DXC

(3ALPHA,5BETA,12ALPHA)-3,12-DIHYDROXYCHOLAN-24-OIC ACID

Created: 2000-06-26
Last modified:  2020-06-05

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Chemical Details

Formal Charge0
Atom Count68
Chiral Atom Count10
Bond Count71
Aromatic Bond Count0
2D diagram of DXC
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Chemical Component Summary

Name(3ALPHA,5BETA,12ALPHA)-3,12-DIHYDROXYCHOLAN-24-OIC ACID
SynonymsDEOXYCHOLIC ACID
Systematic Name (OpenEye OEToolkits)(4R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
FormulaC24 H40 O4
Molecular Weight392.572
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O=C(O)CCC(C4CCC3C2C(C1(C)CCC(O)CC1CC2)CC(O)C34C)C
SMILESCACTVS3.341C[CH](CCC(O)=O)[CH]1CC[CH]2[CH]3CC[CH]4C[CH](O)CC[C]4(C)[CH]3C[CH](O)[C]12C
SMILESOpenEye OEToolkits1.5.0CC(CCC(=O)O)C1CCC2C1(C(CC3C2CCC4C3(CCC(C4)O)C)O)C
Canonical SMILESCACTVS3.341 C[C@H](CCC(O)=O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@]12C
Canonical SMILESOpenEye OEToolkits1.5.0 C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2CC[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C
InChIInChI1.03 InChI=1S/C24H40O4/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/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,21+,23+,24-/m1/s1
InChIKeyInChI1.03 KXGVEGMKQFWNSR-LLQZFEROSA-N

Drug Info: DrugBank

DrugBank IDDB03619 
NameDeoxycholic acid
Groups approved
DescriptionDeoxycholic acid is a a bile acid which emulsifies and solubilizes dietary fats in the intestine, and when injected subcutaneously, it disrupts cell membranes in adipocytes and destroys fat cells in that tissue. In April 2015, deoxycholic acid was approved by the FDA for the treatment submental fat to improve aesthetic appearance and reduce facial fullness or convexity. It is marketed under the brand name Kybella by Kythera Biopharma and is the first pharmacological agent available for submental fat reduction, allowing for a safer and less invasive alternative than surgical procedures.
Synonyms
  • Desoxycholic acid
  • (3α,5β,12α)-3,12-dihydroxycholan-24-oic acid
  • Deoxycholate
  • 3alpha,12alpha-Dihydroxy-5beta-cholanic acid
  • Desoxycholsäure
Brand Names
  • Belkyra
  • Kybella
  • Duchol Ect
  • Debiline
  • Medichol
IndicationFor improvement in appearance of moderate to severe fullness associated with submental fat in adults.
Categories
  • Bile Acids and Salts
  • BSEP/ABCB11 inducers
  • Cholagogues and Choleretics
  • Cholanes
  • Cholic Acids
ATC-CodeD11AX24
CAS number83-44-3

Drug Targets

NameTarget SequencePharmacological ActionActions
Steroid Delta-isomeraseMNLPTAQEVQGLMARYIELVDVGDIEAIVQMYADDATVEDPFGQPPIHGR...unknown
PpcAMKKVIASLALSVFCAGLAFAADDIVLKAKNGDVKFPHKAHQKAVPDCKKC...unknown
Elongation factor Tu GTP-binding domain-containing protein 1MVLNSLDKMIQLQKNTANIRNICVLAHVDHGKTTLADCLISSNGIISSRL...unknown
Choloylglycine hydrolaseMCTGLALETKDGLHLFGRNMDIEYSFNQSIIFIPRNFKCVNKSNKKELTT...unknown
Lactaldehyde dehydrogenaseMSVPVQHPMYIDGQFVTWRGDAWIDVVNPATEAVISRIPDGQAEDARKAI...unknown
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 222528
ChEMBL CHEMBL406393
ChEBI CHEBI:28834
CCDC/CSD SORXED, RAVVUF, YOMKAN, FEHYAS02, FEHYAS03, TOFBUO, BARPUG, FEHYAS01, DADKUP, TOFBOI, FEHYAS04, YECPUT, UBOCOF, QQQDFA01, DANSEQ, PEJBOW
COD 2006240, 4501232, 7203350, 7216029