NP-MRD: Showing NP-Card for 2-(hydroxymethyl)-2,6a,8a,9,12b,14a-hexamethyl-10-oxo-tetradecahydro-1h-picene-4a-carboxylic acid (NP0306133)

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Record Information

Version

2.0

Created at

2022-09-10 22:25:35 UTC

Updated at

2022-09-10 22:25:35 UTC

NP-MRD ID

NP0306133

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(hydroxymethyl)-2,6a,8a,9,12b,14a-hexamethyl-10-oxo-tetradecahydro-1h-picene-4a-carboxylic acid

Description

2-(Hydroxymethyl)-2,6a,8a,9,12b,14a-hexamethyl-10-oxo-docosahydropicene-4a-carboxylic acid belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 2-(Hydroxymethyl)-2,6a,8a,9,12b,14a-hexamethyl-10-oxo-docosahydropicene-4a-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004191518352D          

 34 38  0  0  0  0            999 V2000
    6.4895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4452   -1.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4733   -0.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6165   -1.3966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    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
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 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
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 21 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 19 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 12 30  1  0  0  0  0
 17 30  1  0  0  0  0
 30 31  1  0  0  0  0
 27 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
M  END


  Mrv1533004191518352D          

 34 38  0  0  0  0            999 V2000
    6.4895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4452   -1.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4733   -0.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6165   -1.3966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    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
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 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
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 21 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 19 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 12 30  1  0  0  0  0
 17 30  1  0  0  0  0
 30 31  1  0  0  0  0
 27 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0306133

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C(=O)CCC2C1(C)CCC1C2(C)CCC2(C)C3CC(C)(CO)CCC3(CCC12C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O4/c1-19-20(32)7-8-21-26(19,3)10-9-22-27(21,4)12-13-29(6)23-17-25(2,18-31)11-15-30(23,24(33)34)16-14-28(22,29)5/h19,21-23,31H,7-18H2,1-6H3,(H,33,34)

> <INCHI_KEY>
QIVLJUFPYIANQG-UHFFFAOYSA-N

> <FORMULA>
C30H48O4

> <MOLECULAR_WEIGHT>
472.71

> <EXACT_MASS>
472.355260026

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
55.59676189922158

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(hydroxymethyl)-2,6a,8a,9,12b,14a-hexamethyl-10-oxo-docosahydropicene-4a-carboxylic acid

> <ALOGPS_LOGP>
5.06

> <JCHEM_LOGP>
6.027202281666666

> <ALOGPS_LOGS>
-5.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.219745177375973

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.588133961285865

> <JCHEM_PKA_STRONGEST_BASIC>
-1.390483534138482

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
133.70099999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.34e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(hydroxymethyl)-2,6a,8a,9,12b,14a-hexamethyl-10-oxo-tetradecahydro-1H-picene-4a-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      12.114   3.437   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.344   2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.114   0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      13.654   0.770   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      11.344  -0.564   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.804  -0.564   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.804   2.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.574   3.437   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.034   3.437   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.494   3.437   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.264  -0.564   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.831  -2.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.883  -1.090   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.151  -2.607   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.334   3.437   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.104   4.771   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -0.206   3.437   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    2    9   10                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   30                                                  
CONECT   13   12    7   14   15                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   30                                             
CONECT   18   17                                                            
CONECT   19   17   20   27                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23   25                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23                                                            
CONECT   25   21   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   19   28   32                                             
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   12   17   31                                             
CONECT   31   30                                                            
CONECT   32   27   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Value	Source
2-(Hydroxymethyl)-2,6a,8a,9,12b,14a-hexamethyl-10-oxo-docosahydropicene-4a-carboxylate	Generator

Chemical Formula

C₃₀H₄₈O₄

Average Mass

472.7100 Da

Monoisotopic Mass

472.35526 Da

IUPAC Name

2-(hydroxymethyl)-2,6a,8a,9,12b,14a-hexamethyl-10-oxo-docosahydropicene-4a-carboxylic acid

Traditional Name

2-(hydroxymethyl)-2,6a,8a,9,12b,14a-hexamethyl-10-oxo-tetradecahydro-1H-picene-4a-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1C(=O)CCC2C1(C)CCC1C2(C)CCC2(C)C3CC(C)(CO)CCC3(CCC12C)C(O)=O

InChI Identifier

InChI=1S/C30H48O4/c1-19-20(32)7-8-21-26(19,3)10-9-22-27(21,4)12-13-29(6)23-17-25(2,18-31)11-15-30(23,24(33)34)16-14-28(22,29)5/h19,21-23,31H,7-18H2,1-6H3,(H,33,34)

InChI Key

QIVLJUFPYIANQG-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Cyclic ketone
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
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	5.06	ALOGPS
logP	6.03	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	4.59	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	133.7 m³·mol⁻¹	ChemAxon
Polarizability	55.6 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

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References

General References

LOTUS database [Link]

Showing NP-Card for 2-(hydroxymethyl)-2,6a,8a,9,12b,14a-hexamethyl-10-oxo-tetradecahydro-1h-picene-4a-carboxylic acid (NP0306133)

MOL for NP0306133 (2-(hydroxymethyl)-2,6a,8a,9,12b,14a-hexamethyl-10-oxo-tetradecahydro-1h-picene-4a-carboxylic acid)

3D MOL for NP0306133 (2-(hydroxymethyl)-2,6a,8a,9,12b,14a-hexamethyl-10-oxo-tetradecahydro-1h-picene-4a-carboxylic acid)

3D SDF for NP0306133 (2-(hydroxymethyl)-2,6a,8a,9,12b,14a-hexamethyl-10-oxo-tetradecahydro-1h-picene-4a-carboxylic acid)

3D-SDF for NP0306133 (2-(hydroxymethyl)-2,6a,8a,9,12b,14a-hexamethyl-10-oxo-tetradecahydro-1h-picene-4a-carboxylic acid)

PDB for NP0306133 (2-(hydroxymethyl)-2,6a,8a,9,12b,14a-hexamethyl-10-oxo-tetradecahydro-1h-picene-4a-carboxylic acid)

3D PDB for NP0306133 (2-(hydroxymethyl)-2,6a,8a,9,12b,14a-hexamethyl-10-oxo-tetradecahydro-1h-picene-4a-carboxylic acid)

SMILES for NP0306133 (2-(hydroxymethyl)-2,6a,8a,9,12b,14a-hexamethyl-10-oxo-tetradecahydro-1h-picene-4a-carboxylic acid)

INCHI for NP0306133 (2-(hydroxymethyl)-2,6a,8a,9,12b,14a-hexamethyl-10-oxo-tetradecahydro-1h-picene-4a-carboxylic acid)

Structure for NP0306133 (2-(hydroxymethyl)-2,6a,8a,9,12b,14a-hexamethyl-10-oxo-tetradecahydro-1h-picene-4a-carboxylic acid)

3D Structure for NP0306133 (2-(hydroxymethyl)-2,6a,8a,9,12b,14a-hexamethyl-10-oxo-tetradecahydro-1h-picene-4a-carboxylic acid)