NP-MRD: Showing NP-Card for 12-Ketodeoxycholic acid (NP0086552)

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Record Information

Version

2.0

Created at

2022-05-11 16:24:11 UTC

Updated at

2022-05-11 16:24:11 UTC

NP-MRD ID

NP0086552

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12-Ketodeoxycholic acid

Description

12-Ketodeoxycholic acid, also known as 12-dehydrodeoxycholate or 12-ketolithocholate, belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. 12-Ketodeoxycholic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 12-Ketodeoxycholic acid exists in all living organisms, ranging from bacteria to humans. Bile acids are steroid acids found predominantly in bile of mammals. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. 12-Ketodeoxycholic acid was first documented in 1988 (PMID: 3133222). Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit (PMID: 2545348) (PMID: 8173925).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231218272D          

 33 36  0  0  1  0            999 V2000
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   10.7283  -14.7822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   18.6360  -10.7182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4630  -13.5017    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv0541 02231218272D          

 33 36  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0086552

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

> <INCHI_IDENTIFIER>
InChI=1S/C24H38O4/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/h14-20,25H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,23+,24-/m1/s1

> <INCHI_KEY>
CVNYHSDFZXHMMJ-VPUMZWJWSA-N

> <FORMULA>
C24H38O4

> <MOLECULAR_WEIGHT>
390.5561

> <EXACT_MASS>
390.277009704

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
45.515900800801035

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.78

> <JCHEM_LOGP>
4.3547869593333335

> <ALOGPS_LOGS>
-4.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.296396219790154

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.556916959655809

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3569565006749031

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
108.37449999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.26e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-ketolithocholic 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  O   UNK     0      26.998 -20.583   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      20.026 -27.593   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      34.237 -17.398   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      34.787 -20.007   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      26.998 -25.203   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.331 -24.433   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.664 -24.433   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      28.331 -22.893   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      24.263 -25.214   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.250 -26.818   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      29.788 -22.424   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      27.022 -26.807   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      29.788 -24.902   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.664 -22.893   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      25.639 -27.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      30.687 -23.663   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      26.998 -22.123   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      22.835 -24.345   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      22.810 -27.664   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      30.267 -20.960   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      28.331 -21.353   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      24.275 -23.674   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      21.376 -25.158   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      21.363 -26.829   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      31.773 -20.643   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      29.238 -19.814   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      32.252 -19.179   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      33.759 -18.861   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0      28.069 -25.811   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0      28.462 -25.658   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0      26.731 -23.817   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0      24.255 -28.049   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      31.006 -22.233   0.000  0.00  0.00           H+0
CONECT    1   17                                                            
CONECT    2   24                                                            
CONECT    3   28                                                            
CONECT    4   28                                                            
CONECT    5    6    7   12   29                                             
CONECT    6    5    8   13   30                                             
CONECT    7    5    9   14   31                                             
CONECT    8    6   11   17   21                                             
CONECT    9    7   10   18   22                                             
CONECT   10    9   15   19   32                                             
CONECT   11    8   16   20   33                                             
CONECT   12    5   15                                                       
CONECT   13    6   16                                                       
CONECT   14    7   17                                                       
CONECT   15   10   12                                                       
CONECT   16   11   13                                                       
CONECT   17    1    8   14                                                  
CONECT   18    9   23                                                       
CONECT   19   10   24                                                       
CONECT   20   11   25   26                                                  
CONECT   21    8                                                            
CONECT   22    9                                                            
CONECT   23   18   24                                                       
CONECT   24    2   19   23                                                  
CONECT   25   20   27                                                       
CONECT   26   20                                                            
CONECT   27   25   28                                                       
CONECT   28    3    4   27                                                  
CONECT   29    5                                                            
CONECT   30    6                                                            
CONECT   31    7                                                            
CONECT   32   10                                                            
CONECT   33   11                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
12-Ketodeoxycholate	Generator
(3a,5b)-3-Hydroxy-12-oxo-cholan-24-Oate	HMDB
(3a,5b)-3-Hydroxy-12-oxo-cholan-24-Oic acid	HMDB
(3alpha,5beta)-3-Hydroxy-12-oxo-cholan-24-Oate	HMDB
(3alpha,5beta)-3-Hydroxy-12-oxo-cholan-24-Oic acid	HMDB
12-Dehydrodeoxycholate	HMDB
12-Dehydrodeoxycholic acid	HMDB
12-Ketolithocholate	HMDB
12-Ketolithocholic acid	HMDB
12-oxo-3a-Hydroxy-5b-cholanate	HMDB
12-oxo-3a-Hydroxy-5b-cholanic acid	HMDB
12-Oxolithocholate	HMDB
12-Oxolithocholic acid	HMDB
3a-Hydroxy-12-oxo-5b-cholan-24-Oate	HMDB
3a-Hydroxy-12-oxo-5b-cholan-24-Oic acid	HMDB
3a-Hydroxy-12-oxo-5b-cholanate	HMDB
3a-Hydroxy-12-oxo-5b-cholanic acid	HMDB
3a-Hydroxy-12-oxo-5b-cholanoate	HMDB
3a-Hydroxy-12-oxo-5b-cholanoic acid	HMDB
3-Hydroxy-12-ketocholanoic acid	HMDB
12-Ketolithocholic acid, (3beta,5beta)-isomer	HMDB
3 alpha-Hydroxy-12-keto-5 beta-cholanoic acid	HMDB
(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-Hydroxy-2,15-dimethyl-16-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate	HMDB

Chemical Formula

C₂₄H₃₈O₄

Average Mass

390.5561 Da

Monoisotopic Mass

390.27701 Da

IUPAC Name

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

Traditional Name

12-ketolithocholic 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])CC(=O)[C@]12C)[C@H](C)CCC(O)=O

InChI Identifier

InChI=1S/C24H38O4/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/h14-20,25H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,23+,24-/m1/s1

InChI Key

CVNYHSDFZXHMMJ-VPUMZWJWSA-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 monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Monohydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Monohydroxy bile acid, alcohol, or derivatives
3-hydroxysteroid
Hydroxysteroid
3-alpha-hydroxysteroid
Oxosteroid
12-oxosteroid
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

C24 bile acids, alcohols, and derivatives (LMST04010155 )

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	3.78	ALOGPS
logP	4.35	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	4.56	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	108.37 m³·mol⁻¹	ChemAxon
Polarizability	45.52 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

HMDB0000328

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021953

KNApSAcK ID

Not Available

Chemspider ID

2338365

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5317

PubChem Compound

3080612

PDB ID

Not Available

ChEBI ID

803536

Good Scents ID

Not Available

References

General References

Reddy B, Engle A, Katsifis S, Simi B, Bartram HP, Perrino P, Mahan C: Biochemical epidemiology of colon cancer: effect of types of dietary fiber on fecal mutagens, acid, and neutral sterols in healthy subjects. Cancer Res. 1989 Aug 15;49(16):4629-35. [PubMed:2545348 ]
Barker GM, Radley S, Bain I, Davis A, Lawson AM, Keighley MR, Neoptolemos JP: Biliary bile acid profiles in patients with familial adenomatous polyposis before and after colectomy. Br J Surg. 1994 Mar;81(3):441-4. doi: 10.1002/bjs.1800810340. [PubMed:8173925 ]
Andersen E, Karlaganis G, Sjovall J: Altered bile acid profiles in duodenal bile and urine in diabetic subjects. Eur J Clin Invest. 1988 Apr;18(2):166-72. doi: 10.1111/j.1365-2362.1988.tb02408.x. [PubMed:3133222 ]

Showing NP-Card for 12-Ketodeoxycholic acid (NP0086552)

MOL for NP0086552 (12-Ketodeoxycholic acid)

3D MOL for NP0086552 (12-Ketodeoxycholic acid)

3D SDF for NP0086552 (12-Ketodeoxycholic acid)

3D-SDF for NP0086552 (12-Ketodeoxycholic acid)

PDB for NP0086552 (12-Ketodeoxycholic acid)

3D PDB for NP0086552 (12-Ketodeoxycholic acid)

SMILES for NP0086552 (12-Ketodeoxycholic acid)

INCHI for NP0086552 (12-Ketodeoxycholic acid)

Structure for NP0086552 (12-Ketodeoxycholic acid)

3D Structure for NP0086552 (12-Ketodeoxycholic acid)