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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 12:25:29 UTC

Update Date

2021-09-26 23:06:58 UTC

HMDB ID

HMDB0253626

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Isocupressic acid

Description

Isocupressic acid, also known as isocupressate, belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Isocupressic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Isocupressic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Isocupressic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0253626
     RDKit          3D
Isocupressic acid
 55 56  0  0  0  0  0  0  0  0999 V2000
    0.5186    2.1904   -1.7100 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2123    0.9417   -1.4389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5342    0.1068   -2.4541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5107   -0.7342   -1.6079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8816    0.0869   -0.4177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2398   -0.1686    0.1453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6518   -1.6280    0.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2362    0.5783   -0.6762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8661    1.2737   -1.6563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5956    0.5405   -0.4010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3478    0.2771    1.5871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4566    1.4407    1.9100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0214    1.2467    1.5329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7811    0.0829    0.6365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7093   -1.1633    1.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5208    0.2380   -0.1689 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6195    0.7824    0.6344 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9460    0.7827   -0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5238   -0.5106   -0.4243 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9141   -1.4291   -1.4448 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6680   -0.9204    0.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5221   -0.2362    1.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7816   -0.0514    0.4521 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2440    2.6179   -2.6447 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0367    2.8046   -0.9945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1614    0.7571   -3.0812 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1233   -0.5674   -3.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3718   -1.0021   -2.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9863   -1.6449   -1.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9043    1.1630   -0.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7318   -2.0702    1.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6988   -1.7497   -0.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0165   -2.2308   -0.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2503   -0.0829   -0.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4019    0.6357    1.7219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2433   -0.5794    2.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4994    1.5902    3.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9058    2.3604    1.4597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3410    1.1942    2.4070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7094    2.1710    0.9677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3369   -1.9879    1.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3483   -1.5633    1.4322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8938   -0.9760    2.5420 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7710   -0.8184   -0.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3878    1.8070    1.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7292    0.1033    1.5386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8636    1.3717   -1.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6448    1.4609    0.5129 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7739   -1.8438   -2.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4296   -2.3124   -1.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3239   -0.8635   -2.1853 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0095   -1.9331   -0.2646 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7626   -0.8725    1.9638 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1698    0.7465    1.3427 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4400    0.2897    1.1309 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  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  3
 21 22  1  0
 22 23  1  0
 16  2  1  0
 14  5  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  7 31  1  0
  7 32  1  0
  7 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 15 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
 20 49  1  0
 20 50  1  0
 20 51  1  0
 21 52  1  0
 22 53  1  0
 22 54  1  0
 23 55  1  0
M  END

  Mrv1533004191523032D          

 23 24  0  0  0  0            999 V2000
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   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
    0.0000    0.8250    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
   -0.7145   -0.4125    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
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -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
    0.7145    0.4125    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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8163   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0416   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4788   -3.0781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2171   -2.4072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  4  0  0  0
  4  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 13 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253626

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(CCC1C(=C)CCC2C1(C)CCCC2(C)C(O)=O)=CCO

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O3/c1-14(10-13-21)6-8-16-15(2)7-9-17-19(16,3)11-5-12-20(17,4)18(22)23/h10,16-17,21H,2,5-9,11-13H2,1,3-4H3,(H,22,23)

> <INCHI_KEY>
DOYKMKZYLAAOGH-UHFFFAOYSA-N

> <FORMULA>
C20H32O3

> <MOLECULAR_WEIGHT>
320.473

> <EXACT_MASS>
320.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
37.66248036159922

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(5-hydroxy-3-methylpent-3-en-1-yl)-1,4a-dimethyl-6-methylidene-decahydronaphthalene-1-carboxylic acid

> <ALOGPS_LOGP>
4.26

> <JCHEM_LOGP>
4.351003045333334

> <ALOGPS_LOGS>
-4.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.33003036041821

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.858441990530014

> <JCHEM_PKA_STRONGEST_BASIC>
-2.217044720353715

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
93.77099999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.91e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-(5-hydroxy-3-methylpent-3-en-1-yl)-1,4a-dimethyl-6-methylidene-hexahydro-2H-naphthalene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0253626
     RDKit          3D
Isocupressic acid
 55 56  0  0  0  0  0  0  0  0999 V2000
    0.5186    2.1904   -1.7100 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2123    0.9417   -1.4389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5342    0.1068   -2.4541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5107   -0.7342   -1.6079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8816    0.0869   -0.4177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2398   -0.1686    0.1453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6518   -1.6280    0.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2362    0.5783   -0.6762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8661    1.2737   -1.6563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5956    0.5405   -0.4010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3478    0.2771    1.5871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4566    1.4407    1.9100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0214    1.2467    1.5329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7811    0.0829    0.6365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7093   -1.1633    1.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5208    0.2380   -0.1689 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6195    0.7824    0.6344 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9460    0.7827   -0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5238   -0.5106   -0.4243 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9141   -1.4291   -1.4448 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6680   -0.9204    0.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5221   -0.2362    1.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7816   -0.0514    0.4521 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2440    2.6179   -2.6447 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0367    2.8046   -0.9945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1614    0.7571   -3.0812 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1233   -0.5674   -3.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3718   -1.0021   -2.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9863   -1.6449   -1.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9043    1.1630   -0.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7318   -2.0702    1.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6988   -1.7497   -0.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0165   -2.2308   -0.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2503   -0.0829   -0.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4019    0.6357    1.7219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2433   -0.5794    2.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4994    1.5902    3.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9058    2.3604    1.4597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3410    1.1942    2.4070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7094    2.1710    0.9677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3369   -1.9879    1.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3483   -1.5633    1.4322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8938   -0.9760    2.5420 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7710   -0.8184   -0.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3878    1.8070    1.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7292    0.1033    1.5386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8636    1.3717   -1.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6448    1.4609    0.5129 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7739   -1.8438   -2.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4296   -2.3124   -1.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3239   -0.8635   -2.1853 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0095   -1.9331   -0.2646 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7626   -0.8725    1.9638 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1698    0.7465    1.3427 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4400    0.2897    1.1309 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  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  3
 21 22  1  0
 22 23  1  0
 16  2  1  0
 14  5  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  7 31  1  0
  7 32  1  0
  7 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 15 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
 20 49  1  0
 20 50  1  0
 20 51  1  0
 21 52  1  0
 22 53  1  0
 22 54  1  0
 23 55  1  0
M  END

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.390  -4.440   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.944  -4.440   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.760  -5.746   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.405  -4.493   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    2    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13    8   15   16                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   13   20   21                                             
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0253626
HETATM    1  C1  UNL     1       0.519   2.190  -1.710  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.212   0.942  -1.439  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.534   0.107  -2.454  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.511  -0.734  -1.608  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.882   0.087  -0.418  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.240  -0.169   0.145  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.652  -1.628   0.091  1.00  0.00           C  
HETATM    8  C8  UNL     1      -4.236   0.578  -0.676  1.00  0.00           C  
HETATM    9  O1  UNL     1      -3.866   1.274  -1.656  1.00  0.00           O  
HETATM   10  O2  UNL     1      -5.596   0.541  -0.401  1.00  0.00           O  
HETATM   11  C9  UNL     1      -3.348   0.277   1.587  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.457   1.441   1.910  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.021   1.247   1.533  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.781   0.083   0.636  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.709  -1.163   1.443  1.00  0.00           C  
HETATM   16  C14 UNL     1       0.521   0.238  -0.169  1.00  0.00           C  
HETATM   17  C15 UNL     1       1.619   0.782   0.634  1.00  0.00           C  
HETATM   18  C16 UNL     1       2.946   0.783  -0.052  1.00  0.00           C  
HETATM   19  C17 UNL     1       3.524  -0.511  -0.424  1.00  0.00           C  
HETATM   20  C18 UNL     1       2.914  -1.429  -1.445  1.00  0.00           C  
HETATM   21  C19 UNL     1       4.668  -0.920   0.101  1.00  0.00           C  
HETATM   22  C20 UNL     1       5.522  -0.236   1.076  1.00  0.00           C  
HETATM   23  O3  UNL     1       6.782  -0.051   0.452  1.00  0.00           O  
HETATM   24  H1  UNL     1       0.244   2.618  -2.645  1.00  0.00           H  
HETATM   25  H2  UNL     1       1.037   2.805  -0.995  1.00  0.00           H  
HETATM   26  H3  UNL     1      -1.161   0.757  -3.081  1.00  0.00           H  
HETATM   27  H4  UNL     1       0.123  -0.567  -3.012  1.00  0.00           H  
HETATM   28  H5  UNL     1      -2.372  -1.002  -2.219  1.00  0.00           H  
HETATM   29  H6  UNL     1      -0.986  -1.645  -1.269  1.00  0.00           H  
HETATM   30  H7  UNL     1      -1.904   1.163  -0.774  1.00  0.00           H  
HETATM   31  H8  UNL     1      -3.732  -2.070   1.127  1.00  0.00           H  
HETATM   32  H9  UNL     1      -4.699  -1.750  -0.317  1.00  0.00           H  
HETATM   33  H10 UNL     1      -3.017  -2.231  -0.576  1.00  0.00           H  
HETATM   34  H11 UNL     1      -6.250  -0.083  -0.837  1.00  0.00           H  
HETATM   35  H12 UNL     1      -4.402   0.636   1.722  1.00  0.00           H  
HETATM   36  H13 UNL     1      -3.243  -0.579   2.284  1.00  0.00           H  
HETATM   37  H14 UNL     1      -2.499   1.590   3.009  1.00  0.00           H  
HETATM   38  H15 UNL     1      -2.906   2.360   1.460  1.00  0.00           H  
HETATM   39  H16 UNL     1      -0.341   1.194   2.407  1.00  0.00           H  
HETATM   40  H17 UNL     1      -0.709   2.171   0.968  1.00  0.00           H  
HETATM   41  H18 UNL     1      -1.337  -1.988   1.117  1.00  0.00           H  
HETATM   42  H19 UNL     1       0.348  -1.563   1.432  1.00  0.00           H  
HETATM   43  H20 UNL     1      -0.894  -0.976   2.542  1.00  0.00           H  
HETATM   44  H21 UNL     1       0.771  -0.818  -0.433  1.00  0.00           H  
HETATM   45  H22 UNL     1       1.388   1.807   1.037  1.00  0.00           H  
HETATM   46  H23 UNL     1       1.729   0.103   1.539  1.00  0.00           H  
HETATM   47  H24 UNL     1       2.864   1.372  -1.048  1.00  0.00           H  
HETATM   48  H25 UNL     1       3.645   1.461   0.513  1.00  0.00           H  
HETATM   49  H26 UNL     1       3.774  -1.844  -2.087  1.00  0.00           H  
HETATM   50  H27 UNL     1       2.430  -2.312  -1.010  1.00  0.00           H  
HETATM   51  H28 UNL     1       2.324  -0.864  -2.185  1.00  0.00           H  
HETATM   52  H29 UNL     1       5.009  -1.933  -0.265  1.00  0.00           H  
HETATM   53  H30 UNL     1       5.763  -0.872   1.964  1.00  0.00           H  
HETATM   54  H31 UNL     1       5.170   0.747   1.343  1.00  0.00           H  
HETATM   55  H32 UNL     1       7.440   0.290   1.131  1.00  0.00           H  
CONECT    1    2    2   24   25
CONECT    2    3   16
CONECT    3    4   26   27
CONECT    4    5   28   29
CONECT    5    6   14   30
CONECT    6    7    8   11
CONECT    7   31   32   33
CONECT    8    9    9   10
CONECT   10   34
CONECT   11   12   35   36
CONECT   12   13   37   38
CONECT   13   14   39   40
CONECT   14   15   16
CONECT   15   41   42   43
CONECT   16   17   44
CONECT   17   18   45   46
CONECT   18   19   47   48
CONECT   19   20   21   21
CONECT   20   49   50   51
CONECT   21   22   52
CONECT   22   23   53   54
CONECT   23   55
END

HMDB0253626
     RDKit          3D
Isocupressic acid
 55 56  0  0  0  0  0  0  0  0999 V2000
    0.5186    2.1904   -1.7100 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2123    0.9417   -1.4389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5342    0.1068   -2.4541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5107   -0.7342   -1.6079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8816    0.0869   -0.4177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2398   -0.1686    0.1453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6518   -1.6280    0.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2362    0.5783   -0.6762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8661    1.2737   -1.6563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5956    0.5405   -0.4010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3478    0.2771    1.5871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4566    1.4407    1.9100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0214    1.2467    1.5329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7811    0.0829    0.6365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7093   -1.1633    1.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5208    0.2380   -0.1689 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6195    0.7824    0.6344 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9460    0.7827   -0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5238   -0.5106   -0.4243 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9141   -1.4291   -1.4448 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6680   -0.9204    0.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5221   -0.2362    1.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7816   -0.0514    0.4521 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2440    2.6179   -2.6447 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0367    2.8046   -0.9945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1614    0.7571   -3.0812 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1233   -0.5674   -3.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3718   -1.0021   -2.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9863   -1.6449   -1.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9043    1.1630   -0.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7318   -2.0702    1.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6988   -1.7497   -0.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0165   -2.2308   -0.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2503   -0.0829   -0.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4019    0.6357    1.7219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2433   -0.5794    2.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4994    1.5902    3.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9058    2.3604    1.4597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3410    1.1942    2.4070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7094    2.1710    0.9677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3369   -1.9879    1.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3483   -1.5633    1.4322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8938   -0.9760    2.5420 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7710   -0.8184   -0.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3878    1.8070    1.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7292    0.1033    1.5386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8636    1.3717   -1.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6448    1.4609    0.5129 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7739   -1.8438   -2.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4296   -2.3124   -1.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3239   -0.8635   -2.1853 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0095   -1.9331   -0.2646 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7626   -0.8725    1.9638 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1698    0.7465    1.3427 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4400    0.2897    1.1309 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  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  3
 21 22  1  0
 22 23  1  0
 16  2  1  0
 14  5  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  7 31  1  0
  7 32  1  0
  7 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 15 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
 20 49  1  0
 20 50  1  0
 20 51  1  0
 21 52  1  0
 22 53  1  0
 22 54  1  0
 23 55  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Isocupressate	Generator
15-Hydroxylabda-8(17),13-dien-19-Oic acid	MeSH
5-(5-Hydroxy-3-methylpent-3-en-1-yl)-1,4a-dimethyl-6-methylidene-decahydronaphthalene-1-carboxylate	Generator

Chemical Formula

C₂₀H₃₂O₃

Average Molecular Weight

320.473

Monoisotopic Molecular Weight

320.23514489

IUPAC Name

5-(5-hydroxy-3-methylpent-3-en-1-yl)-1,4a-dimethyl-6-methylidene-decahydronaphthalene-1-carboxylic acid

Traditional Name

5-(5-hydroxy-3-methylpent-3-en-1-yl)-1,4a-dimethyl-6-methylidene-hexahydro-2H-naphthalene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(CCC1C(=C)CCC2C1(C)CCCC2(C)C(O)=O)=CCO

InChI Identifier

InChI=1S/C20H32O3/c1-14(10-13-21)6-8-16-15(2)7-9-17-19(16,3)11-5-12-20(17,4)18(22)23/h10,16-17,21H,2,5-9,11-13H2,1,3-4H3,(H,22,23)

InChI Key

DOYKMKZYLAAOGH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Labdane diterpenoid
Fatty alcohol
Fatty acyl
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

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
logP	4.26	ALOGPS
logP	4.35	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	4.86	ChemAxon
pKa (Strongest Basic)	-2.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	93.77 m³·mol⁻¹	ChemAxon
Polarizability	37.66 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
DeepCCS	[M+H]+	176.404	30932474
DeepCCS	[M-H]-	174.024	30932474
DeepCCS	[M-2H]-	207.507	30932474
DeepCCS	[M+Na]+	183.314	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isocupressic acid	CC(CCC1C(=C)CCC2C1(C)CCCC2(C)C(O)=O)=CCO	3065.6	Standard polar	33892256
Isocupressic acid	CC(CCC1C(=C)CCC2C1(C)CCCC2(C)C(O)=O)=CCO	2380.4	Standard non polar	33892256
Isocupressic acid	CC(CCC1C(=C)CCC2C1(C)CCCC2(C)C(O)=O)=CCO	2594.1	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 - Isocupressic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-3193000000-0c722c31ef33c05ad943	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isocupressic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isocupressic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isocupressic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isocupressic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isocupressic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isocupressic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isocupressic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-04	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 - Isocupressic acid 10V, Positive-QTOF	splash10-056r-0292000000-bd44c802a80dd6d935c1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocupressic acid 20V, Positive-QTOF	splash10-000i-1950000000-15f3598bdfd06b24a763	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocupressic acid 40V, Positive-QTOF	splash10-053r-9310000000-aa9002d8d42bc1fd27aa	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocupressic acid 10V, Negative-QTOF	splash10-014i-0009000000-e9172f49e67d0b8f9e55	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocupressic acid 20V, Negative-QTOF	splash10-014i-0039000000-da18bd347dbc7edc2ef2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocupressic acid 40V, Negative-QTOF	splash10-0002-2091000000-228a66b197ee60c9dc47	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Isocupressic acid

METLIN ID

Not Available

PubChem Compound

73678322

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Isocupressic acid (HMDB0253626)

MOL for HMDB0253626 (Isocupressic acid)

3D MOL for HMDB0253626 (Isocupressic acid)

3D SDF for HMDB0253626 (Isocupressic acid)

3D-SDF for HMDB0253626 (Isocupressic acid)

PDB for HMDB0253626 (Isocupressic acid)

3D PDB for HMDB0253626 (Isocupressic acid)

SMILES for HMDB0253626 (Isocupressic acid)

INCHI for HMDB0253626 (Isocupressic acid)

Structure for HMDB0253626 (Isocupressic acid)

3D Structure for HMDB0253626 (Isocupressic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra