NP-MRD: Showing NP-Card for (4as)-5-hydroxy-7-isopropyl-6-methoxy-1,1-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid (NP0180096)

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Record Information

Version

2.0

Created at

2022-09-03 18:24:42 UTC

Updated at

2022-09-03 18:24:42 UTC

NP-MRD ID

NP0180096

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4as)-5-hydroxy-7-isopropyl-6-methoxy-1,1-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid

Description

12-Methoxycarnosic acid belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (4as)-5-hydroxy-7-isopropyl-6-methoxy-1,1-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid is found in Salvia apiana, Salvia lanigera, Salvia officinalis and Salvia tomentosa. (4as)-5-hydroxy-7-isopropyl-6-methoxy-1,1-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid was first documented in 2015 (PMID: 25537192). Based on a literature review a small amount of articles have been published on 12-Methoxycarnosic acid (PMID: 33228164) (PMID: 25801906) (PMID: 31547166) (PMID: 27059447).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032220242D          

 25 27  0  0  1  0            999 V2000
    3.5664   -1.7780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9906   -1.0703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5899   -0.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0140    0.3584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8389    0.3449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2397   -0.3763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2631    1.0525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6133    1.0795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7884    1.0931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3642    0.3855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0165   -0.0923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3408   -1.0433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5394    0.3990    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9401   -0.3222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7650   -0.3357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5159   -1.0298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1152   -0.3086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2903   -0.2951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1104    0.4260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3137    1.1336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4568    1.4285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4703    1.9436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1386    1.1201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5628    1.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3877    1.8142    0.0000 C   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  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 13 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  9 25  1  0  0  0  0
M  END

     RDKit          3D

 55 57  0  0  0  0  0  0  0  0999 V2000
   -3.6174    0.8829   -3.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3188   -0.2677   -2.2515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4412   -0.1221   -1.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9159    0.2089    0.0582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3713    0.4136    0.2736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6648    0.7980    1.7112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0618   -0.8850   -0.0876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0334    0.3547    1.1269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6833    0.1734    0.9709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1688   -0.1684   -0.2877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0645   -0.3046   -1.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6354   -0.6336   -2.5946 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2857   -0.3886   -0.4166 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5955   -0.4163   -1.8738 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8779    0.6441   -2.4728 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5959   -1.5929   -2.6302 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5937   -1.7811    0.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8673   -2.0449    0.7369 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5765   -0.9202    1.3887 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4692    0.3370    0.6178 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0373    1.5065    1.4185 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3128    0.2320   -0.6263 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0396    0.6955    0.2459 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3380    1.3047    1.4574 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3193    0.3606    2.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7195    0.9451   -3.1867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0808    0.8652   -4.0045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3152    1.7984   -2.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7519    1.2060   -0.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7496    0.9325    1.8462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1421    1.7033    2.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3753   -0.0716    2.3464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9794   -1.0465    0.5129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3026   -0.8533   -1.1679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3360   -1.7323    0.0442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4129    0.6193    2.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2957   -0.7277   -3.3408 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3114   -1.8575   -3.2674 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4888   -2.4980   -0.7892 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7514   -2.0947    0.7310 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7536   -2.8484    1.5292 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6024   -2.5249    0.0193 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6675   -1.1585    1.4913 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2264   -0.8226    2.4568 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0292    1.3172    2.5050 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5186    2.4364    1.1087 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1125    1.6680    1.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9525   -0.5987   -1.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2215    1.1674   -1.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3856    0.0392   -0.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1590    1.5502   -0.4498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7688    2.1867    1.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0387    1.5967    2.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1649    0.9513    2.8849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7058   -0.5352    2.5060 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  8  1  0
  8  9  2  0
  9 25  1  0
 25 24  1  0
 24 23  1  0
 23 20  1  0
 20 21  1  0
 20 22  1  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 13  1  0
 13 14  1  6
 14 16  1  0
 14 15  2  0
 13 10  1  0
 10 11  2  0
 11 12  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
 11  3  1  0
 10  9  1  0
 13 23  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  8 36  1  0
 25 54  1  0
 25 55  1  0
 24 52  1  0
 24 53  1  0
 23 51  1  6
 21 45  1  0
 21 46  1  0
 21 47  1  0
 22 48  1  0
 22 49  1  0
 22 50  1  0
 19 43  1  0
 19 44  1  0
 18 41  1  0
 18 42  1  0
 17 39  1  0
 17 40  1  0
 16 38  1  0
 12 37  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  7 35  1  0
M  END


  Mrv1652309032220242D          

 25 27  0  0  1  0            999 V2000
    3.5664   -1.7780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9906   -1.0703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5899   -0.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0140    0.3584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8389    0.3449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2397   -0.3763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2631    1.0525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6133    1.0795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7884    1.0931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3642    0.3855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0165   -0.0923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3408   -1.0433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5394    0.3990    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9401   -0.3222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7650   -0.3357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5159   -1.0298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1152   -0.3086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2903   -0.2951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1104    0.4260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3137    1.1336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4568    1.4285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4703    1.9436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1386    1.1201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5628    1.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3877    1.8142    0.0000 C   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  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 13 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  9 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0180096

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C=C2CCC3C(C)(C)CCC[C@@]3(C(O)=O)C2=C1O)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O4/c1-12(2)14-11-13-7-8-15-20(3,4)9-6-10-21(15,19(23)24)16(13)17(22)18(14)25-5/h11-12,15,22H,6-10H2,1-5H3,(H,23,24)/t15?,21-/m0/s1

> <INCHI_KEY>
QQNSARJGBPMQDI-FXMQYSIJSA-N

> <FORMULA>
C21H30O4

> <MOLECULAR_WEIGHT>
346.467

> <EXACT_MASS>
346.214409446

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
39.20748024308163

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4aS)-5-hydroxy-6-methoxy-1,1-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-4a-carboxylic acid

> <JCHEM_LOGP>
5.287528140666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.954102851953087

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.331572871998162

> <JCHEM_PKA_STRONGEST_BASIC>
-4.884940048366394

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
97.8881

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(4aS)-5-hydroxy-7-isopropyl-6-methoxy-1,1-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       6.657  -3.319   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.449  -1.998   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.701  -0.652   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.493   0.669   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.033   0.644   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.781  -0.702   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.824   1.965   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.745   2.015   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.205   2.040   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.413   0.720   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.631  -0.172   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.370  -1.947   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.873   0.745   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.622  -0.601   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.161  -0.627   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.830  -1.922   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.082  -0.576   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.542  -0.551   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.206   0.795   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.586   2.116   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.853   2.666   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.878   3.628   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.125   2.091   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.917   3.412   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.457   3.387   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    4    9                                                       
CONECT    9    8   10   25                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10    3   12                                                  
CONECT   12   11                                                            
CONECT   13   10   14   17   23                                             
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   13   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20   13   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24    9                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Value	Source
12-Methoxycarnosate	Generator

Chemical Formula

C₂₁H₃₀O₄

Average Mass

346.4670 Da

Monoisotopic Mass

346.21441 Da

IUPAC Name

(4aS)-5-hydroxy-6-methoxy-1,1-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-4a-carboxylic acid

Traditional Name

(4aS)-5-hydroxy-7-isopropyl-6-methoxy-1,1-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid

CAS Registry Number

Not Available

SMILES

COC1=C(C=C2CCC3C(C)(C)CCC[C@@]3(C(O)=O)C2=C1O)C(C)C

InChI Identifier

InChI=1S/C21H30O4/c1-12(2)14-11-13-7-8-15-20(3,4)9-6-10-21(15,19(23)24)16(13)17(22)18(14)25-5/h11-12,15,22H,6-10H2,1-5H3,(H,23,24)/t15?,21-/m0/s1

InChI Key

QQNSARJGBPMQDI-FXMQYSIJSA-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
Salvia apiana	LOTUS Database	35616633
Salvia lanigera	LOTUS Database	35616633
Salvia officinalis	LOTUS Database	35616633
Salvia tomentosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Abietane diterpenoid
Phenanthrene
Hydrophenanthrene
1-naphthalenecarboxylic acid or derivatives
1-naphthalenecarboxylic acid
Tetralin
Anisole
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

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	5.29	ChemAxon
pKa (Strongest Acidic)	4.33	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	97.89 m³·mol⁻¹	ChemAxon
Polarizability	39.21 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

78430546

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

133554352

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Etsassala NGER, Badmus JA, Marnewick JL, Iwuoha EI, Nchu F, Hussein AA: Alpha-Glucosidase and Alpha-Amylase Inhibitory Activities, Molecular Docking, and Antioxidant Capacities of Salvia aurita Constituents. Antioxidants (Basel). 2020 Nov 19;9(11). pii: antiox9111149. doi: 10.3390/antiox9111149. [PubMed:33228164 ]
Exarchou V, Kanetis L, Charalambous Z, Apers S, Pieters L, Gekas V, Goulas V: HPLC-SPE-NMR characterization of major metabolites in Salvia fruticosa Mill. extract with antifungal potential: relevance of carnosic acid, carnosol, and hispidulin. J Agric Food Chem. 2015 Jan 21;63(2):457-63. doi: 10.1021/jf5050734. Epub 2015 Jan 12. [PubMed:25537192 ]
Borras-Linares I, Perez-Sanchez A, Lozano-Sanchez J, Barrajon-Catalan E, Arraez-Roman D, Cifuentes A, Micol V, Carretero AS: A bioguided identification of the active compounds that contribute to the antiproliferative/cytotoxic effects of rosemary extract on colon cancer cells. Food Chem Toxicol. 2015 Jun;80:215-222. doi: 10.1016/j.fct.2015.03.013. Epub 2015 Mar 20. [PubMed:25801906 ]
Etsassala NGER, Badmus JA, Waryo TT, Marnewick JL, Cupido CN, Hussein AA, Iwuoha EI: Alpha-Glucosidase and Alpha-Amylase Inhibitory Activities of Novel Abietane Diterpenes from Salvia africana-lutea. Antioxidants (Basel). 2019 Sep 20;8(10):421. doi: 10.3390/antiox8100421. [PubMed:31547166 ]
Kanetis L, Exarchou V, Charalambous Z, Goulas V: Edible coating composed of chitosan and Salvia fruticosa Mill. extract for the control of grey mould of table grapes. J Sci Food Agric. 2017 Jan;97(2):452-460. doi: 10.1002/jsfa.7745. Epub 2016 May 17. [PubMed:27059447 ]
LOTUS database [Link]

Showing NP-Card for (4as)-5-hydroxy-7-isopropyl-6-methoxy-1,1-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid (NP0180096)

MOL for NP0180096 ((4as)-5-hydroxy-7-isopropyl-6-methoxy-1,1-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid)

3D MOL for NP0180096 ((4as)-5-hydroxy-7-isopropyl-6-methoxy-1,1-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid)

3D SDF for NP0180096 ((4as)-5-hydroxy-7-isopropyl-6-methoxy-1,1-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid)

3D-SDF for NP0180096 ((4as)-5-hydroxy-7-isopropyl-6-methoxy-1,1-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid)

PDB for NP0180096 ((4as)-5-hydroxy-7-isopropyl-6-methoxy-1,1-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid)

3D PDB for NP0180096 ((4as)-5-hydroxy-7-isopropyl-6-methoxy-1,1-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid)

SMILES for NP0180096 ((4as)-5-hydroxy-7-isopropyl-6-methoxy-1,1-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid)

INCHI for NP0180096 ((4as)-5-hydroxy-7-isopropyl-6-methoxy-1,1-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid)

Structure for NP0180096 ((4as)-5-hydroxy-7-isopropyl-6-methoxy-1,1-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid)

3D Structure for NP0180096 ((4as)-5-hydroxy-7-isopropyl-6-methoxy-1,1-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid)