.00           H  
HETATM   67  H31 UNL     1      -1.604  -1.902   0.918  1.00  0.00           H  
HETATM   68  H32 UNL     1       0.711  -1.548   0.635  1.00  0.00           H  
HETATM   69  H33 UNL     1       0.621   0.170   1.068  1.00  0.00           H  
HETATM   70  H34 UNL     1      -1.104  -0.865  -2.653  1.00  0.00           H  
HETATM   71  H35 UNL     1       0.117  -1.971  -2.042  1.00  0.00           H  
HETATM   72  H36 UNL     1      -1.345  -1.835  -1.079  1.00  0.00           H  
HETATM   73  H37 UNL     1       3.435  -2.026   0.273  1.00  0.00           H  
HETATM   74  H38 UNL     1       2.808  -0.692   1.371  1.00  0.00           H  
CONECT    1    2   37   38   39
CONECT    2    3    3   36
CONECT    3    4    5
CONECT    4   40   41   42
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   36   43
CONECT    9   10   11   12
CONECT   10   44   45   46
CONECT   11   47
CONECT   12   13   14   34
CONECT   13   48
CONECT   14   15   49   50
CONECT   15   16   51   52
CONECT   16   17   18   34
CONECT   17   53
CONECT   18   19   31   54
CONECT   19   20   55   56
CONECT   20   21   22   57
CONECT   21   22
CONECT   22   23   29
CONECT   23   24   58   59
CONECT   24   25   26   60
CONECT   25   26
CONECT   26   27   61
CONECT   27   28   28   29
CONECT   29   30   31
CONECT   30   62   63   64
CONECT   31   32   65
CONECT   32   33   66   67
CONECT   33   34   68   69
CONECT   34   35
CONECT   35   70   71   72
CONECT   36   73   74
END

HMDB0033943
     RDKit          3D
Withaperuvin G
 74 80  0  0  0  0  0  0  0  0999 V2000
    5.3866   -2.0478    2.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8281   -0.8610    1.3419 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3861    0.3347    1.4020 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6263    0.4238    2.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8668    1.4925    0.6747 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4394    2.6085    0.7794 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7260    1.2925   -0.1206 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5550   -0.0201   -0.5884 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6040   -0.2412   -1.6880 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7846   -1.6538   -2.2007 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1840    0.5510   -2.7587 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2368    0.2567   -1.7151 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8738   -0.0633   -3.0874 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2131    1.7997   -1.8234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3115    1.9859   -1.9628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7353    1.1260   -0.8446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3660    1.8004    0.3468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1219    0.7075   -0.6954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1795    1.7580   -0.8685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5102    1.0152   -0.8894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3481   -0.4491   -1.2197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6442   -0.0425    0.0651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0388   -0.4064    0.5153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1107   -1.8275    1.0316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0586   -2.0447    2.4111 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9113   -2.3562    1.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8189   -1.4178    1.8472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0693   -1.7631    2.7158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6226   -0.1162    1.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0469    0.9260    2.2327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2465    0.2020    0.7561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2229   -0.8584    1.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1234   -0.6279    0.4384 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1110   -0.1706   -0.9552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6944   -1.2518   -1.7076 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5504   -0.9648    0.5732 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4259   -1.8494    2.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7270   -2.2859    2.8714 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3367   -2.8904    1.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9378    1.4761    2.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4500   -0.0092    3.2281 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4254   -0.1671    1.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5848   -0.2611   -1.0566 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2770   -1.7022   -3.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4200   -2.4224   -1.5243 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8773   -1.7689   -2.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2450    0.0567   -3.5823 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2782    0.5500   -3.7122 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7045    2.1566   -2.7276 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6278    2.2906   -0.9627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5271    3.0434   -1.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6232    1.6716   -2.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2316    2.7604    0.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4481   -0.1544   -1.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2213    2.4605   -0.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0735    2.2520   -1.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3583    1.4137   -1.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7000   -0.3458   -0.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4724    0.3014    1.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8312   -2.4997    0.5291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6916   -3.4228    1.5428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2496    1.7226    2.3160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1127    0.4906    3.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9544    1.4491    1.9595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8546    1.1066    1.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0442   -0.8094    2.1709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6037   -1.9018    0.9177 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7108   -1.5485    0.6347 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6207    0.1700    1.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1042   -0.8655   -2.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1174   -1.9712   -2.0420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3453   -1.8354   -1.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4349   -2.0255    0.2732 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8077   -0.6915    1.3707 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
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 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  2  0
 27 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
  8 36  1  0
 36  2  1  0
 34 12  1  0
 34 16  1  0
 31 18  1  0
 22 20  1  0
 26 24  1  0
 29 22  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  4 40  1  0
  4 41  1  0
  4 42  1  0
  8 43  1  0
 10 44  1  0
 10 45  1  0
 10 46  1  0
 11 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 15 52  1  0
 17 53  1  0
 18 54  1  0
 19 55  1  0
 19 56  1  0
 20 57  1  0
 23 58  1  0
 23 59  1  0
 24 60  1  0
 26 61  1  0
 30 62  1  0
 30 63  1  0
 30 64  1  0
 31 65  1  0
 32 66  1  0
 32 67  1  0
 33 68  1  0
 33 69  1  0
 35 70  1  0
 35 71  1  0
 35 72  1  0
 36 73  1  0
 36 74  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2b,3B;5,6b-diepoxy-14,17b,20R-trihydroxy-1-oxo-5b,22R-with-24-enolide	HMDB

Chemical Formula

C₂₈H₃₈O₈

Average Molecular Weight

502.5965

Monoisotopic Molecular Weight

502.256668192

IUPAC Name

16-[1-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-hydroxyethyl]-13,16-dihydroxy-2,17-dimethyl-5,9-dioxahexacyclo[10.7.0.0²,⁸.0⁴,⁶.0⁸,¹⁰.0¹³,¹⁷]nonadecan-3-one

Traditional Name

16-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-13,16-dihydroxy-2,17-dimethyl-5,9-dioxahexacyclo[10.7.0.0²,⁸.0⁴,⁶.0⁸,¹⁰.0¹³,¹⁷]nonadecan-3-one

CAS Registry Number

Not Available

SMILES

CC1=C(C)C(=O)OC(C1)C(C)(O)C1(O)CCC2(O)C3CC4OC44CC5OC5C(=O)C4(C)C3CCC12C

InChI Identifier

InChI=1S/C28H38O8/c1-13-10-18(35-22(30)14(13)2)25(5,31)28(33)9-8-26(32)16-11-19-27(36-19)12-17-20(34-17)21(29)24(27,4)15(16)6-7-23(26,28)3/h15-20,31-33H,6-12H2,1-5H3

InChI Key

FHBPSLRPQVOBMG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Withanolides and derivatives

Alternative Parents

Substituents

Withanolide-skeleton
5,6-epoxysteroid
Dihydropyranone
Oxepane
Pyran
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Carboxylic acid ester
Ketone
Lactone
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxygen compound
Organic oxide
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0033943)
Cell membrane (HMDB: HMDB0033943)

Biofluid or Excreta

Urine (HMDB: HMDB0033943)

Tissue substructure

Hepatic tissue (HMDB: HMDB0033943)

Cellular substructure

Extracellular (HMDB: HMDB0033943)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033943)

Source

Endogenous

Endogenous (HMDB: HMDB0033943)

Plant

Plant (HMDB: HMDB0033943)

Animal

Animal (HMDB: HMDB0033943)

Exogenous

Food

Food (HMDB: HMDB0033943)

Fruit

Fruits (FooDB: FOOD00871)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0033943)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0033943)

Cellular process

Cell signaling (HMDB: HMDB0033943)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0033943)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0033943)

Nutrient

Nutrient (HMDB: HMDB0033943)

Molecular messenger

Signaling molecule (HMDB: HMDB0033943)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0033943)

Emulsifier (HMDB: HMDB0033943)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	163 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.32 g/L	ALOGPS
logP	1.2	ALOGPS
logP	1.84	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	12.72	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	129.12 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	126.62 m³·mol⁻¹	ChemAxon
Polarizability	53.66 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	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]+	215.827	31661259
DarkChem	[M-H]-	205.26	31661259
DeepCCS	[M-2H]-	247.305	30932474
DeepCCS	[M+Na]+	222.729	30932474
AllCCS	[M+H]+	217.6	32859911
AllCCS	[M+H-H2O]+	215.9	32859911
AllCCS	[M+NH4]+	219.1	32859911
AllCCS	[M+Na]+	219.5	32859911
AllCCS	[M-H]-	220.5	32859911
AllCCS	[M+Na-2H]-	222.4	32859911
AllCCS	[M+HCOO]-	224.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Withaperuvin G	CC1=C(C)C(=O)OC(C1)C(C)(O)C1(O)CCC2(O)C3CC4OC44CC5OC5C(=O)C4(C)C3CCC12C	4098.5	Standard polar	33892256
Withaperuvin G	CC1=C(C)C(=O)OC(C1)C(C)(O)C1(O)CCC2(O)C3CC4OC44CC5OC5C(=O)C4(C)C3CCC12C	3642.3	Standard non polar	33892256
Withaperuvin G	CC1=C(C)C(=O)OC(C1)C(C)(O)C1(O)CCC2(O)C3CC4OC44CC5OC5C(=O)C4(C)C3CCC12C	4315.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Withaperuvin G,1TMS,isomer #1	CC1=C(C)C(=O)OC(C(C)(O[Si](C)(C)C)C2(O)CCC3(O)C4CC5OC56CC5OC5C(=O)C6(C)C4CCC32C)C1	4134.3	Semi standard non polar	33892256
Withaperuvin G,1TMS,isomer #2	CC1=C(C)C(=O)OC(C(C)(O)C2(O[Si](C)(C)C)CCC3(O)C4CC5OC56CC5OC5C(=O)C6(C)C4CCC32C)C1	4141.0	Semi standard non polar	33892256
Withaperuvin G,1TMS,isomer #3	CC1=C(C)C(=O)OC(C(C)(O)C2(O)CCC3(O[Si](C)(C)C)C4CC5OC56CC5OC5C(=O)C6(C)C4CCC32C)C1	4165.7	Semi standard non polar	33892256
Withaperuvin G,1TMS,isomer #4	CC1=C(C)C(=O)OC(C(C)(O)C2(O)CCC3(O)C4CC5OC56CC5OC5=C(O[Si](C)(C)C)C6(C)C4CCC32C)C1	4039.8	Semi standard non polar	33892256
Withaperuvin G,2TMS,isomer #1	CC1=C(C)C(=O)OC(C(C)(O[Si](C)(C)C)C2(O[Si](C)(C)C)CCC3(O)C4CC5OC56CC5OC5C(=O)C6(C)C4CCC32C)C1	4115.9	Semi standard non polar	33892256
Withaperuvin G,2TMS,isomer #2	CC1=C(C)C(=O)OC(C(C)(O[Si](C)(C)C)C2(O)CCC3(O[Si](C)(C)C)C4CC5OC56CC5OC5C(=O)C6(C)C4CCC32C)C1	4137.6	Semi standard non polar	33892256
Withaperuvin G,2TMS,isomer #3	CC1=C(C)C(=O)OC(C(C)(O[Si](C)(C)C)C2(O)CCC3(O)C4CC5OC56CC5OC5=C(O[Si](C)(C)C)C6(C)C4CCC32C)C1	4001.9	Semi standard non polar	33892256
Withaperuvin G,2TMS,isomer #4	CC1=C(C)C(=O)OC(C(C)(O)C2(O[Si](C)(C)C)CCC3(O[Si](C)(C)C)C4CC5OC56CC5OC5C(=O)C6(C)C4CCC32C)C1	4139.8	Semi standard non polar	33892256
Withaperuvin G,2TMS,isomer #5	CC1=C(C)C(=O)OC(C(C)(O)C2(O[Si](C)(C)C)CCC3(O)C4CC5OC56CC5OC5=C(O[Si](C)(C)C)C6(C)C4CCC32C)C1	4006.4	Semi standard non polar	33892256
Withaperuvin G,2TMS,isomer #6	CC1=C(C)C(=O)OC(C(C)(O)C2(O)CCC3(O[Si](C)(C)C)C4CC5OC56CC5OC5=C(O[Si](C)(C)C)C6(C)C4CCC32C)C1	4008.1	Semi standard non polar	33892256
Withaperuvin G,3TMS,isomer #1	CC1=C(C)C(=O)OC(C(C)(O[Si](C)(C)C)C2(O[Si](C)(C)C)CCC3(O[Si](C)(C)C)C4CC5OC56CC5OC5C(=O)C6(C)C4CCC32C)C1	4096.4	Semi standard non polar	33892256
Withaperuvin G,3TMS,isomer #2	CC1=C(C)C(=O)OC(C(C)(O[Si](C)(C)C)C2(O[Si](C)(C)C)CCC3(O)C4CC5OC56CC5OC5=C(O[Si](C)(C)C)C6(C)C4CCC32C)C1	3962.6	Semi standard non polar	33892256
Withaperuvin G,3TMS,isomer #3	CC1=C(C)C(=O)OC(C(C)(O[Si](C)(C)C)C2(O)CCC3(O[Si](C)(C)C)C4CC5OC56CC5OC5=C(O[Si](C)(C)C)C6(C)C4CCC32C)C1	3972.6	Semi standard non polar	33892256
Withaperuvin G,3TMS,isomer #4	CC1=C(C)C(=O)OC(C(C)(O)C2(O[Si](C)(C)C)CCC3(O[Si](C)(C)C)C4CC5OC56CC5OC5=C(O[Si](C)(C)C)C6(C)C4CCC32C)C1	3969.4	Semi standard non polar	33892256
Withaperuvin G,4TMS,isomer #1	CC1=C(C)C(=O)OC(C(C)(O[Si](C)(C)C)C2(O[Si](C)(C)C)CCC3(O[Si](C)(C)C)C4CC5OC56CC5OC5=C(O[Si](C)(C)C)C6(C)C4CCC32C)C1	3934.5	Semi standard non polar	33892256
Withaperuvin G,4TMS,isomer #1	CC1=C(C)C(=O)OC(C(C)(O[Si](C)(C)C)C2(O[Si](C)(C)C)CCC3(O[Si](C)(C)C)C4CC5OC56CC5OC5=C(O[Si](C)(C)C)C6(C)C4CCC32C)C1	3980.1	Standard non polar	33892256
Withaperuvin G,1TBDMS,isomer #1	CC1=C(C)C(=O)OC(C(C)(O[Si](C)(C)C(C)(C)C)C2(O)CCC3(O)C4CC5OC56CC5OC5C(=O)C6(C)C4CCC32C)C1	4364.0	Semi standard non polar	33892256
Withaperuvin G,1TBDMS,isomer #2	CC1=C(C)C(=O)OC(C(C)(O)C2(O[Si](C)(C)C(C)(C)C)CCC3(O)C4CC5OC56CC5OC5C(=O)C6(C)C4CCC32C)C1	4364.3	Semi standard non polar	33892256
Withaperuvin G,1TBDMS,isomer #3	CC1=C(C)C(=O)OC(C(C)(O)C2(O)CCC3(O[Si](C)(C)C(C)(C)C)C4CC5OC56CC5OC5C(=O)C6(C)C4CCC32C)C1	4381.6	Semi standard non polar	33892256
Withaperuvin G,1TBDMS,isomer #4	CC1=C(C)C(=O)OC(C(C)(O)C2(O)CCC3(O)C4CC5OC56CC5OC5=C(O[Si](C)(C)C(C)(C)C)C6(C)C4CCC32C)C1	4266.0	Semi standard non polar	33892256
Withaperuvin G,2TBDMS,isomer #1	CC1=C(C)C(=O)OC(C(C)(O[Si](C)(C)C(C)(C)C)C2(O[Si](C)(C)C(C)(C)C)CCC3(O)C4CC5OC56CC5OC5C(=O)C6(C)C4CCC32C)C1	4578.1	Semi standard non polar	33892256
Withaperuvin G,2TBDMS,isomer #2	CC1=C(C)C(=O)OC(C(C)(O[Si](C)(C)C(C)(C)C)C2(O)CCC3(O[Si](C)(C)C(C)(C)C)C4CC5OC56CC5OC5C(=O)C6(C)C4CCC32C)C1	4585.4	Semi standard non polar	33892256
Withaperuvin G,2TBDMS,isomer #3	CC1=C(C)C(=O)OC(C(C)(O[Si](C)(C)C(C)(C)C)C2(O)CCC3(O)C4CC5OC56CC5OC5=C(O[Si](C)(C)C(C)(C)C)C6(C)C4CCC32C)C1	4451.5	Semi standard non polar	33892256
Withaperuvin G,2TBDMS,isomer #4	CC1=C(C)C(=O)OC(C(C)(O)C2(O[Si](C)(C)C(C)(C)C)CCC3(O[Si](C)(C)C(C)(C)C)C4CC5OC56CC5OC5C(=O)C6(C)C4CCC32C)C1	4581.1	Semi standard non polar	33892256
Withaperuvin G,2TBDMS,isomer #5	CC1=C(C)C(=O)OC(C(C)(O)C2(O[Si](C)(C)C(C)(C)C)CCC3(O)C4CC5OC56CC5OC5=C(O[Si](C)(C)C(C)(C)C)C6(C)C4CCC32C)C1	4446.9	Semi standard non polar	33892256
Withaperuvin G,2TBDMS,isomer #6	CC1=C(C)C(=O)OC(C(C)(O)C2(O)CCC3(O[Si](C)(C)C(C)(C)C)C4CC5OC56CC5OC5=C(O[Si](C)(C)C(C)(C)C)C6(C)C4CCC32C)C1	4448.1	Semi standard non polar	33892256
Withaperuvin G,3TBDMS,isomer #1	CC1=C(C)C(=O)OC(C(C)(O[Si](C)(C)C(C)(C)C)C2(O[Si](C)(C)C(C)(C)C)CCC3(O[Si](C)(C)C(C)(C)C)C4CC5OC56CC5OC5C(=O)C6(C)C4CCC32C)C1	4785.5	Semi standard non polar	33892256
Withaperuvin G,3TBDMS,isomer #2	CC1=C(C)C(=O)OC(C(C)(O[Si](C)(C)C(C)(C)C)C2(O[Si](C)(C)C(C)(C)C)CCC3(O)C4CC5OC56CC5OC5=C(O[Si](C)(C)C(C)(C)C)C6(C)C4CCC32C)C1	4611.1	Semi standard non polar	33892256
Withaperuvin G,3TBDMS,isomer #3	CC1=C(C)C(=O)OC(C(C)(O[Si](C)(C)C(C)(C)C)C2(O)CCC3(O[Si](C)(C)C(C)(C)C)C4CC5OC56CC5OC5=C(O[Si](C)(C)C(C)(C)C)C6(C)C4CCC32C)C1	4603.3	Semi standard non polar	33892256
Withaperuvin G,3TBDMS,isomer #4	CC1=C(C)C(=O)OC(C(C)(O)C2(O[Si](C)(C)C(C)(C)C)CCC3(O[Si](C)(C)C(C)(C)C)C4CC5OC56CC5OC5=C(O[Si](C)(C)C(C)(C)C)C6(C)C4CCC32C)C1	4601.0	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 - Withaperuvin G GC-MS (Non-derivatized) - 70eV, Positive	splash10-00pi-3496500000-573ffd6746d2f8a0930b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Withaperuvin G GC-MS (2 TMS) - 70eV, Positive	splash10-001i-8252669000-81d87f2eb4b540f9f47a	2017-10-06	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 - Withaperuvin G 10V, Positive-QTOF	splash10-0f79-0003940000-8317eb63df9417021b73	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withaperuvin G 20V, Positive-QTOF	splash10-0gb9-9105700000-8fc24190f0bf5d716703	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withaperuvin G 40V, Positive-QTOF	splash10-0gb9-7195100000-3e5f9401273ac3fd099b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withaperuvin G 10V, Negative-QTOF	splash10-0zfr-0205980000-fab9dd752ea28fc4ef07	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withaperuvin G 20V, Negative-QTOF	splash10-0159-1906200000-e00d7b8893d83ea8ae81	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withaperuvin G 40V, Negative-QTOF	splash10-02t9-9503000000-c977bb67ace66275f443	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withaperuvin G 10V, Positive-QTOF	splash10-0udi-0000590000-3012d5eba687a6a7730e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withaperuvin G 20V, Positive-QTOF	splash10-0udr-6009230000-2a36323d6a36f1cbd4cb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withaperuvin G 40V, Positive-QTOF	splash10-0ikc-6629000000-3b2b565e2a43d3da2ffe	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withaperuvin G 10V, Negative-QTOF	splash10-0udi-0002290000-9c2130218a90ed784bb1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withaperuvin G 20V, Negative-QTOF	splash10-1029-2109140000-3589b28532554911688e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withaperuvin G 40V, Negative-QTOF	splash10-0ktf-9402000000-1093694b4b6ce8d781de	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

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

FDB012151

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751505

PDB ID

Not Available

ChEBI ID

Not Available

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 Withaperuvin G (HMDB0033943)

MOL for HMDB0033943 (Withaperuvin G)

3D MOL for HMDB0033943 (Withaperuvin G)

3D SDF for HMDB0033943 (Withaperuvin G)

3D-SDF for HMDB0033943 (Withaperuvin G)

PDB for HMDB0033943 (Withaperuvin G)

3D PDB for HMDB0033943 (Withaperuvin G)

SMILES for HMDB0033943 (Withaperuvin G)

INCHI for HMDB0033943 (Withaperuvin G)

Structure for HMDB0033943 (Withaperuvin G)

3D Structure for HMDB0033943 (Withaperuvin G)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra