NP-MRD: Showing NP-Card for 13,14-dihydroxymulin-11-en-20-oic acid (NP0027680)

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Record Information

Version

2.0

Created at

2021-06-19 19:46:11 UTC

Updated at

2021-06-29 23:53:56 UTC

NP-MRD ID

NP0027680

Secondary Accession Numbers

None

Natural Product Identification

Common Name

13,14-dihydroxymulin-11-en-20-oic acid

Provided By

JEOL Database JEOL Logo

Description

13,14-dihydroxymulin-11-en-20-oic acid is found in Azorella compacta and Azorella prolifera. 13,14-dihydroxymulin-11-en-20-oic acid was first documented in 2004 (Loyola, L. A., et al.). Based on a literature review very few articles have been published on 14-Hydroxymulin-11-en-20-oic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192121463D          

 56 58  0  0  0  0            999 V2000
    4.1519   -1.4661   -2.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6989   -1.0074   -2.5151 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.8957    1.2999    0.4486 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5702    0.5606    0.2868 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7494    1.2811    0.6178 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6441    2.0988    1.8782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7759    1.7308    3.1597 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306192121463D          

 56 58  0  0  0  0            999 V2000
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    2.6989   -1.0074   -2.5151 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9337   -2.1343   -3.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2387    1.2767    1.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8323    2.3531    0.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6514   -0.2842    0.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9177    2.0341   -0.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3972    3.1475    1.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6269    2.5251    3.8930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5388    1.0463    5.7526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4375   -0.4489    5.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2845    1.0825    5.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8797    0.1745    3.7792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1644    0.1496    3.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5314   -2.0377    3.8489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0899   -1.4363    1.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7977   -1.5173    1.3355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4078    1.6538    1.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1491    0.4160    0.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3405    1.8069   -0.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1485    0.2983   -1.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6685   -1.2007   -0.9413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6158   -1.4967   -2.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3333   -1.8984   -0.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5827    2.7140   -2.8765 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 17  1  0  0  0  0
 16 14  1  0  0  0  0
  7  6  1  0  0  0  0
 10 11  1  0  0  0  0
 14 11  1  0  0  0  0
  6  5  1  0  0  0  0
 11 12  1  0  0  0  0
  5  4  1  0  0  0  0
 17 18  1  6  0  0  0
  4 21  1  0  0  0  0
  8 38  1  6  0  0  0
 21  7  1  0  0  0  0
  4  2  1  0  0  0  0
 21 22  1  6  0  0  0
 17  8  1  0  0  0  0
  2  1  1  0  0  0  0
  7  8  1  0  0  0  0
  2  3  1  0  0  0  0
  8  9  1  0  0  0  0
 22 24  1  0  0  0  0
 21 20  1  0  0  0  0
  7 37  1  1  0  0  0
 17 16  1  0  0  0  0
 22 23  2  0  0  0  0
 20 19  1  0  0  0  0
 14 15  1  0  0  0  0
  9 10  2  0  0  0  0
 11 13  1  1  0  0  0
 20 54  1  0  0  0  0
 20 55  1  0  0  0  0
 19 52  1  0  0  0  0
 19 53  1  0  0  0  0
  6 35  1  0  0  0  0
  6 36  1  0  0  0  0
  5 33  1  0  0  0  0
  5 34  1  0  0  0  0
  4 32  1  1  0  0  0
  9 39  1  0  0  0  0
 16 47  1  0  0  0  0
 16 48  1  0  0  0  0
 10 40  1  0  0  0  0
 14 45  1  6  0  0  0
 12 41  1  0  0  0  0
 12 42  1  0  0  0  0
 12 43  1  0  0  0  0
 18 49  1  0  0  0  0
 18 50  1  0  0  0  0
 18 51  1  0  0  0  0
  2 28  1  6  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  3 29  1  0  0  0  0
  3 30  1  0  0  0  0
  3 31  1  0  0  0  0
 24 56  1  0  0  0  0
 15 46  1  0  0  0  0
 13 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0027680

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@]12C([H])([H])C([H])([H])[C@@]3(C([H])([H])[H])C([H])([H])[C@@]([H])(O[H])[C@@](O[H])(C([H])=C([H])[C@@]3([H])[C@]1([H])C([H])([H])C([H])([H])[C@]2([H])C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O4/c1-12(2)13-5-6-15-14-7-8-19(4,24)16(21)11-18(14,3)9-10-20(13,15)17(22)23/h7-8,12-16,21,24H,5-6,9-11H2,1-4H3,(H,22,23)/t13-,14+,15+,16-,18+,19+,20+/m1/s1

> <INCHI_KEY>
VCHZZEWOPLDLLE-DXGFZXISSA-N

> <FORMULA>
C20H32O4

> <MOLECULAR_WEIGHT>
336.472

> <EXACT_MASS>
336.23005951

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
37.8094164812591

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,3aS,5aS,7R,8S,10aS,10bS)-7,8-dihydroxy-5a,8-dimethyl-3-(propan-2-yl)-1H,2H,3H,3aH,4H,5H,5aH,6H,7H,8H,10aH,10bH-cyclohepta[e]indene-3a-carboxylic acid

> <ALOGPS_LOGP>
3.01

> <JCHEM_LOGP>
3.089645264333334

> <ALOGPS_LOGS>
-3.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.496990991250254

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.6717593515931535

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2639645542156517

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
93.59739999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.13e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,3aS,5aS,7R,8S,10aS,10bS)-7,8-dihydroxy-3-isopropyl-5a,8-dimethyl-1H,2H,3H,4H,5H,6H,7H,10aH,10bH-cyclohepta[e]indene-3a-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 56 58  0  0  0  0  0  0  0  0999 V2000
    4.1519   -1.4661   -2.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6989   -1.0074   -2.5151 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9337   -2.1343   -3.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0586   -0.5827   -1.1672 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8688    0.5405   -0.4619 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8957    1.2999    0.4486 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5702    0.5606    0.2868 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7494    1.2811    0.6178 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6441    2.0988    1.8782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7759    1.7308    3.1597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0690    0.3717    3.7367 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3587    0.5245    5.2431 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1243   -0.4231    3.6429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2257   -0.4058    3.0552 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4251   -1.6491    3.7654 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9911   -0.8143    1.5955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9598    0.2934    0.5082 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2877    1.0870    0.5472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8954   -0.4234   -0.8832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5326   -1.0604   -1.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6062   -0.0249   -1.1487 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4163    0.9739   -2.3035 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0338    0.6988   -3.4311 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7389    2.2473   -2.0283 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7799   -0.6561   -1.9290 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5944   -1.7907   -3.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2076   -2.3044   -1.6093 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7271   -0.1463   -3.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9831   -1.7815   -3.6159 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7367   -2.9659   -2.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5018   -2.5273   -4.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0858   -1.4622   -0.5053 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6935    0.1168    0.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042    1.2362   -1.1889 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2387    1.2767    1.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8323    2.3531    0.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6514   -0.2842    0.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9177    2.0341   -0.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3972    3.1475    1.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6269    2.5251    3.8930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5388    1.0463    5.7526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4375   -0.4489    5.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2845    1.0825    5.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8797    0.1745    3.7792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1644    0.1496    3.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5314   -2.0377    3.8489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0899   -1.4363    1.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7977   -1.5173    1.3355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4078    1.6538    1.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1491    0.4160    0.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3405    1.8069   -0.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1485    0.2983   -1.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6685   -1.2007   -0.9413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6158   -1.4967   -2.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3333   -1.8984   -0.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5827    2.7140   -2.8765 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 17  1  0
 16 14  1  0
  7  6  1  0
 10 11  1  0
 14 11  1  0
  6  5  1  0
 11 12  1  0
  5  4  1  0
 17 18  1  6
  4 21  1  0
  8 38  1  6
 21  7  1  0
  4  2  1  0
 21 22  1  6
 17  8  1  0
  2  1  1  0
  7  8  1  0
  2  3  1  0
  8  9  1  0
 22 24  1  0
 21 20  1  0
  7 37  1  1
 17 16  1  0
 22 23  2  0
 20 19  1  0
 14 15  1  0
  9 10  2  0
 11 13  1  1
 20 54  1  0
 20 55  1  0
 19 52  1  0
 19 53  1  0
  6 35  1  0
  6 36  1  0
  5 33  1  0
  5 34  1  0
  4 32  1  1
  9 39  1  0
 16 47  1  0
 16 48  1  0
 10 40  1  0
 14 45  1  6
 12 41  1  0
 12 42  1  0
 12 43  1  0
 18 49  1  0
 18 50  1  0
 18 51  1  0
  2 28  1  6
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
 24 56  1  0
 15 46  1  0
 13 44  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       4.152  -1.466  -2.312  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.699  -1.007  -2.515  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.934  -2.134  -3.212  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.059  -0.583  -1.167  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.869   0.541  -0.462  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.896   1.300   0.449  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.570   0.561   0.287  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.749   1.281   0.618  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.644   2.099   1.878  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.776   1.731   3.160  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.069   0.372   3.737  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.359   0.525   5.243  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.124  -0.423   3.643  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.226  -0.406   3.055  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.425  -1.649   3.765  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.991  -0.814   1.595  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.960   0.293   0.508  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.288   1.087   0.547  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.895  -0.423  -0.883  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.533  -1.060  -1.226  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.606  -0.025  -1.149  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.416   0.974  -2.304  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.034   0.699  -3.431  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.739   2.247  -2.028  0.00  0.00           O+0
HETATM   25  H   UNK     0       4.780  -0.656  -1.929  0.00  0.00           H+0
HETATM   26  H   UNK     0       4.594  -1.791  -3.260  0.00  0.00           H+0
HETATM   27  H   UNK     0       4.208  -2.304  -1.609  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.727  -0.146  -3.194  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.983  -1.782  -3.616  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.737  -2.966  -2.527  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.502  -2.527  -4.063  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.086  -1.462  -0.505  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.693   0.117   0.122  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.304   1.236  -1.189  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.239   1.277   1.489  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.832   2.353   0.158  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.651  -0.284   0.987  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.918   2.034  -0.165  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.397   3.147   1.698  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.627   2.525   3.893  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.539   1.046   5.753  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.438  -0.449   5.740  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.285   1.083   5.421  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.880   0.175   3.779  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.164   0.150   3.151  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.531  -2.038   3.849  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.090  -1.436   1.546  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.798  -1.517   1.335  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.408   1.654   1.475  0.00  0.00           H+0
HETATM   50  H   UNK     0      -4.149   0.416   0.453  0.00  0.00           H+0
HETATM   51  H   UNK     0      -3.341   1.807  -0.278  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.148   0.298  -1.671  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.668  -1.201  -0.941  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.616  -1.497  -2.225  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.333  -1.898  -0.548  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.583   2.714  -2.877  0.00  0.00           H+0
CONECT    1    2   25   26   27                                             
CONECT    2    4    1    3   28                                             
CONECT    3    2   29   30   31                                             
CONECT    4    5   21    2   32                                             
CONECT    5    6    4   33   34                                             
CONECT    6    7    5   35   36                                             
CONECT    7    6   21    8   37                                             
CONECT    8   38   17    7    9                                             
CONECT    9    8   10   39                                                  
CONECT   10   11    9   40                                                  
CONECT   11   10   14   12   13                                             
CONECT   12   11   41   42   43                                             
CONECT   13   11   44                                                       
CONECT   14   16   11   15   45                                             
CONECT   15   14   46                                                       
CONECT   16   14   17   47   48                                             
CONECT   17   19   18    8   16                                             
CONECT   18   17   49   50   51                                             
CONECT   19   17   20   52   53                                             
CONECT   20   21   19   54   55                                             
CONECT   21    4    7   22   20                                             
CONECT   22   21   24   23                                                  
CONECT   23   22                                                            
CONECT   24   22   56                                                       
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    2                                                            
CONECT   29    3                                                            
CONECT   30    3                                                            
CONECT   31    3                                                            
CONECT   32    4                                                            
CONECT   33    5                                                            
CONECT   34    5                                                            
CONECT   35    6                                                            
CONECT   36    6                                                            
CONECT   37    7                                                            
CONECT   38    8                                                            
CONECT   39    9                                                            
CONECT   40   10                                                            
CONECT   41   12                                                            
CONECT   42   12                                                            
CONECT   43   12                                                            
CONECT   44   13                                                            
CONECT   45   14                                                            
CONECT   46   15                                                            
CONECT   47   16                                                            
CONECT   48   16                                                            
CONECT   49   18                                                            
CONECT   50   18                                                            
CONECT   51   18                                                            
CONECT   52   19                                                            
CONECT   53   19                                                            
CONECT   54   20                                                            
CONECT   55   20                                                            
CONECT   56   24                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  116    0
END

RDKit          3D

56 58  0  0  0  0  0  0  0  0999 V2000
    4.1519   -1.4661   -2.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6989   -1.0074   -2.5151 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.8688    0.5405   -0.4619 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8957    1.2999    0.4486 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5702    0.5606    0.2868 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.1243   -0.4231    3.6429 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6062   -0.0249   -1.1487 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4163    0.9739   -2.3035 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0338    0.6988   -3.4311 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7389    2.2473   -2.0283 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7799   -0.6561   -1.9290 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5944   -1.7907   -3.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2076   -2.3044   -1.6093 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7271   -0.1463   -3.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9831   -1.7815   -3.6159 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7367   -2.9659   -2.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5018   -2.5273   -4.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0858   -1.4622   -0.5053 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6935    0.1168    0.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042    1.2362   -1.1889 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2387    1.2767    1.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8323    2.3531    0.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6514   -0.2842    0.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9177    2.0341   -0.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3972    3.1475    1.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6269    2.5251    3.8930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5388    1.0463    5.7526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4375   -0.4489    5.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2845    1.0825    5.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8797    0.1745    3.7792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1644    0.1496    3.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5314   -2.0377    3.8489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0899   -1.4363    1.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7977   -1.5173    1.3355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4078    1.6538    1.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1491    0.4160    0.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3405    1.8069   -0.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1485    0.2983   -1.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6685   -1.2007   -0.9413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6158   -1.4967   -2.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3333   -1.8984   -0.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5827    2.7140   -2.8765 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 17  1  0
 16 14  1  0
  7  6  1  0
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 11 12  1  0
  5  4  1  0
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  4 21  1  0
  8 38  1  6
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  4  2  1  0
 21 22  1  6
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  2  1  1  0
  7  8  1  0
  2  3  1  0
  8  9  1  0
 22 24  1  0
 21 20  1  0
  7 37  1  1
 17 16  1  0
 22 23  2  0
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 14 15  1  0
  9 10  2  0
 11 13  1  1
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  6 35  1  0
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  5 33  1  0
  5 34  1  0
  4 32  1  1
  9 39  1  0
 16 47  1  0
 16 48  1  0
 10 40  1  0
 14 45  1  6
 12 41  1  0
 12 42  1  0
 12 43  1  0
 18 49  1  0
 18 50  1  0
 18 51  1  0
  2 28  1  6
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
 24 56  1  0
 15 46  1  0
 13 44  1  0
M  END

View in JSmol

Synonyms

Value	Source
14-Hydroxymulin-11-en-20-Oate	Generator

Chemical Formula

C₂₀H₃₂O₄

Average Mass

336.4720 Da

Monoisotopic Mass

336.23006 Da

IUPAC Name

(3R,3aS,5aS,7R,8S,10aS,10bS)-7,8-dihydroxy-5a,8-dimethyl-3-(propan-2-yl)-1H,2H,3H,3aH,4H,5H,5aH,6H,7H,8H,10aH,10bH-cyclohepta[e]indene-3a-carboxylic acid

Traditional Name

(3R,3aS,5aS,7R,8S,10aS,10bS)-7,8-dihydroxy-3-isopropyl-5a,8-dimethyl-1H,2H,3H,4H,5H,6H,7H,10aH,10bH-cyclohepta[e]indene-3a-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)[C@]12C([H])([H])C([H])([H])[C@@]3(C([H])([H])[H])C([H])([H])[C@@]([H])(O[H])[C@@](O[H])(C([H])=C([H])[C@@]3([H])[C@]1([H])C([H])([H])C([H])([H])[C@]2([H])C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C20H32O4/c1-12(2)13-5-6-15-14-7-8-19(4,24)16(21)11-18(14,3)9-10-20(13,15)17(22)23/h7-8,12-16,21,24H,5-6,9-11H2,1-4H3,(H,22,23)/t13-,14+,15+,16-,18+,19+,20+/m1/s1

InChI Key

VCHZZEWOPLDLLE-DXGFZXISSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₅D₅N, 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
Azorella compacta	JEOL database	Loyola, L. A., et al, Phytochemistry 65, 1931 (2004)
Azorella prolifera	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as valparane and mulinane diterpenoids. These are diterpenoids with a structure based on either the valparane or mulinane skeleton. Valparane and mulinane are tricyclic compounds containing a tetradecahydrocyclohepta[e]indene skeleton. Valparane carries a 1-methylethyl at the 3-position, as well as three methyl groups at the 5a-, 8-, and 10b-position of the ring system. Mulinane carries a 1-methylethyl at the 3-position, as well as three methyl groups at the 3a-, 5a-, and 8-position of the ring system.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Valparane and mulinane diterpenoids

Alternative Parents

Substituents

Valparane or mulinane diterpenoid
Tertiary alcohol
Secondary alcohol
1,2-diol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	3.01	ALOGPS
logP	3.09	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	4.67	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	93.6 m³·mol⁻¹	ChemAxon
Polarizability	37.81 Å³	ChemAxon
Number of Rings	3	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

9177406

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11002214

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Loyola, L. A., et al. (2004). Loyola, L. A., et al, Phytochemistry 65, 1931 (2004). Phytochem..

Showing NP-Card for 13,14-dihydroxymulin-11-en-20-oic acid (NP0027680)

MOL for NP0027680 (13,14-dihydroxymulin-11-en-20-oic acid)

3D MOL for NP0027680 (13,14-dihydroxymulin-11-en-20-oic acid)

3D SDF for NP0027680 (13,14-dihydroxymulin-11-en-20-oic acid)

3D-SDF for NP0027680 (13,14-dihydroxymulin-11-en-20-oic acid)

PDB for NP0027680 (13,14-dihydroxymulin-11-en-20-oic acid)

3D PDB for NP0027680 (13,14-dihydroxymulin-11-en-20-oic acid)

SMILES for NP0027680 (13,14-dihydroxymulin-11-en-20-oic acid)

INCHI for NP0027680 (13,14-dihydroxymulin-11-en-20-oic acid)

Structure for NP0027680 (13,14-dihydroxymulin-11-en-20-oic acid)

3D Structure for NP0027680 (13,14-dihydroxymulin-11-en-20-oic acid)