NP-MRD: Showing NP-Card for (4ar,10as)-8-hydroxy-7-isopropyl-1,1-dimethyl-5,6-dioxo-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid (NP0275686)

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Record Information

Version

2.0

Created at

2022-09-08 23:30:34 UTC

Updated at

2022-09-08 23:30:34 UTC

NP-MRD ID

NP0275686

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4ar,10as)-8-hydroxy-7-isopropyl-1,1-dimethyl-5,6-dioxo-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid

Description

Royleanonic acid, also known as royleanonate, belongs to the class of organic compounds known as 19-oxosteroids. These are steroid derivatives carrying a C=O group at the 19-position of the steroid skeleton. (4ar,10as)-8-hydroxy-7-isopropyl-1,1-dimethyl-5,6-dioxo-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid is found in Salvia plebeia. (4ar,10as)-8-hydroxy-7-isopropyl-1,1-dimethyl-5,6-dioxo-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid was first documented in 2004 (PMID: 15050633). Based on a literature review a small amount of articles have been published on Royleanonic acid (PMID: 29909523) (PMID: 22927089).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092201302D          

 25 27  0  0  1  0            999 V2000
    5.2397   -0.3763    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
    5.2631    1.0525    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
    3.6133    1.0795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0374    1.7872    0.0000 O   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
    3.5899   -0.3492    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
    1.5394    0.3990    0.0000 C   0  0  1  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
    1.5159   -1.0298    0.0000 O   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
    1.1152   -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  2  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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  6  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  6  0  0  0
 24 25  1  0  0  0  0
  7 25  1  0  0  0  0
M  END

     RDKit          3D

 51 53  0  0  0  0  0  0  0  0999 V2000
    5.4640    1.0121    0.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6456    0.4008   -0.6809 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2117   -0.9375   -0.9938 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2014    0.4329   -0.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4200   -0.5958   -0.4079 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9691   -1.8463   -0.7040 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9564   -0.5741   -0.1248 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3409    0.5472    0.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1530    1.7649    0.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6933    2.9137    0.4571 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5853    1.7342   -0.0838 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2482    2.7881   -0.0503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1298    0.6707    0.4789 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1902    0.9145    1.9332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6903    0.0707    2.6951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6896    2.0826    2.4570 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7186    1.8029   -0.3188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1926    1.6995   -0.5546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8687    0.7307    0.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2644   -0.6541    0.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9229   -1.2908   -0.9803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7188   -1.4598    1.4538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8075   -0.5996    0.0441 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0423   -1.8091    0.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2242   -1.8641   -0.2045 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4672    2.1214    0.3961 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5157    0.6941    0.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1607    0.6122    1.4215 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8020    1.0497   -1.5907 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2124   -1.6560   -0.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3133   -0.7663   -1.2073 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8485   -1.3714   -1.9705 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0045   -2.5964   -0.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2255    2.9221    2.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2141    1.8204   -1.3050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5546    2.7920    0.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4343    1.3921   -1.5925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7212    2.6793   -0.4157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9334    0.6541    0.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9013    1.0728    1.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2296   -2.0185   -1.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2042   -0.4888   -1.6796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8199   -1.8575   -0.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1983   -0.8485    2.2564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5649   -2.1268    1.1068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9675   -2.1726    1.8420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6435   -0.6329   -1.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8343   -1.7959    1.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6621   -2.6965    0.2563 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8857   -2.7155    0.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0211   -2.0011   -1.3116 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
  8 13  1  0
 13 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 13 14  1  1
 14 16  1  0
 14 15  2  0
 11  4  1  0
 23 13  1  0
 25  7  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  6 33  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
 19 40  1  0
 21 41  1  0
 21 42  1  0
 21 43  1  0
 22 44  1  0
 22 45  1  0
 22 46  1  0
 23 47  1  6
 24 48  1  0
 24 49  1  0
 25 50  1  0
 25 51  1  0
 16 34  1  0
M  END


  Mrv1652309092201302D          

 25 27  0  0  1  0            999 V2000
    5.2397   -0.3763    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
    5.2631    1.0525    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
    3.6133    1.0795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0374    1.7872    0.0000 O   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
    3.5899   -0.3492    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
    1.5394    0.3990    0.0000 C   0  0  1  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
    1.5159   -1.0298    0.0000 O   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
    1.1152   -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  2  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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  6  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  6  0  0  0
 24 25  1  0  0  0  0
  7 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0275686

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=C(O)C2=C(C(=O)C1=O)[C@]1(CCCC(C)(C)[C@@H]1CC2)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O5/c1-10(2)13-15(21)11-6-7-12-19(3,4)8-5-9-20(12,18(24)25)14(11)17(23)16(13)22/h10,12,21H,5-9H2,1-4H3,(H,24,25)/t12-,20+/m0/s1

> <INCHI_KEY>
LFNJOAMWXNMXHJ-FKIZINRSSA-N

> <FORMULA>
C20H26O5

> <MOLECULAR_WEIGHT>
346.423

> <EXACT_MASS>
346.178023937

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
37.28369245838141

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4aR,10aS)-8-hydroxy-1,1-dimethyl-5,6-dioxo-7-(propan-2-yl)-1,2,3,4,4a,5,6,9,10,10a-decahydrophenanthrene-4a-carboxylic acid

> <JCHEM_LOGP>
3.927362342

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.193608426952536

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.222172898833278

> <JCHEM_PKA_STRONGEST_BASIC>
-7.178060652430006

> <JCHEM_POLAR_SURFACE_AREA>
91.67

> <JCHEM_REFRACTIVITY>
94.3299

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4aR,10aS)-8-hydroxy-7-isopropyl-1,1-dimethyl-5,6-dioxo-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       9.781  -0.702   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.033   0.644   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.824   1.965   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       6.745   2.015   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       7.537   3.336   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.205   2.040   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.413   0.720   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.631  -0.172   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.370  -1.947   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.701  -0.652   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.449  -1.998   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       2.830  -1.922   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       5.161  -0.627   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    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   11                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   25                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    4   12                                                  
CONECT   12   11                                                            
CONECT   13    8   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    7                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Value	Source
Royleanonate	Generator

Chemical Formula

C₂₀H₂₆O₅

Average Mass

346.4230 Da

Monoisotopic Mass

346.17802 Da

IUPAC Name

(4aR,10aS)-8-hydroxy-1,1-dimethyl-5,6-dioxo-7-(propan-2-yl)-1,2,3,4,4a,5,6,9,10,10a-decahydrophenanthrene-4a-carboxylic acid

Traditional Name

(4aR,10aS)-8-hydroxy-7-isopropyl-1,1-dimethyl-5,6-dioxo-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(C)C1=C(O)C2=C(C(=O)C1=O)[C@]1(CCCC(C)(C)[C@@H]1CC2)C(O)=O

InChI Identifier

InChI=1S/C20H26O5/c1-10(2)13-15(21)11-6-7-12-19(3,4)8-5-9-20(12,18(24)25)14(11)17(23)16(13)22/h10,12,21H,5-9H2,1-4H3,(H,24,25)/t12-,20+/m0/s1

InChI Key

LFNJOAMWXNMXHJ-FKIZINRSSA-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 plebeia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 19-oxosteroids. These are steroid derivatives carrying a C=O group at the 19-position of the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Oxosteroids

Direct Parent

19-oxosteroids

Alternative Parents

Substituents

Abietane diterpenoid
Diterpenoid
19-oxosteroid
Phenanthrene
Hydrophenanthrene
Vinylogous acid
Cyclic ketone
Ketone
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Enol
Carboxylic acid
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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	3.93	ChemAxon
pKa (Strongest Acidic)	4.22	ChemAxon
pKa (Strongest Basic)	-7.2	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.67 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	94.33 m³·mol⁻¹	ChemAxon
Polarizability	37.28 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

C00035386

Chemspider ID

8558435

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10382993

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ninomiya K, Matsuda H, Shimoda H, Nishida N, Kasajima N, Yoshino T, Morikawa T, Yoshikawa M: Carnosic acid, a new class of lipid absorption inhibitor from sage. Bioorg Med Chem Lett. 2004 Apr 19;14(8):1943-6. doi: 10.1016/j.bmcl.2004.01.091. [PubMed:15050633 ]
Li CJ, Xia F, Wu R, Tan HS, Xu HX, Xu G, Qin HB: Synthesis and Cytotoxicities of Royleanone Derivatives. Nat Prod Bioprospect. 2018 Dec;8(6):453-456. doi: 10.1007/s13659-018-0173-y. Epub 2018 Jun 16. [PubMed:29909523 ]
Yun YS, Noda S, Shigemori G, Kuriyama R, Takahashi S, Umemura M, Takahashi Y, Inoue H: Phenolic diterpenes from rosemary suppress cAMP responsiveness of gluconeogenic gene promoters. Phytother Res. 2013 Jun;27(6):906-10. doi: 10.1002/ptr.4794. Epub 2012 Aug 23. [PubMed:22927089 ]
LOTUS database [Link]

Showing NP-Card for (4ar,10as)-8-hydroxy-7-isopropyl-1,1-dimethyl-5,6-dioxo-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid (NP0275686)

MOL for NP0275686 ((4ar,10as)-8-hydroxy-7-isopropyl-1,1-dimethyl-5,6-dioxo-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid)

3D MOL for NP0275686 ((4ar,10as)-8-hydroxy-7-isopropyl-1,1-dimethyl-5,6-dioxo-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid)

3D SDF for NP0275686 ((4ar,10as)-8-hydroxy-7-isopropyl-1,1-dimethyl-5,6-dioxo-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid)

3D-SDF for NP0275686 ((4ar,10as)-8-hydroxy-7-isopropyl-1,1-dimethyl-5,6-dioxo-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid)

PDB for NP0275686 ((4ar,10as)-8-hydroxy-7-isopropyl-1,1-dimethyl-5,6-dioxo-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid)

3D PDB for NP0275686 ((4ar,10as)-8-hydroxy-7-isopropyl-1,1-dimethyl-5,6-dioxo-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid)

SMILES for NP0275686 ((4ar,10as)-8-hydroxy-7-isopropyl-1,1-dimethyl-5,6-dioxo-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid)

INCHI for NP0275686 ((4ar,10as)-8-hydroxy-7-isopropyl-1,1-dimethyl-5,6-dioxo-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid)

Structure for NP0275686 ((4ar,10as)-8-hydroxy-7-isopropyl-1,1-dimethyl-5,6-dioxo-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid)

3D Structure for NP0275686 ((4ar,10as)-8-hydroxy-7-isopropyl-1,1-dimethyl-5,6-dioxo-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid)