NP-MRD: Showing NP-Card for 3beta,7alpha-Dihydroxy-5-cholestenoate (NP0334816)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2024-09-10 20:05:10 UTC

Updated at

2024-09-10 20:05:10 UTC

NP-MRD ID

NP0334816

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3beta,7alpha-Dihydroxy-5-cholestenoate

Description

3Beta,7alpha-Dihydroxy-5-cholestenoate, also known as 3β,7α-dihydroxy-5-cholestenoic 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. 3Beta,7alpha-Dihydroxy-5-cholestenoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241204052D          

 31 34  0  0  1  0            999 V2000
    8.6866   -6.2139    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.4011   -6.6264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1156   -6.2139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1156   -5.3889    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.4011   -4.9764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6866   -5.3889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8301   -6.6264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5446   -6.2139    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.5446   -5.3889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8301   -4.9764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2590   -4.9764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2590   -4.1514    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.5446   -3.7389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8301   -4.1514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0436   -5.2313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5286   -4.5639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0436   -3.8964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4035   -3.3391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2986   -3.1118    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.1055   -2.9403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1156   -4.5639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6576   -3.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4646   -3.3819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0166   -3.9950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7466   -2.4988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8236   -3.8234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7617   -4.7796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3756   -4.4365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0785   -3.0388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2590   -6.6264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9722   -6.6264    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  3  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 12 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
  4 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 25  1  6  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 29  2  0  0  0  0
  8 30  1  6  0  0  0
  1 31  1  1  0  0  0
M  END


  Mrv0541 02241204052D          

 31 34  0  0  1  0            999 V2000
    8.6866   -6.2139    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.4011   -6.6264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1156   -6.2139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1156   -5.3889    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.4011   -4.9764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6866   -5.3889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8301   -6.6264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5446   -6.2139    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.5446   -5.3889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8301   -4.9764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2590   -4.9764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2590   -4.1514    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.5446   -3.7389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8301   -4.1514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0436   -5.2313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5286   -4.5639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0436   -3.8964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4035   -3.3391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2986   -3.1118    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.1055   -2.9403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1156   -4.5639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6576   -3.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4646   -3.3819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0166   -3.9950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7466   -2.4988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8236   -3.8234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7617   -4.7796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3756   -4.4365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0785   -3.0388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2590   -6.6264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9722   -6.6264    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  3  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 12 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
  4 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 25  1  6  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 29  2  0  0  0  0
  8 30  1  6  0  0  0
  1 31  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0334816

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](CCCC(C)C(O)=O)C1CCC2C3[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O4/c1-16(6-5-7-17(2)25(30)31)20-8-9-21-24-22(11-13-27(20,21)4)26(3)12-10-19(28)14-18(26)15-23(24)29/h15-17,19-24,28-29H,5-14H2,1-4H3,(H,30,31)/t16-,17?,19+,20?,21?,22?,23-,24?,26+,27-/m1/s1

> <INCHI_KEY>
GYJSAWZGYQXRBS-BJGNZVHYSA-N

> <FORMULA>
C27H44O4

> <MOLECULAR_WEIGHT>
432.6359

> <EXACT_MASS>
432.323959896

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
51.243883655646684

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6R)-6-[(2R,5S,9S,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]-2-methylheptanoic acid

> <ALOGPS_LOGP>
3.92

> <JCHEM_LOGP>
4.8957571106666675

> <ALOGPS_LOGS>
-4.80

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.204233421519334

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.828921693673492

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8269284491353041

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
123.74629999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.90e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6R)-6-[(2R,5S,9S,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]-2-methylheptanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      16.215 -11.599   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      17.549 -12.369   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.882 -11.599   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.882 -10.059   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.549  -9.289   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.215 -10.059   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.216 -12.369   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      21.550 -11.599   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.550 -10.059   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.216  -9.289   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.883  -9.289   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.883  -7.749   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.550  -6.979   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.216  -7.749   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      24.348  -9.765   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      25.253  -8.519   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      24.348  -7.273   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      23.153  -6.233   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      24.824  -5.809   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      26.330  -5.489   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      18.882  -8.519   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      27.361  -6.633   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      28.867  -6.313   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      29.898  -7.457   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      23.794  -4.664   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      31.404  -7.137   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      29.422  -8.922   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      32.434  -8.281   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      31.880  -5.672   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      22.883 -12.369   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      14.881 -12.369   0.000  0.00  0.00           O+0
CONECT    1    2    6   31                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5   10   21                                             
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    3    8                                                       
CONECT    8    7    9   30                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    4   14                                                  
CONECT   11    9   12   15                                                  
CONECT   12   11   13   17   18                                             
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   19                                                  
CONECT   18   12                                                            
CONECT   19   17   20   25                                                  
CONECT   20   19   22                                                       
CONECT   21    4                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   26   27                                                  
CONECT   25   19                                                            
CONECT   26   24   28   29                                                  
CONECT   27   24                                                            
CONECT   28   26                                                            
CONECT   29   26                                                            
CONECT   30    8                                                            
CONECT   31    1                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
3b,7a-Dihydroxy-5-cholestenoate	Generator
3b,7a-Dihydroxy-5-cholestenoic acid	Generator
3beta,7alpha-Dihydroxy-5-cholestenoic acid	Generator
3Β,7α-dihydroxy-5-cholestenoate	Generator
3Β,7α-dihydroxy-5-cholestenoic acid	Generator
(3beta,7alpha)-3,7-Dihydroxy-cholest-5-en-26-Oate	HMDB
(3beta,7alpha)-3,7-Dihydroxy-cholest-5-en-26-Oic acid	HMDB
3 beta,7 alpha-Dihydroxy-5-cholesten-26-Oate	HMDB
3 beta,7 alpha-Dihydroxy-5-cholesten-26-Oic acid	HMDB
3,7-Dihydroxy-5-cholestenoate	HMDB
3,7-Dihydroxy-5-cholestenoic acid	HMDB
3beta,7alpha-Dihydroxy-5-cholesten-26-Oate	HMDB
3beta,7alpha-Dihydroxy-5-cholesten-26-Oic acid	HMDB

Chemical Formula

C₂₇H₄₄O₄

Average Mass

432.6359 Da

Monoisotopic Mass

432.32396 Da

IUPAC Name

(6R)-6-[(2R,5S,9S,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]-2-methylheptanoic acid

Traditional Name

(6R)-6-[(2R,5S,9S,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]-2-methylheptanoic acid

CAS Registry Number

Not Available

SMILES

C[C@H](CCCC(C)C(O)=O)C1CCC2C3[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C

InChI Identifier

InChI=1S/C27H44O4/c1-16(6-5-7-17(2)25(30)31)20-8-9-21-24-22(11-13-27(20,21)4)26(3)12-10-19(28)14-18(26)15-23(24)29/h15-17,19-24,28-29H,5-14H2,1-4H3,(H,30,31)/t16-,17?,19+,20?,21?,22?,23-,24?,26+,27-/m1/s1

InChI Key

GYJSAWZGYQXRBS-BJGNZVHYSA-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 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.

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
Steroid acid
3-hydroxy-delta-5-steroid
3-hydroxysteroid
7-hydroxysteroid
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
Hydroxysteroid
Delta-5-steroid
Medium-chain fatty acid
Hydroxy fatty acid
Fatty acyl
Cyclic alcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
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	3.92	ALOGPS
logP	4.9	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	4.83	ChemAxon
pKa (Strongest Basic)	-0.83	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	6	ChemAxon
Refractivity	123.75 m³·mol⁻¹	ChemAxon
Polarizability	51.24 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029070

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

53481408

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3beta,7alpha-Dihydroxy-5-cholestenoate (NP0334816)

MOL for NP0334816 (3beta,7alpha-Dihydroxy-5-cholestenoate)

3D MOL for NP0334816 (3beta,7alpha-Dihydroxy-5-cholestenoate)

3D SDF for NP0334816 (3beta,7alpha-Dihydroxy-5-cholestenoate)

3D-SDF for NP0334816 (3beta,7alpha-Dihydroxy-5-cholestenoate)

PDB for NP0334816 (3beta,7alpha-Dihydroxy-5-cholestenoate)

3D PDB for NP0334816 (3beta,7alpha-Dihydroxy-5-cholestenoate)

SMILES for NP0334816 (3beta,7alpha-Dihydroxy-5-cholestenoate)

INCHI for NP0334816 (3beta,7alpha-Dihydroxy-5-cholestenoate)

Structure for NP0334816 (3beta,7alpha-Dihydroxy-5-cholestenoate)

3D Structure for NP0334816 (3beta,7alpha-Dihydroxy-5-cholestenoate)