NP-MRD: Showing NP-Card for laricinolic acid (NP0030204)

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Record Information

Version

1.0

Created at

2021-06-19 21:37:15 UTC

Updated at

2021-06-29 23:58:02 UTC

NP-MRD ID

NP0030204

Secondary Accession Numbers

None

Natural Product Identification

Common Name

laricinolic acid

Provided By

JEOL Database JEOL Logo

Description

(1R,3S,4aS,8aS)-3-hydroxy-5,5,8a-trimethyl-2-methylidene-decahydronaphthalene-1-carboxylic acid belongs to the class of organic compounds known as cyclic alcohols and derivatives. These are organic compounds containing an aliphatic ring substituted with at least one hydroxyl group. laricinolic acid is found in Fomitopsis officinalis and Stereum ostrea. It was first documented in 2006 (Kim, Y.-H., et al.). Based on a literature review very few articles have been published on (1R,3S,4aS,8aS)-3-hydroxy-5,5,8a-trimethyl-2-methylidene-decahydronaphthalene-1-carboxylic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192123373D          

 42 43  0  0  0  0            999 V2000
   -1.9834    0.5483   -2.5025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3969    0.2274   -1.3333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0903   -1.2063   -0.9353 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3304   -2.1138   -2.0060 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3591   -1.3936   -0.4651 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7422   -0.3837    0.6364 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0985   -0.6977    1.3653 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9776   -2.0448    2.1281 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3128   -0.8453    0.4291 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3778    0.3912    2.4308 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2473    1.8172    1.9123 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8731    2.0665    1.2974 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5286    1.0986    0.1360 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3928    1.4680   -1.0963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9983    1.2343   -0.2459 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4062    2.6914   -0.5120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1639    3.3765   -1.4920 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0893    3.2285    0.5233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2124    1.5688   -2.7915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2805   -0.2102   -3.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7703   -1.4895   -0.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7270   -1.8656   -2.7268 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0426   -1.3255   -1.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4574   -2.4236   -0.1050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0157   -0.5225    1.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8505   -2.2125    2.7704 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9154   -2.8982    1.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0911   -2.0619    2.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1835   -1.2168    0.9840 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6282    0.0955   -0.0193 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1225   -1.5618   -0.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6737    0.2708    3.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3795    0.2561    2.8586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3937    2.5134    2.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0416    2.0375    1.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1182    1.9704    2.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8315    3.1081    0.9559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1807    2.4866   -1.4370 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2217    0.8049   -1.9486 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4605    1.4563   -0.8868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5882    0.9400    0.6374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2813    4.1429    0.2266 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  3  2  1  0  0  0  0
  2 15  1  0  0  0  0
 13  6  1  0  0  0  0
 13 14  1  6  0  0  0
  7  8  1  1  0  0  0
 11 10  1  0  0  0  0
 15 16  1  0  0  0  0
 11 12  1  0  0  0  0
  7  9  1  0  0  0  0
 10  7  1  0  0  0  0
  2  1  2  3  0  0  0
  7  6  1  0  0  0  0
 16 18  1  0  0  0  0
 13 12  1  0  0  0  0
 16 17  2  0  0  0  0
 13 15  1  0  0  0  0
  3  4  1  0  0  0  0
  6  5  1  0  0  0  0
  6 25  1  1  0  0  0
 11 34  1  0  0  0  0
 11 35  1  0  0  0  0
 10 32  1  0  0  0  0
 10 33  1  0  0  0  0
 12 36  1  0  0  0  0
 12 37  1  0  0  0  0
  5 23  1  0  0  0  0
  5 24  1  0  0  0  0
  3 21  1  1  0  0  0
 15 41  1  1  0  0  0
 14 38  1  0  0  0  0
 14 39  1  0  0  0  0
 14 40  1  0  0  0  0
  8 26  1  0  0  0  0
  8 27  1  0  0  0  0
  8 28  1  0  0  0  0
  9 29  1  0  0  0  0
  9 30  1  0  0  0  0
  9 31  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
 18 42  1  0  0  0  0
  4 22  1  0  0  0  0
M  END

     RDKit          3D

 42 43  0  0  0  0  0  0  0  0999 V2000
   -1.9834    0.5483   -2.5025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3969    0.2274   -1.3333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0903   -1.2063   -0.9353 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3304   -2.1138   -2.0060 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3591   -1.3936   -0.4651 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7422   -0.3837    0.6364 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0985   -0.6977    1.3653 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9776   -2.0448    2.1281 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3128   -0.8453    0.4291 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3778    0.3912    2.4308 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2473    1.8172    1.9123 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8731    2.0665    1.2974 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5286    1.0986    0.1360 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3928    1.4680   -1.0963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9983    1.2343   -0.2459 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4062    2.6914   -0.5120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1639    3.3765   -1.4920 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0893    3.2285    0.5233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2124    1.5688   -2.7915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2805   -0.2102   -3.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7703   -1.4895   -0.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7270   -1.8656   -2.7268 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0426   -1.3255   -1.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4574   -2.4236   -0.1050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0157   -0.5225    1.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8505   -2.2125    2.7704 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9154   -2.8982    1.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0911   -2.0619    2.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1835   -1.2168    0.9840 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6282    0.0955   -0.0193 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1225   -1.5618   -0.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6737    0.2708    3.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3795    0.2561    2.8586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3937    2.5134    2.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0416    2.0375    1.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1182    1.9704    2.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8315    3.1081    0.9559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1807    2.4866   -1.4370 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2217    0.8049   -1.9486 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4605    1.4563   -0.8868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5882    0.9400    0.6374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2813    4.1429    0.2266 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0
  3  2  1  0
  2 15  1  0
 13  6  1  0
 13 14  1  6
  7  8  1  1
 11 10  1  0
 15 16  1  0
 11 12  1  0
  7  9  1  0
 10  7  1  0
  2  1  2  3
  7  6  1  0
 16 18  1  0
 13 12  1  0
 16 17  2  0
 13 15  1  0
  3  4  1  0
  6  5  1  0
  6 25  1  1
 11 34  1  0
 11 35  1  0
 10 32  1  0
 10 33  1  0
 12 36  1  0
 12 37  1  0
  5 23  1  0
  5 24  1  0
  3 21  1  1
 15 41  1  1
 14 38  1  0
 14 39  1  0
 14 40  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
  9 31  1  0
  1 19  1  0
  1 20  1  0
 18 42  1  0
  4 22  1  0
M  END


  Mrv1652306192123373D          

 42 43  0  0  0  0            999 V2000
   -1.9834    0.5483   -2.5025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3969    0.2274   -1.3333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0903   -1.2063   -0.9353 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3304   -2.1138   -2.0060 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3591   -1.3936   -0.4651 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7422   -0.3837    0.6364 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0985   -0.6977    1.3653 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9776   -2.0448    2.1281 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3128   -0.8453    0.4291 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3778    0.3912    2.4308 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2473    1.8172    1.9123 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8731    2.0665    1.2974 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5286    1.0986    0.1360 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3928    1.4680   -1.0963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9983    1.2343   -0.2459 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4062    2.6914   -0.5120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1639    3.3765   -1.4920 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0893    3.2285    0.5233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2124    1.5688   -2.7915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2805   -0.2102   -3.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7703   -1.4895   -0.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7270   -1.8656   -2.7268 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0426   -1.3255   -1.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4574   -2.4236   -0.1050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0157   -0.5225    1.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8505   -2.2125    2.7704 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9154   -2.8982    1.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0911   -2.0619    2.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1835   -1.2168    0.9840 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6282    0.0955   -0.0193 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1225   -1.5618   -0.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6737    0.2708    3.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3795    0.2561    2.8586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3937    2.5134    2.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0416    2.0375    1.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1182    1.9704    2.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8315    3.1081    0.9559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1807    2.4866   -1.4370 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2217    0.8049   -1.9486 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4605    1.4563   -0.8868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5882    0.9400    0.6374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2813    4.1429    0.2266 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  3  2  1  0  0  0  0
  2 15  1  0  0  0  0
 13  6  1  0  0  0  0
 13 14  1  6  0  0  0
  7  8  1  1  0  0  0
 11 10  1  0  0  0  0
 15 16  1  0  0  0  0
 11 12  1  0  0  0  0
  7  9  1  0  0  0  0
 10  7  1  0  0  0  0
  2  1  2  3  0  0  0
  7  6  1  0  0  0  0
 16 18  1  0  0  0  0
 13 12  1  0  0  0  0
 16 17  2  0  0  0  0
 13 15  1  0  0  0  0
  3  4  1  0  0  0  0
  6  5  1  0  0  0  0
  6 25  1  1  0  0  0
 11 34  1  0  0  0  0
 11 35  1  0  0  0  0
 10 32  1  0  0  0  0
 10 33  1  0  0  0  0
 12 36  1  0  0  0  0
 12 37  1  0  0  0  0
  5 23  1  0  0  0  0
  5 24  1  0  0  0  0
  3 21  1  1  0  0  0
 15 41  1  1  0  0  0
 14 38  1  0  0  0  0
 14 39  1  0  0  0  0
 14 40  1  0  0  0  0
  8 26  1  0  0  0  0
  8 27  1  0  0  0  0
  8 28  1  0  0  0  0
  9 29  1  0  0  0  0
  9 30  1  0  0  0  0
  9 31  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
 18 42  1  0  0  0  0
  4 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0030204

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O3/c1-9-10(16)8-11-14(2,3)6-5-7-15(11,4)12(9)13(17)18/h10-12,16H,1,5-8H2,2-4H3,(H,17,18)/t10-,11-,12+,15-/m0/s1

> <INCHI_KEY>
HHNLQWOVCRXGMP-OHTBPHCPSA-N

> <FORMULA>
C15H24O3

> <MOLECULAR_WEIGHT>
252.354

> <EXACT_MASS>
252.172544633

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
28.2596663407965

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3S,4aS,8aS)-3-hydroxy-5,5,8a-trimethyl-2-methylidene-decahydronaphthalene-1-carboxylic acid

> <ALOGPS_LOGP>
2.63

> <JCHEM_LOGP>
2.4852816779999998

> <ALOGPS_LOGS>
-2.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.621392565102909

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.724890348234033

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9753542671147057

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
69.6833

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.73e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3S,4aS,8aS)-3-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1H-naphthalene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 42 43  0  0  0  0  0  0  0  0999 V2000
   -1.9834    0.5483   -2.5025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3969    0.2274   -1.3333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0903   -1.2063   -0.9353 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3304   -2.1138   -2.0060 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3591   -1.3936   -0.4651 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7422   -0.3837    0.6364 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0985   -0.6977    1.3653 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9776   -2.0448    2.1281 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3128   -0.8453    0.4291 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3778    0.3912    2.4308 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2473    1.8172    1.9123 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8731    2.0665    1.2974 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5286    1.0986    0.1360 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3928    1.4680   -1.0963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9983    1.2343   -0.2459 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4062    2.6914   -0.5120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1639    3.3765   -1.4920 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0893    3.2285    0.5233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2124    1.5688   -2.7915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2805   -0.2102   -3.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7703   -1.4895   -0.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7270   -1.8656   -2.7268 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0426   -1.3255   -1.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4574   -2.4236   -0.1050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0157   -0.5225    1.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8505   -2.2125    2.7704 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9154   -2.8982    1.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0911   -2.0619    2.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1835   -1.2168    0.9840 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6282    0.0955   -0.0193 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1225   -1.5618   -0.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6737    0.2708    3.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3795    0.2561    2.8586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3937    2.5134    2.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0416    2.0375    1.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1182    1.9704    2.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8315    3.1081    0.9559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1807    2.4866   -1.4370 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2217    0.8049   -1.9486 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4605    1.4563   -0.8868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5882    0.9400    0.6374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2813    4.1429    0.2266 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0
  3  2  1  0
  2 15  1  0
 13  6  1  0
 13 14  1  6
  7  8  1  1
 11 10  1  0
 15 16  1  0
 11 12  1  0
  7  9  1  0
 10  7  1  0
  2  1  2  3
  7  6  1  0
 16 18  1  0
 13 12  1  0
 16 17  2  0
 13 15  1  0
  3  4  1  0
  6  5  1  0
  6 25  1  1
 11 34  1  0
 11 35  1  0
 10 32  1  0
 10 33  1  0
 12 36  1  0
 12 37  1  0
  5 23  1  0
  5 24  1  0
  3 21  1  1
 15 41  1  1
 14 38  1  0
 14 39  1  0
 14 40  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
  9 31  1  0
  1 19  1  0
  1 20  1  0
 18 42  1  0
  4 22  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.983   0.548  -2.502  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.397   0.227  -1.333  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.090  -1.206  -0.935  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.330  -2.114  -2.006  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.359  -1.394  -0.465  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.742  -0.384   0.636  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.099  -0.698   1.365  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.978  -2.045   2.128  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.313  -0.845   0.429  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.378   0.391   2.431  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.247   1.817   1.912  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.873   2.067   1.297  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.529   1.099   0.136  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.393   1.468  -1.096  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.998   1.234  -0.246  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.406   2.691  -0.512  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.164   3.377  -1.492  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.089   3.228   0.523  0.00  0.00           O+0
HETATM   19  H   UNK     0      -2.212   1.569  -2.792  0.00  0.00           H+0
HETATM   20  H   UNK     0      -2.281  -0.210  -3.221  0.00  0.00           H+0
HETATM   21  H   UNK     0      -1.770  -1.490  -0.123  0.00  0.00           H+0
HETATM   22  H   UNK     0      -0.727  -1.866  -2.727  0.00  0.00           H+0
HETATM   23  H   UNK     0       1.043  -1.325  -1.319  0.00  0.00           H+0
HETATM   24  H   UNK     0       0.457  -2.424  -0.105  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.016  -0.523   1.426  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.850  -2.212   2.770  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.915  -2.898   1.445  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.091  -2.062   2.772  0.00  0.00           H+0
HETATM   29  H   UNK     0       4.184  -1.217   0.984  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.628   0.096  -0.019  0.00  0.00           H+0
HETATM   31  H   UNK     0       3.123  -1.562  -0.376  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.674   0.271   3.266  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.380   0.256   2.859  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.394   2.513   2.747  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.042   2.038   1.192  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.118   1.970   2.089  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.832   3.108   0.956  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.181   2.487  -1.437  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.222   0.805  -1.949  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.461   1.456  -0.887  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.588   0.940   0.637  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.281   4.143   0.227  0.00  0.00           H+0
CONECT    1    2   19   20                                                  
CONECT    2    3   15    1                                                  
CONECT    3    5    2    4   21                                             
CONECT    4    3   22                                                       
CONECT    5    3    6   23   24                                             
CONECT    6   13    7    5   25                                             
CONECT    7    8    9   10    6                                             
CONECT    8    7   26   27   28                                             
CONECT    9    7   29   30   31                                             
CONECT   10   11    7   32   33                                             
CONECT   11   10   12   34   35                                             
CONECT   12   11   13   36   37                                             
CONECT   13    6   14   12   15                                             
CONECT   14   13   38   39   40                                             
CONECT   15    2   16   13   41                                             
CONECT   16   15   18   17                                                  
CONECT   17   16                                                            
CONECT   18   16   42                                                       
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    3                                                            
CONECT   22    4                                                            
CONECT   23    5                                                            
CONECT   24    5                                                            
CONECT   25    6                                                            
CONECT   26    8                                                            
CONECT   27    8                                                            
CONECT   28    8                                                            
CONECT   29    9                                                            
CONECT   30    9                                                            
CONECT   31    9                                                            
CONECT   32   10                                                            
CONECT   33   10                                                            
CONECT   34   11                                                            
CONECT   35   11                                                            
CONECT   36   12                                                            
CONECT   37   12                                                            
CONECT   38   14                                                            
CONECT   39   14                                                            
CONECT   40   14                                                            
CONECT   41   15                                                            
CONECT   42   18                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   86    0
END

RDKit          3D

42 43  0  0  0  0  0  0  0  0999 V2000
   -1.9834    0.5483   -2.5025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3969    0.2274   -1.3333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0903   -1.2063   -0.9353 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3304   -2.1138   -2.0060 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3591   -1.3936   -0.4651 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7422   -0.3837    0.6364 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0985   -0.6977    1.3653 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9776   -2.0448    2.1281 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3128   -0.8453    0.4291 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3778    0.3912    2.4308 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2473    1.8172    1.9123 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8731    2.0665    1.2974 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5286    1.0986    0.1360 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3928    1.4680   -1.0963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9983    1.2343   -0.2459 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4062    2.6914   -0.5120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1639    3.3765   -1.4920 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0893    3.2285    0.5233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2124    1.5688   -2.7915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2805   -0.2102   -3.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7703   -1.4895   -0.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7270   -1.8656   -2.7268 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0426   -1.3255   -1.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4574   -2.4236   -0.1050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0157   -0.5225    1.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8505   -2.2125    2.7704 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9154   -2.8982    1.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0911   -2.0619    2.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1835   -1.2168    0.9840 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6282    0.0955   -0.0193 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1225   -1.5618   -0.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6737    0.2708    3.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3795    0.2561    2.8586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3937    2.5134    2.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0416    2.0375    1.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1182    1.9704    2.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8315    3.1081    0.9559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1807    2.4866   -1.4370 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2217    0.8049   -1.9486 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4605    1.4563   -0.8868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5882    0.9400    0.6374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2813    4.1429    0.2266 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0
  3  2  1  0
  2 15  1  0
 13  6  1  0
 13 14  1  6
  7  8  1  1
 11 10  1  0
 15 16  1  0
 11 12  1  0
  7  9  1  0
 10  7  1  0
  2  1  2  3
  7  6  1  0
 16 18  1  0
 13 12  1  0
 16 17  2  0
 13 15  1  0
  3  4  1  0
  6  5  1  0
  6 25  1  1
 11 34  1  0
 11 35  1  0
 10 32  1  0
 10 33  1  0
 12 36  1  0
 12 37  1  0
  5 23  1  0
  5 24  1  0
  3 21  1  1
 15 41  1  1
 14 38  1  0
 14 39  1  0
 14 40  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
  9 31  1  0
  1 19  1  0
  1 20  1  0
 18 42  1  0
  4 22  1  0
M  END

View in JSmol

Synonyms

Value	Source
(1R,3S,4AS,8as)-3-hydroxy-5,5,8a-trimethyl-2-methylidene-decahydronaphthalene-1-carboxylate	Generator
Laricinolate	Generator

Chemical Formula

C₁₅H₂₄O₃

Average Mass

252.3540 Da

Monoisotopic Mass

252.17254 Da

IUPAC Name

(1R,3S,4aS,8aS)-3-hydroxy-5,5,8a-trimethyl-2-methylidene-decahydronaphthalene-1-carboxylic acid

Traditional Name

(1R,3S,4aS,8aS)-3-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1H-naphthalene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H24O3/c1-9-10(16)8-11-14(2,3)6-5-7-15(11,4)12(9)13(17)18/h10-12,16H,1,5-8H2,2-4H3,(H,17,18)/t10-,11-,12+,15-/m0/s1

InChI Key

HHNLQWOVCRXGMP-OHTBPHCPSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, 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
Fomitopsis officinalis	LOTUS Database	35616633
Stereum ostrea	JEOL database	Kim, Y.-H., et al, J. Antibiotics 59, 432 (2006).

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic alcohols and derivatives. These are organic compounds containing an aliphatic ring substituted with at least one hydroxyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Cyclic alcohols and derivatives

Alternative Parents

Substituents

Cyclic alcohol
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	2.63	ALOGPS
logP	2.49	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	4.72	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	69.68 m³·mol⁻¹	ChemAxon
Polarizability	28.26 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8690381

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10514980

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kim, Y.-H., et al. (2006). Kim, Y.-H., et al, J. Antibiotics 59, 432 (2006).. J. Antibiotics.

Showing NP-Card for laricinolic acid (NP0030204)

MOL for NP0030204 (laricinolic acid)

3D MOL for NP0030204 (laricinolic acid)

3D SDF for NP0030204 (laricinolic acid)

3D-SDF for NP0030204 (laricinolic acid)

PDB for NP0030204 (laricinolic acid)

3D PDB for NP0030204 (laricinolic acid)

SMILES for NP0030204 (laricinolic acid)

INCHI for NP0030204 (laricinolic acid)

Structure for NP0030204 (laricinolic acid)

3D Structure for NP0030204 (laricinolic acid)