NP-MRD: Showing NP-Card for 3,7-Dihydroxy-12-oxocholanoic acid (NP0086573)

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Record Information

Version

2.0

Created at

2022-05-11 16:24:51 UTC

Updated at

2022-05-11 16:24:52 UTC

NP-MRD ID

NP0086573

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,7-Dihydroxy-12-oxocholanoic acid

Description

3,7-Dihydroxy-12-oxocholanoic acid, also known as 12-keto-chenodeoxycholate or 3a,7a-dihydroxy-12-ketocholanate, 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. 3,7-Dihydroxy-12-oxocholanoic 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. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. 3,7-Dihydroxy-12-oxocholanoic acid was first documented in 1990 (PMID: 2079611). 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 02231218302D          

 33 36  0  0  1  0            999 V2000
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    9.4750   -6.8175    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   10.9039   -6.8175    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.9039   -5.9925    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.1894   -5.5800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6184   -7.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  9 33  1  6  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv0541 02231218302D          

 33 36  0  0  1  0            999 V2000
    9.4750   -5.9925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0086573

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C24H38O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-19,22,25-26H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19-,22+,23+,24-/m1/s1

> <INCHI_KEY>
MIHNUBCEFJLAGN-DMMBONCOSA-N

> <FORMULA>
C24H38O5

> <MOLECULAR_WEIGHT>
406.5555

> <EXACT_MASS>
406.271924326

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
46.4394192970417

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyl-16-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

> <ALOGPS_LOGP>
2.56

> <JCHEM_LOGP>
3.046022162333333

> <ALOGPS_LOGS>
-3.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.296339807159416

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.385323492622886

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5149500746765611

> <JCHEM_POLAR_SURFACE_AREA>
94.83000000000001

> <JCHEM_REFRACTIVITY>
109.96699999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.25e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-ketochenodeoxycholic 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      17.687 -11.186   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      17.687 -12.726   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      19.020 -13.496   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      20.354 -12.726   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.354 -11.186   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.020 -10.416   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      21.688 -13.496   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      23.021 -12.726   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.688 -10.416   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.355 -10.416   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      24.355  -8.876   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.021  -8.106   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.688  -8.876   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.820 -10.892   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.725  -9.646   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      26.034  -8.542   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      26.642  -7.133   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.167  -6.955   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      28.775  -5.546   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      30.300  -5.369   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      30.908  -3.959   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      31.216  -6.600   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      24.197 -13.713   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      20.308  -9.698   0.000  0.00  0.00           C+0
HETATM   25  H   UNK     0      20.354 -14.261   0.000  0.00  0.00           H+0
HETATM   26  C   UNK     0      24.355  -7.336   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      16.357 -13.493   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      23.021 -11.186   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0      22.997  -9.714   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0      24.420 -11.750   0.000  0.00  0.00           H+0
HETATM   31  O   UNK     0      23.021  -6.571   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      25.726  -5.902   0.000  0.00  0.00           C+0
HETATM   33  H   UNK     0      21.690 -11.893   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    3   27                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7   25                                             
CONECT    5    4    6    9   24                                             
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7   23   28                                                  
CONECT    9    5   13   28   33                                             
CONECT   10   11   14   28   30                                             
CONECT   11   10   12   16   26                                             
CONECT   12   11   13   31                                                  
CONECT   13   12    9                                                       
CONECT   14   10   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11   17                                                  
CONECT   17   16   18   32                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23    8                                                            
CONECT   24    5                                                            
CONECT   25    4                                                            
CONECT   26   11                                                            
CONECT   27    2                                                            
CONECT   28    9    8   10   29                                             
CONECT   29   28                                                            
CONECT   30   10                                                            
CONECT   31   12                                                            
CONECT   32   17                                                            
CONECT   33    9                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
(3alpha,5beta,7alpha)-3,7-Dihydroxy-12-oxocholan-24-Oic acid	ChEBI
3alpha,7alpha-Dihydroxy-12-oxo-5beta-cholanate	ChEBI
(3a,5b,7a)-3,7-Dihydroxy-12-oxocholan-24-Oate	Generator
(3a,5b,7a)-3,7-Dihydroxy-12-oxocholan-24-Oic acid	Generator
(3alpha,5beta,7alpha)-3,7-Dihydroxy-12-oxocholan-24-Oate	Generator
(3Α,5β,7α)-3,7-dihydroxy-12-oxocholan-24-Oate	Generator
(3Α,5β,7α)-3,7-dihydroxy-12-oxocholan-24-Oic acid	Generator
3a,7a-Dihydroxy-12-oxo-5b-cholanate	Generator
3a,7a-Dihydroxy-12-oxo-5b-cholanic acid	Generator
3alpha,7alpha-Dihydroxy-12-oxo-5beta-cholanic acid	Generator
3Α,7α-dihydroxy-12-oxo-5β-cholanate	Generator
3Α,7α-dihydroxy-12-oxo-5β-cholanic acid	Generator
3,7-Dihydroxy-12-oxocholanoate	Generator
(3a,5b,7a)-3,7-Dihydroxy-12-oxo-cholan-24-Oate	HMDB
(3a,5b,7a)-3,7-Dihydroxy-12-oxo-cholan-24-Oic acid	HMDB
12-Keto-3a,7a-dihydroxy-5b-cholanate	HMDB
12-Keto-3a,7a-dihydroxy-5b-cholanic acid	HMDB
12-Keto-chenodeoxycholate	HMDB
12-Keto-chenodeoxycholic acid	HMDB
12-Ketochenodeoxycholate	HMDB
12-Ketochenodeoxycholic acid	HMDB
12-oxo-3a,7a-Dihydroxy-5b-cholan-24-Oate	HMDB
12-oxo-3a,7a-Dihydroxy-5b-cholan-24-Oic acid	HMDB
12-Oxochenodeoxycholate	HMDB
12-Oxochenodeoxycholic acid	HMDB
3a,7a-Dihydroxy-12-keto-5b-cholanate	HMDB
3a,7a-Dihydroxy-12-keto-5b-cholanic acid	HMDB
3a,7a-Dihydroxy-12-ketocholanate	HMDB
3a,7a-Dihydroxy-12-ketocholanic acid	HMDB
3a,7a-Dihydroxy-12-ketocholate	HMDB
3a,7a-Dihydroxy-12-ketocholic acid	HMDB
3a,7a-Dihydroxy-12-oxo-5b-cholan-24-Oate	HMDB
3a,7a-Dihydroxy-12-oxo-5b-cholan-24-Oic acid	HMDB
3a,7a-Dihydroxy-12-oxo-5b-cholanoate	HMDB
3a,7a-Dihydroxy-12-oxo-5b-cholanoic acid	HMDB
3a,7a-Dihydroxy-12-oxocholate	HMDB
3a,7a-Dihydroxy-12-oxocholic acid	HMDB
5b-Cholanic acid-3a,7a-diol-12-one	HMDB
12-Monoketocholate	HMDB
12-Monoketocholic acid	HMDB
12-oxo-3,7-Dihydroxycholanoic acid	HMDB
3 alpha, 7 alpha-Dihydroxy-12-one-5 beta-cholanoic acid	HMDB
3 alpha,7 alpha-Dihydroxy-12-keto-5 beta-cholanoic acid	HMDB
3alpha,7alpha-Dihydroxy-12-keto-5beta-cholanoic acid	HMDB
Sodium monoketocholate	HMDB
(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-Dihydroxy-2,15-dimethyl-16-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate	HMDB
3,7-Dihydroxy-12-oxocholanoic acid	ChEBI

Chemical Formula

C₂₄H₃₈O₅

Average Mass

406.5555 Da

Monoisotopic Mass

406.27192 Da

IUPAC Name

(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyl-16-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

Traditional Name

12-ketochenodeoxycholic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C24H38O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-19,22,25-26H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19-,22+,23+,24-/m1/s1

InChI Key

MIHNUBCEFJLAGN-DMMBONCOSA-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
3-hydroxysteroid
7-hydroxysteroid
3-alpha-hydroxysteroid
Oxosteroid
12-oxosteroid
Hydroxysteroid
Cyclic alcohol
Secondary alcohol
Ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

oxo-5beta-cholanic acid (CHEBI:16312 )
C24 bile acids, alcohols, and derivatives (LMST04010176 )

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	2.56	ALOGPS
logP	3.05	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	4.39	ChemAxon
pKa (Strongest Basic)	-0.51	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	109.97 m³·mol⁻¹	ChemAxon
Polarizability	46.44 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

HMDB0000400

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022017

KNApSAcK ID

Not Available

Chemspider ID

85044

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5389

PubChem Compound

94235

PDB ID

Not Available

ChEBI ID

16312

Good Scents ID

Not Available

References

General References

Kuramoto T, Furukawa Y, Nishina T, Sugimoto T, Mahara R, Tohma M, Kihira K, Hoshita T: Identification of short side chain bile acids in urine of patients with cerebrotendinous xanthomatosis. J Lipid Res. 1990 Oct;31(10):1895-902. [PubMed:2079611 ]

Showing NP-Card for 3,7-Dihydroxy-12-oxocholanoic acid (NP0086573)

MOL for NP0086573 (3,7-Dihydroxy-12-oxocholanoic acid)

3D MOL for NP0086573 (3,7-Dihydroxy-12-oxocholanoic acid)

3D SDF for NP0086573 (3,7-Dihydroxy-12-oxocholanoic acid)

3D-SDF for NP0086573 (3,7-Dihydroxy-12-oxocholanoic acid)

PDB for NP0086573 (3,7-Dihydroxy-12-oxocholanoic acid)

3D PDB for NP0086573 (3,7-Dihydroxy-12-oxocholanoic acid)

SMILES for NP0086573 (3,7-Dihydroxy-12-oxocholanoic acid)

INCHI for NP0086573 (3,7-Dihydroxy-12-oxocholanoic acid)

Structure for NP0086573 (3,7-Dihydroxy-12-oxocholanoic acid)

3D Structure for NP0086573 (3,7-Dihydroxy-12-oxocholanoic acid)