NP-MRD: Showing NP-Card for Allochenodeoxycholic acid (NP0334650)

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Record Information

Version

2.0

Created at

2024-09-10 19:18:48 UTC

Updated at

2024-09-10 19:18:48 UTC

NP-MRD ID

NP0334650

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Allochenodeoxycholic acid

Description

Allochenodeoxycholic acid, also known as 3a,7a-dihydroxy-5a-cholanate, 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. Allochenodeoxycholic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. Allochenodeoxycholic acid was first documented in 1984 (PMID: 6708561). Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02231218342D          

 32 35  0  0  1  0            999 V2000
   13.0257   -8.9340    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.0257   -8.1091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7401   -7.6966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7401   -9.3466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4546   -8.9340    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.1692   -9.3466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8836   -8.9340    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.8836   -8.1091    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.5980   -7.6966    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.3826   -7.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8676   -7.2841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3826   -6.6165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6376   -5.8320    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.0542   -5.2486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2677   -4.4518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0646   -4.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4446   -5.6604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5980   -6.8716    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.5980   -6.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8836   -6.4590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1692   -6.8716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1692   -7.6966    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.4546   -8.1091    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.4546   -7.2841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2782   -3.4413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6480   -4.8216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5980   -9.3466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3112   -9.3466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4546   -9.7591    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.1692   -8.5215    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.8836   -7.2841    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.5980   -8.5215    0.0000 H   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
  1  4  1  0  0  0  0
  4  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
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  0  0  0  0
 12 13  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
 13 17  1  1  0  0  0
 12 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  8 22  1  0  0  0  0
 22 23  1  0  0  0  0
  3 23  1  0  0  0  0
  5 23  1  0  0  0  0
 23 24  1  1  0  0  0
 16 25  2  0  0  0  0
 16 26  1  0  0  0  0
  7 27  1  6  0  0  0
  1 28  1  6  0  0  0
  5 29  1  6  0  0  0
 22 30  1  6  0  0  0
  8 31  1  1  0  0  0
  9 32  1  6  0  0  0
M  END


  Mrv0541 02231218342D          

 32 35  0  0  1  0            999 V2000
   13.0257   -8.9340    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.0257   -8.1091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7401   -7.6966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7401   -9.3466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4546   -8.9340    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.1692   -9.3466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8836   -8.9340    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.8836   -8.1091    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.5980   -7.6966    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.3826   -7.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8676   -7.2841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3826   -6.6165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6376   -5.8320    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.0542   -5.2486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2677   -4.4518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0646   -4.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4446   -5.6604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5980   -6.8716    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.5980   -6.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8836   -6.4590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1692   -6.8716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1692   -7.6966    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.4546   -8.1091    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.4546   -7.2841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2782   -3.4413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6480   -4.8216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5980   -9.3466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3112   -9.3466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4546   -9.7591    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.1692   -8.5215    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.8836   -7.2841    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.5980   -8.5215    0.0000 H   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
  1  4  1  0  0  0  0
  4  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
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  0  0  0  0
 12 13  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
 13 17  1  1  0  0  0
 12 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  8 22  1  0  0  0  0
 22 23  1  0  0  0  0
  3 23  1  0  0  0  0
  5 23  1  0  0  0  0
 23 24  1  1  0  0  0
 16 25  2  0  0  0  0
 16 26  1  0  0  0  0
  7 27  1  6  0  0  0
  1 28  1  6  0  0  0
  5 29  1  6  0  0  0
 22 30  1  6  0  0  0
  8 31  1  1  0  0  0
  9 32  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0334650

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17?,18+,19+,20-,22+,23+,24-/m1/s1

> <INCHI_KEY>
RUDATBOHQWOJDD-FBMQJMKYSA-N

> <FORMULA>
C24H40O4

> <MOLECULAR_WEIGHT>
392.572

> <EXACT_MASS>
392.292659768

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
46.56906570374015

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R)-4-[(1S,2S,5R,7R,9R,10R,11S,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

> <ALOGPS_LOGP>
3.01

> <JCHEM_LOGP>
3.7133055236666674

> <ALOGPS_LOGS>
-4.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.296339908541825

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.595945733487658

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5356636301705279

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
109.27379999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.97e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-4-[(1S,2S,5R,7R,9R,10R,11S,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      24.315 -16.677   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      24.315 -15.137   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      25.648 -14.367   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      25.648 -17.447   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      26.982 -16.677   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.316 -17.447   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      29.649 -16.677   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      29.649 -15.137   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      30.983 -14.367   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      32.448 -14.843   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      33.353 -13.597   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      32.448 -12.351   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      32.924 -10.886   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      31.835  -9.797   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      32.233  -8.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      33.721  -7.911   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      34.430 -10.566   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      30.983 -12.827   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      30.983 -11.287   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      29.649 -12.057   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      28.316 -12.827   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      28.316 -14.367   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      26.982 -15.137   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      26.982 -13.597   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      34.119  -6.424   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      34.810  -9.000   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      30.983 -17.447   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      22.981 -17.447   0.000  0.00  0.00           O+0
HETATM   29  H   UNK     0      26.982 -18.217   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0      28.316 -15.907   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0      29.649 -13.597   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0      30.983 -15.907   0.000  0.00  0.00           H+0
CONECT    1    2    4   28                                                  
CONECT    2    1    3                                                       
CONECT    3    2   23                                                       
CONECT    4    1    5                                                       
CONECT    5    4    6   23   29                                             
CONECT    6    5    7                                                       
CONECT    7    6    8   27                                                  
CONECT    8    7    9   22   31                                             
CONECT    9    8   10   18   32                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   25   26                                                  
CONECT   17   13                                                            
CONECT   18   12    9   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    8   23   30                                             
CONECT   23   22    3    5   24                                             
CONECT   24   23                                                            
CONECT   25   16                                                            
CONECT   26   16                                                            
CONECT   27    7                                                            
CONECT   28    1                                                            
CONECT   29    5                                                            
CONECT   30   22                                                            
CONECT   31    8                                                            
CONECT   32    9                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
Allochenodeoxycholate	Generator
3a,7a-Dihydroxy-(5a)-cholan-24-Oate	HMDB
3a,7a-Dihydroxy-(5a)-cholan-24-Oic acid	HMDB
3a,7a-Dihydroxy-5a-cholanate	HMDB
3a,7a-Dihydroxy-5a-cholanic acid	HMDB
(4R)-4-[(1S,2S,5R,7R,9R,10R,11S,15R)-5,9-Dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate	HMDB

Chemical Formula

C₂₄H₄₀O₄

Average Mass

392.5720 Da

Monoisotopic Mass

392.29266 Da

IUPAC Name

(4R)-4-[(1S,2S,5R,7R,9R,10R,11S,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

Traditional Name

(4R)-4-[(1S,2S,5R,7R,9R,10R,11S,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17?,18+,19+,20-,22+,23+,24-/m1/s1

InChI Key

RUDATBOHQWOJDD-FBMQJMKYSA-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
3-hydroxysteroid
Hydroxysteroid
3-alpha-hydroxysteroid
7-hydroxysteroid
Cyclic alcohol
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
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	3.01	ALOGPS
logP	3.71	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	4.6	ChemAxon
pKa (Strongest Basic)	-0.54	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	109.27 m³·mol⁻¹	ChemAxon
Polarizability	46.57 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

HMDB0000514

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022086

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

5500

PubChem Compound

53477701

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Huijghebaert S, Parmentier G, Eyssen H: Specificity of bile salt sulfatase activity in man, mouse and rat intestinal microflora. J Steroid Biochem. 1984 Apr;20(4A):907-12. doi: 10.1016/0022-4731(84)90404-7. [PubMed:6708561 ]

Showing NP-Card for Allochenodeoxycholic acid (NP0334650)

MOL for NP0334650 (Allochenodeoxycholic acid)

3D MOL for NP0334650 (Allochenodeoxycholic acid)

3D SDF for NP0334650 (Allochenodeoxycholic acid)

3D-SDF for NP0334650 (Allochenodeoxycholic acid)

PDB for NP0334650 (Allochenodeoxycholic acid)

3D PDB for NP0334650 (Allochenodeoxycholic acid)

SMILES for NP0334650 (Allochenodeoxycholic acid)

INCHI for NP0334650 (Allochenodeoxycholic acid)

Structure for NP0334650 (Allochenodeoxycholic acid)

3D Structure for NP0334650 (Allochenodeoxycholic acid)