NP-MRD: Showing NP-Card for (1s,2s)-6-[(3e,5e,7e,9e,11e,13e,15e)-16-[(2r,6s,7ar)-6-hydroxy-4,4-dimethyl-5,6,7,7a-tetrahydro-2h-1-benzofuran-2-yl]-3,7,12-trimethylheptadeca-1,3,5,7,9,11,13,15-octaen-1-ylidene]-1,5,5-trimethylcyclohexane-1,2-diol (NP0220478)

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Record Information

Version

2.0

Created at

2022-09-05 21:48:10 UTC

Updated at

2022-09-05 21:48:10 UTC

NP-MRD ID

NP0220478

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s)-6-[(3e,5e,7e,9e,11e,13e,15e)-16-[(2r,6s,7ar)-6-hydroxy-4,4-dimethyl-5,6,7,7a-tetrahydro-2h-1-benzofuran-2-yl]-3,7,12-trimethylheptadeca-1,3,5,7,9,11,13,15-octaen-1-ylidene]-1,5,5-trimethylcyclohexane-1,2-diol

Description

(1S,2S)-6-[(3E,5E,7E,9E,11E,13E,15E)-16-[(2R,6S,7aR)-6-hydroxy-4,4-dimethyl-2,4,5,6,7,7a-hexahydro-1-benzofuran-2-yl]-3,7,12-trimethylheptadeca-1,3,5,7,9,11,13,15-octaen-1-ylidene]-1,5,5-trimethylcyclohexane-1,2-diol belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (1s,2s)-6-[(3e,5e,7e,9e,11e,13e,15e)-16-[(2r,6s,7ar)-6-hydroxy-4,4-dimethyl-5,6,7,7a-tetrahydro-2h-1-benzofuran-2-yl]-3,7,12-trimethylheptadeca-1,3,5,7,9,11,13,15-octaen-1-ylidene]-1,5,5-trimethylcyclohexane-1,2-diol is found in Rosa villosa. Based on a literature review very few articles have been published on (1S,2S)-6-[(3E,5E,7E,9E,11E,13E,15E)-16-[(2R,6S,7aR)-6-hydroxy-4,4-dimethyl-2,4,5,6,7,7a-hexahydro-1-benzofuran-2-yl]-3,7,12-trimethylheptadeca-1,3,5,7,9,11,13,15-octaen-1-ylidene]-1,5,5-trimethylcyclohexane-1,2-diol.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052223482D          

 43 45  0  0  1  0            999 V2000
   -8.8784    5.0178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2909    4.3034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1159    4.3034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5284    5.0178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9409    5.7323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7659    5.7323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6227    4.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5412    5.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1784    6.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7659    7.1612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9409    7.1612    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  -10.5284    7.8757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5284    6.4468    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.8000    6.8341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8000    6.0595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8784    3.5889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0534    3.5889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6409    2.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8159    2.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4034    3.5889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4034    2.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5784    2.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1659    1.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3409    1.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9284    0.7310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3409    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1034    0.7310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7845    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7429   -2.2514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9683   -2.2514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  1  0  0  0
  2 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
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 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
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 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 32 30  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  1  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 34 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
 35 43  1  6  0  0  0
 32 43  1  0  0  0  0
M  END


  Mrv1652309052223482D          

 43 45  0  0  1  0            999 V2000
   -8.8784    5.0178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2909    4.3034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1159    4.3034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5284    5.0178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9409    5.7323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7659    5.7323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6227    4.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5412    5.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1784    6.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7659    7.1612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9409    7.1612    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  -10.5284    7.8757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5284    6.4468    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.8000    6.8341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8000    6.0595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8784    3.5889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0534    3.5889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6409    2.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8159    2.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4034    3.5889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4034    2.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5784    2.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1659    1.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3409    1.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9284    0.7310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3409    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1034    0.7310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7845    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7429   -2.2514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9683   -2.2514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  1  0  0  0
  2 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 32 30  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  1  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 34 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
 35 43  1  6  0  0  0
 32 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0220478

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(\C=C\C=C(/C)C=C=C1C(C)(C)CC[C@H](O)[C@@]1(C)O)=C/C=C/C=C(\C)/C=C/C=C(\C)[C@@H]1O[C@@H]2C[C@@H](O)CC(C)(C)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C39H54O4/c1-27(16-12-17-29(3)20-21-35-37(5,6)23-22-36(41)39(35,9)42)14-10-11-15-28(2)18-13-19-30(4)33-25-32-34(43-33)24-31(40)26-38(32,7)8/h10-20,25,31,33-34,36,40-42H,22-24,26H2,1-9H3/b11-10+,16-12+,18-13+,27-14+,28-15+,29-17+,30-19+/t21?,31-,33-,34-,36+,39+/m1/s1

> <INCHI_KEY>
PVEQEACTAZYHGN-XWEYLWSRSA-N

> <FORMULA>
C39H54O4

> <MOLECULAR_WEIGHT>
586.857

> <EXACT_MASS>
586.402210219

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
97

> <JCHEM_AVERAGE_POLARIZABILITY>
71.9654681413822

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S)-6-[(3E,5E,7E,9E,11E,13E,15E)-16-[(2R,6S,7aR)-6-hydroxy-4,4-dimethyl-2,4,5,6,7,7a-hexahydro-1-benzofuran-2-yl]-3,7,12-trimethylheptadeca-1,3,5,7,9,11,13,15-octaen-1-ylidene]-1,5,5-trimethylcyclohexane-1,2-diol

> <JCHEM_LOGP>
6.524893561999999

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.632050742694496

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.132826565547404

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7384960057591785

> <JCHEM_POLAR_SURFACE_AREA>
69.92

> <JCHEM_REFRACTIVITY>
189.00330000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S)-6-[(3E,5E,7E,9E,11E,13E,15E)-16-[(2R,6S,7aR)-6-hydroxy-4,4-dimethyl-5,6,7,7a-tetrahydro-2H-1-benzofuran-2-yl]-3,7,12-trimethylheptadeca-1,3,5,7,9,11,13,15-octaen-1-ylidene]-1,5,5-trimethylcyclohexane-1,2-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0     -16.573   9.367   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -17.343   8.033   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -18.883   8.033   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -19.653   9.367   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -20.423  10.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -21.963  10.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -21.696   9.184   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -23.410  10.174   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -22.733  12.034   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -21.963  13.368   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -20.423  13.368   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0     -19.653  14.701   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0     -19.653  12.034   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -18.293  12.757   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0     -18.293  11.311   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0     -16.573   6.699   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -15.033   6.699   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -14.263   5.366   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -12.723   5.366   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -11.953   6.699   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -11.953   4.032   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -10.413   4.032   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -9.643   2.698   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -8.103   2.698   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -7.333   1.365   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -8.103   0.031   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -5.793   1.365   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.023   0.031   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.483   0.031   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.713  -1.303   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -3.483  -2.637   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.268  -2.549   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       5.198   0.237   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       3.253  -4.203   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       1.807  -4.203   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -0.268  -0.057   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    5   14   15                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    2   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   43                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   40                                                  
CONECT   35   34   36   43                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40                                                       
CONECT   40   39   34   41   42                                             
CONECT   41   40                                                            
CONECT   42   40                                                            
CONECT   43   35   32                                                       
MASTER        0    0    0    0    0    0    0    0   43    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₉H₅₄O₄

Average Mass

586.8570 Da

Monoisotopic Mass

586.40221 Da

IUPAC Name

Traditional Name

(1S,2S)-6-[(3E,5E,7E,9E,11E,13E,15E)-16-[(2R,6S,7aR)-6-hydroxy-4,4-dimethyl-5,6,7,7a-tetrahydro-2H-1-benzofuran-2-yl]-3,7,12-trimethylheptadeca-1,3,5,7,9,11,13,15-octaen-1-ylidene]-1,5,5-trimethylcyclohexane-1,2-diol

CAS Registry Number

Not Available

SMILES

C\C(\C=C\C=C(/C)C=C=C1C(C)(C)CC[C@H](O)[C@@]1(C)O)=C/C=C/C=C(\C)/C=C/C=C(\C)[C@@H]1O[C@@H]2C[C@@H](O)CC(C)(C)C2=C1

InChI Identifier

InChI=1S/C39H54O4/c1-27(16-12-17-29(3)20-21-35-37(5,6)23-22-36(41)39(35,9)42)14-10-11-15-28(2)18-13-19-30(4)33-25-32-34(43-33)24-31(40)26-38(32,7)8/h10-20,25,31,33-34,36,40-42H,22-24,26H2,1-9H3/b11-10+,16-12+,18-13+,27-14+,28-15+,29-17+,30-19+/t21?,31-,33-,34-,36+,39+/m1/s1

InChI Key

PVEQEACTAZYHGN-XWEYLWSRSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Rosa villosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Benzofuran
Tertiary alcohol
Dihydrofuran
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	6.52	ChemAxon
pKa (Strongest Acidic)	13.13	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.92 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	189 m³·mol⁻¹	ChemAxon
Polarizability	71.97 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163017400

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2s)-6-[(3e,5e,7e,9e,11e,13e,15e)-16-[(2r,6s,7ar)-6-hydroxy-4,4-dimethyl-5,6,7,7a-tetrahydro-2h-1-benzofuran-2-yl]-3,7,12-trimethylheptadeca-1,3,5,7,9,11,13,15-octaen-1-ylidene]-1,5,5-trimethylcyclohexane-1,2-diol (NP0220478)

MOL for NP0220478 ((1s,2s)-6-[(3e,5e,7e,9e,11e,13e,15e)-16-[(2r,6s,7ar)-6-hydroxy-4,4-dimethyl-5,6,7,7a-tetrahydro-2h-1-benzofuran-2-yl]-3,7,12-trimethylheptadeca-1,3,5,7,9,11,13,15-octaen-1-ylidene]-1,5,5-trimethylcyclohexane-1,2-diol)

3D MOL for NP0220478 ((1s,2s)-6-[(3e,5e,7e,9e,11e,13e,15e)-16-[(2r,6s,7ar)-6-hydroxy-4,4-dimethyl-5,6,7,7a-tetrahydro-2h-1-benzofuran-2-yl]-3,7,12-trimethylheptadeca-1,3,5,7,9,11,13,15-octaen-1-ylidene]-1,5,5-trimethylcyclohexane-1,2-diol)

3D SDF for NP0220478 ((1s,2s)-6-[(3e,5e,7e,9e,11e,13e,15e)-16-[(2r,6s,7ar)-6-hydroxy-4,4-dimethyl-5,6,7,7a-tetrahydro-2h-1-benzofuran-2-yl]-3,7,12-trimethylheptadeca-1,3,5,7,9,11,13,15-octaen-1-ylidene]-1,5,5-trimethylcyclohexane-1,2-diol)

3D-SDF for NP0220478 ((1s,2s)-6-[(3e,5e,7e,9e,11e,13e,15e)-16-[(2r,6s,7ar)-6-hydroxy-4,4-dimethyl-5,6,7,7a-tetrahydro-2h-1-benzofuran-2-yl]-3,7,12-trimethylheptadeca-1,3,5,7,9,11,13,15-octaen-1-ylidene]-1,5,5-trimethylcyclohexane-1,2-diol)

PDB for NP0220478 ((1s,2s)-6-[(3e,5e,7e,9e,11e,13e,15e)-16-[(2r,6s,7ar)-6-hydroxy-4,4-dimethyl-5,6,7,7a-tetrahydro-2h-1-benzofuran-2-yl]-3,7,12-trimethylheptadeca-1,3,5,7,9,11,13,15-octaen-1-ylidene]-1,5,5-trimethylcyclohexane-1,2-diol)

3D PDB for NP0220478 ((1s,2s)-6-[(3e,5e,7e,9e,11e,13e,15e)-16-[(2r,6s,7ar)-6-hydroxy-4,4-dimethyl-5,6,7,7a-tetrahydro-2h-1-benzofuran-2-yl]-3,7,12-trimethylheptadeca-1,3,5,7,9,11,13,15-octaen-1-ylidene]-1,5,5-trimethylcyclohexane-1,2-diol)

SMILES for NP0220478 ((1s,2s)-6-[(3e,5e,7e,9e,11e,13e,15e)-16-[(2r,6s,7ar)-6-hydroxy-4,4-dimethyl-5,6,7,7a-tetrahydro-2h-1-benzofuran-2-yl]-3,7,12-trimethylheptadeca-1,3,5,7,9,11,13,15-octaen-1-ylidene]-1,5,5-trimethylcyclohexane-1,2-diol)

INCHI for NP0220478 ((1s,2s)-6-[(3e,5e,7e,9e,11e,13e,15e)-16-[(2r,6s,7ar)-6-hydroxy-4,4-dimethyl-5,6,7,7a-tetrahydro-2h-1-benzofuran-2-yl]-3,7,12-trimethylheptadeca-1,3,5,7,9,11,13,15-octaen-1-ylidene]-1,5,5-trimethylcyclohexane-1,2-diol)

Structure for NP0220478 ((1s,2s)-6-[(3e,5e,7e,9e,11e,13e,15e)-16-[(2r,6s,7ar)-6-hydroxy-4,4-dimethyl-5,6,7,7a-tetrahydro-2h-1-benzofuran-2-yl]-3,7,12-trimethylheptadeca-1,3,5,7,9,11,13,15-octaen-1-ylidene]-1,5,5-trimethylcyclohexane-1,2-diol)

3D Structure for NP0220478 ((1s,2s)-6-[(3e,5e,7e,9e,11e,13e,15e)-16-[(2r,6s,7ar)-6-hydroxy-4,4-dimethyl-5,6,7,7a-tetrahydro-2h-1-benzofuran-2-yl]-3,7,12-trimethylheptadeca-1,3,5,7,9,11,13,15-octaen-1-ylidene]-1,5,5-trimethylcyclohexane-1,2-diol)