NP-MRD: Showing NP-Card for Isodeoxycholic acid (NP0086987)

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Record Information

Version

2.0

Created at

2022-05-11 16:36:35 UTC

Updated at

2022-05-11 16:36:35 UTC

NP-MRD ID

NP0086987

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isodeoxycholic acid

Description

Isodeoxycholic acid, also known as isodeoxycholate, 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. Isodeoxycholic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are steroid acids found predominantly in bile of mammals. Bile acids have potent toxic properties (e.G., Membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231219332D          

 33 36  0  0  1  0            999 V2000
   15.9151  -11.6908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9151  -12.5158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6296  -12.9283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3440  -12.5158    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.3440  -11.6908    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.6296  -11.2783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0585  -12.9283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7730  -12.5158    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.7730  -11.6908    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.0585  -11.2783    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.4875  -11.2783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.4875  -10.4533    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.7730  -10.0408    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.0585  -10.4533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2721  -11.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7570  -10.8658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2721  -10.1984    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.5270   -9.4138    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.9750   -8.8007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   22.9479   -8.8992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3440  -10.8658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 17 30  1  6  0  0  0
 11 31  1  6  0  0  0
  8 32  1  6  0  0  0
 10 33  1  6  0  0  0
M  END

     RDKit          3D

 68 71  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv0541 02231219332D          

 33 36  0  0  1  0            999 V2000
   15.9151  -11.6908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9151  -12.5158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.3440  -11.6908    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0086987

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C24H40O4/c1-14(7-10-21(27)28)16-8-9-17-22-18(13-20(26)24(16,17)3)23(2)11-5-4-6-15(23)12-19(22)25/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>
ZHCAAZIHTDCFJX-QLEQUTGBSA-N

> <FORMULA>
C24H40O4

> <MOLECULAR_WEIGHT>
392.572

> <EXACT_MASS>
392.292659768

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
46.10888446064601

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R)-4-[(1S,2S,7S,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

> <ALOGPS_LOGP>
3.16

> <JCHEM_LOGP>
3.869212983666668

> <ALOGPS_LOGS>
-4.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.475011784581372

> <JCHEM_PKA_STRONGEST_BASIC>
-0.1879036357499263

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
109.11979999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.49e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-4-[(1S,2S,7S,9R,10R,11S,14R,15R,16S)-9,16-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      29.708 -21.823   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      29.708 -23.363   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      31.042 -24.133   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      32.375 -23.363   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      32.375 -21.823   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      31.042 -21.053   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      33.709 -24.133   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      35.043 -23.363   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      35.043 -21.823   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      33.709 -21.053   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      36.377 -21.053   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      36.377 -19.513   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      35.043 -18.743   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      33.709 -19.513   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      37.841 -21.529   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      38.746 -20.283   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      37.841 -19.037   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      38.317 -17.572   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      37.287 -16.428   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      39.823 -17.252   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      40.854 -18.397   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      42.360 -18.076   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      43.391 -19.221   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      42.836 -16.612   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      32.375 -20.283   0.000  0.00  0.00           C+0
HETATM   26  H   UNK     0      32.375 -24.903   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0      35.043 -20.283   0.000  0.00  0.00           H+0
HETATM   28  C   UNK     0      36.538 -17.981   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      35.043 -17.203   0.000  0.00  0.00           O+0
HETATM   30  H   UNK     0      39.362 -18.796   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0      36.538 -22.584   0.000  0.00  0.00           H+0
HETATM   32  O   UNK     0      36.377 -24.133   0.000  0.00  0.00           O+0
HETATM   33  H   UNK     0      33.709 -22.593   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7   26                                             
CONECT    5    4    6   10   25                                             
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   32                                                  
CONECT    9    8   10   11   27                                             
CONECT   10    9    5   14   33                                             
CONECT   11    9   12   15   31                                             
CONECT   12   11   13   17   28                                             
CONECT   13   12   14   29                                                  
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18   30                                             
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25    5                                                            
CONECT   26    4                                                            
CONECT   27    9                                                            
CONECT   28   12                                                            
CONECT   29   13                                                            
CONECT   30   17                                                            
CONECT   31   11                                                            
CONECT   32    8                                                            
CONECT   33   10                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
7alpha,12alpha-Dihydroxy-5beta-cholanic acid	Kegg
7alpha,12alpha-Dihydroxycholanoic acid	Kegg
7a,12a-Dihydroxy-5b-cholanate	Generator
7a,12a-Dihydroxy-5b-cholanic acid	Generator
7alpha,12alpha-Dihydroxy-5beta-cholanate	Generator
7Α,12α-dihydroxy-5β-cholanate	Generator
7Α,12α-dihydroxy-5β-cholanic acid	Generator
7a,12a-Dihydroxycholanoate	Generator
7a,12a-Dihydroxycholanoic acid	Generator
7alpha,12alpha-Dihydroxycholanoate	Generator
7Α,12α-dihydroxycholanoate	Generator
7Α,12α-dihydroxycholanoic acid	Generator
Isodeoxycholate	Generator
3-Deoxycholic acid	HMDB
7a,12a-Dihydroxy-5b-cholan-24-Oate	HMDB
7a,12a-Dihydroxy-5b-cholan-24-Oic acid	HMDB
7a,12a-Dihydroxy-5b-cholanoate	HMDB
7a,12a-Dihydroxy-5b-cholanoic acid	HMDB
7alpha,12alpha-Dihydroxy-5beta-cholan-24-Oate	HMDB
7alpha,12alpha-Dihydroxy-5beta-cholan-24-Oic acid	HMDB
(4R)-4-[(1S,2S,7S,9R,10R,11S,14R,15R,16S)-9,16-Dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate	HMDB
Isodeoxycholic acid	KEGG

Chemical Formula

C₂₄H₄₀O₄

Average Mass

392.5720 Da

Monoisotopic Mass

392.29266 Da

IUPAC Name

(4R)-4-[(1S,2S,7S,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

Traditional Name

(4R)-4-[(1S,2S,7S,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

ZHCAAZIHTDCFJX-QLEQUTGBSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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
12-hydroxysteroid
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

cholanoid (CHEBI:81256 )
C24 bile acids, alcohols, and derivatives (C17661 )
C24 bile acids, alcohols, and derivatives (LMST04010049 )

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	3.16	ALOGPS
logP	3.87	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	4.48	ChemAxon
pKa (Strongest Basic)	-0.19	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	109.12 m³·mol⁻¹	ChemAxon
Polarizability	46.11 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

HMDB0002536

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023024

KNApSAcK ID

Not Available

Chemspider ID

144358

KEGG Compound ID

C17661

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

164672

PDB ID

Not Available

ChEBI ID

81256

Good Scents ID

Not Available

References

General References

Showing NP-Card for Isodeoxycholic acid (NP0086987)

MOL for NP0086987 (Isodeoxycholic acid)

3D MOL for NP0086987 (Isodeoxycholic acid)

3D SDF for NP0086987 (Isodeoxycholic acid)

3D-SDF for NP0086987 (Isodeoxycholic acid)

PDB for NP0086987 (Isodeoxycholic acid)

3D PDB for NP0086987 (Isodeoxycholic acid)

SMILES for NP0086987 (Isodeoxycholic acid)

INCHI for NP0086987 (Isodeoxycholic acid)

Structure for NP0086987 (Isodeoxycholic acid)

3D Structure for NP0086987 (Isodeoxycholic acid)