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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:34:12 UTC

Update Date

2022-03-07 02:52:24 UTC

HMDB ID

HMDB0030020

Secondary Accession Numbers

HMDB30020

Metabolite Identification

Common Name

Withanolide B

Description

Menatetrenone, also known as vitamin K2 or menaquinone 4, belongs to the class of organic compounds known as menaquinones. These are vitamin K2 compounds consisting of a naphtho-1,4-quinone ring system, which is substituted at the 2-position by an isoprenyl side-chain, and usually, at the 3-position by a methyl group. Menatetrenone 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 02241211162D          

 33 38  0  0  0  0            999 V2000
    2.0507    0.5657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4993    1.1789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7536    1.9626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5607    2.1344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8151    2.9195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1079    1.5901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6923    1.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4365    0.2220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9218   -0.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4365   -1.1129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3471   -0.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4905   -0.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4905   -1.2696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2055   -0.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2055   -0.0323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9191   -1.2696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9191   -2.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2055   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4905   -2.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7770   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0620   -2.9195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0620   -2.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0620   -1.2696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7770   -0.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7770   -0.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0620    0.3802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3471   -0.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2618    0.7884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4905   -2.9195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9191    1.6932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1121    1.5213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578    0.7362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4091    0.1244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 32  1  0  0  0  0
  2  3  1  0  0  0  0
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 31  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 27  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 23  1  0  0  0  0
 11 27  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 19  1  0  0  0  0
 13 24  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 29  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
M  END

HMDB0030020
     RDKit          3D
Withanolide B
 71 76  0  0  0  0  0  0  0  0999 V2000
   -4.8383    1.7787   -2.1442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8940    0.8634   -0.9444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0211    0.7955   -0.2908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2333    1.5790   -0.6847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0688   -0.0883    0.8648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1527   -0.1756    1.5214 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9451   -0.7779    1.1832 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5962   -0.4856    1.5850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7790    0.8482    2.2290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2624   -0.9637    1.3265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1468   -2.4842    1.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3055   -2.7010    0.7188 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8679   -1.3248    0.7037 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1055   -1.1128   -0.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1897   -1.8523    0.7704 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8373   -0.9967    1.7812 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5112   -1.3887    0.6502 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7241   -0.4785   -0.5072 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4086   -1.1756   -1.6786 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1506   -0.0021   -0.6581 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2315    0.8889   -1.8421 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1726    1.4841   -2.3856 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8377    1.2911   -1.8367 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8659    1.6148   -2.5509 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7747    0.7240   -0.4717 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3564    1.8088    0.4479 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4312    0.3821    0.0341 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2913    1.1026   -0.5970 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0567    0.9318    0.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3584   -0.4953    0.2741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6365   -0.9077   -1.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6800    0.1233   -0.6072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8523    1.7936   -2.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6437    1.4447   -2.8598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0978    2.8170   -1.8495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8268    1.0069   -1.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8368    1.7056    0.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9639    2.5936   -1.0311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5338   -1.8655    0.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9920   -1.1728    2.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8490    0.9159    2.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1793    0.8592    3.1639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6333    1.7061    1.5821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6592   -0.8093    2.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7730   -2.8824    0.3833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3447   -2.9842    2.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3697   -3.2546   -0.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7960   -3.3247    1.5162 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0320   -1.0220    1.7770 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1838   -1.5060   -1.0434 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9240   -2.8483    1.1846 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3552   -2.1202    0.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2102   -1.7380   -1.8735 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5622    0.4465    0.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7963   -0.8822   -0.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2008    1.0820   -2.3099 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3338    2.1282   -3.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6322    2.6322    0.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4109    1.4072    1.4991 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3657    2.0953    0.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3784    0.6132    1.1413 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4910    2.1851   -0.7568 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3992    1.2741    1.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2646   -1.3104   -1.6731 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8564    0.8728   -0.6193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4584   -0.5104   -1.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
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  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
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 17 18  1  0
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 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  2  0
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 24 25  2  0
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 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
  8 33  1  0
 33  2  1  0
 31 11  1  0
 31 14  1  0
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  1 34  1  0
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 29 64  1  0
 30 65  1  0
 30 66  1  0
 32 67  1  0
 32 68  1  0
 32 69  1  0
 33 70  1  0
 33 71  1  0
M  END


  Mrv0541 02241211162D          

 33 38  0  0  0  0            999 V2000
    2.0507    0.5657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4993    1.1789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7536    1.9626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5607    2.1344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8151    2.9195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1079    1.5901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6923    1.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4365    0.2220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9218   -0.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4365   -1.1129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3471   -0.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4905   -0.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4905   -1.2696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2055   -0.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2055   -0.0323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9191   -1.2696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9191   -2.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4091    0.1244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1 32  1  0  0  0  0
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  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 31  2  0  0  0  0
  6  7  1  0  0  0  0
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 27 28  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030020

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C1CCC2C3C4OC4C4(O)CC=CC(=O)C4(C)C3CCC12C)C1CC(C)=C(C)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C28H38O5/c1-14-13-20(32-25(30)15(14)2)16(3)17-8-9-18-22-19(10-12-26(17,18)4)27(5)21(29)7-6-11-28(27,31)24-23(22)33-24/h6-7,16-20,22-24,31H,8-13H2,1-5H3

> <INCHI_KEY>
ZTEVDTFJUUJBLP-UHFFFAOYSA-N

> <FORMULA>
C28H38O5

> <MOLECULAR_WEIGHT>
454.5983

> <EXACT_MASS>
454.271924326

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
51.51873816111223

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
15-[1-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.0²,⁴.0⁵,¹⁰.0¹⁴,¹⁸]octadec-7-en-9-one

> <ALOGPS_LOGP>
3.51

> <JCHEM_LOGP>
4.784791540999999

> <ALOGPS_LOGS>
-5.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.699548427795087

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.097605729263176

> <JCHEM_PKA_STRONGEST_BASIC>
-3.619906614954558

> <JCHEM_POLAR_SURFACE_AREA>
76.13

> <JCHEM_REFRACTIVITY>
125.49699999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.95e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.0²,⁴.0⁵,¹⁰.0¹⁴,¹⁸]octadec-7-en-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030020
     RDKit          3D
Withanolide B
 71 76  0  0  0  0  0  0  0  0999 V2000
   -4.8383    1.7787   -2.1442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8940    0.8634   -0.9444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0211    0.7955   -0.2908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2333    1.5790   -0.6847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0688   -0.0883    0.8648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1527   -0.1756    1.5214 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9451   -0.7779    1.1832 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6898   -0.7787    0.5454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5962   -0.4856    1.5850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7790    0.8482    2.2290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2624   -0.9637    1.3265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1468   -2.4842    1.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3055   -2.7010    0.7188 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8679   -1.3248    0.7037 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1055   -1.1128   -0.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1897   -1.8523    0.7704 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8373   -0.9967    1.7812 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5112   -1.3887    0.6502 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7241   -0.4785   -0.5072 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4086   -1.1756   -1.6786 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1506   -0.0021   -0.6581 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2315    0.8889   -1.8421 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1726    1.4841   -2.3856 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8377    1.2911   -1.8367 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8659    1.6148   -2.5509 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7747    0.7240   -0.4717 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3564    1.8088    0.4479 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4312    0.3821    0.0341 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2913    1.1026   -0.5970 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0567    0.9318    0.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3584   -0.4953    0.2741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6365   -0.9077   -1.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6800    0.1233   -0.6072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8523    1.7936   -2.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6437    1.4447   -2.8598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0978    2.8170   -1.8495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8268    1.0069   -1.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8368    1.7056    0.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9639    2.5936   -1.0311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5338   -1.8655    0.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9920   -1.1728    2.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8490    0.9159    2.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1793    0.8592    3.1639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6333    1.7061    1.5821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6592   -0.8093    2.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7730   -2.8824    0.3833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3447   -2.9842    2.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3697   -3.2546   -0.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7960   -3.3247    1.5162 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0320   -1.0220    1.7770 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1838   -1.5060   -1.0434 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9240   -2.8483    1.1846 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3552   -2.1202    0.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2102   -1.7380   -1.8735 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5622    0.4465    0.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7963   -0.8822   -0.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2008    1.0820   -2.3099 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3338    2.1282   -3.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6322    2.6322    0.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4109    1.4072    1.4991 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3657    2.0953    0.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3784    0.6132    1.1413 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4910    2.1851   -0.7568 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9658    0.6880   -1.5720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3992    1.2741    1.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6523    1.6484   -0.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2646   -1.3104   -1.6731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9350   -0.0159   -1.7139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4003   -1.6956   -1.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8564    0.8728   -0.6193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4584   -0.5104   -1.5248 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
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
  8 33  1  0
 33  2  1  0
 31 11  1  0
 31 14  1  0
 28 15  1  0
 18 16  1  0
 26 19  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  4 38  1  0
  4 39  1  0
  8 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 10 44  1  0
 11 45  1  0
 12 46  1  0
 12 47  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  0
 15 51  1  0
 16 52  1  0
 18 53  1  0
 20 54  1  0
 21 55  1  0
 21 56  1  0
 22 57  1  0
 23 58  1  0
 27 59  1  0
 27 60  1  0
 27 61  1  0
 28 62  1  0
 29 63  1  0
 29 64  1  0
 30 65  1  0
 30 66  1  0
 32 67  1  0
 32 68  1  0
 32 69  1  0
 33 70  1  0
 33 71  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       3.828   1.056   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.799   2.201   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.273   3.664   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.780   3.984   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.255   5.450   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.201   2.968   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.292   1.880   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.815   0.414   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.721  -0.830   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.815  -2.077   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.648  -1.600   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.649  -0.830   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.649  -2.370   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.984  -1.600   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -5.984  -0.060   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -7.316  -2.370   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -7.316  -3.910   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.984  -4.680   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.649  -3.910   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.317  -4.680   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.982  -5.450   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.982  -3.910   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.982  -2.370   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.317  -1.600   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.317  -0.060   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.982   0.710   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.648  -0.060   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.489   1.472   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -4.649  -5.450   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       7.316   3.161   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.809   2.840   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.335   1.374   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       6.364   0.232   0.000  0.00  0.00           O+0
CONECT    1    2   32                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   31                                                  
CONECT    5    4                                                            
CONECT    6    7                                                            
CONECT    7    2    6    8                                                  
CONECT    8    7    9   27                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   23   27                                                  
CONECT   12   13                                                            
CONECT   13   12   14   19   24                                             
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   13   18   20   29                                             
CONECT   20   19   21   22                                                  
CONECT   21   20   22                                                       
CONECT   22   20   21   23                                                  
CONECT   23   11   22   24                                                  
CONECT   24   13   23   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27    8   11   26   28                                             
CONECT   28   27                                                            
CONECT   29   19                                                            
CONECT   30   31                                                            
CONECT   31    4   30   32                                                  
CONECT   32    1   31   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   76    0
END

COMPND    HMDB0030020
HETATM    1  C1  UNL     1      -4.838   1.779  -2.144  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.894   0.863  -0.944  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.021   0.795  -0.291  1.00  0.00           C  
HETATM    4  C4  UNL     1      -7.233   1.579  -0.685  1.00  0.00           C  
HETATM    5  C5  UNL     1      -6.069  -0.088   0.865  1.00  0.00           C  
HETATM    6  O1  UNL     1      -7.153  -0.176   1.521  1.00  0.00           O  
HETATM    7  O2  UNL     1      -4.945  -0.778   1.183  1.00  0.00           O  
HETATM    8  C6  UNL     1      -3.690  -0.779   0.545  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.596  -0.486   1.585  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.779   0.848   2.229  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.262  -0.964   1.326  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.147  -2.484   1.171  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.306  -2.701   0.719  1.00  0.00           C  
HETATM   14  C12 UNL     1       0.868  -1.325   0.704  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.106  -1.113  -0.033  1.00  0.00           C  
HETATM   16  C14 UNL     1       3.190  -1.852   0.770  1.00  0.00           C  
HETATM   17  O3  UNL     1       3.837  -0.997   1.781  1.00  0.00           O  
HETATM   18  C15 UNL     1       4.511  -1.389   0.650  1.00  0.00           C  
HETATM   19  C16 UNL     1       4.724  -0.479  -0.507  1.00  0.00           C  
HETATM   20  O4  UNL     1       4.409  -1.176  -1.679  1.00  0.00           O  
HETATM   21  C17 UNL     1       6.151  -0.002  -0.658  1.00  0.00           C  
HETATM   22  C18 UNL     1       6.232   0.889  -1.842  1.00  0.00           C  
HETATM   23  C19 UNL     1       5.173   1.484  -2.386  1.00  0.00           C  
HETATM   24  C20 UNL     1       3.838   1.291  -1.837  1.00  0.00           C  
HETATM   25  O5  UNL     1       2.866   1.615  -2.551  1.00  0.00           O  
HETATM   26  C21 UNL     1       3.775   0.724  -0.472  1.00  0.00           C  
HETATM   27  C22 UNL     1       4.356   1.809   0.448  1.00  0.00           C  
HETATM   28  C23 UNL     1       2.431   0.382   0.034  1.00  0.00           C  
HETATM   29  C24 UNL     1       1.291   1.103  -0.597  1.00  0.00           C  
HETATM   30  C25 UNL     1       0.057   0.932   0.312  1.00  0.00           C  
HETATM   31  C26 UNL     1      -0.358  -0.495   0.274  1.00  0.00           C  
HETATM   32  C27 UNL     1      -0.636  -0.908  -1.127  1.00  0.00           C  
HETATM   33  C28 UNL     1      -3.680   0.123  -0.607  1.00  0.00           C  
HETATM   34  H1  UNL     1      -3.852   1.794  -2.606  1.00  0.00           H  
HETATM   35  H2  UNL     1      -5.644   1.445  -2.860  1.00  0.00           H  
HETATM   36  H3  UNL     1      -5.098   2.817  -1.850  1.00  0.00           H  
HETATM   37  H4  UNL     1      -7.827   1.007  -1.423  1.00  0.00           H  
HETATM   38  H5  UNL     1      -7.837   1.706   0.233  1.00  0.00           H  
HETATM   39  H6  UNL     1      -6.964   2.594  -1.031  1.00  0.00           H  
HETATM   40  H7  UNL     1      -3.534  -1.865   0.261  1.00  0.00           H  
HETATM   41  H8  UNL     1      -2.992  -1.173   2.430  1.00  0.00           H  
HETATM   42  H9  UNL     1      -3.849   0.916   2.591  1.00  0.00           H  
HETATM   43  H10 UNL     1      -2.179   0.859   3.164  1.00  0.00           H  
HETATM   44  H11 UNL     1      -2.633   1.706   1.582  1.00  0.00           H  
HETATM   45  H12 UNL     1      -0.659  -0.809   2.293  1.00  0.00           H  
HETATM   46  H13 UNL     1      -1.773  -2.882   0.383  1.00  0.00           H  
HETATM   47  H14 UNL     1      -1.345  -2.984   2.139  1.00  0.00           H  
HETATM   48  H15 UNL     1       0.370  -3.255  -0.216  1.00  0.00           H  
HETATM   49  H16 UNL     1       0.796  -3.325   1.516  1.00  0.00           H  
HETATM   50  H17 UNL     1       1.032  -1.022   1.777  1.00  0.00           H  
HETATM   51  H18 UNL     1       2.184  -1.506  -1.043  1.00  0.00           H  
HETATM   52  H19 UNL     1       2.924  -2.848   1.185  1.00  0.00           H  
HETATM   53  H20 UNL     1       5.355  -2.120   0.792  1.00  0.00           H  
HETATM   54  H21 UNL     1       5.210  -1.738  -1.873  1.00  0.00           H  
HETATM   55  H22 UNL     1       6.562   0.447   0.257  1.00  0.00           H  
HETATM   56  H23 UNL     1       6.796  -0.882  -0.890  1.00  0.00           H  
HETATM   57  H24 UNL     1       7.201   1.082  -2.310  1.00  0.00           H  
HETATM   58  H25 UNL     1       5.334   2.128  -3.264  1.00  0.00           H  
HETATM   59  H26 UNL     1       3.632   2.632   0.480  1.00  0.00           H  
HETATM   60  H27 UNL     1       4.411   1.407   1.499  1.00  0.00           H  
HETATM   61  H28 UNL     1       5.366   2.095   0.166  1.00  0.00           H  
HETATM   62  H29 UNL     1       2.378   0.613   1.141  1.00  0.00           H  
HETATM   63  H30 UNL     1       1.491   2.185  -0.757  1.00  0.00           H  
HETATM   64  H31 UNL     1       0.966   0.688  -1.572  1.00  0.00           H  
HETATM   65  H32 UNL     1       0.399   1.274   1.309  1.00  0.00           H  
HETATM   66  H33 UNL     1      -0.652   1.648  -0.152  1.00  0.00           H  
HETATM   67  H34 UNL     1       0.265  -1.310  -1.673  1.00  0.00           H  
HETATM   68  H35 UNL     1      -0.935  -0.016  -1.714  1.00  0.00           H  
HETATM   69  H36 UNL     1      -1.400  -1.696  -1.233  1.00  0.00           H  
HETATM   70  H37 UNL     1      -2.856   0.873  -0.619  1.00  0.00           H  
HETATM   71  H38 UNL     1      -3.458  -0.510  -1.525  1.00  0.00           H  
CONECT    1    2   34   35   36
CONECT    2    3    3   33
CONECT    3    4    5
CONECT    4   37   38   39
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   33   40
CONECT    9   10   11   41
CONECT   10   42   43   44
CONECT   11   12   31   45
CONECT   12   13   46   47
CONECT   13   14   48   49
CONECT   14   15   31   50
CONECT   15   16   28   51
CONECT   16   17   18   52
CONECT   17   18
CONECT   18   19   53
CONECT   19   20   21   26
CONECT   20   54
CONECT   21   22   55   56
CONECT   22   23   23   57
CONECT   23   24   58
CONECT   24   25   25   26
CONECT   26   27   28
CONECT   27   59   60   61
CONECT   28   29   62
CONECT   29   30   63   64
CONECT   30   31   65   66
CONECT   31   32
CONECT   32   67   68   69
CONECT   33   70   71
END

HMDB0030020
     RDKit          3D
Withanolide B
 71 76  0  0  0  0  0  0  0  0999 V2000
   -4.8383    1.7787   -2.1442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8940    0.8634   -0.9444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0211    0.7955   -0.2908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2333    1.5790   -0.6847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0688   -0.0883    0.8648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1527   -0.1756    1.5214 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9451   -0.7779    1.1832 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6898   -0.7787    0.5454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5962   -0.4856    1.5850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7790    0.8482    2.2290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2624   -0.9637    1.3265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1468   -2.4842    1.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3055   -2.7010    0.7188 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8679   -1.3248    0.7037 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1055   -1.1128   -0.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1897   -1.8523    0.7704 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8373   -0.9967    1.7812 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5112   -1.3887    0.6502 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7241   -0.4785   -0.5072 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4086   -1.1756   -1.6786 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1506   -0.0021   -0.6581 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2315    0.8889   -1.8421 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1726    1.4841   -2.3856 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8377    1.2911   -1.8367 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8659    1.6148   -2.5509 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7747    0.7240   -0.4717 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3564    1.8088    0.4479 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4312    0.3821    0.0341 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2913    1.1026   -0.5970 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0567    0.9318    0.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3584   -0.4953    0.2741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6365   -0.9077   -1.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6800    0.1233   -0.6072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8523    1.7936   -2.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6437    1.4447   -2.8598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0978    2.8170   -1.8495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8268    1.0069   -1.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8368    1.7056    0.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9639    2.5936   -1.0311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5338   -1.8655    0.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9920   -1.1728    2.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8490    0.9159    2.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1793    0.8592    3.1639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6333    1.7061    1.5821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6592   -0.8093    2.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7730   -2.8824    0.3833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3447   -2.9842    2.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3697   -3.2546   -0.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7960   -3.3247    1.5162 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0320   -1.0220    1.7770 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1838   -1.5060   -1.0434 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9240   -2.8483    1.1846 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3552   -2.1202    0.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2102   -1.7380   -1.8735 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5622    0.4465    0.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7963   -0.8822   -0.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2008    1.0820   -2.3099 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3338    2.1282   -3.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6322    2.6322    0.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4109    1.4072    1.4991 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3657    2.0953    0.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3784    0.6132    1.1413 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4910    2.1851   -0.7568 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9658    0.6880   -1.5720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3992    1.2741    1.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6523    1.6484   -0.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2646   -1.3104   -1.6731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9350   -0.0159   -1.7139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4003   -1.6956   -1.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8564    0.8728   -0.6193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4584   -0.5104   -1.5248 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
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
  8 33  1  0
 33  2  1  0
 31 11  1  0
 31 14  1  0
 28 15  1  0
 18 16  1  0
 26 19  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  4 38  1  0
  4 39  1  0
  8 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 10 44  1  0
 11 45  1  0
 12 46  1  0
 12 47  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  0
 15 51  1  0
 16 52  1  0
 18 53  1  0
 20 54  1  0
 21 55  1  0
 21 56  1  0
 22 57  1  0
 23 58  1  0
 27 59  1  0
 27 60  1  0
 27 61  1  0
 28 62  1  0
 29 63  1  0
 29 64  1  0
 30 65  1  0
 30 66  1  0
 32 67  1  0
 32 68  1  0
 32 69  1  0
 33 70  1  0
 33 71  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Methyl-3-(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl)-1,4-naphthoquinone	ChEBI
2-Methyl-3-geranylgeranyl-1,4-naphthoquinone	ChEBI
2-Methyl-3-trans-tetraprenyl-1,4-naphthoquinone	ChEBI
Menaquinone 4	ChEBI
Menaquinone K4	ChEBI
Menaquinone-4	ChEBI
Menatetrenona	ChEBI
Menatetrenonum	ChEBI
MK-4	ChEBI
MK4	ChEBI
Vitamin K2	ChEBI
Vitamin MK 4	ChEBI
2-Methyl-3-all-trans-tetraprenyl-1,4-naphthoquinone	HMDB
Vitamin K2(20)	HMDB
Kefton-2	HMDB
(e,e,e)-Isomer OF menatetrenone	HMDB
Vitamin MK-4	HMDB
Menaquinones	MeSH
Vitamin K quinone	MeSH
Vitamin K 2	MeSH
Menaquinone	MeSH
Lycium substance b	HMDB

Chemical Formula

C₂₈H₃₈O₅

Average Molecular Weight

454.5983

Monoisotopic Molecular Weight

454.271924326

IUPAC Name

15-[1-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.0²,⁴.0⁵,¹⁰.0¹⁴,¹⁸]octadec-7-en-9-one

Traditional Name

15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.0²,⁴.0⁵,¹⁰.0¹⁴,¹⁸]octadec-7-en-9-one

CAS Registry Number

56973-41-2

SMILES

CC(C1CCC2C3C4OC4C4(O)CC=CC(=O)C4(C)C3CCC12C)C1CC(C)=C(C)C(=O)O1

InChI Identifier

InChI=1S/C28H38O5/c1-14-13-20(32-25(30)15(14)2)16(3)17-8-9-18-22-19(10-12-26(17,18)4)27(5)21(29)7-6-11-28(27,31)24-23(22)33-24/h6-7,16-20,22-24,31H,8-13H2,1-5H3

InChI Key

ZTEVDTFJUUJBLP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as menaquinones. These are vitamin K2 compounds consisting of a naphtho-1,4-quinone ring system, which is substituted at the 2-position by an isoprenyl side-chain, and usually, at the 3-position by a methyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Menaquinones

Alternative Parents

Substituents

Menaquinone
Diterpenoid
Naphthoquinone
Naphthalene
Aryl ketone
Quinone
Benzenoid
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

menaquinone (CHEBI:78277 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0030020)
Cell membrane (HMDB: HMDB0030020)

Biofluid or Excreta

Urine (HMDB: HMDB0030020)

Tissue substructure

Hepatic tissue (HMDB: HMDB0030020)

Cellular substructure

Extracellular (HMDB: HMDB0030020)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030020)

Source

Endogenous

Endogenous (HMDB: HMDB0030020)

Plant

Plant (HMDB: HMDB0030020)

Animal

Animal (HMDB: HMDB0030020)

Exogenous

Food

Food (HMDB: HMDB0030020)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0030020)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0030020)

Cellular process

Cell signaling (HMDB: HMDB0030020)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0030020)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0030020)

Molecular messenger

Signaling molecule (HMDB: HMDB0030020)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0030020)

Emulsifier (HMDB: HMDB0030020)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	260 - 265 °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	0.004 g/L	ALOGPS
logP	3.51	ALOGPS
logP	4.78	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	13.1	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	76.13 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	125.5 m³·mol⁻¹	ChemAxon
Polarizability	51.52 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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]+	205.872	31661259
DarkChem	[M-H]-	200.272	31661259
DeepCCS	[M-2H]-	236.533	30932474
DeepCCS	[M+Na]+	211.762	30932474
AllCCS	[M+H]+	212.6	32859911
AllCCS	[M+H-H2O]+	210.5	32859911
AllCCS	[M+NH4]+	214.4	32859911
AllCCS	[M+Na]+	214.9	32859911
AllCCS	[M-H]-	214.8	32859911
AllCCS	[M+Na-2H]-	216.4	32859911
AllCCS	[M+HCOO]-	218.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Withanolide B	CC(C1CCC2C3C4OC4C4(O)CC=CC(=O)C4(C)C3CCC12C)C1CC(C)=C(C)C(=O)O1	4439.0	Standard polar	33892256
Withanolide B	CC(C1CCC2C3C4OC4C4(O)CC=CC(=O)C4(C)C3CCC12C)C1CC(C)=C(C)C(=O)O1	3223.8	Standard non polar	33892256
Withanolide B	CC(C1CCC2C3C4OC4C4(O)CC=CC(=O)C4(C)C3CCC12C)C1CC(C)=C(C)C(=O)O1	3887.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Withanolide B,1TMS,isomer #1	CC1=C(C)C(=O)OC(C(C)C2CCC3C4C5OC5C5(O[Si](C)(C)C)CC=CC(=O)C5(C)C4CCC23C)C1	3857.0	Semi standard non polar	33892256
Withanolide B,1TBDMS,isomer #1	CC1=C(C)C(=O)OC(C(C)C2CCC3C4C5OC5C5(O[Si](C)(C)C(C)(C)C)CC=CC(=O)C5(C)C4CCC23C)C1	4056.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Withanolide B GC-MS (Non-derivatized) - 70eV, Positive	splash10-02br-3594800000-342201064ab3ced44f46	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Withanolide B GC-MS (1 TMS) - 70eV, Positive	splash10-03dr-7395750000-310dbfd34ec4e713cd0d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Withanolide B GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Withanolide B GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withanolide B 10V, Positive-QTOF	splash10-0a4i-0005900000-688ecb047eeaf70aecd1	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withanolide B 20V, Positive-QTOF	splash10-000l-4019400000-c975545f7209b4f8488a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withanolide B 40V, Positive-QTOF	splash10-0uy3-8439300000-f0185769a0d0164097dd	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withanolide B 10V, Positive-QTOF	splash10-0a4i-0005900000-688ecb047eeaf70aecd1	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withanolide B 20V, Positive-QTOF	splash10-000l-4019400000-c975545f7209b4f8488a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withanolide B 40V, Positive-QTOF	splash10-0uy3-8439300000-f0185769a0d0164097dd	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withanolide B 10V, Negative-QTOF	splash10-0udi-0001900000-88b2d268530467097752	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withanolide B 20V, Negative-QTOF	splash10-0zfr-1002900000-fdadf8b6714187301cf8	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withanolide B 40V, Negative-QTOF	splash10-014r-9104200000-bdd23549b698a72f5ac1	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withanolide B 10V, Negative-QTOF	splash10-0udi-0001900000-88b2d268530467097752	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withanolide B 20V, Negative-QTOF	splash10-0zfr-1002900000-fdadf8b6714187301cf8	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withanolide B 40V, Negative-QTOF	splash10-014r-9104200000-bdd23549b698a72f5ac1	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withanolide B 10V, Positive-QTOF	splash10-0a4i-0103900000-aef2673bbbbb0075640b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withanolide B 20V, Positive-QTOF	splash10-0a4i-3215900000-dcd8d40fda1ce41a7f6a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withanolide B 40V, Positive-QTOF	splash10-056s-3595500000-e4ba507f537b364f99b3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withanolide B 10V, Negative-QTOF	splash10-0udi-0000900000-c658cb9af4dd9a98de68	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withanolide B 20V, Negative-QTOF	splash10-0udi-0002900000-928ede65d5278775a412	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withanolide B 40V, Negative-QTOF	splash10-0udi-7109800000-c966b2d9ad2935e3cb57	2021-09-22	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

DB12148

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029792

KNApSAcK ID

Not Available

Chemspider ID

4445530

KEGG Compound ID

C00828

BioCyc ID

CPD-9726

BiGG ID

Not Available

Wikipedia Link

Menatetrenone

METLIN ID

Not Available

PubChem Compound

5282367

PDB ID

Not Available

ChEBI ID

78277

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 Withanolide B (HMDB0030020)

MOL for HMDB0030020 (Withanolide B)

3D MOL for HMDB0030020 (Withanolide B)

3D SDF for HMDB0030020 (Withanolide B)

3D-SDF for HMDB0030020 (Withanolide B)

PDB for HMDB0030020 (Withanolide B)

3D PDB for HMDB0030020 (Withanolide B)

SMILES for HMDB0030020 (Withanolide B)

INCHI for HMDB0030020 (Withanolide B)

Structure for HMDB0030020 (Withanolide B)

3D Structure for HMDB0030020 (Withanolide B)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra