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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:41:37 UTC

Update Date

2022-03-07 02:54:35 UTC

HMDB ID

HMDB0035685

Secondary Accession Numbers

HMDB35685

Metabolite Identification

Common Name

beta-Citraurol

Description

beta-Citraurol, also known as β-citraurol, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Based on a literature review a small amount of articles have been published on beta-Citraurol.

Structure

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


  Mrv0541 05061308382D          

 32 32  0  0  0  0            999 V2000
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  2  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  2  0  0  0  0
 15 11  2  0  0  0  0
 16 10  1  0  0  0  0
 17 11  1  0  0  0  0
 19 18  2  0  0  0  0
 23  1  1  0  0  0  0
 23 12  2  0  0  0  0
 23 14  1  0  0  0  0
 24  2  1  0  0  0  0
 24 13  2  0  0  0  0
 24 15  1  0  0  0  0
 25  3  1  0  0  0  0
 25 16  2  0  0  0  0
 25 18  1  0  0  0  0
 26  4  1  0  0  0  0
 26 17  2  0  0  0  0
 26 22  1  0  0  0  0
 27  5  1  0  0  0  0
 27 20  1  0  0  0  0
 28 20  1  0  0  0  0
 28 21  1  0  0  0  0
 29 19  1  0  0  0  0
 29 27  2  0  0  0  0
 30  6  1  0  0  0  0
 30  7  1  0  0  0  0
 30 21  1  0  0  0  0
 30 29  1  0  0  0  0
 31 22  1  0  0  0  0
 32 28  1  0  0  0  0
M  END

HMDB0035685
     RDKit          3D
beta-Citraurol
 74 74  0  0  0  0  0  0  0  0999 V2000
   -8.1542   -2.7089    0.7979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8400   -1.2620    0.7775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5281   -0.8867    0.6759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5831   -1.9561    0.5892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2650   -1.9052    0.4619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4218   -3.0796    0.3872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9753   -4.4480    0.4892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1154   -2.9758    0.2495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4485   -1.7476    0.1685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3425   -1.2228    0.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7931   -0.4396   -0.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6457    1.0921   -0.1415 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0160   -0.8400   -0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0914    0.1177   -0.3197 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3334   -0.2159   -0.4719 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.5817    0.5534   -0.7168 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0017   -0.8514   -0.7855 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4961    1.6712   -0.7916 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7975    1.5621   -0.9403 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6624    2.7248   -1.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9523    2.7420   -1.1620 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6475    1.4137   -1.2915 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7943    3.9531   -1.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0355    5.1236   -1.0858 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3480    0.5532    0.7199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8627    1.0514    2.0981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0113    1.1556    0.5112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3091    1.1610   -0.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7298    0.9314    0.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3585    2.0490    0.5744 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9631   -0.3308    0.8115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6713   -3.2236    1.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7841   -3.1850   -0.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2459   -2.8846    0.9453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9475   -3.0061    0.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8586   -0.9213    0.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1736   -0.8539   -0.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7701   -0.3836    1.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0343    1.3692   -1.1407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4367    1.2928   -0.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1051    1.5740    0.7118 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2387   -1.8872   -0.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8402    1.1875   -0.2670 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5803   -1.2709   -0.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9956    1.8867   -0.5180 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0235   -0.9249   -1.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9796   -1.3719    0.1979 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3586   -1.3977   -1.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1184    2.7132   -0.7200 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2228    0.5652   -0.9994 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1834    3.7210   -0.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.7474    1.5632   -1.2501 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3338    0.8034   -0.4247 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3320    0.9260   -2.2401 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.5712    3.9621   -0.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2740    3.9667   -2.2384 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5578    5.0276   -0.2030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1643    0.1839    2.6838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9915    1.4899    2.6727 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.5679    1.0878   -0.4653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1936    2.2977    0.6309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3558    0.9513    1.3927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0892    2.2253   -0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  2  0
  3  4  1  0
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  5  6  1  0
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  6  8  2  0
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 11 12  1  0
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 21 22  2  0
 22 23  1  0
 22 24  1  0
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  3 26  1  0
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 26 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 32  2  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  5 37  1  0
  7 38  1  0
  7 39  1  0
  7 40  1  0
  8 41  1  0
  9 42  1  0
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 29 69  1  0
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 30 71  1  0
 31 72  1  0
 32 73  1  0
 32 74  1  0
M  END


  Mrv0541 05061308382D          

 32 32  0  0  0  0            999 V2000
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
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 23  1  1  0  0  0  0
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 23 14  1  0  0  0  0
 24  2  1  0  0  0  0
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 24 15  1  0  0  0  0
 25  3  1  0  0  0  0
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 25 18  1  0  0  0  0
 26  4  1  0  0  0  0
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 26 22  1  0  0  0  0
 27  5  1  0  0  0  0
 27 20  1  0  0  0  0
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 28 21  1  0  0  0  0
 29 19  1  0  0  0  0
 29 27  2  0  0  0  0
 30  6  1  0  0  0  0
 30  7  1  0  0  0  0
 30 21  1  0  0  0  0
 30 29  1  0  0  0  0
 31 22  1  0  0  0  0
 32 28  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035685

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C(CO)=C/C=C/C(/C)=C/C=C/C=C(\C)/C=C/C=C(/C)\C=C\C1=C(C)CC(O)CC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C30H42O2/c1-23(12-8-9-13-24(2)15-11-17-26(4)22-31)14-10-16-25(3)18-19-29-27(5)20-28(32)21-30(29,6)7/h8-19,28,31-32H,20-22H2,1-7H3/b9-8+,14-10+,15-11+,19-18+,23-12+,24-13+,25-16-,26-17+

> <INCHI_KEY>
FNAJVVMDXCOSFY-STNACPSUSA-N

> <FORMULA>
C30H42O2

> <MOLECULAR_WEIGHT>
434.6533

> <EXACT_MASS>
434.318480588

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
55.857127853620064

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[(1E,3Z,5E,7E,9E,11E,13E,15E)-17-hydroxy-3,7,12,16-tetramethylheptadeca-1,3,5,7,9,11,13,15-octaen-1-yl]-3,5,5-trimethylcyclohex-3-en-1-ol

> <ALOGPS_LOGP>
6.84

> <JCHEM_LOGP>
5.902959882666668

> <ALOGPS_LOGS>
-5.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.907213404525137

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.75904463664036

> <JCHEM_PKA_STRONGEST_BASIC>
-1.089784856860705

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
149.43130000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.57e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(1E,3Z,5E,7E,9E,11E,13E,15E)-17-hydroxy-3,7,12,16-tetramethylheptadeca-1,3,5,7,9,11,13,15-octaen-1-yl]-3,5,5-trimethylcyclohex-3-en-1-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035685
     RDKit          3D
beta-Citraurol
 74 74  0  0  0  0  0  0  0  0999 V2000
   -8.1542   -2.7089    0.7979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8400   -1.2620    0.7775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5281   -0.8867    0.6759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5831   -1.9561    0.5892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2650   -1.9052    0.4619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4218   -3.0796    0.3872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9753   -4.4480    0.4892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1154   -2.9758    0.2495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4485   -1.7476    0.1685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3425   -1.2228    0.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7931   -0.4396   -0.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6457    1.0921   -0.1415 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0160   -0.8400   -0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0914    0.1177   -0.3197 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3334   -0.2159   -0.4719 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2856    0.8710   -0.5658 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5817    0.5534   -0.7168 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0017   -0.8514   -0.7855 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4961    1.6712   -0.7916 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7975    1.5621   -0.9403 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6624    2.7248   -1.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9523    2.7420   -1.1620 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6475    1.4137   -1.2915 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7943    3.9531   -1.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0355    5.1236   -1.0858 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3480    0.5532    0.7199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8627    1.0514    2.0981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0113    1.1556    0.5112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3091    1.1610   -0.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7298    0.9314    0.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3585    2.0490    0.5744 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9631   -0.3308    0.8115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6713   -3.2236    1.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7841   -3.1850   -0.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2459   -2.8846    0.9453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9475   -3.0061    0.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8586   -0.9213    0.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3786   -4.7433   -0.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7434   -4.4514    1.3083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1989   -5.1685    0.8289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4909   -3.8908    0.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1736   -0.8539   -0.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7701   -0.3836    1.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0343    1.3692   -1.1407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4367    1.2928   -0.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1051    1.5740    0.7118 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2387   -1.8872   -0.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8402    1.1875   -0.2670 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5803   -1.2709   -0.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9956    1.8867   -0.5180 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0235   -0.9249   -1.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9796   -1.3719    0.1979 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3586   -1.3977   -1.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1184    2.7132   -0.7200 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2228    0.5652   -0.9994 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1834    3.7210   -0.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.7474    1.5632   -1.2501 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3338    0.8034   -0.4247 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3320    0.9260   -2.2401 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.5712    3.9621   -0.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2740    3.9667   -2.2384 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5578    5.0276   -0.2030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1643    0.1839    2.6838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9915    1.4899    2.6727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5833    1.8501    1.9568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5679    1.0878   -0.4653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1936    2.2977    0.6309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3558    0.9513    1.3927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0892    2.2253   -0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0654    0.7067   -1.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2738    0.7916   -0.9669 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2771    1.7804    0.8344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8667   -0.8774    0.3889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2465   -0.0918    1.8410 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
  3 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 32  2  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  5 37  1  0
  7 38  1  0
  7 39  1  0
  7 40  1  0
  8 41  1  0
  9 42  1  0
 10 43  1  0
 12 44  1  0
 12 45  1  0
 12 46  1  0
 13 47  1  0
 14 48  1  0
 15 49  1  0
 16 50  1  0
 18 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 20 55  1  0
 21 56  1  0
 23 57  1  0
 23 58  1  0
 23 59  1  0
 24 60  1  0
 24 61  1  0
 25 62  1  0
 27 63  1  0
 27 64  1  0
 27 65  1  0
 28 66  1  0
 28 67  1  0
 28 68  1  0
 29 69  1  0
 29 70  1  0
 30 71  1  0
 31 72  1  0
 32 73  1  0
 32 74  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.667 -12.320   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1   23                                                            
CONECT    2   24                                                            
CONECT    3   25                                                            
CONECT    4   26                                                            
CONECT    5   27                                                            
CONECT    6   30                                                            
CONECT    7   30                                                            
CONECT    8    9   12                                                       
CONECT    9    8   13                                                       
CONECT   10   14   16                                                       
CONECT   11   15   17                                                       
CONECT   12    8   23                                                       
CONECT   13    9   24                                                       
CONECT   14   10   23                                                       
CONECT   15   11   24                                                       
CONECT   16   10   25                                                       
CONECT   17   11   26                                                       
CONECT   18   19   25                                                       
CONECT   19   18   29                                                       
CONECT   20   27   28                                                       
CONECT   21   28   30                                                       
CONECT   22   26   31                                                       
CONECT   23    1   12   14                                                  
CONECT   24    2   13   15                                                  
CONECT   25    3   16   18                                                  
CONECT   26    4   17   22                                                  
CONECT   27    5   20   29                                                  
CONECT   28   20   21   32                                                  
CONECT   29   19   27   30                                                  
CONECT   30    6    7   21   29                                             
CONECT   31   22                                                            
CONECT   32   28                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   64    0
END

COMPND    HMDB0035685
HETATM    1  C1  UNL     1      -8.154  -2.709   0.798  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.840  -1.262   0.777  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.528  -0.887   0.676  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.583  -1.956   0.589  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.265  -1.905   0.462  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.422  -3.080   0.387  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.975  -4.448   0.489  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.115  -2.976   0.250  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.448  -1.748   0.168  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.342  -1.223   0.048  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.793  -0.440  -0.071  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.646   1.092  -0.141  1.00  0.00           C  
HETATM   13  C13 UNL     1       2.016  -0.840  -0.210  1.00  0.00           C  
HETATM   14  C14 UNL     1       3.091   0.118  -0.320  1.00  0.00           C  
HETATM   15  C15 UNL     1       4.333  -0.216  -0.472  1.00  0.00           C  
HETATM   16  C16 UNL     1       5.286   0.871  -0.566  1.00  0.00           C  
HETATM   17  C17 UNL     1       6.582   0.553  -0.717  1.00  0.00           C  
HETATM   18  C18 UNL     1       7.002  -0.851  -0.785  1.00  0.00           C  
HETATM   19  C19 UNL     1       7.496   1.671  -0.792  1.00  0.00           C  
HETATM   20  C20 UNL     1       8.798   1.562  -0.940  1.00  0.00           C  
HETATM   21  C21 UNL     1       9.662   2.725  -1.006  1.00  0.00           C  
HETATM   22  C22 UNL     1      10.952   2.742  -1.162  1.00  0.00           C  
HETATM   23  C23 UNL     1      11.647   1.414  -1.291  1.00  0.00           C  
HETATM   24  C24 UNL     1      11.794   3.953  -1.222  1.00  0.00           C  
HETATM   25  O1  UNL     1      11.036   5.124  -1.086  1.00  0.00           O  
HETATM   26  C25 UNL     1      -6.348   0.553   0.720  1.00  0.00           C  
HETATM   27  C26 UNL     1      -6.863   1.051   2.098  1.00  0.00           C  
HETATM   28  C27 UNL     1      -5.011   1.156   0.511  1.00  0.00           C  
HETATM   29  C28 UNL     1      -7.309   1.161  -0.325  1.00  0.00           C  
HETATM   30  C29 UNL     1      -8.730   0.931   0.021  1.00  0.00           C  
HETATM   31  O2  UNL     1      -9.358   2.049   0.574  1.00  0.00           O  
HETATM   32  C30 UNL     1      -8.963  -0.331   0.811  1.00  0.00           C  
HETATM   33  H1  UNL     1      -7.671  -3.224   1.679  1.00  0.00           H  
HETATM   34  H2  UNL     1      -7.784  -3.185  -0.114  1.00  0.00           H  
HETATM   35  H3  UNL     1      -9.246  -2.885   0.945  1.00  0.00           H  
HETATM   36  H4  UNL     1      -5.948  -3.006   0.621  1.00  0.00           H  
HETATM   37  H5  UNL     1      -3.859  -0.921   0.402  1.00  0.00           H  
HETATM   38  H6  UNL     1      -4.379  -4.743  -0.473  1.00  0.00           H  
HETATM   39  H7  UNL     1      -4.743  -4.451   1.308  1.00  0.00           H  
HETATM   40  H8  UNL     1      -3.199  -5.169   0.829  1.00  0.00           H  
HETATM   41  H9  UNL     1      -1.491  -3.891   0.195  1.00  0.00           H  
HETATM   42  H10 UNL     1      -2.174  -0.854  -0.098  1.00  0.00           H  
HETATM   43  H11 UNL     1      -0.770  -0.384   1.164  1.00  0.00           H  
HETATM   44  H12 UNL     1       1.034   1.369  -1.141  1.00  0.00           H  
HETATM   45  H13 UNL     1      -0.437   1.293  -0.081  1.00  0.00           H  
HETATM   46  H14 UNL     1       1.105   1.574   0.712  1.00  0.00           H  
HETATM   47  H15 UNL     1       2.239  -1.887  -0.242  1.00  0.00           H  
HETATM   48  H16 UNL     1       2.840   1.188  -0.267  1.00  0.00           H  
HETATM   49  H17 UNL     1       4.580  -1.271  -0.522  1.00  0.00           H  
HETATM   50  H18 UNL     1       4.996   1.887  -0.518  1.00  0.00           H  
HETATM   51  H19 UNL     1       8.023  -0.925  -1.169  1.00  0.00           H  
HETATM   52  H20 UNL     1       6.980  -1.372   0.198  1.00  0.00           H  
HETATM   53  H21 UNL     1       6.359  -1.398  -1.535  1.00  0.00           H  
HETATM   54  H22 UNL     1       7.118   2.713  -0.720  1.00  0.00           H  
HETATM   55  H23 UNL     1       9.223   0.565  -0.999  1.00  0.00           H  
HETATM   56  H24 UNL     1       9.183   3.721  -0.916  1.00  0.00           H  
HETATM   57  H25 UNL     1      12.747   1.563  -1.250  1.00  0.00           H  
HETATM   58  H26 UNL     1      11.334   0.803  -0.425  1.00  0.00           H  
HETATM   59  H27 UNL     1      11.332   0.926  -2.240  1.00  0.00           H  
HETATM   60  H28 UNL     1      12.571   3.962  -0.452  1.00  0.00           H  
HETATM   61  H29 UNL     1      12.274   3.967  -2.238  1.00  0.00           H  
HETATM   62  H30 UNL     1      10.558   5.028  -0.203  1.00  0.00           H  
HETATM   63  H31 UNL     1      -7.164   0.184   2.684  1.00  0.00           H  
HETATM   64  H32 UNL     1      -5.991   1.490   2.673  1.00  0.00           H  
HETATM   65  H33 UNL     1      -7.583   1.850   1.957  1.00  0.00           H  
HETATM   66  H34 UNL     1      -4.568   1.088  -0.465  1.00  0.00           H  
HETATM   67  H35 UNL     1      -5.194   2.298   0.631  1.00  0.00           H  
HETATM   68  H36 UNL     1      -4.356   0.951   1.393  1.00  0.00           H  
HETATM   69  H37 UNL     1      -7.089   2.225  -0.368  1.00  0.00           H  
HETATM   70  H38 UNL     1      -7.065   0.707  -1.323  1.00  0.00           H  
HETATM   71  H39 UNL     1      -9.274   0.792  -0.967  1.00  0.00           H  
HETATM   72  H40 UNL     1     -10.277   1.780   0.834  1.00  0.00           H  
HETATM   73  H41 UNL     1      -9.867  -0.877   0.389  1.00  0.00           H  
HETATM   74  H42 UNL     1      -9.247  -0.092   1.841  1.00  0.00           H  
CONECT    1    2   33   34   35
CONECT    2    3    3   32
CONECT    3    4   26
CONECT    4    5    5   36
CONECT    5    6   37
CONECT    6    7    8    8
CONECT    7   38   39   40
CONECT    8    9   41
CONECT    9   10   10   42
CONECT   10   11   43
CONECT   11   12   13   13
CONECT   12   44   45   46
CONECT   13   14   47
CONECT   14   15   15   48
CONECT   15   16   49
CONECT   16   17   17   50
CONECT   17   18   19
CONECT   18   51   52   53
CONECT   19   20   20   54
CONECT   20   21   55
CONECT   21   22   22   56
CONECT   22   23   24
CONECT   23   57   58   59
CONECT   24   25   60   61
CONECT   25   62
CONECT   26   27   28   29
CONECT   27   63   64   65
CONECT   28   66   67   68
CONECT   29   30   69   70
CONECT   30   31   32   71
CONECT   31   72
CONECT   32   73   74
END

HMDB0035685
     RDKit          3D
beta-Citraurol
 74 74  0  0  0  0  0  0  0  0999 V2000
   -8.1542   -2.7089    0.7979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8400   -1.2620    0.7775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5281   -0.8867    0.6759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5831   -1.9561    0.5892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2650   -1.9052    0.4619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4218   -3.0796    0.3872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9753   -4.4480    0.4892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1154   -2.9758    0.2495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4485   -1.7476    0.1685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3425   -1.2228    0.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7931   -0.4396   -0.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6457    1.0921   -0.1415 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0160   -0.8400   -0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0914    0.1177   -0.3197 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3334   -0.2159   -0.4719 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2856    0.8710   -0.5658 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5817    0.5534   -0.7168 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0017   -0.8514   -0.7855 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4961    1.6712   -0.7916 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7975    1.5621   -0.9403 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6624    2.7248   -1.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9523    2.7420   -1.1620 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6475    1.4137   -1.2915 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7943    3.9531   -1.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0355    5.1236   -1.0858 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3480    0.5532    0.7199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8627    1.0514    2.0981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0113    1.1556    0.5112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3091    1.1610   -0.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7298    0.9314    0.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3585    2.0490    0.5744 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9631   -0.3308    0.8115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6713   -3.2236    1.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7841   -3.1850   -0.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2459   -2.8846    0.9453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9475   -3.0061    0.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8586   -0.9213    0.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3786   -4.7433   -0.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7434   -4.4514    1.3083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1989   -5.1685    0.8289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4909   -3.8908    0.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1736   -0.8539   -0.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7701   -0.3836    1.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0343    1.3692   -1.1407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4367    1.2928   -0.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1051    1.5740    0.7118 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2387   -1.8872   -0.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8402    1.1875   -0.2670 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5803   -1.2709   -0.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9956    1.8867   -0.5180 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0235   -0.9249   -1.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9796   -1.3719    0.1979 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3586   -1.3977   -1.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1184    2.7132   -0.7200 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2228    0.5652   -0.9994 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1834    3.7210   -0.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.7474    1.5632   -1.2501 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3338    0.8034   -0.4247 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3320    0.9260   -2.2401 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.5712    3.9621   -0.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2740    3.9667   -2.2384 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5578    5.0276   -0.2030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1643    0.1839    2.6838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9915    1.4899    2.6727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5833    1.8501    1.9568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5679    1.0878   -0.4653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1936    2.2977    0.6309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3558    0.9513    1.3927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0892    2.2253   -0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0654    0.7067   -1.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2738    0.7916   -0.9669 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2771    1.7804    0.8344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8667   -0.8774    0.3889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2465   -0.0918    1.8410 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
  3 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 32  2  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  5 37  1  0
  7 38  1  0
  7 39  1  0
  7 40  1  0
  8 41  1  0
  9 42  1  0
 10 43  1  0
 12 44  1  0
 12 45  1  0
 12 46  1  0
 13 47  1  0
 14 48  1  0
 15 49  1  0
 16 50  1  0
 18 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 20 55  1  0
 21 56  1  0
 23 57  1  0
 23 58  1  0
 23 59  1  0
 24 60  1  0
 24 61  1  0
 25 62  1  0
 27 63  1  0
 27 64  1  0
 27 65  1  0
 28 66  1  0
 28 67  1  0
 28 68  1  0
 29 69  1  0
 29 70  1  0
 30 71  1  0
 31 72  1  0
 32 73  1  0
 32 74  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
b-Citraurol	Generator
Β-citraurol	Generator
8'-apo-b-Carotene-3,8'-diol	HMDB
b-Citraurinol	HMDB

Chemical Formula

C₃₀H₄₂O₂

Average Molecular Weight

434.6533

Monoisotopic Molecular Weight

434.318480588

IUPAC Name

4-[(1E,3Z,5E,7E,9E,11E,13E,15E)-17-hydroxy-3,7,12,16-tetramethylheptadeca-1,3,5,7,9,11,13,15-octaen-1-yl]-3,5,5-trimethylcyclohex-3-en-1-ol

Traditional Name

4-[(1E,3Z,5E,7E,9E,11E,13E,15E)-17-hydroxy-3,7,12,16-tetramethylheptadeca-1,3,5,7,9,11,13,15-octaen-1-yl]-3,5,5-trimethylcyclohex-3-en-1-ol

CAS Registry Number

57593-78-9

SMILES

C\C(CO)=C/C=C/C(/C)=C/C=C/C=C(\C)/C=C/C=C(/C)\C=C\C1=C(C)CC(O)CC1(C)C

InChI Identifier

InChI=1S/C30H42O2/c1-23(12-8-9-13-24(2)15-11-17-26(4)22-31)14-10-16-25(3)18-19-29-27(5)20-28(32)21-30(29,6)7/h8-19,28,31-32H,20-22H2,1-7H3/b9-8+,14-10+,15-11+,19-18+,23-12+,24-13+,25-16-,26-17+

InChI Key

FNAJVVMDXCOSFY-STNACPSUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Long chain fatty alcohol
Fatty alcohol
Fatty acyl
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0035685)
Cell membrane (HMDB: HMDB0035685)

Cellular substructure

Extracellular (HMDB: HMDB0035685)
Membrane (HMDB: HMDB0035685)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035685)

Source

Endogenous

Endogenous (HMDB: HMDB0035685)

Plant

Plant (HMDB: HMDB0035685)

Animal

Animal (HMDB: HMDB0035685)

Exogenous

Food

Food (HMDB: HMDB0035685)

Fruit

Citrus

Citrus (FooDB: FOOD00859)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0035685)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0035685)

Cellular process

Cell signaling (HMDB: HMDB0035685)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0035685)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0035685)

Nutrient

Nutrient (HMDB: HMDB0035685)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035685)

Emulsifier (HMDB: HMDB0035685)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.5e-06 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0016 g/L	ALOGPS
logP	6.84	ALOGPS
logP	5.9	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	16.76	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	149.43 m³·mol⁻¹	ChemAxon
Polarizability	55.86 Å³	ChemAxon
Number of Rings	1	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]+	216.484	31661259
DarkChem	[M-H]-	214.898	31661259
DeepCCS	[M+H]+	230.479	30932474
DeepCCS	[M-H]-	228.083	30932474
DeepCCS	[M-2H]-	260.967	30932474
DeepCCS	[M+Na]+	236.391	30932474
AllCCS	[M+H]+	219.0	32859911
AllCCS	[M+H-H2O]+	216.7	32859911
AllCCS	[M+NH4]+	221.1	32859911
AllCCS	[M+Na]+	221.7	32859911
AllCCS	[M-H]-	208.3	32859911
AllCCS	[M+Na-2H]-	210.4	32859911
AllCCS	[M+HCOO]-	213.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
beta-Citraurol	C\C(CO)=C/C=C/C(/C)=C/C=C/C=C(\C)/C=C/C=C(/C)\C=C\C1=C(C)CC(O)CC1(C)C	4987.0	Standard polar	33892256
beta-Citraurol	C\C(CO)=C/C=C/C(/C)=C/C=C/C=C(\C)/C=C/C=C(/C)\C=C\C1=C(C)CC(O)CC1(C)C	3680.9	Standard non polar	33892256
beta-Citraurol	C\C(CO)=C/C=C/C(/C)=C/C=C/C=C(\C)/C=C/C=C(/C)\C=C\C1=C(C)CC(O)CC1(C)C	3541.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
beta-Citraurol,1TMS,isomer #1	CC1=C(/C=C/C(C)=C\C=C\C(C)=C\C=C\C=C(C)\C=C\C=C(/C)CO[Si](C)(C)C)C(C)(C)CC(O)C1	3800.3	Semi standard non polar	33892256
beta-Citraurol,1TMS,isomer #2	CC1=C(/C=C/C(C)=C\C=C\C(C)=C\C=C\C=C(C)\C=C\C=C(/C)CO)C(C)(C)CC(O[Si](C)(C)C)C1	3738.1	Semi standard non polar	33892256
beta-Citraurol,2TMS,isomer #1	CC1=C(/C=C/C(C)=C\C=C\C(C)=C\C=C\C=C(C)\C=C\C=C(/C)CO[Si](C)(C)C)C(C)(C)CC(O[Si](C)(C)C)C1	3767.7	Semi standard non polar	33892256
beta-Citraurol,1TBDMS,isomer #1	CC1=C(/C=C/C(C)=C\C=C\C(C)=C\C=C\C=C(C)\C=C\C=C(/C)CO[Si](C)(C)C(C)(C)C)C(C)(C)CC(O)C1	4011.6	Semi standard non polar	33892256
beta-Citraurol,1TBDMS,isomer #2	CC1=C(/C=C/C(C)=C\C=C\C(C)=C\C=C\C=C(C)\C=C\C=C(/C)CO)C(C)(C)CC(O[Si](C)(C)C(C)(C)C)C1	3957.3	Semi standard non polar	33892256
beta-Citraurol,2TBDMS,isomer #1	CC1=C(/C=C/C(C)=C\C=C\C(C)=C\C=C\C=C(C)\C=C\C=C(/C)CO[Si](C)(C)C(C)(C)C)C(C)(C)CC(O[Si](C)(C)C(C)(C)C)C1	4206.8	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 - beta-Citraurol GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-1004900000-27e0f0509770afba2a2c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-Citraurol GC-MS (2 TMS) - 70eV, Positive	splash10-03di-4200390000-b44cff969b6e857a3e78	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-Citraurol 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 - beta-Citraurol 10V, Positive-QTOF	splash10-014i-1233900000-b3fec74872434e5acf4f	2016-06-20	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Citraurol 20V, Positive-QTOF	splash10-00ls-2895200000-8d27963de177060fbe11	2016-06-20	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Citraurol 40V, Positive-QTOF	splash10-00xs-4963000000-9b9646af522ba8ac8577	2016-06-20	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Citraurol 10V, Negative-QTOF	splash10-001i-0000900000-8bed77f4a05a6ce4ce4c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Citraurol 20V, Negative-QTOF	splash10-00lr-0001900000-2c44cb7bd12a69d0859d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Citraurol 40V, Negative-QTOF	splash10-0uy0-4459600000-6684066fa395153ebdc4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Citraurol 10V, Positive-QTOF	splash10-0h09-0139200000-e66fede75ef0d85632de	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Citraurol 20V, Positive-QTOF	splash10-01ot-2279100000-8d64ebb73d911265c507	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Citraurol 40V, Positive-QTOF	splash10-0040-0971000000-5f9fd6bce440b83cb8c3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Citraurol 10V, Negative-QTOF	splash10-014i-0001900000-02a34da352570985a57f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Citraurol 20V, Negative-QTOF	splash10-0udr-0408900000-e8511dfbc901f1893c15	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Citraurol 40V, Negative-QTOF	splash10-000i-1129000000-0bb507140ad5fc196300	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB014402

KNApSAcK ID

C00054859

Chemspider ID

35013995

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751847

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1850911

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 beta-Citraurol (HMDB0035685)

MOL for HMDB0035685 (beta-Citraurol)

3D MOL for HMDB0035685 (beta-Citraurol)

3D SDF for HMDB0035685 (beta-Citraurol)

3D-SDF for HMDB0035685 (beta-Citraurol)

PDB for HMDB0035685 (beta-Citraurol)

3D PDB for HMDB0035685 (beta-Citraurol)

SMILES for HMDB0035685 (beta-Citraurol)

INCHI for HMDB0035685 (beta-Citraurol)

Structure for HMDB0035685 (beta-Citraurol)

3D Structure for HMDB0035685 (beta-Citraurol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra