NP-MRD: Showing NP-Card for 3b,12b-Dihydroxy-5b-cholanoic acid (NP0334713)

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Record Information

Version

2.0

Created at

2024-09-10 19:38:35 UTC

Updated at

2024-09-10 19:38:35 UTC

NP-MRD ID

NP0334713

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3b,12b-Dihydroxy-5b-cholanoic acid

Description

3B,12b-Dihydroxy-5b-cholanoic acid belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups. Based on a literature review very few articles have been published on 3b,12b-Dihydroxy-5b-cholanoic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05252322102D          

 33 36  0  0  0  0            999 V2000
10000.354710001.0443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.641710001.4589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2167 9999.7949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0750 9997.7270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2167 9997.3135    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9291 9998.5603    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6417 9999.7949    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.3547 9998.5603    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2151 9998.9668    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.2151 9998.1417    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.9296 9997.7293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6441 9998.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.642310000.6257    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.927810000.2132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9278 9999.3881    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.6423 9998.9757    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.5034 9999.3793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7889 9998.9668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7889 9998.1417    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.5034 9997.7293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.356810000.2132    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.3568 9999.3882    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.1414 9999.1332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.6263 9999.8007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.141410000.4682    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.141410001.2932    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.857110001.7057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.570710001.2932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.286410001.7057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.000010001.2932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.286410002.5307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.427710001.7057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.857110000.8807    0.0000 H   0  0  0  0  0  0  0  0  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
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  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
 19  4  1  1  0  0  0
 20 10  1  0  0  0  0
 10  5  1  1  0  0  0
 17  9  1  0  0  0  0
  9  3  1  1  0  0  0
 13  2  1  1  0  0  0
 15  9  1  0  0  0  0
 15  6  1  6  0  0  0
 12 16  1  0  0  0  0
 16  7  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 26  1  0  0  0  0
 25 33  1  6  0  0  0
 26 27  1  0  0  0  0
 26 32  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 25 21  1  0  0  0  0
 25 24  1  0  0  0  0
 16 22  1  0  0  0  0
 22  8  1  6  0  0  0
 13 21  1  0  0  0  0
 21  1  1  1  0  0  0
M  END


  Mrv2104 05252322102D          

 33 36  0  0  0  0            999 V2000
10000.354710001.0443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.641710001.4589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2167 9999.7949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0750 9997.7270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2167 9997.3135    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9291 9998.5603    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6417 9999.7949    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.3547 9998.5603    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2151 9998.9668    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.2151 9998.1417    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.9296 9997.7293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6441 9998.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.642310000.6257    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.927810000.2132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9278 9999.3881    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.6423 9998.9757    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.5034 9999.3793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7889 9998.9668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7889 9998.1417    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.5034 9997.7293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.356810000.2132    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.3568 9999.3882    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.1414 9999.1332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.6263 9999.8007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.141410000.4682    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.141410001.2932    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.857110001.7057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.570710001.2932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.286410001.7057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.000010001.2932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.286410002.5307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.427710001.7057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.857110000.8807    0.0000 H   0  0  0  0  0  0  0  0  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
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  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
 19  4  1  1  0  0  0
 20 10  1  0  0  0  0
 10  5  1  1  0  0  0
 17  9  1  0  0  0  0
  9  3  1  1  0  0  0
 13  2  1  1  0  0  0
 15  9  1  0  0  0  0
 15  6  1  6  0  0  0
 12 16  1  0  0  0  0
 16  7  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 26  1  0  0  0  0
 25 33  1  6  0  0  0
 26 27  1  0  0  0  0
 26 32  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 25 21  1  0  0  0  0
 25 24  1  0  0  0  0
 16 22  1  0  0  0  0
 22  8  1  6  0  0  0
 13 21  1  0  0  0  0
 21  1  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0334713

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])C[C@@H](O)[C@]12C)[C@H](C)CCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16+,17+,18-,19+,20+,21-,23+,24-/s2

> <INCHI_KEY>
KXGVEGMKQFWNSR-PAPZHAMDNA-N

> <FORMULA>
C24H40O4

> <MOLECULAR_WEIGHT>
392.58

> <EXACT_MASS>
392.292659768

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
46.23099306763176

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R)-4-[(1R,3aS,3bR,5aR,7S,9aS,9bS,11R,11aR)-7,11-dihydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanoic acid

> <JCHEM_LOGP>
3.7912592536666683

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.296396318179

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.651656794864149

> <JCHEM_PKA_STRONGEST_BASIC>
-0.3511899140388809

> <JCHEM_POLAR_SURFACE_AREA>
77.75999999999999

> <JCHEM_REFRACTIVITY>
109.19679999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-4-[(1R,3aS,3bR,5aR,7S,9aS,9bS,11R,11aR)-7,11-dihydroxy-9a,11a-dimethyl-tetradecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-MAY-23         0                                  
HETATM    1  C   UNK     0    8667.3298668.616   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8665.9988669.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8663.3388666.284   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8659.3408662.424   0.000  0.00  0.00           O+0
HETATM    5  H   UNK     0    8663.3388661.652   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8664.6688663.979   0.000  0.00  0.00           H+0
HETATM    7  H   UNK     0    8665.9988666.284   0.000  0.00  0.00           H+0
HETATM    8  H   UNK     0    8667.3298663.979   0.000  0.00  0.00           H+0
HETATM    9  C   UNK     0    8663.3358664.738   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8663.3358663.198   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8664.6698662.428   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8666.0028663.198   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8665.9998667.835   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8664.6658667.065   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8664.6658665.524   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8665.9998664.755   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8662.0068665.508   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8660.6738664.738   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8660.6738663.198   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8662.0068662.428   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8667.3338667.065   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8667.3338665.525   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8668.7978665.049   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8669.7028666.295   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8668.7978667.541   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8668.7978669.081   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8670.1338669.851   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8671.4658669.081   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8672.8018669.851   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0    8674.1338669.081   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0    8672.8018671.391   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0    8667.4658669.851   0.000  0.00  0.00           C+0
HETATM   33  H   UNK     0    8670.1338668.311   0.000  0.00  0.00           H+0
CONECT    1   21                                                            
CONECT    2   13                                                            
CONECT    3    9                                                            
CONECT    4   19                                                            
CONECT    5   10                                                            
CONECT    6   15                                                            
CONECT    7   16                                                            
CONECT    8   22                                                            
CONECT    9   10   17    3   15                                             
CONECT   10    9   11   20    5                                             
CONECT   11   10   12                                                       
CONECT   12   11   16                                                       
CONECT   13   14    2   21                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16    9    6                                             
CONECT   16   15   12    7   22                                             
CONECT   17   18    9                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20    4                                                  
CONECT   20   19   10                                                       
CONECT   21   22   25   13    1                                             
CONECT   22   21   23   16    8                                             
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   26   33   21   24                                             
CONECT   26   25   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   26                                                            
CONECT   33   25                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
3b,12b-Dihydroxy-5b-cholanoate	Generator

Chemical Formula

C₂₄H₄₀O₄

Average Mass

392.5800 Da

Monoisotopic Mass

392.29266 Da

IUPAC Name

(4R)-4-[(1R,3aS,3bR,5aR,7S,9aS,9bS,11R,11aR)-7,11-dihydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanoic acid

Traditional Name

(4R)-4-[(1R,3aS,3bR,5aR,7S,9aS,9bS,11R,11aR)-7,11-dihydroxy-9a,11a-dimethyl-tetradecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])C[C@@H](O)[C@]12C)[C@H](C)CCC(O)=O

InChI Identifier

InChI=1/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16+,17+,18-,19+,20+,21-,23+,24-/s2

InChI Key

KXGVEGMKQFWNSR-PAPZHAMDNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. These are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Dihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Dihydroxy bile acid, alcohol, or derivatives
3-hydroxysteroid
3-beta-hydroxysteroid
12-hydroxysteroid
Hydroxysteroid
Cyclic alcohol
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

C24 bile acids, alcohols, and derivatives (LMST04010043 )

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	3.79	ChemAxon
pKa (Strongest Acidic)	4.65	ChemAxon
pKa (Strongest Basic)	-0.35	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	4	ChemAxon
Refractivity	109.2 m³·mol⁻¹	ChemAxon
Polarizability	46.23 Å³	ChemAxon
Number of Rings	4	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

Showing NP-Card for 3b,12b-Dihydroxy-5b-cholanoic acid (NP0334713)

MOL for NP0334713 (3b,12b-Dihydroxy-5b-cholanoic acid)

3D MOL for NP0334713 (3b,12b-Dihydroxy-5b-cholanoic acid)

3D SDF for NP0334713 (3b,12b-Dihydroxy-5b-cholanoic acid)

3D-SDF for NP0334713 (3b,12b-Dihydroxy-5b-cholanoic acid)

PDB for NP0334713 (3b,12b-Dihydroxy-5b-cholanoic acid)

3D PDB for NP0334713 (3b,12b-Dihydroxy-5b-cholanoic acid)

SMILES for NP0334713 (3b,12b-Dihydroxy-5b-cholanoic acid)

INCHI for NP0334713 (3b,12b-Dihydroxy-5b-cholanoic acid)

Structure for NP0334713 (3b,12b-Dihydroxy-5b-cholanoic acid)

3D Structure for NP0334713 (3b,12b-Dihydroxy-5b-cholanoic acid)