Dehydrolithocholic Acid

HCID 5283906
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Basic information

CAS
1553-56-6
Standard SMILES
C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C
InChIKey
KIQFUORWRVZTHT-OPTMKGCMSA-N
Molecular formula
C24H38O3
Average molar mass
374.6 g/mol
Monoisotopic mass
374.28209508

Overview

3-oxo-5beta-cholanic acid is an oxo-5beta-cholanic acid. It is a conjugate acid of a 3-oxo-5beta-cholanate.

Names & identifiers

Preferred name
Dehydrolithocholic Acid
IUPAC
(4R)-4-[(5R,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid
English name
3-Oxo-5beta-cholanoic Acid
Molecular formula
C24H38O3
Molecular weight
374.56

Names & synonyms

Dehydrolithocholic acid1553-56-63-Oxocholanic acid3-Oxolithocholic acid3-Oxocholan-24-oic acid3-Oxo-5beta-cholan-24-oic Acid96JBM35FXFDTXSID609351823-oxo-5 beta-cholan-24-oic acidRefChem:585658DTXCID7017839393-Oxo-5beta-cholanoic Acid
Show more names
3-KETOCHOLANIC ACID3-Keto-5β-cholanic acid3-oxocholanicacid3-oxolithocholicacid3-ketolithocholicacid3-Oxo-5β-cholanic acid5β-CHOLANIC acid-3-ONE5-B-CHOLANIC ACID-3-ONE
3-Ketolithocholic acid3-keto-lithocholic acid3-Oxo-5|A-cholanoic AcidMFCD00046265(4R)-4-[(5R,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid5.beta.-Cholanic acid-3-oneCholan-24-oic acid, 3-oxo-, (5beta)-CHEMBL410893

Database identifiers

CAS
1553-56-6
PubChem CID
5283906
DTXSID
DTXSID60935182
ChEMBL
CHEMBL410893
ChEBI
CHEBI:17639
UNII
96JBM35FXF
EC Number
833-832-5
Nikkaji
J39.835G

Properties

Computed structural properties

XLogP
5.8
Topological polar surface area
54.4 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
4
Heavy atoms
27

Experimental & physicochemical properties

Chemical ClassesBile Acids -> Canonical Bile Acids
LipidsLipids -> Sterol Lipids [ST] -> Bile acids and derivatives [ST04] -> C24 bile acids, alcohols, and derivatives [ST0401]
Collision Cross Section · 2 items

205.6 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: Bile Acids]

214.3 Ų [M+K-H+Cl]- [CCS Type: DT; Method: single field calibrated]

Physicochemical properties

Melting point
140 · 140-141 °C
Boiling point
509.3 · 509.3±23.0 °C(Predicted)
Density
1.069 · 1.069±0.06 g/cm3(Predicted)
storage temp.
Refrigerator
solubility
Chloroform (Slightly), Methanol (Slightly)
pka
4.76 · 4.76±0.10(Predicted)

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

wgk
3
rtecs
FZ2281400
hs_code
2918.30.9000
Signal word
Warning
Symbol(GHS)
GHS07
Storage Class
11 - Combustible Solids

Chemistry & industry

Applications

Uses3-Oxo-5β-cholanoic Acid is a steroid compound with pharmacological activity. It is a bile acid. Also used in the preparation of lithocholic acid derivatives used as proteasome regulators.

Uses3-Oxo-5beta-cholanoic Acid is a steroid compound with pharmacological activity. It is a bile acid. Also used in the preparation of lithocholic acid derivatives used as proteasome regulators.

Suppliers61 total

韶远科技(上海)有限公司021-50795510 4000665055 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
重庆欣博曜生物科技有限公司19122915778 · [email protected]
艾吉析科技（上海）有限公司17717235263 · [email protected]
广州佳途科技股份有限公司81960175 18933936954 · [email protected]

Additional notes

DefinitionChEBI: 3-oxo-5beta-cholanic acid is an oxo-5beta-cholanic acid. It is a conjugate acid of a 3-oxo-5beta-cholanate.

Related reactions

2 records
New reaction record

Compound notes

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