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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:34:34 UTC

Update Date

2022-03-07 02:56:49 UTC

HMDB ID

HMDB0040954

Secondary Accession Numbers

HMDB40954

Metabolite Identification

Common Name

9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one

Description

9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a small amount of articles have been published on 9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one.

Structure

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

  Mrv0541 05061312162D          

 25 26  0  0  0  0            999 V2000
   -0.7194    1.1826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0050    0.7701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0050   -0.0549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7194   -0.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7194   -1.2924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2804    1.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4735    1.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2185    1.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4339    0.7701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4339   -0.0549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2185   -0.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7034    0.3576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5284    0.3576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0803    2.4790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6605    2.0076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0050    2.4201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7095   -0.4674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1277    2.4227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7095   -1.2924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4240   -1.7049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0050   -1.7049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4240   -2.5299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1385   -2.9424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7095   -2.9424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8529   -2.5299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  9  1  0  0  0  0
  1 15  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 17  1  0  0  0  0
  4  5  2  0  0  0  0
  4 10  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 18  1  0  0  0  0
  8  9  1  0  0  0  0
  8 12  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 23 25  1  0  0  0  0
M  END

HMDB0040954
     RDKit          3D
9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one
 57 58  0  0  0  0  0  0  0  0999 V2000
    0.9546    2.2411    0.9790 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1589    1.1678    0.8187 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7414   -0.2022    0.7884 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1297   -0.1463    0.5406 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9590   -0.7735    1.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4273   -1.3551    2.4732 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3989   -0.8291    1.3728 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0356   -0.2757    0.3703 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2960    0.4136   -0.6889 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5410   -0.3290    0.2733 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0621    1.0816    0.2661 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0650   -0.8674   -0.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4791   -0.9104   -0.1199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8647   -2.0831   -0.9288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2802   -2.5060   -0.9548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2369   -2.0589   -2.3297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9416    0.4442   -0.4170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2573    1.3156    0.6863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0911    0.8882    1.8912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4103    0.4096    1.3127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2832   -0.2036    1.8398 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2916    0.9256   -0.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4467    0.8018   -0.9470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6581    1.4585   -0.2388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3634    1.5009   -2.1484 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0057    2.0699    1.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5314    3.2358    1.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4980   -0.7711    1.7095 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9887   -1.3395    2.1503 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9891    0.7698   -1.4917 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6117   -0.2966   -1.2366 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7647    1.2954   -0.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9354   -0.9507    1.0821 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7954   -0.7915   -0.7080 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2828    1.7996    0.6251 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9292    1.1386    0.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4565    1.3776   -0.7238 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4591   -1.8804   -0.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1657   -0.3105   -1.3200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5983   -1.1605    0.9501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3160   -2.9643   -0.4522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8064   -2.2269   -1.9152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4153   -3.6283   -0.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8013   -2.1338   -0.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211   -2.4555   -2.3504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2696   -1.0497   -2.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8746   -2.7341   -2.9478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5129    0.8612   -1.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5134    2.3634    0.4220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6107    0.1401    2.5153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2821    1.8332    2.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1962    2.0622    0.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8203   -0.2256   -1.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7351    2.5416   -0.5540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4799    1.4883    0.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5915    0.9907   -0.5633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5337    0.8434   -2.8665 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
  3 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 13 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 18  2  1  0
 22 17  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  7 29  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 22 52  1  0
 23 53  1  0
 24 54  1  0
 24 55  1  0
 24 56  1  0
 25 57  1  0
M  END

  Mrv0541 05061312162D          

 25 26  0  0  0  0            999 V2000
   -0.7194    1.1826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0050    0.7701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0050   -0.0549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7194   -0.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7194   -1.2924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2804    1.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4735    1.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2185    1.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4339    0.7701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4339   -0.0549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2185   -0.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7034    0.3576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5284    0.3576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0803    2.4790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6605    2.0076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0050    2.4201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7095   -0.4674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1277    2.4227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7095   -1.2924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4240   -1.7049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0050   -1.7049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4240   -2.5299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1385   -2.9424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7095   -2.9424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8529   -2.5299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  9  1  0  0  0  0
  1 15  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 17  1  0  0  0  0
  4  5  2  0  0  0  0
  4 10  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 18  1  0  0  0  0
  8  9  1  0  0  0  0
  8 12  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 23 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040954

> <DATABASE_NAME>
hmdb

> <SMILES>
CC\C(C)=C\C(=O)OC1CC(C(C)C)C2C(CC(=O)C2C(C)O)C1=C

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O4/c1-7-12(4)8-19(24)25-18-10-15(11(2)3)21-16(13(18)5)9-17(23)20(21)14(6)22/h8,11,14-16,18,20-22H,5,7,9-10H2,1-4,6H3/b12-8+

> <INCHI_KEY>
AIZCSTFUIXPHFD-XYOKQWHBSA-N

> <FORMULA>
C21H32O4

> <MOLECULAR_WEIGHT>
348.4764

> <EXACT_MASS>
348.230059512

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
39.996651873177456

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(1-hydroxyethyl)-4-methylidene-2-oxo-7-(propan-2-yl)-octahydro-1H-inden-5-yl (2E)-3-methylpent-2-enoate

> <ALOGPS_LOGP>
2.49

> <JCHEM_LOGP>
3.954351123999999

> <ALOGPS_LOGS>
-4.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.726092562440606

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.089769374616104

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7591051494121643

> <JCHEM_POLAR_SURFACE_AREA>
63.6

> <JCHEM_REFRACTIVITY>
98.80689999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.37e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(1-hydroxyethyl)-7-isopropyl-4-methylidene-2-oxo-hexahydro-1H-inden-5-yl (2E)-3-methylpent-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040954
     RDKit          3D
9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one
 57 58  0  0  0  0  0  0  0  0999 V2000
    0.9546    2.2411    0.9790 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1589    1.1678    0.8187 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7414   -0.2022    0.7884 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1297   -0.1463    0.5406 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9590   -0.7735    1.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4273   -1.3551    2.4732 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3989   -0.8291    1.3728 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0356   -0.2757    0.3703 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2960    0.4136   -0.6889 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5410   -0.3290    0.2733 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0621    1.0816    0.2661 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0650   -0.8674   -0.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4791   -0.9104   -0.1199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8647   -2.0831   -0.9288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2802   -2.5060   -0.9548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2369   -2.0589   -2.3297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9416    0.4442   -0.4170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2573    1.3156    0.6863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0911    0.8882    1.8912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4103    0.4096    1.3127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2832   -0.2036    1.8398 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2916    0.9256   -0.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4467    0.8018   -0.9470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6581    1.4585   -0.2388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3634    1.5009   -2.1484 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0057    2.0699    1.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5314    3.2358    1.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4980   -0.7711    1.7095 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9887   -1.3395    2.1503 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9891    0.7698   -1.4917 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6117   -0.2966   -1.2366 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7647    1.2954   -0.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9354   -0.9507    1.0821 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7954   -0.7915   -0.7080 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2828    1.7996    0.6251 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9292    1.1386    0.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4565    1.3776   -0.7238 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4591   -1.8804   -0.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1657   -0.3105   -1.3200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5983   -1.1605    0.9501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3160   -2.9643   -0.4522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8064   -2.2269   -1.9152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4153   -3.6283   -0.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8013   -2.1338   -0.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211   -2.4555   -2.3504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2696   -1.0497   -2.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8746   -2.7341   -2.9478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5129    0.8612   -1.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5134    2.3634    0.4220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6107    0.1401    2.5153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2821    1.8332    2.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1962    2.0622    0.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8203   -0.2256   -1.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7351    2.5416   -0.5540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4799    1.4883    0.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5915    0.9907   -0.5633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5337    0.8434   -2.8665 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
  3 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 13 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 18  2  1  0
 22 17  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  7 29  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 22 52  1  0
 23 53  1  0
 24 54  1  0
 24 55  1  0
 24 56  1  0
 25 57  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      -1.343   2.208   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.009   1.438   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.009  -0.102   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.343  -0.872   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.343  -2.412   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.123   3.698   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.617   3.378   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.141   1.913   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.677   1.438   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.677  -0.102   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.141  -0.578   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.046   0.668   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -6.586   0.668   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.017   4.627   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.233   3.748   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.009   4.518   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.324  -0.872   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -3.972   4.522   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.324  -2.412   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.658  -3.182   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.009  -3.182   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.658  -4.722   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.992  -5.492   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.324  -5.492   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.325  -4.722   0.000  0.00  0.00           C+0
CONECT    1    2    9   15                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4                                                            
CONECT    6    7                                                            
CONECT    7    6    8   18                                                  
CONECT    8    7    9   12                                                  
CONECT    9    1    8   10                                                  
CONECT   10    4    9   11                                                  
CONECT   11   10   12                                                       
CONECT   12    8   11   13                                                  
CONECT   13   12                                                            
CONECT   14   15                                                            
CONECT   15    1   14   16                                                  
CONECT   16   15                                                            
CONECT   17    3   19                                                       
CONECT   18    7                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19   22                                                       
CONECT   21   19                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22   25                                                       
CONECT   24   22                                                            
CONECT   25   23                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

COMPND    HMDB0040954
HETATM    1  C1  UNL     1       0.955   2.241   0.979  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.159   1.168   0.819  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.741  -0.202   0.788  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.130  -0.146   0.541  1.00  0.00           O  
HETATM    5  C4  UNL     1       2.959  -0.773   1.460  1.00  0.00           C  
HETATM    6  O2  UNL     1       2.427  -1.355   2.473  1.00  0.00           O  
HETATM    7  C5  UNL     1       4.399  -0.829   1.373  1.00  0.00           C  
HETATM    8  C6  UNL     1       5.036  -0.276   0.370  1.00  0.00           C  
HETATM    9  C7  UNL     1       4.296   0.414  -0.689  1.00  0.00           C  
HETATM   10  C8  UNL     1       6.541  -0.329   0.273  1.00  0.00           C  
HETATM   11  C9  UNL     1       7.062   1.082   0.266  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.065  -0.867  -0.368  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.479  -0.910  -0.120  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.865  -2.083  -0.929  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.280  -2.506  -0.955  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.237  -2.059  -2.330  1.00  0.00           C  
HETATM   17  C15 UNL     1      -1.942   0.444  -0.417  1.00  0.00           C  
HETATM   18  C16 UNL     1      -1.257   1.316   0.686  1.00  0.00           C  
HETATM   19  C17 UNL     1      -2.091   0.888   1.891  1.00  0.00           C  
HETATM   20  C18 UNL     1      -3.410   0.410   1.313  1.00  0.00           C  
HETATM   21  O3  UNL     1      -4.283  -0.204   1.840  1.00  0.00           O  
HETATM   22  C19 UNL     1      -3.292   0.926  -0.090  1.00  0.00           C  
HETATM   23  C20 UNL     1      -4.447   0.802  -0.947  1.00  0.00           C  
HETATM   24  C21 UNL     1      -5.658   1.459  -0.239  1.00  0.00           C  
HETATM   25  O4  UNL     1      -4.363   1.501  -2.148  1.00  0.00           O  
HETATM   26  H1  UNL     1       2.006   2.070   1.082  1.00  0.00           H  
HETATM   27  H2  UNL     1       0.531   3.236   1.001  1.00  0.00           H  
HETATM   28  H3  UNL     1       0.498  -0.771   1.710  1.00  0.00           H  
HETATM   29  H4  UNL     1       4.989  -1.339   2.150  1.00  0.00           H  
HETATM   30  H5  UNL     1       4.989   0.770  -1.492  1.00  0.00           H  
HETATM   31  H6  UNL     1       3.612  -0.297  -1.237  1.00  0.00           H  
HETATM   32  H7  UNL     1       3.765   1.295  -0.300  1.00  0.00           H  
HETATM   33  H8  UNL     1       6.935  -0.951   1.082  1.00  0.00           H  
HETATM   34  H9  UNL     1       6.795  -0.792  -0.708  1.00  0.00           H  
HETATM   35  H10 UNL     1       6.283   1.800   0.625  1.00  0.00           H  
HETATM   36  H11 UNL     1       7.929   1.139   0.973  1.00  0.00           H  
HETATM   37  H12 UNL     1       7.456   1.378  -0.724  1.00  0.00           H  
HETATM   38  H13 UNL     1       0.459  -1.880  -0.517  1.00  0.00           H  
HETATM   39  H14 UNL     1       0.166  -0.310  -1.320  1.00  0.00           H  
HETATM   40  H15 UNL     1      -1.598  -1.161   0.950  1.00  0.00           H  
HETATM   41  H16 UNL     1      -1.316  -2.964  -0.452  1.00  0.00           H  
HETATM   42  H17 UNL     1      -3.806  -2.227  -1.915  1.00  0.00           H  
HETATM   43  H18 UNL     1      -3.415  -3.628  -0.917  1.00  0.00           H  
HETATM   44  H19 UNL     1      -3.801  -2.134  -0.058  1.00  0.00           H  
HETATM   45  H20 UNL     1      -0.221  -2.455  -2.350  1.00  0.00           H  
HETATM   46  H21 UNL     1      -1.270  -1.050  -2.763  1.00  0.00           H  
HETATM   47  H22 UNL     1      -1.875  -2.734  -2.948  1.00  0.00           H  
HETATM   48  H23 UNL     1      -1.513   0.861  -1.356  1.00  0.00           H  
HETATM   49  H24 UNL     1      -1.513   2.363   0.422  1.00  0.00           H  
HETATM   50  H25 UNL     1      -1.611   0.140   2.515  1.00  0.00           H  
HETATM   51  H26 UNL     1      -2.282   1.833   2.477  1.00  0.00           H  
HETATM   52  H27 UNL     1      -3.196   2.062   0.099  1.00  0.00           H  
HETATM   53  H28 UNL     1      -4.820  -0.226  -1.083  1.00  0.00           H  
HETATM   54  H29 UNL     1      -5.735   2.542  -0.554  1.00  0.00           H  
HETATM   55  H30 UNL     1      -5.480   1.488   0.835  1.00  0.00           H  
HETATM   56  H31 UNL     1      -6.592   0.991  -0.563  1.00  0.00           H  
HETATM   57  H32 UNL     1      -4.534   0.843  -2.867  1.00  0.00           H  
CONECT    1    2    2   26   27
CONECT    2    3   18
CONECT    3    4   12   28
CONECT    4    5
CONECT    5    6    6    7
CONECT    7    8    8   29
CONECT    8    9   10
CONECT    9   30   31   32
CONECT   10   11   33   34
CONECT   11   35   36   37
CONECT   12   13   38   39
CONECT   13   14   17   40
CONECT   14   15   16   41
CONECT   15   42   43   44
CONECT   16   45   46   47
CONECT   17   18   22   48
CONECT   18   19   49
CONECT   19   20   50   51
CONECT   20   21   21   22
CONECT   22   23   52
CONECT   23   24   25   53
CONECT   24   54   55   56
CONECT   25   57
END

HMDB0040954
     RDKit          3D
9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one
 57 58  0  0  0  0  0  0  0  0999 V2000
    0.9546    2.2411    0.9790 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1589    1.1678    0.8187 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7414   -0.2022    0.7884 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1297   -0.1463    0.5406 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9590   -0.7735    1.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4273   -1.3551    2.4732 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3989   -0.8291    1.3728 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0356   -0.2757    0.3703 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2960    0.4136   -0.6889 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5410   -0.3290    0.2733 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0621    1.0816    0.2661 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0650   -0.8674   -0.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4791   -0.9104   -0.1199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8647   -2.0831   -0.9288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2802   -2.5060   -0.9548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2369   -2.0589   -2.3297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9416    0.4442   -0.4170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2573    1.3156    0.6863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0911    0.8882    1.8912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4103    0.4096    1.3127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2832   -0.2036    1.8398 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2916    0.9256   -0.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4467    0.8018   -0.9470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6581    1.4585   -0.2388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3634    1.5009   -2.1484 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0057    2.0699    1.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5314    3.2358    1.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4980   -0.7711    1.7095 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9887   -1.3395    2.1503 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9891    0.7698   -1.4917 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6117   -0.2966   -1.2366 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7647    1.2954   -0.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9354   -0.9507    1.0821 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7954   -0.7915   -0.7080 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2828    1.7996    0.6251 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9292    1.1386    0.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4565    1.3776   -0.7238 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4591   -1.8804   -0.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1657   -0.3105   -1.3200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5983   -1.1605    0.9501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3160   -2.9643   -0.4522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8064   -2.2269   -1.9152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4153   -3.6283   -0.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8013   -2.1338   -0.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211   -2.4555   -2.3504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2696   -1.0497   -2.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8746   -2.7341   -2.9478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5129    0.8612   -1.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5134    2.3634    0.4220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6107    0.1401    2.5153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2821    1.8332    2.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1962    2.0622    0.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8203   -0.2256   -1.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7351    2.5416   -0.5540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4799    1.4883    0.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5915    0.9907   -0.5633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5337    0.8434   -2.8665 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
  3 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 13 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 18  2  1  0
 22 17  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  7 29  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 22 52  1  0
 23 53  1  0
 24 54  1  0
 24 55  1  0
 24 56  1  0
 25 57  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
9a-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one	Generator
9Α-(3-methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one	Generator
1-(1-Hydroxyethyl)-4-methylidene-2-oxo-7-(propan-2-yl)-octahydro-1H-inden-5-yl (2E)-3-methylpent-2-enoic acid	Generator

Chemical Formula

C₂₁H₃₂O₄

Average Molecular Weight

348.4764

Monoisotopic Molecular Weight

348.230059512

IUPAC Name

1-(1-hydroxyethyl)-4-methylidene-2-oxo-7-(propan-2-yl)-octahydro-1H-inden-5-yl (2E)-3-methylpent-2-enoate

Traditional Name

1-(1-hydroxyethyl)-7-isopropyl-4-methylidene-2-oxo-hexahydro-1H-inden-5-yl (2E)-3-methylpent-2-enoate

CAS Registry Number

147742-07-2

SMILES

CC\C(C)=C\C(=O)OC1CC(C(C)C)C2C(CC(=O)C2C(C)O)C1=C

InChI Identifier

InChI=1S/C21H32O4/c1-7-12(4)8-19(24)25-18-10-15(11(2)3)21-16(13(18)5)9-17(23)20(21)14(6)22/h8,11,14-16,18,20-22H,5,7,9-10H2,1-4,6H3/b12-8+

InChI Key

AIZCSTFUIXPHFD-XYOKQWHBSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Oplopane sesquiterpenoid
Fatty acid ester
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Ketone
Secondary alcohol
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organooxygen compound
Organic oxygen compound
Alcohol
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040954)

Source

Endogenous

Endogenous (HMDB: HMDB0040954)

Plant

Plant (HMDB: HMDB0040954)

Animal

Animal (HMDB: HMDB0040954)

Exogenous

Food

Food (HMDB: HMDB0040954)

Tea

Exogenous (HMDB: HMDB0040954)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0040954)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0040954)

Lipid metabolism pathway (HMDB: HMDB0040954)

Cellular process

Cell signaling (HMDB: HMDB0040954)

Biochemical process

Lipid transport (HMDB: HMDB0040954)

Role

Biological role

Energy source (HMDB: HMDB0040954)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0040954)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.024 g/L	ALOGPS
logP	2.49	ALOGPS
logP	3.95	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	15.09	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	98.81 m³·mol⁻¹	ChemAxon
Polarizability	40 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	185.024	31661259
DarkChem	[M-H]-	179.97	31661259
DeepCCS	[M+H]+	191.455	30932474
DeepCCS	[M-H]-	188.913	30932474
DeepCCS	[M-2H]-	223.389	30932474
DeepCCS	[M+Na]+	199.036	30932474
AllCCS	[M+H]+	187.5	32859911
AllCCS	[M+H-H2O]+	185.0	32859911
AllCCS	[M+NH4]+	189.8	32859911
AllCCS	[M+Na]+	190.5	32859911
AllCCS	[M-H]-	187.2	32859911
AllCCS	[M+Na-2H]-	188.1	32859911
AllCCS	[M+HCOO]-	189.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one	CC\C(C)=C\C(=O)OC1CC(C(C)C)C2C(CC(=O)C2C(C)O)C1=C	3272.1	Standard polar	33892256
9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one	CC\C(C)=C\C(=O)OC1CC(C(C)C)C2C(CC(=O)C2C(C)O)C1=C	2280.4	Standard non polar	33892256
9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one	CC\C(C)=C\C(=O)OC1CC(C(C)C)C2C(CC(=O)C2C(C)O)C1=C	2409.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one,1TMS,isomer #1	C=C1C(OC(=O)/C=C(\C)CC)CC(C(C)C)C2C1CC(=O)C2C(C)O[Si](C)(C)C	2431.1	Semi standard non polar	33892256
9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one,1TMS,isomer #2	C=C1C(OC(=O)/C=C(\C)CC)CC(C(C)C)C2C(C(C)O)=C(O[Si](C)(C)C)CC12	2489.7	Semi standard non polar	33892256
9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one,1TMS,isomer #3	C=C1C(OC(=O)/C=C(\C)CC)CC(C(C)C)C2C1C=C(O[Si](C)(C)C)C2C(C)O	2445.9	Semi standard non polar	33892256
9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one,2TMS,isomer #1	C=C1C(OC(=O)/C=C(\C)CC)CC(C(C)C)C2C(C(C)O[Si](C)(C)C)=C(O[Si](C)(C)C)CC12	2502.0	Semi standard non polar	33892256
9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one,2TMS,isomer #1	C=C1C(OC(=O)/C=C(\C)CC)CC(C(C)C)C2C(C(C)O[Si](C)(C)C)=C(O[Si](C)(C)C)CC12	2602.0	Standard non polar	33892256
9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one,2TMS,isomer #2	C=C1C(OC(=O)/C=C(\C)CC)CC(C(C)C)C2C1C=C(O[Si](C)(C)C)C2C(C)O[Si](C)(C)C	2460.1	Semi standard non polar	33892256
9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one,2TMS,isomer #2	C=C1C(OC(=O)/C=C(\C)CC)CC(C(C)C)C2C1C=C(O[Si](C)(C)C)C2C(C)O[Si](C)(C)C	2552.1	Standard non polar	33892256
9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one,1TBDMS,isomer #1	C=C1C(OC(=O)/C=C(\C)CC)CC(C(C)C)C2C1CC(=O)C2C(C)O[Si](C)(C)C(C)(C)C	2652.6	Semi standard non polar	33892256
9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one,1TBDMS,isomer #2	C=C1C(OC(=O)/C=C(\C)CC)CC(C(C)C)C2C(C(C)O)=C(O[Si](C)(C)C(C)(C)C)CC12	2703.0	Semi standard non polar	33892256
9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one,1TBDMS,isomer #3	C=C1C(OC(=O)/C=C(\C)CC)CC(C(C)C)C2C1C=C(O[Si](C)(C)C(C)(C)C)C2C(C)O	2656.7	Semi standard non polar	33892256
9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one,2TBDMS,isomer #1	C=C1C(OC(=O)/C=C(\C)CC)CC(C(C)C)C2C(C(C)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)CC12	2923.6	Semi standard non polar	33892256
9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one,2TBDMS,isomer #1	C=C1C(OC(=O)/C=C(\C)CC)CC(C(C)C)C2C(C(C)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)CC12	3017.4	Standard non polar	33892256
9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one,2TBDMS,isomer #2	C=C1C(OC(=O)/C=C(\C)CC)CC(C(C)C)C2C1C=C(O[Si](C)(C)C(C)(C)C)C2C(C)O[Si](C)(C)C(C)(C)C	2888.6	Semi standard non polar	33892256
9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one,2TBDMS,isomer #2	C=C1C(OC(=O)/C=C(\C)CC)CC(C(C)C)C2C1C=C(O[Si](C)(C)C(C)(C)C)C2C(C)O[Si](C)(C)C(C)(C)C	2903.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-7295000000-7624b4fb55542b303fbc	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one GC-MS (1 TMS) - 70eV, Positive	splash10-066r-9143200000-7c8b7f8f4af3fccf7d54	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one 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 - 9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one 10V, Positive-QTOF	splash10-0532-8039000000-950bfba8e20c7122ec72	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one 20V, Positive-QTOF	splash10-0pb9-9020000000-2902c76eca4a213087a1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one 40V, Positive-QTOF	splash10-0pb9-9210000000-c045fe45041334246949	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one 10V, Negative-QTOF	splash10-0002-1039000000-e9b83c0e689342a17ca9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one 20V, Negative-QTOF	splash10-0uea-3294000000-3b910f4b36b99005dd39	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one 40V, Negative-QTOF	splash10-0a4l-7190000000-8eec3e1db39088f922cf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one 10V, Negative-QTOF	splash10-0zfr-0294000000-852163bb49c3fffa6f47	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one 20V, Negative-QTOF	splash10-115j-1391000000-feb0b1d7910b4498c07b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one 40V, Negative-QTOF	splash10-067i-2190000000-9d53ce0b1edebb468a80	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one 10V, Positive-QTOF	splash10-00kv-0393000000-8d97db82622fa215ce74	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one 20V, Positive-QTOF	splash10-0udr-0491000000-8a5cb0781f6b44f73ed6	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one 40V, Positive-QTOF	splash10-0pbc-9520000000-a9f8ba8f24467c354a37	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB020802

KNApSAcK ID

Not Available

Chemspider ID

35015057

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752994

PDB ID

Not Available

ChEBI ID

175460

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 9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one (HMDB0040954)

MOL for HMDB0040954 (9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one)

3D MOL for HMDB0040954 (9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one)

3D SDF for HMDB0040954 (9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one)

3D-SDF for HMDB0040954 (9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one)

PDB for HMDB0040954 (9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one)

3D PDB for HMDB0040954 (9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one)

SMILES for HMDB0040954 (9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one)

INCHI for HMDB0040954 (9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one)

Structure for HMDB0040954 (9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one)

3D Structure for HMDB0040954 (9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra