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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2014-10-09 19:54:24 UTC

Update Date

2021-09-14 15:15:54 UTC

HMDB ID

HMDB0061925

Secondary Accession Numbers

HMDB61925

Metabolite Identification

Common Name

Dehydroabietic acid

Description

Dehydroabietic acid, also known as dehydroabietate, belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Dehydroabietic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

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

HMDB0061925
     RDKit          3D
Dehydroabietic acid
 50 52  0  0  0  0  0  0  0  0999 V2000
    5.4865   -0.7156   -0.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6478    0.5119   -0.2677 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0491    1.2598    0.9919 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1952    0.1982   -0.1400 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7541   -0.6162    0.8820 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3913   -0.9180    1.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4793   -0.4031    0.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8971    0.4075   -0.9020 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2439    0.6898   -1.0090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0385    1.0052   -1.9145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4070    0.3661   -1.7744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7431    0.3559   -0.2958 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9577   -0.7684    0.3219 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1671   -2.0950   -0.3439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2249   -0.8552    1.7941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7178   -0.9212    2.0770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4160    0.2699    1.4936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1781    0.4350    0.0293 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0505   -0.5409   -0.7196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6825    1.8047   -0.3474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1338    2.6068    0.5399 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7018    2.2969   -1.6336 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9473   -1.4354   -1.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7971   -1.1846    0.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4049   -0.4145   -1.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7565    1.1754   -1.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8863    2.3510    0.8118 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4317    0.8693    1.8152 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1269    1.1171    1.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4885   -1.0098    1.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1460   -1.5636    1.8436 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6060    1.3291   -1.8077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0858    2.1180   -1.7443 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3704    0.8031   -2.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1339    0.8590   -2.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2889   -0.6651   -2.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2770    1.3051    0.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0217   -2.1652   -1.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2348   -2.8737    0.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2717   -2.4164   -0.9521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8321   -1.8527    2.1333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7800   -0.0409    2.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8291   -0.8916    3.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1510   -1.8797    1.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5223    0.0864    1.6235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1365    1.1759    2.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0758   -0.1068   -0.7360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1620   -1.5028   -0.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7409   -0.6741   -1.7632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1434    3.1137   -1.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  6
 20 21  2  0
 20 22  1  0
  9  4  1  0
 18 12  1  0
 13  7  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  5 30  1  0
  6 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  1
 14 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  0
 17 46  1  0
 19 47  1  0
 19 48  1  0
 19 49  1  0
 22 50  1  0
M  END


  Mrv1652309272006282D          

 23 25  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
10002.878110001.4535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3030 9998.6779    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.589410000.6285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.874910000.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8749 9999.3909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3039 9999.3909    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.303910000.2160    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.018110000.6286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0181 9998.9786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7326 9999.3910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.732610000.2161    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  0  0  0  0  0  0  0  0  0  0
10002.162710002.6910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.0733 9998.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1153 9998.3447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5894 9998.9785    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.2578 9998.4598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.3727 9997.5660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  6  7  1  0  0  0  0
  8  9  1  0  0  0  0
 10 13  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 14 17  2  0  0  0  0
 16 17  1  0  0  0  0
 17  2  1  0  0  0  0
 15 10  2  0  0  0  0
 13 16  2  0  0  0  0
 10  9  1  0  0  0  0
  9  1  1  1  0  0  0
  8 11  1  0  0  0  0
  8  4  1  6  0  0  0
  2 18  1  0  0  0  0
  2  3  1  0  0  0  0
 21 19  1  6  0  0  0
 21 20  1  0  0  0  0
 19 23  2  0  0  0  0
 19 22  1  0  0  0  0
  7 21  1  0  0  0  0
 21  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061925

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CCC3=CC(=CC=C3[C@@]1(C)CCC[C@@]2(C)C(O)=O)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O2/c1-13(2)14-6-8-16-15(12-14)7-9-17-19(16,3)10-5-11-20(17,4)18(21)22/h6,8,12-13,17H,5,7,9-11H2,1-4H3,(H,21,22)/t17-,19-,20-/m1/s1

> <INCHI_KEY>
NFWKVWVWBFBAOV-MISYRCLQSA-N

> <FORMULA>
C20H28O2

> <MOLECULAR_WEIGHT>
300.442

> <EXACT_MASS>
300.208930142

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
35.86166281984195

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,4aS,10aR)-1,4a-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid

> <ALOGPS_LOGP>
5.45

> <JCHEM_LOGP>
5.748764728000001

> <ALOGPS_LOGS>
-5.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.545782514802334

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
89.44399999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.54e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-dehydroabietic acid

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0061925
     RDKit          3D
Dehydroabietic acid
 50 52  0  0  0  0  0  0  0  0999 V2000
    5.4865   -0.7156   -0.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6478    0.5119   -0.2677 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0491    1.2598    0.9919 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1952    0.1982   -0.1400 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7541   -0.6162    0.8820 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3913   -0.9180    1.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4793   -0.4031    0.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8971    0.4075   -0.9020 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2439    0.6898   -1.0090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0385    1.0052   -1.9145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4070    0.3661   -1.7744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7431    0.3559   -0.2958 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9577   -0.7684    0.3219 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1671   -2.0950   -0.3439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2249   -0.8552    1.7941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7178   -0.9212    2.0770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4160    0.2699    1.4936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1781    0.4350    0.0293 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0505   -0.5409   -0.7196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6825    1.8047   -0.3474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1338    2.6068    0.5399 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7018    2.2969   -1.6336 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9473   -1.4354   -1.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7971   -1.1846    0.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4049   -0.4145   -1.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7565    1.1754   -1.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8863    2.3510    0.8118 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4317    0.8693    1.8152 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1269    1.1171    1.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4885   -1.0098    1.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1460   -1.5636    1.8436 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6060    1.3291   -1.8077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0858    2.1180   -1.7443 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3704    0.8031   -2.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1339    0.8590   -2.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2889   -0.6651   -2.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2770    1.3051    0.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0217   -2.1652   -1.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2348   -2.8737    0.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2717   -2.4164   -0.9521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8321   -1.8527    2.1333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7800   -0.0409    2.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8291   -0.8916    3.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1510   -1.8797    1.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5223    0.0864    1.6235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1365    1.1759    2.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0758   -0.1068   -0.7360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1620   -1.5028   -0.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7409   -0.6741   -1.7632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1434    3.1137   -1.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  6
 20 21  2  0
 20 22  1  0
  9  4  1  0
 18 12  1  0
 13  7  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  5 30  1  0
  6 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  1
 14 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  0
 17 46  1  0
 19 47  1  0
 19 48  1  0
 19 49  1  0
 22 50  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  H   UNK     0    8665.3668664.199   0.000  0.00  0.00           H+0
HETATM    5  C   UNK     0    8664.0348667.840   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8662.7008667.070   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8662.7008665.530   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8665.3678665.530   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8665.3678667.070   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8666.7008667.840   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8666.7008664.760   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8668.0348665.530   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8668.0348667.070   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8668.0358670.150   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8666.7028669.380   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8669.3698667.840   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8669.3698669.380   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8670.7048671.690   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8663.0708663.558   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8665.0158663.577   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8664.0348664.760   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0    8661.5488663.792   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0    8663.6298662.123   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   17   18    3                                                  
CONECT    3    2                                                            
CONECT    4    8                                                            
CONECT    5    6    9                                                       
CONECT    6    5    7                                                       
CONECT    7    6   21                                                       
CONECT    8    9   11    4   21                                             
CONECT    9    5    8   10    1                                             
CONECT   10   13   15    9                                                  
CONECT   11   12    8                                                       
CONECT   12   11   13                                                       
CONECT   13   10   12   16                                                  
CONECT   14   15   17                                                       
CONECT   15   14   10                                                       
CONECT   16   17   13                                                       
CONECT   17   14   16    2                                                  
CONECT   18    2                                                            
CONECT   19   21   23   22                                                  
CONECT   20   21                                                            
CONECT   21   19   20    7    8                                             
CONECT   22   19                                                            
CONECT   23   19                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0061925
HETATM    1  C1  UNL     1       5.487  -0.716  -0.447  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.648   0.512  -0.268  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.049   1.260   0.992  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.195   0.198  -0.140  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.754  -0.616   0.882  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.391  -0.918   1.012  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.479  -0.403   0.120  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.897   0.408  -0.902  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.244   0.690  -1.009  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.039   1.005  -1.914  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.407   0.366  -1.774  1.00  0.00           C  
HETATM   12  C12 UNL     1      -1.743   0.356  -0.296  1.00  0.00           C  
HETATM   13  C13 UNL     1      -0.958  -0.768   0.322  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.167  -2.095  -0.344  1.00  0.00           C  
HETATM   15  C15 UNL     1      -1.225  -0.855   1.794  1.00  0.00           C  
HETATM   16  C16 UNL     1      -2.718  -0.921   2.077  1.00  0.00           C  
HETATM   17  C17 UNL     1      -3.416   0.270   1.494  1.00  0.00           C  
HETATM   18  C18 UNL     1      -3.178   0.435   0.029  1.00  0.00           C  
HETATM   19  C19 UNL     1      -4.051  -0.541  -0.720  1.00  0.00           C  
HETATM   20  C20 UNL     1      -3.682   1.805  -0.347  1.00  0.00           C  
HETATM   21  O1  UNL     1      -4.134   2.607   0.540  1.00  0.00           O  
HETATM   22  O2  UNL     1      -3.702   2.297  -1.634  1.00  0.00           O  
HETATM   23  H1  UNL     1       4.947  -1.435  -1.087  1.00  0.00           H  
HETATM   24  H2  UNL     1       5.797  -1.185   0.507  1.00  0.00           H  
HETATM   25  H3  UNL     1       6.405  -0.414  -1.012  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.757   1.175  -1.152  1.00  0.00           H  
HETATM   27  H5  UNL     1       4.886   2.351   0.812  1.00  0.00           H  
HETATM   28  H6  UNL     1       4.432   0.869   1.815  1.00  0.00           H  
HETATM   29  H7  UNL     1       6.127   1.117   1.141  1.00  0.00           H  
HETATM   30  H8  UNL     1       3.489  -1.010   1.572  1.00  0.00           H  
HETATM   31  H9  UNL     1       1.146  -1.564   1.844  1.00  0.00           H  
HETATM   32  H10 UNL     1       2.606   1.329  -1.808  1.00  0.00           H  
HETATM   33  H11 UNL     1      -0.086   2.118  -1.744  1.00  0.00           H  
HETATM   34  H12 UNL     1       0.370   0.803  -2.922  1.00  0.00           H  
HETATM   35  H13 UNL     1      -2.134   0.859  -2.409  1.00  0.00           H  
HETATM   36  H14 UNL     1      -1.289  -0.665  -2.173  1.00  0.00           H  
HETATM   37  H15 UNL     1      -1.277   1.305   0.111  1.00  0.00           H  
HETATM   38  H16 UNL     1      -2.022  -2.165  -1.005  1.00  0.00           H  
HETATM   39  H17 UNL     1      -1.235  -2.874   0.463  1.00  0.00           H  
HETATM   40  H18 UNL     1      -0.272  -2.416  -0.952  1.00  0.00           H  
HETATM   41  H19 UNL     1      -0.832  -1.853   2.133  1.00  0.00           H  
HETATM   42  H20 UNL     1      -0.780  -0.041   2.364  1.00  0.00           H  
HETATM   43  H21 UNL     1      -2.829  -0.892   3.177  1.00  0.00           H  
HETATM   44  H22 UNL     1      -3.151  -1.880   1.727  1.00  0.00           H  
HETATM   45  H23 UNL     1      -4.522   0.086   1.624  1.00  0.00           H  
HETATM   46  H24 UNL     1      -3.136   1.176   2.075  1.00  0.00           H  
HETATM   47  H25 UNL     1      -5.076  -0.107  -0.736  1.00  0.00           H  
HETATM   48  H26 UNL     1      -4.162  -1.503  -0.160  1.00  0.00           H  
HETATM   49  H27 UNL     1      -3.741  -0.674  -1.763  1.00  0.00           H  
HETATM   50  H28 UNL     1      -3.143   3.114  -1.909  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    4   26
CONECT    3   27   28   29
CONECT    4    5    5    9
CONECT    5    6   30
CONECT    6    7    7   31
CONECT    7    8   13
CONECT    8    9    9   10
CONECT    9   32
CONECT   10   11   33   34
CONECT   11   12   35   36
CONECT   12   13   18   37
CONECT   13   14   15
CONECT   14   38   39   40
CONECT   15   16   41   42
CONECT   16   17   43   44
CONECT   17   18   45   46
CONECT   18   19   20
CONECT   19   47   48   49
CONECT   20   21   21   22
CONECT   22   50
END

HMDB0061925
     RDKit          3D
Dehydroabietic acid
 50 52  0  0  0  0  0  0  0  0999 V2000
    5.4865   -0.7156   -0.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6478    0.5119   -0.2677 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0491    1.2598    0.9919 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1952    0.1982   -0.1400 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7541   -0.6162    0.8820 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3913   -0.9180    1.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4793   -0.4031    0.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8971    0.4075   -0.9020 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2439    0.6898   -1.0090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0385    1.0052   -1.9145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4070    0.3661   -1.7744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7431    0.3559   -0.2958 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9577   -0.7684    0.3219 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1671   -2.0950   -0.3439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2249   -0.8552    1.7941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7178   -0.9212    2.0770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4160    0.2699    1.4936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1781    0.4350    0.0293 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0505   -0.5409   -0.7196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6825    1.8047   -0.3474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1338    2.6068    0.5399 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7018    2.2969   -1.6336 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9473   -1.4354   -1.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7971   -1.1846    0.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4049   -0.4145   -1.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7565    1.1754   -1.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8863    2.3510    0.8118 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4317    0.8693    1.8152 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1269    1.1171    1.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4885   -1.0098    1.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1460   -1.5636    1.8436 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6060    1.3291   -1.8077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0858    2.1180   -1.7443 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3704    0.8031   -2.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1339    0.8590   -2.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2889   -0.6651   -2.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2770    1.3051    0.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0217   -2.1652   -1.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2348   -2.8737    0.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2717   -2.4164   -0.9521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8321   -1.8527    2.1333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7800   -0.0409    2.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8291   -0.8916    3.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1510   -1.8797    1.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5223    0.0864    1.6235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1365    1.1759    2.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0758   -0.1068   -0.7360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1620   -1.5028   -0.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7409   -0.6741   -1.7632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1434    3.1137   -1.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  6
 20 21  2  0
 20 22  1  0
  9  4  1  0
 18 12  1  0
 13  7  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  5 30  1  0
  6 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  1
 14 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  0
 17 46  1  0
 19 47  1  0
 19 48  1  0
 19 49  1  0
 22 50  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-Dehydroabietic acid	ChEBI
1,2,3,4,4a,9,10,10a-Octahydro-1,4a-dimethyl-7-(1-methylethyl)-1-phenanthrenecarboxylic acid	ChEBI
13-Isopropylpodocarpa-8,11,13-trien-15-Oic acid	ChEBI
Abieta-8,11,13-trien-18-Oic acid	ChEBI
Dehydroabietate	ChEBI
(-)-Dehydroabietate	Generator
1,2,3,4,4a,9,10,10a-Octahydro-1,4a-dimethyl-7-(1-methylethyl)-1-phenanthrenecarboxylate	Generator
13-Isopropylpodocarpa-8,11,13-trien-15-Oate	Generator
Abieta-8,11,13-trien-18-Oate	Generator
(+)-Dehydroabietic acid	PhytoBank

Chemical Formula

C₂₀H₂₈O₂

Average Molecular Weight

300.442

Monoisotopic Molecular Weight

300.208930142

IUPAC Name

(1R,4aS,10aR)-1,4a-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid

Traditional Name

(-)-dehydroabietic acid

CAS Registry Number

1740-19-8

SMILES

[H][C@@]12CCC3=CC(=CC=C3[C@@]1(C)CCC[C@@]2(C)C(O)=O)C(C)C

InChI Identifier

InChI=1S/C20H28O2/c1-13(2)14-6-8-16-15(12-14)7-9-17-19(16,3)10-5-11-20(17,4)18(21)22/h6,8,12-13,17H,5,7,9-11H2,1-4H3,(H,21,22)/t17-,19-,20-/m1/s1

InChI Key

NFWKVWVWBFBAOV-MISYRCLQSA-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
Abietane diterpenoid
Phenanthrene
Hydrophenanthrene
Tetralin
Benzenoid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:29571 )
abietane diterpenoid (CHEBI:29571 )
carbotricyclic compound (CHEBI:29571 )
Abietane diterpenoids (C12078 )
Podocarpanes (C12078 )
Abietane diterpenoids (LMPR0104050005 )

Ontology

Not Available

Non-excretory biofluid

Saliva (HMDB: HMDB0061925)

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
Water Solubility	0.00045 g/L	ALOGPS
logP	5.45	ALOGPS
logP	5.75	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	4.55	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	89.44 m³·mol⁻¹	ChemAxon
Polarizability	35.86 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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]-	216.419	30932474
DeepCCS	[M+Na]+	191.638	30932474
AllCCS	[M+H]+	174.4	32859911
AllCCS	[M+H-H2O]+	171.2	32859911
AllCCS	[M+NH4]+	177.4	32859911
AllCCS	[M+Na]+	178.2	32859911
AllCCS	[M-H]-	183.1	32859911
AllCCS	[M+Na-2H]-	183.4	32859911
AllCCS	[M+HCOO]-	183.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dehydroabietic acid	[H][C@@]12CCC3=CC(=CC=C3[C@@]1(C)CCC[C@@]2(C)C(O)=O)C(C)C	3282.2	Standard polar	33892256
Dehydroabietic acid	[H][C@@]12CCC3=CC(=CC=C3[C@@]1(C)CCC[C@@]2(C)C(O)=O)C(C)C	2343.6	Standard non polar	33892256
Dehydroabietic acid	[H][C@@]12CCC3=CC(=CC=C3[C@@]1(C)CCC[C@@]2(C)C(O)=O)C(C)C	2447.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dehydroabietic acid,1TMS,isomer #1	CC(C)C1=CC=C2C(=C1)CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(=O)O[Si](C)(C)C	2389.1	Semi standard non polar	33892256
Dehydroabietic acid,1TBDMS,isomer #1	CC(C)C1=CC=C2C(=C1)CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(=O)O[Si](C)(C)C(C)(C)C	2651.7	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 - Dehydroabietic 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 - Dehydroabietic acid 10V, Positive-QTOF	splash10-114i-0094000000-65169464f0a52a0f4fd2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroabietic acid 20V, Positive-QTOF	splash10-08fr-0390000000-5be19c5b48244be1a888	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroabietic acid 40V, Positive-QTOF	splash10-02ni-1950000000-13b1d3e1a4d3a447a83e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroabietic acid 10V, Negative-QTOF	splash10-0002-0090000000-344a11f406f20d02412c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroabietic acid 20V, Negative-QTOF	splash10-0002-0090000000-3a240567ab7edc092860	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroabietic acid 40V, Negative-QTOF	splash10-0002-1190000000-bc5ae92c2fc41baf0b5f	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

94391

PDB ID

Not Available

ChEBI ID

29571

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

Villeneuve DC, Yagminas AP, Marino IA, Becking GC: Toxicity studies on dehydroabietic acid. Bull Environ Contam Toxicol. 1977 Jul;18(1):42-7. [PubMed:884336 ]
Matsumoto T, Hayashi N, Ishida T, Asakawa Y: Metabolites of (+)-dehydroabietic acid in rabbits. J Pharm Sci. 1990 Jun;79(6):540-7. [PubMed:2395101 ]
Wada H, Kodato S, Kawamori M, Morikawa T, Nakai H, Takeda M, Saito S, Onoda Y, Tamaki H: Antiulcer activity of dehydroabietic acid derivatives. Chem Pharm Bull (Tokyo). 1985 Apr;33(4):1472-87. [PubMed:4042223 ]
Biellmann JF, Wennig R: [Microbial degradation of dehydroabietic acid]. Bull Soc Chim Fr. 1971 May;5:1676-86. [PubMed:5559065 ]
Tapia AA, Vallejo MD, Gouiric SC, Feresin GE, Rossomando PC, Bustos DA: Hydroxylation of dehydroabietic acid by Fusarium species. Phytochemistry. 1997 Sep;46(1):131-3. [PubMed:9276983 ]
OHTA M, OHMORI L: Studies on abietic acid derivatives. I. Deisopropylation of dehydroabietic acid. Pharm Bull. 1957 Apr;5(2):91-5. [PubMed:13452774 ]
van Beek TA, Claassen FW, Dorado J, Godejohann M, Sierra-Alvarez R, Wijnberg JB: Fungal biotransformation products of dehydroabietic acid. J Nat Prod. 2007 Feb;70(2):154-9. [PubMed:17315956 ]
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 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
MetaCyc: dehydroabietic acid biosynthesis [Link]
Toshimitsu Sakuma, Kozo Sato, 'NOVEL DEHYDROABIETIC ACID POLYMER.' U.S. Patent US20120101250, issued April 26, 2012. [Link]
Kozo Sato, Toshimitsu Sakuma, 'DEHYDROABIETIC ACID POLYMER, COMPACT, METHOD FOR PRODUCING DEHYDROABIETIC ACID POLYMER, AND DEHYDROABIETIC ACID COMPOUND.' U.S. Patent US20120322969, issued December 20, 2012. [Link]

Showing metabocard for Dehydroabietic acid (HMDB0061925)

MOL for HMDB0061925 (Dehydroabietic acid)

3D MOL for HMDB0061925 (Dehydroabietic acid)

3D SDF for HMDB0061925 (Dehydroabietic acid)

3D-SDF for HMDB0061925 (Dehydroabietic acid)

PDB for HMDB0061925 (Dehydroabietic acid)

3D PDB for HMDB0061925 (Dehydroabietic acid)

SMILES for HMDB0061925 (Dehydroabietic acid)

INCHI for HMDB0061925 (Dehydroabietic acid)

Structure for HMDB0061925 (Dehydroabietic acid)

3D Structure for HMDB0061925 (Dehydroabietic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra