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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 21:59:14 UTC

Update Date

2022-03-07 02:55:04 UTC

HMDB ID

HMDB0036811

Secondary Accession Numbers

HMDB36811

Metabolite Identification

Common Name

Isopimaric acid

Description

Isopimaric acid, also known as 4-epi-isopimarate, belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Based on a literature review a significant number of articles have been published on Isopimaric acid.

Structure

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

HMDB0036811
     RDKit          3D
Isopimaric acid
 52 54  0  0  0  0  0  0  0  0999 V2000
    4.8415    0.6147   -0.8932 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6632    0.1834    0.3461 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3186   -0.1016    0.9051 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4982   -0.8922    2.2068 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7075    1.2158    1.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2370    0.9770    1.6728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5247    0.6992    0.4086 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2526   -0.3044   -0.4540 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6128   -0.6193   -1.5804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7080   -0.0072   -1.9189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5418    0.3441   -0.7462 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9456   -0.1824   -0.7943 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0496   -1.6619   -0.9872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5421    0.4412   -2.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9944   -0.1858   -2.9877 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5870    1.8253   -2.0374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7579    0.2440    0.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0694    0.4489    1.6518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6596    0.9002    1.5975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8681    0.1113    0.5948 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7653   -1.3232    0.9723 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5455   -0.8840   -0.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8045    0.8267   -1.3166 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9650    0.7605   -1.5098 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5421    0.0399    0.9584 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7367   -1.6863    2.3022 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5218   -1.3616    2.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4219   -0.2436    3.0932 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6933    1.8564    0.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2840    1.6232    2.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1522    0.1931    2.4423 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8817    1.9581    2.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4813    1.6311   -0.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0993   -1.3414   -2.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1916   -0.7148   -2.6287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4471    0.8855   -2.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6721    1.4724   -0.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0509   -1.8481   -1.4816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0956   -2.2405   -0.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3060   -2.1062   -1.6391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4761    2.3876   -2.8491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5597   -0.5371    0.5330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3575    1.1753    0.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1168   -0.4875    2.2822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6354    1.2051    2.2740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6404    1.9754    1.2696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2058    0.8258    2.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7136   -2.0339    0.1541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5526   -1.6588    1.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1985   -1.4425    1.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1200   -1.0373   -1.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4061   -1.9194    0.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  3  2  1  6
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  6
 14 15  2  0
 14 16  1  0
 12 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  1
  8 22  1  0
 22  3  1  0
 20  7  1  0
 20 11  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  4 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  6
  9 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  6
 13 38  1  0
 13 39  1  0
 13 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 18 45  1  0
 19 46  1  0
 19 47  1  0
 21 48  1  0
 21 49  1  0
 21 50  1  0
 22 51  1  0
 22 52  1  0
M  END


  Mrv1652309272006432D          

 24 26  0  0  0  0            999 V2000
 9999.303010001.0410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.162510001.8660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.878210001.4535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.448910002.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0195 9999.8031    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.589310000.6286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.874810000.2161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.733210001.8660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.018710001.4535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.447710000.6284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.447710001.4535    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.018310000.6285    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.303810000.2160    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.0183 9998.9785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7328 9999.3909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.732810000.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3023 9998.6784    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8755 9999.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3032 9999.3908    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.0732 9998.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1153 9998.3451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5892 9998.9788    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.2579 9998.4601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.3726 9997.5665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0  0  0  0
  6  7  1  0  0  0  0
  8  9  1  0  0  0  0
  8 11  1  0  0  0  0
 10 11  1  0  0  0  0
 11  2  1  0  0  0  0
 11  4  1  1  0  0  0
 12 13  1  0  0  0  0
 12 16  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
  6 13  1  0  0  0  0
 13  1  1  1  0  0  0
  9 12  1  0  0  0  0
 12  5  1  6  0  0  0
 16 10  1  0  0  0  0
 19 17  1  6  0  0  0
 22 20  1  6  0  0  0
 22 21  1  0  0  0  0
 20 23  1  0  0  0  0
 18 22  1  0  0  0  0
 22 19  1  0  0  0  0
 20 24  2  0  0  0  0
  7 18  1  0  0  0  0
 13 19  1  0  0  0  0
 19 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036811

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12CC[C@@](C)(CC1=CC[C@@]1([H])[C@@](C)(CCC[C@]21C)C(O)=O)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O2/c1-5-18(2)12-9-15-14(13-18)7-8-16-19(15,3)10-6-11-20(16,4)17(21)22/h5,7,15-16H,1,6,8-13H2,2-4H3,(H,21,22)/t15-,16+,18-,19+,20+/m0/s1

> <INCHI_KEY>
MXYATHGRPJZBNA-KRFUXDQASA-N

> <FORMULA>
C20H30O2

> <MOLECULAR_WEIGHT>
302.458

> <EXACT_MASS>
302.224580206

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
35.97471324547094

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4aR,4bS,7S,10aR)-7-ethenyl-1,4a,7-trimethyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydrophenanthrene-1-carboxylic acid

> <ALOGPS_LOGP>
5.28

> <JCHEM_LOGP>
5.067184579000001

> <ALOGPS_LOGS>
-5.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.804501147597557

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
90.33479999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.53e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isopimaric acid

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0036811
     RDKit          3D
Isopimaric acid
 52 54  0  0  0  0  0  0  0  0999 V2000
    4.8415    0.6147   -0.8932 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6632    0.1834    0.3461 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3186   -0.1016    0.9051 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4982   -0.8922    2.2068 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7075    1.2158    1.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2370    0.9770    1.6728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5247    0.6992    0.4086 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2526   -0.3044   -0.4540 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6128   -0.6193   -1.5804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7080   -0.0072   -1.9189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5418    0.3441   -0.7462 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9456   -0.1824   -0.7943 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0496   -1.6619   -0.9872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5421    0.4412   -2.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9944   -0.1858   -2.9877 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5870    1.8253   -2.0374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7579    0.2440    0.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0694    0.4489    1.6518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6596    0.9002    1.5975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8681    0.1113    0.5948 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7653   -1.3232    0.9723 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5455   -0.8840   -0.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8045    0.8267   -1.3166 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9650    0.7605   -1.5098 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5421    0.0399    0.9584 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7367   -1.6863    2.3022 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5218   -1.3616    2.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4219   -0.2436    3.0932 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6933    1.8564    0.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2840    1.6232    2.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1522    0.1931    2.4423 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8817    1.9581    2.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4813    1.6311   -0.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0993   -1.3414   -2.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1916   -0.7148   -2.6287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4471    0.8855   -2.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6721    1.4724   -0.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0509   -1.8481   -1.4816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0956   -2.2405   -0.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3060   -2.1062   -1.6391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4761    2.3876   -2.8491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5597   -0.5371    0.5330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3575    1.1753    0.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1168   -0.4875    2.2822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6354    1.2051    2.2740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6404    1.9754    1.2696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2058    0.8258    2.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7136   -2.0339    0.1541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5526   -1.6588    1.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1985   -1.4425    1.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1200   -1.0373   -1.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4061   -1.9194    0.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  3  2  1  6
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  6
 14 15  2  0
 14 16  1  0
 12 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  1
  8 22  1  0
 22  3  1  0
 20  7  1  0
 20 11  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  4 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  6
  9 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  6
 13 38  1  0
 13 39  1  0
 13 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 18 45  1  0
 19 46  1  0
 19 47  1  0
 21 48  1  0
 21 49  1  0
 21 50  1  0
 22 51  1  0
 22 52  1  0
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8665.3668668.610   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8670.7038670.150   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8672.0398669.380   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8669.3718670.920   0.000  0.00  0.00           C+0
HETATM    5  H   UNK     0    8666.7038666.299   0.000  0.00  0.00           H+0
HETATM    6  C   UNK     0    8664.0338667.840   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8662.7008667.070   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8668.0358670.150   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8666.7028669.380   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8669.3698667.840   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8669.3698669.380   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8666.7018667.840   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8665.3678667.070   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8666.7018664.760   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8668.0358665.530   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8668.0358667.070   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0    8665.3648664.200   0.000  0.00  0.00           H+0
HETATM   18  C   UNK     0    8662.7018665.529   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8665.3668665.529   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8663.0708663.559   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8665.0158663.578   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8664.0338664.760   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0    8661.5488663.792   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0    8663.6298662.124   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2    3   11                                                       
CONECT    3    2                                                            
CONECT    4   11                                                            
CONECT    5   12                                                            
CONECT    6    7   13                                                       
CONECT    7    6   18                                                       
CONECT    8    9   11                                                       
CONECT    9    8   12                                                       
CONECT   10   11   16                                                       
CONECT   11    8   10    2    4                                             
CONECT   12   13   16    9    5                                             
CONECT   13   12    6    1   19                                             
CONECT   14   15   19                                                       
CONECT   15   14   16                                                       
CONECT   16   12   15   10                                                  
CONECT   17   19                                                            
CONECT   18   22    7                                                       
CONECT   19   17   22   13   14                                             
CONECT   20   22   23   24                                                  
CONECT   21   22                                                            
CONECT   22   20   21   18   19                                             
CONECT   23   20                                                            
CONECT   24   20                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0036811
HETATM    1  C1  UNL     1       4.842   0.615  -0.893  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.663   0.183   0.346  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.319  -0.102   0.905  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.498  -0.892   2.207  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.708   1.216   1.297  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.237   0.977   1.673  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.525   0.699   0.409  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.253  -0.304  -0.454  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.613  -0.619  -1.580  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.708  -0.007  -1.919  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.542   0.344  -0.746  1.00  0.00           C  
HETATM   12  C12 UNL     1      -2.946  -0.182  -0.794  1.00  0.00           C  
HETATM   13  C13 UNL     1      -3.050  -1.662  -0.987  1.00  0.00           C  
HETATM   14  C14 UNL     1      -3.542   0.441  -2.011  1.00  0.00           C  
HETATM   15  O1  UNL     1      -3.994  -0.186  -2.988  1.00  0.00           O  
HETATM   16  O2  UNL     1      -3.587   1.825  -2.037  1.00  0.00           O  
HETATM   17  C15 UNL     1      -3.758   0.244   0.367  1.00  0.00           C  
HETATM   18  C16 UNL     1      -3.069   0.449   1.652  1.00  0.00           C  
HETATM   19  C17 UNL     1      -1.660   0.900   1.598  1.00  0.00           C  
HETATM   20  C18 UNL     1      -0.868   0.111   0.595  1.00  0.00           C  
HETATM   21  C19 UNL     1      -0.765  -1.323   0.972  1.00  0.00           C  
HETATM   22  C20 UNL     1       2.546  -0.884  -0.091  1.00  0.00           C  
HETATM   23  H1  UNL     1       5.804   0.827  -1.317  1.00  0.00           H  
HETATM   24  H2  UNL     1       3.965   0.760  -1.510  1.00  0.00           H  
HETATM   25  H3  UNL     1       5.542   0.040   0.958  1.00  0.00           H  
HETATM   26  H4  UNL     1       2.737  -1.686   2.302  1.00  0.00           H  
HETATM   27  H5  UNL     1       4.522  -1.362   2.240  1.00  0.00           H  
HETATM   28  H6  UNL     1       3.422  -0.244   3.093  1.00  0.00           H  
HETATM   29  H7  UNL     1       2.693   1.856   0.392  1.00  0.00           H  
HETATM   30  H8  UNL     1       3.284   1.623   2.131  1.00  0.00           H  
HETATM   31  H9  UNL     1       1.152   0.193   2.442  1.00  0.00           H  
HETATM   32  H10 UNL     1       0.882   1.958   2.079  1.00  0.00           H  
HETATM   33  H11 UNL     1       0.481   1.631  -0.191  1.00  0.00           H  
HETATM   34  H12 UNL     1       1.099  -1.341  -2.238  1.00  0.00           H  
HETATM   35  H13 UNL     1      -1.192  -0.715  -2.629  1.00  0.00           H  
HETATM   36  H14 UNL     1      -0.447   0.885  -2.566  1.00  0.00           H  
HETATM   37  H15 UNL     1      -1.672   1.472  -0.772  1.00  0.00           H  
HETATM   38  H16 UNL     1      -4.051  -1.848  -1.482  1.00  0.00           H  
HETATM   39  H17 UNL     1      -3.096  -2.240  -0.045  1.00  0.00           H  
HETATM   40  H18 UNL     1      -2.306  -2.106  -1.639  1.00  0.00           H  
HETATM   41  H19 UNL     1      -3.476   2.388  -2.849  1.00  0.00           H  
HETATM   42  H20 UNL     1      -4.560  -0.537   0.533  1.00  0.00           H  
HETATM   43  H21 UNL     1      -4.357   1.175   0.138  1.00  0.00           H  
HETATM   44  H22 UNL     1      -3.117  -0.487   2.282  1.00  0.00           H  
HETATM   45  H23 UNL     1      -3.635   1.205   2.274  1.00  0.00           H  
HETATM   46  H24 UNL     1      -1.640   1.975   1.270  1.00  0.00           H  
HETATM   47  H25 UNL     1      -1.206   0.826   2.594  1.00  0.00           H  
HETATM   48  H26 UNL     1      -0.714  -2.034   0.154  1.00  0.00           H  
HETATM   49  H27 UNL     1      -1.553  -1.659   1.697  1.00  0.00           H  
HETATM   50  H28 UNL     1       0.198  -1.443   1.551  1.00  0.00           H  
HETATM   51  H29 UNL     1       3.120  -1.037  -1.050  1.00  0.00           H  
HETATM   52  H30 UNL     1       2.406  -1.919   0.309  1.00  0.00           H  
CONECT    1    2    2   23   24
CONECT    2    3   25
CONECT    3    4    5   22
CONECT    4   26   27   28
CONECT    5    6   29   30
CONECT    6    7   31   32
CONECT    7    8   20   33
CONECT    8    9    9   22
CONECT    9   10   34
CONECT   10   11   35   36
CONECT   11   12   20   37
CONECT   12   13   14   17
CONECT   13   38   39   40
CONECT   14   15   15   16
CONECT   16   41
CONECT   17   18   42   43
CONECT   18   19   44   45
CONECT   19   20   46   47
CONECT   20   21
CONECT   21   48   49   50
CONECT   22   51   52
END

HMDB0036811
     RDKit          3D
Isopimaric acid
 52 54  0  0  0  0  0  0  0  0999 V2000
    4.8415    0.6147   -0.8932 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6632    0.1834    0.3461 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3186   -0.1016    0.9051 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4982   -0.8922    2.2068 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7075    1.2158    1.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2370    0.9770    1.6728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5247    0.6992    0.4086 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2526   -0.3044   -0.4540 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6128   -0.6193   -1.5804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7080   -0.0072   -1.9189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5418    0.3441   -0.7462 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9456   -0.1824   -0.7943 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0496   -1.6619   -0.9872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5421    0.4412   -2.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9944   -0.1858   -2.9877 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5870    1.8253   -2.0374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7579    0.2440    0.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0694    0.4489    1.6518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6596    0.9002    1.5975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8681    0.1113    0.5948 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7653   -1.3232    0.9723 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5455   -0.8840   -0.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8045    0.8267   -1.3166 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9650    0.7605   -1.5098 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5421    0.0399    0.9584 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7367   -1.6863    2.3022 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5218   -1.3616    2.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4219   -0.2436    3.0932 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6933    1.8564    0.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2840    1.6232    2.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1522    0.1931    2.4423 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8817    1.9581    2.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4813    1.6311   -0.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0993   -1.3414   -2.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1916   -0.7148   -2.6287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4471    0.8855   -2.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6721    1.4724   -0.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0509   -1.8481   -1.4816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0956   -2.2405   -0.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3060   -2.1062   -1.6391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4761    2.3876   -2.8491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5597   -0.5371    0.5330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3575    1.1753    0.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1168   -0.4875    2.2822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6354    1.2051    2.2740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6404    1.9754    1.2696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2058    0.8258    2.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7136   -2.0339    0.1541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5526   -1.6588    1.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1985   -1.4425    1.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1200   -1.0373   -1.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4061   -1.9194    0.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  3  2  1  6
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  6
 14 15  2  0
 14 16  1  0
 12 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  1
  8 22  1  0
 22  3  1  0
 20  7  1  0
 20 11  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  4 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  6
  9 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  6
 13 38  1  0
 13 39  1  0
 13 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 18 45  1  0
 19 46  1  0
 19 47  1  0
 21 48  1  0
 21 49  1  0
 21 50  1  0
 22 51  1  0
 22 52  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(1R,4AR,4BS,7S,10ar)-7-ethenyl-1,4a,7-trimethyl-3,4,4b,5,6,8,10,10a-octahydro-2H-phenanthrene-1-carboxylic acid	ChEBI
4-Epi-isopimaric acid	ChEBI
(1R,4AR,4BS,7S,10ar)-7-ethenyl-1,4a,7-trimethyl-3,4,4b,5,6,8,10,10a-octahydro-2H-phenanthrene-1-carboxylate	Generator
4-Epi-isopimarate	Generator
Isopimarate	Generator
13beta-Methyl-13-vinylpodocarp-7-en-15-Oic acid	HMDB
13Β-methyl-13-vinylpodocarp-7-en-15-Oic acid	HMDB
(-)-13beta-Methyl-13-vinylpodocarp-7-en-15-Oic acid	HMDB
(-)-13Β-methyl-13-vinylpodocarp-7-en-15-Oic acid	HMDB
(+)-Isopimaric acid	HMDB
7,15-Isopimaradien-18-Oic acid	HMDB
Isopimaric acid a	HMDB
delta7,15-Isopimaric acid	HMDB
Δ7,15-isopimaric acid	HMDB

Chemical Formula

C₂₀H₃₀O₂

Average Molecular Weight

302.458

Monoisotopic Molecular Weight

302.224580206

IUPAC Name

(1R,4aR,4bS,7S,10aR)-7-ethenyl-1,4a,7-trimethyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydrophenanthrene-1-carboxylic acid

Traditional Name

isopimaric acid

CAS Registry Number

5835-26-7

SMILES

[H][C@]12CC[C@@](C)(CC1=CC[C@@]1([H])[C@@](C)(CCC[C@]21C)C(O)=O)C=C

InChI Identifier

InChI=1S/C20H30O2/c1-5-18(2)12-9-15-14(13-18)7-8-16-19(15,3)10-6-11-20(16,4)17(21)22/h5,7,15-16H,1,6,8-13H2,2-4H3,(H,21,22)/t15-,16+,18-,19+,20+/m0/s1

InChI Key

MXYATHGRPJZBNA-KRFUXDQASA-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

Pimarane diterpenoid
Diterpenoid
Phenanthrene
Hydrophenanthrene
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:6039 )
diterpenoid (CHEBI:6039 )
carbotricyclic compound (CHEBI:6039 )
Pimarane diterpenoids (C09118 )
Pimaranes (C09118 )
Pimarane diterpenoids (LMPR0104080010 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0036811)
Cell membrane (HMDB: HMDB0036811)

Biofluid or Excreta

Non-excretory biofluid

Saliva (HMDB: HMDB0036811)

Cellular substructure

Extracellular (HMDB: HMDB0036811)
Membrane (HMDB: HMDB0036811)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036811)

Source

Endogenous

Endogenous (HMDB: HMDB0036811)

Animal

Animal (HMDB: HMDB0036811)

Exogenous

Food

Food (HMDB: HMDB0036811)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0036811)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0036811)

Cellular process

Cell signaling (HMDB: HMDB0036811)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0036811)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0036811)

Nutrient

Nutrient (HMDB: HMDB0036811)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036811)

Emulsifier (HMDB: HMDB0036811)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	162 - 164 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00065 g/L	ALOGPS
logP	5.28	ALOGPS
logP	5.07	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	90.33 m³·mol⁻¹	ChemAxon
Polarizability	35.97 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	202.959	30932474
DeepCCS	[M+Na]+	178.262	30932474
AllCCS	[M+H]+	177.0	32859911
AllCCS	[M+H-H2O]+	173.9	32859911
AllCCS	[M+NH4]+	179.8	32859911
AllCCS	[M+Na]+	180.7	32859911
AllCCS	[M-H]-	183.2	32859911
AllCCS	[M+Na-2H]-	183.6	32859911
AllCCS	[M+HCOO]-	184.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isopimaric acid	[H][C@]12CC[C@@](C)(CC1=CC[C@@]1([H])[C@@](C)(CCC[C@]21C)C(O)=O)C=C	2972.0	Standard polar	33892256
Isopimaric acid	[H][C@]12CC[C@@](C)(CC1=CC[C@@]1([H])[C@@](C)(CCC[C@]21C)C(O)=O)C=C	2239.4	Standard non polar	33892256
Isopimaric acid	[H][C@]12CC[C@@](C)(CC1=CC[C@@]1([H])[C@@](C)(CCC[C@]21C)C(O)=O)C=C	2361.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isopimaric acid,1TMS,isomer #1	C=C[C@@]1(C)CC[C@H]2C(=CC[C@H]3[C@](C)(C(=O)O[Si](C)(C)C)CCC[C@]23C)C1	2367.3	Semi standard non polar	33892256
Isopimaric acid,1TBDMS,isomer #1	C=C[C@@]1(C)CC[C@H]2C(=CC[C@H]3[C@](C)(C(=O)O[Si](C)(C)C(C)(C)C)CCC[C@]23C)C1	2656.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Isopimaric acid 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 - Isopimaric acid 10V, Positive-QTOF	splash10-0zfr-0194000000-6accdee6fd7ecb3aaf3d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopimaric acid 20V, Positive-QTOF	splash10-005i-0490000000-975cf74c21d7d3ce9174	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopimaric acid 40V, Positive-QTOF	splash10-014i-8930000000-2d7a80b65b8b2f09efa1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopimaric acid 10V, Negative-QTOF	splash10-0udi-0009000000-16d58525184e918518fa	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopimaric acid 20V, Negative-QTOF	splash10-0udi-0009000000-16d58525184e918518fa	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopimaric acid 40V, Negative-QTOF	splash10-0udj-1095000000-dd8fb46ea5f348ad26ff	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Saliva

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	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

C00003444

Chemspider ID

390596

KEGG Compound ID

C09118

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Isopimaric acid

METLIN ID

Not Available

PubChem Compound

442048

PDB ID

Not Available

ChEBI ID

6039

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 Isopimaric acid (HMDB0036811)

MOL for HMDB0036811 (Isopimaric acid)

3D MOL for HMDB0036811 (Isopimaric acid)

3D SDF for HMDB0036811 (Isopimaric acid)

3D-SDF for HMDB0036811 (Isopimaric acid)

PDB for HMDB0036811 (Isopimaric acid)

3D PDB for HMDB0036811 (Isopimaric acid)

SMILES for HMDB0036811 (Isopimaric acid)

INCHI for HMDB0036811 (Isopimaric acid)

Structure for HMDB0036811 (Isopimaric acid)

3D Structure for HMDB0036811 (Isopimaric acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra