NP-MRD: Showing NP-Card for dehydroabietic acid (NP0032641)

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Record Information

Version

2.0

Created at

2021-06-19 23:23:30 UTC

Updated at

2021-08-20 00:00:26 UTC

NP-MRD ID

NP0032641

Secondary Accession Numbers

None

Natural Product Identification

Common Name

dehydroabietic acid

Provided By

JEOL Database JEOL Logo

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 secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. dehydroabietic acid is found in Abies pinsapo, Abies spectabilis, Cedrus deodara, Cedrus libani, Anisochilus harmandii, Homo sapiens, Isodon interruptus, Isodon nervosus, Juniperus chinensis, Juniperus sabina, Larix decidua, Larix kaempferi, Phlebiopsis gigantea, Picea ajanensis, Sitka spruce, Pinus densiflora, Pinus massoniana, Pinus palustris, Pinus pumila, Pinus resinosa, Pinus strobus, Pinus sylvestris, Pinus yunnanensis, Pistacia lentiscus, Porodaedalea pini, Relhania corymbosa, Salvia tomentosa and Trametes Versicolor. dehydroabietic acid was first documented in 2002 (PMID: 12000325). Based on a literature review a small amount of articles have been published on Dehydroabietic acid (PMID: 19753653) (PMID: 21725812) (PMID: 21742316).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202101233D          

 50 52  0  0  0  0            999 V2000
   -3.5224    4.6071   -0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1467    4.7088   -0.7708 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2216    5.6289    0.0297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5262    3.3401   -0.9816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2505    2.8902   -2.2741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6769    1.6332   -2.4868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3488    0.7824   -1.4152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6417    1.2240   -0.1080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2158    2.4953    0.0913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3146    0.4136    1.1232 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1495   -1.0152    0.8537 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0523   -1.0566   -0.3896 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2391   -0.6276   -1.6646 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9905   -1.5120   -1.9872 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2086   -0.6533   -2.8783 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.7556   -2.3342   -1.7994 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9138   -2.3596   -0.5012 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1020   -3.6689   -0.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8929   -2.3999    0.6857 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9134   -3.2207    1.5896 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.1892    3.9585   -0.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7189   -1.6706    0.7314 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3120   -1.5490    1.5072 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0  0  0  0
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  9 32  1  0  0  0  0
  5 30  1  0  0  0  0
  6 31  1  0  0  0  0
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  2 26  1  6  0  0  0
  1 23  1  0  0  0  0
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  1 25  1  0  0  0  0
  3 27  1  0  0  0  0
  3 28  1  0  0  0  0
  3 29  1  0  0  0  0
 22 50  1  0  0  0  0
M  END

     RDKit          3D

 50 52  0  0  0  0  0  0  0  0999 V2000
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    2.7556   -2.3342   -1.7994 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1020   -3.6689   -0.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9134   -3.2207    1.5896 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7830   -1.3882    0.6978 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1892    3.9585   -0.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7694   -4.5360   -0.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3120   -1.5490    1.5072 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0
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M  END


  Mrv1652306202101233D          

 50 52  0  0  0  0            999 V2000
   -3.5224    4.6071   -0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1467    4.7088   -0.7708 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.2512   -2.7841   -3.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2510   -3.3023   -1.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5681   -1.6008   -1.7152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4366   -3.6998    0.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7694   -4.5360   -0.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5043   -3.8451   -1.3360 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3120   -1.5490    1.5072 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0  0  0  0
  9  4  2  0  0  0  0
 16 17  1  0  0  0  0
  4  5  1  0  0  0  0
 16 15  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
 17 18  1  0  0  0  0
 13 14  1  6  0  0  0
 13  7  1  0  0  0  0
 18 19  1  0  0  0  0
 12 11  1  0  0  0  0
 12 37  1  1  0  0  0
 11 10  1  0  0  0  0
  4  2  1  0  0  0  0
 10  8  1  0  0  0  0
  2  1  1  0  0  0  0
 18 12  1  0  0  0  0
  2  3  1  0  0  0  0
 13 15  1  0  0  0  0
  7  8  2  0  0  0  0
 20 22  1  0  0  0  0
 13 12  1  0  0  0  0
 20 21  2  0  0  0  0
 18 20  1  1  0  0  0
 16 43  1  0  0  0  0
 16 44  1  0  0  0  0
 17 45  1  0  0  0  0
 17 46  1  0  0  0  0
 15 41  1  0  0  0  0
 15 42  1  0  0  0  0
 11 35  1  0  0  0  0
 11 36  1  0  0  0  0
 10 33  1  0  0  0  0
 10 34  1  0  0  0  0
  9 32  1  0  0  0  0
  5 30  1  0  0  0  0
  6 31  1  0  0  0  0
 14 38  1  0  0  0  0
 14 39  1  0  0  0  0
 14 40  1  0  0  0  0
 19 47  1  0  0  0  0
 19 48  1  0  0  0  0
 19 49  1  0  0  0  0
  2 26  1  6  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  3 27  1  0  0  0  0
  3 28  1  0  0  0  0
  3 29  1  0  0  0  0
 22 50  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0032641

> <DATABASE_NAME>
NP-MRD

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

> <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>
35.74502548273904

> <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>
4.545782514802338

> <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

$$$$

     RDKit          3D

 50 52  0  0  0  0  0  0  0  0999 V2000
   -3.5224    4.6071   -0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1467    4.7088   -0.7708 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2216    5.6289    0.0297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5262    3.3401   -0.9816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2505    2.8902   -2.2741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6769    1.6332   -2.4868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3488    0.7824   -1.4152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6417    1.2240   -0.1080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2158    2.4953    0.0913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3146    0.4136    1.1232 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1495   -1.0152    0.8537 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0523   -1.0566   -0.3896 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2391   -0.6276   -1.6646 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9905   -1.5120   -1.9872 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2086   -0.6533   -2.8783 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9507   -1.9787   -3.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7556   -2.3342   -1.7994 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9138   -2.3596   -0.5012 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1020   -3.6689   -0.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8929   -2.3999    0.6857 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9134   -3.2207    1.5896 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7830   -1.3882    0.6978 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1892    3.9585   -0.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4590    4.1997    0.9078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9910    5.5949   -0.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2970    5.1788   -1.7519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6470    6.6360    0.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0630    5.2640    1.0503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2405    5.7121   -0.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4839    3.5118   -3.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5059    1.3290   -3.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4190    2.8256    1.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4841    0.9412    1.6611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1869    0.3808    1.7873 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6747   -1.3768    1.7449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7189   -1.6706    0.7314 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7900   -0.2496   -0.2399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7235   -1.5266   -1.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7319   -2.5430   -2.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5227   -1.1324   -2.8694 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6717   -0.4600   -3.8149 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9480    0.1529   -2.7757 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6334   -1.9001   -3.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2512   -2.7841   -3.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2510   -3.3023   -1.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5681   -1.6008   -1.7152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4366   -3.6998    0.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7694   -4.5360   -0.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5043   -3.8451   -1.3360 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3120   -1.5490    1.5072 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0
  9  4  2  0
 16 17  1  0
  4  5  1  0
 16 15  1  0
  5  6  2  0
  6  7  1  0
 17 18  1  0
 13 14  1  6
 13  7  1  0
 18 19  1  0
 12 11  1  0
 12 37  1  1
 11 10  1  0
  4  2  1  0
 10  8  1  0
  2  1  1  0
 18 12  1  0
  2  3  1  0
 13 15  1  0
  7  8  2  0
 20 22  1  0
 13 12  1  0
 20 21  2  0
 18 20  1  1
 16 43  1  0
 16 44  1  0
 17 45  1  0
 17 46  1  0
 15 41  1  0
 15 42  1  0
 11 35  1  0
 11 36  1  0
 10 33  1  0
 10 34  1  0
  9 32  1  0
  5 30  1  0
  6 31  1  0
 14 38  1  0
 14 39  1  0
 14 40  1  0
 19 47  1  0
 19 48  1  0
 19 49  1  0
  2 26  1  6
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
 22 50  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.522   4.607  -0.107  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.147   4.709  -0.771  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.222   5.629   0.030  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.526   3.340  -0.982  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.250   2.890  -2.274  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.677   1.633  -2.487  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.349   0.782  -1.415  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.642   1.224  -0.108  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.216   2.495   0.091  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.315   0.414   1.123  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.150  -1.015   0.854  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.052  -1.057  -0.390  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.239  -0.628  -1.665  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.991  -1.512  -1.987  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.209  -0.653  -2.878  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.951  -1.979  -3.042  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.756  -2.334  -1.799  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.914  -2.360  -0.501  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.102  -3.669  -0.443  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.893  -2.400   0.686  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.913  -3.221   1.590  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.783  -1.388   0.698  0.00  0.00           O+0
HETATM   23  H   UNK     0      -4.189   3.958  -0.686  0.00  0.00           H+0
HETATM   24  H   UNK     0      -3.459   4.200   0.908  0.00  0.00           H+0
HETATM   25  H   UNK     0      -3.991   5.595  -0.040  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.297   5.179  -1.752  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.647   6.636   0.100  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.063   5.264   1.050  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.241   5.712  -0.451  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.484   3.512  -3.136  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.506   1.329  -3.516  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.419   2.826   1.109  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.484   0.941   1.661  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.187   0.381   1.787  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.675  -1.377   1.745  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.719  -1.671   0.731  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.790  -0.250  -0.240  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.724  -1.527  -1.174  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.732  -2.543  -2.220  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.523  -1.132  -2.869  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.672  -0.460  -3.815  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.948   0.153  -2.776  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.633  -1.900  -3.897  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.251  -2.784  -3.288  0.00  0.00           H+0
HETATM   45  H   UNK     0       3.251  -3.302  -1.950  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.568  -1.601  -1.715  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.437  -3.700   0.426  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.769  -4.536  -0.355  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.504  -3.845  -1.336  0.00  0.00           H+0
HETATM   50  H   UNK     0       4.312  -1.549   1.507  0.00  0.00           H+0
CONECT    1    2   23   24   25                                             
CONECT    2    4    1    3   26                                             
CONECT    3    2   27   28   29                                             
CONECT    4    9    5    2                                                  
CONECT    5    4    6   30                                                  
CONECT    6    5    7   31                                                  
CONECT    7    6   13    8                                                  
CONECT    8    9   10    7                                                  
CONECT    9    8    4   32                                                  
CONECT   10   11    8   33   34                                             
CONECT   11   12   10   35   36                                             
CONECT   12   11   37   18   13                                             
CONECT   13   14    7   15   12                                             
CONECT   14   13   38   39   40                                             
CONECT   15   16   13   41   42                                             
CONECT   16   17   15   43   44                                             
CONECT   17   16   18   45   46                                             
CONECT   18   17   19   12   20                                             
CONECT   19   18   47   48   49                                             
CONECT   20   22   21   18                                                  
CONECT   21   20                                                            
CONECT   22   20   50                                                       
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    2                                                            
CONECT   27    3                                                            
CONECT   28    3                                                            
CONECT   29    3                                                            
CONECT   30    5                                                            
CONECT   31    6                                                            
CONECT   32    9                                                            
CONECT   33   10                                                            
CONECT   34   10                                                            
CONECT   35   11                                                            
CONECT   36   11                                                            
CONECT   37   12                                                            
CONECT   38   14                                                            
CONECT   39   14                                                            
CONECT   40   14                                                            
CONECT   41   15                                                            
CONECT   42   15                                                            
CONECT   43   16                                                            
CONECT   44   16                                                            
CONECT   45   17                                                            
CONECT   46   17                                                            
CONECT   47   19                                                            
CONECT   48   19                                                            
CONECT   49   19                                                            
CONECT   50   22                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  104    0
END

RDKit          3D

50 52  0  0  0  0  0  0  0  0999 V2000
   -3.5224    4.6071   -0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1467    4.7088   -0.7708 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2216    5.6289    0.0297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5262    3.3401   -0.9816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2505    2.8902   -2.2741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6769    1.6332   -2.4868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3488    0.7824   -1.4152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6417    1.2240   -0.1080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2158    2.4953    0.0913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3146    0.4136    1.1232 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1495   -1.0152    0.8537 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0523   -1.0566   -0.3896 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2391   -0.6276   -1.6646 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9905   -1.5120   -1.9872 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2086   -0.6533   -2.8783 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9507   -1.9787   -3.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7556   -2.3342   -1.7994 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9138   -2.3596   -0.5012 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1020   -3.6689   -0.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8929   -2.3999    0.6857 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9134   -3.2207    1.5896 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7830   -1.3882    0.6978 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1892    3.9585   -0.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4590    4.1997    0.9078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9910    5.5949   -0.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2970    5.1788   -1.7519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6470    6.6360    0.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0630    5.2640    1.0503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2405    5.7121   -0.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4839    3.5118   -3.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5059    1.3290   -3.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4190    2.8256    1.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4841    0.9412    1.6611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1869    0.3808    1.7873 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6747   -1.3768    1.7449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7189   -1.6706    0.7314 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7900   -0.2496   -0.2399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7235   -1.5266   -1.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7319   -2.5430   -2.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5227   -1.1324   -2.8694 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6717   -0.4600   -3.8149 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9480    0.1529   -2.7757 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6334   -1.9001   -3.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2512   -2.7841   -3.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2510   -3.3023   -1.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5681   -1.6008   -1.7152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4366   -3.6998    0.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7694   -4.5360   -0.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5043   -3.8451   -1.3360 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3120   -1.5490    1.5072 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0
  9  4  2  0
 16 17  1  0
  4  5  1  0
 16 15  1  0
  5  6  2  0
  6  7  1  0
 17 18  1  0
 13 14  1  6
 13  7  1  0
 18 19  1  0
 12 11  1  0
 12 37  1  1
 11 10  1  0
  4  2  1  0
 10  8  1  0
  2  1  1  0
 18 12  1  0
  2  3  1  0
 13 15  1  0
  7  8  2  0
 20 22  1  0
 13 12  1  0
 20 21  2  0
 18 20  1  1
 16 43  1  0
 16 44  1  0
 17 45  1  0
 17 46  1  0
 15 41  1  0
 15 42  1  0
 11 35  1  0
 11 36  1  0
 10 33  1  0
 10 34  1  0
  9 32  1  0
  5 30  1  0
  6 31  1  0
 14 38  1  0
 14 39  1  0
 14 40  1  0
 19 47  1  0
 19 48  1  0
 19 49  1  0
  2 26  1  6
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
 22 50  1  0
M  END

View in JSmol

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	HMDB

Chemical Formula

C₂₀H₂₈O₂

Average Mass

300.4420 Da

Monoisotopic Mass

300.20893 Da

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

Not Available

SMILES

[H]OC(=O)[C@]1(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@@]2(C3=C(C([H])=C(C([H])=C3[H])C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])[C@@]12[H])C([H])([H])[H]

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₆D₆ (H),CDCl₃ (C), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₆D₆ (H),CDCl₃ (C), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₆D₆ (H),CDCl₃ (C), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₆D₆ (H),CDCl₃ (C), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₆D₆ (H),CDCl₃ (C), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₆D₆ (H),CDCl₃ (C), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₆D₆ (H),CDCl₃ (C), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₆D₆ (H),CDCl₃ (C), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₆D₆ (H),CDCl₃ (C), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₆D₆ (H),CDCl₃ (C), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₆D₆ (H),CDCl₃ (C), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₆D₆ (H),CDCl₃ (C), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₆D₆ (H),CDCl₃ (C), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₆D₆ (H),CDCl₃ (C), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₆D₆ (H),CDCl₃ (C), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₆D₆ (H),CDCl₃ (C), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₆D₆ (H),CDCl₃ (C), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₆D₆ (H),CDCl₃ (C), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₆D₆ (H),CDCl₃ (C), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₆D₆ (H),CDCl₃ (C), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Abies pinsapo	LOTUS Database	35616633
Abies spectabilis	LOTUS Database	35616633
Cedrus deodara	LOTUS Database	35616633
Cedrus libani	LOTUS Database	35616633
Coleus harmandii	LOTUS Database	35616633
Commiphora myrrha	KNApSAcK Database	22123792
Homo sapiens	LOTUS Database	35616633
Isodon interruptus	LOTUS Database	35616633
Isodon nervosus	LOTUS Database	35616633
Juniperus chinensis	LOTUS Database	35616633
Juniperus sabina	LOTUS Database	35616633
Larix decidua	LOTUS Database	35616633
Larix kaempferi	LOTUS Database	35616633
Phlebiopsis gigantea	JEOL database	van Beek, T. A., et al, J. Nat. Prod. 70, 154 (2007)
Picea abies	KNApSAcK Database	22123792
Picea ajanensis	KNApSAcK Database	22123792
Picea glehni	KNApSAcK Database	22123792
Picea glehnii L.	KNApSAcK Database	22123792
Picea jezoensis var. jezoensis	Plant	KNApSAcK
Picea koraiensis	KNApSAcK Database	22123792
Picea sitchensis	-	KNApSAcK
Pinus densiflora	LOTUS Database	35616633
Pinus luchuensis	KNApSAcK Database	22123792
Pinus massoniana	LOTUS Database	35616633
Pinus palustris	LOTUS Database	35616633
Pinus pumila	LOTUS Database	35616633
Pinus resinosa	LOTUS Database	35616633
Pinus sibirica	KNApSAcK Database	22123792
Pinus strobus	LOTUS Database	35616633
Pinus sylvestris	LOTUS Database	35616633
Pinus taeda	KNApSAcK Database	22123792
Pinus yunnanensis	LOTUS Database	35616633
Pistacia lentiscus	LOTUS Database	35616633
Porodaedalea pini	LOTUS Database	35616633
Pseudotsuga wilsoniana	KNApSAcK Database	22123792
Rabdosia nervosa	KNApSAcK Database	22123792
Relhania corymbosa	LOTUS Database	35616633
Salvia tomentosa	LOTUS Database	35616633
Trametes Versicolor	JEOL database	van Beek, T. A., et al, J. Nat. Prod. 70, 154 (2007)
Tripterygium wilfordii	KNApSAcK Database	22123792

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 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	425.08 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	2.41 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	6.120 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
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	35.75 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

External Links

HMDB ID

HMDB0061925

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

rw1450271

References

General References

Johansen JD, Heydorn S, Menne T: Oak moss extracts in the diagnosis of fragrance contact allergy. Contact Dermatitis. 2002 Mar;46(3):157-61. doi: 10.1034/j.1600-0536.2002.460306.x. [PubMed:12000325 ]
Kang MS, Hirai S, Goto T, Kuroyanagi K, Kim YI, Ohyama K, Uemura T, Lee JY, Sakamoto T, Ezaki Y, Yu R, Takahashi N, Kawada T: Dehydroabietic acid, a diterpene, improves diabetes and hyperlipidemia in obese diabetic KK-Ay mice. Biofactors. 2009 Sep-Oct;35(5):442-8. doi: 10.1002/biof.58. [PubMed:19753653 ]
Jang HJ, Yang KS: Inhibition of nitric oxide production in RAW 264.7 macrophages by diterpenoids from Phellinus pini. Arch Pharm Res. 2011 Jun;34(6):913-7. doi: 10.1007/s12272-011-0608-z. Epub 2011 Jul 2. [PubMed:21725812 ]
Xu X, Duan W, Huang M, Li G: Synthesis of cellulose dehydroabietate in ionic liquid [bmim]Br. Carbohydr Res. 2011 Sep 27;346(13):2024-7. doi: 10.1016/j.carres.2011.06.011. Epub 2011 Jun 16. [PubMed:21742316 ]
van Beek, T. A., et al. (2007). van Beek, T. A., et al, J. Nat. Prod. 70, 154 (2007) . J. Nat. Prod..

Showing NP-Card for dehydroabietic acid (NP0032641)

MOL for NP0032641 (dehydroabietic acid)

3D MOL for NP0032641 (dehydroabietic acid)

3D SDF for NP0032641 (dehydroabietic acid)

3D-SDF for NP0032641 (dehydroabietic acid)

PDB for NP0032641 (dehydroabietic acid)

3D PDB for NP0032641 (dehydroabietic acid)

SMILES for NP0032641 (dehydroabietic acid)

INCHI for NP0032641 (dehydroabietic acid)

Structure for NP0032641 (dehydroabietic acid)

3D Structure for NP0032641 (dehydroabietic acid)