NP-MRD: Showing NP-Card for 8a-hydroxy-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-3,4,4b,5,6,9,10,10a-octahydro-2h-phenanthrene-1-carboxylic acid (NP0252115)

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Record Information

Version

2.0

Created at

2022-09-07 15:31:47 UTC

Updated at

2022-09-07 15:31:47 UTC

NP-MRD ID

NP0252115

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8a-hydroxy-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-3,4,4b,5,6,9,10,10a-octahydro-2h-phenanthrene-1-carboxylic acid

Description

8A-hydroxy-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-1,2,3,4,4a,4b,5,6,8a,9,10,10a-dodecahydrophenanthrene-1-carboxylic acid belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 8a-hydroxy-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-3,4,4b,5,6,9,10,10a-octahydro-2h-phenanthrene-1-carboxylic acid is found in Pinus armandii. 8A-hydroxy-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-1,2,3,4,4a,4b,5,6,8a,9,10,10a-dodecahydrophenanthrene-1-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004201503232D          

 24 26  0  0  0  0            999 V2000
   -3.9039   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0789   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0789   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0789    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2539   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0164   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2211   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6336   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2211   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6336   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4586   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8711   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4586   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1582   -1.9767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4874   -2.3640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2158   -2.7513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7877   -2.8012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0164   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414   -0.1105    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
  2  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 12 22  1  0  0  0  0
  7 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  5 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0252115

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)C1=CC2(O)CCC3C(C)(CCCC3(C)C(O)=O)C2CC1

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O4/c1-17(2,23)13-6-7-15-18(3)9-5-10-19(4,16(21)22)14(18)8-11-20(15,24)12-13/h12,14-15,23-24H,5-11H2,1-4H3,(H,21,22)

> <INCHI_KEY>
VBEKTMIFJPKWJA-UHFFFAOYSA-N

> <FORMULA>
C20H32O4

> <MOLECULAR_WEIGHT>
336.472

> <EXACT_MASS>
336.23005951

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
38.284259910229636

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8a-hydroxy-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-1,2,3,4,4a,4b,5,6,8a,9,10,10a-dodecahydrophenanthrene-1-carboxylic acid

> <ALOGPS_LOGP>
2.96

> <JCHEM_LOGP>
2.9615912816666663

> <ALOGPS_LOGS>
-3.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.033762742175568

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.341065038682324

> <JCHEM_PKA_STRONGEST_BASIC>
-2.920450022036297

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
93.4974

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.37e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8a-hydroxy-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthrene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0      -7.287  -1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.747  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.747  -3.080   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -5.747   0.000   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -4.207  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.437  -2.874   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.897  -2.874   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.667  -4.207   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.127  -4.207   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.413  -4.207   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.183  -2.874   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.413  -1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.357  -0.206   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.183  -0.206   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.723  -0.206   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.493  -1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.723  -2.874   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.029  -3.690   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.776  -4.413   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.136  -5.136   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.470  -5.229   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.127  -1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.897  -0.206   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.437  -0.206   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6   24                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9   22                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13   14   22                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   11   18   19                                             
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   12    7   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23    5                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
8a-Hydroxy-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-1,2,3,4,4a,4b,5,6,8a,9,10,10a-dodecahydrophenanthrene-1-carboxylate	Generator

Chemical Formula

C₂₀H₃₂O₄

Average Mass

336.4720 Da

Monoisotopic Mass

336.23006 Da

IUPAC Name

8a-hydroxy-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-1,2,3,4,4a,4b,5,6,8a,9,10,10a-dodecahydrophenanthrene-1-carboxylic acid

Traditional Name

8a-hydroxy-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthrene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(C)(O)C1=CC2(O)CCC3C(C)(CCCC3(C)C(O)=O)C2CC1

InChI Identifier

InChI=1S/C20H32O4/c1-17(2,23)13-6-7-15-18(3)9-5-10-19(4,16(21)22)14(18)8-11-20(15,24)12-13/h12,14-15,23-24H,5-11H2,1-4H3,(H,21,22)

InChI Key

VBEKTMIFJPKWJA-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Pinus armandii	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

Abietane diterpenoid
Diterpenoid
Hydrophenanthrene
Phenanthrene
Cyclic alcohol
Tertiary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen 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	2.96	ALOGPS
logP	2.96	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	4.34	ChemAxon
pKa (Strongest Basic)	-2.9	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	93.5 m³·mol⁻¹	ChemAxon
Polarizability	38.28 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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 8a-hydroxy-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-3,4,4b,5,6,9,10,10a-octahydro-2h-phenanthrene-1-carboxylic acid (NP0252115)

MOL for NP0252115 (8a-hydroxy-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-3,4,4b,5,6,9,10,10a-octahydro-2h-phenanthrene-1-carboxylic acid)

3D MOL for NP0252115 (8a-hydroxy-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-3,4,4b,5,6,9,10,10a-octahydro-2h-phenanthrene-1-carboxylic acid)

3D SDF for NP0252115 (8a-hydroxy-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-3,4,4b,5,6,9,10,10a-octahydro-2h-phenanthrene-1-carboxylic acid)

3D-SDF for NP0252115 (8a-hydroxy-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-3,4,4b,5,6,9,10,10a-octahydro-2h-phenanthrene-1-carboxylic acid)

PDB for NP0252115 (8a-hydroxy-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-3,4,4b,5,6,9,10,10a-octahydro-2h-phenanthrene-1-carboxylic acid)

3D PDB for NP0252115 (8a-hydroxy-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-3,4,4b,5,6,9,10,10a-octahydro-2h-phenanthrene-1-carboxylic acid)

SMILES for NP0252115 (8a-hydroxy-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-3,4,4b,5,6,9,10,10a-octahydro-2h-phenanthrene-1-carboxylic acid)

INCHI for NP0252115 (8a-hydroxy-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-3,4,4b,5,6,9,10,10a-octahydro-2h-phenanthrene-1-carboxylic acid)

Structure for NP0252115 (8a-hydroxy-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-3,4,4b,5,6,9,10,10a-octahydro-2h-phenanthrene-1-carboxylic acid)

3D Structure for NP0252115 (8a-hydroxy-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-3,4,4b,5,6,9,10,10a-octahydro-2h-phenanthrene-1-carboxylic acid)