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Record Information
Version1.0
Created at2020-11-23 19:41:30 UTC
Updated at2021-08-12 19:52:16 UTC
NP-MRD IDNP0002830
Secondary Accession NumbersNone
Natural Product Identification
Common NameGlycodesoxycholic acid
Provided ByBMRBBMRB logo
DescriptionGlycodeoxycholic acid is also known as deoxycholylglycine or GDCA. Glycodesoxycholic acid is found in Streptomyces nigra and Trypanosoma brucei. It was first documented in 1978 (PMID: 659989). Based on a literature review a small amount of articles have been published on glycodeoxycholic acid (PMID: 17984079) (PMID: 22359652) (PMID: 23892997).
Structure
Thumb
Synonyms
ValueSource
Deoxycholic acid glycine conjugateChEBI
DeoxycholylglycineChEBI
GDCAChEBI
GlycodeoxycholateChEBI
Glycodesoxycholic acidChEBI
3alpha,12alpha-Dihydroxy-5beta-cholan-24-oylglycineKegg
Deoxycholate glycine conjugateGenerator
Deoxycholic acid glycine conjugic acidGenerator
GlycodesoxycholateGenerator
3a,12a-Dihydroxy-5b-cholan-24-oylglycineGenerator
3Α,12α-dihydroxy-5β-cholan-24-oylglycineGenerator
Glycodeoxycholic acidGenerator
Acid, glycodeoxycholicMeSH
Glycine deoxycholateMeSH
Deoxycholate, glycineMeSH
Chemical FormulaC26H43NO5
Average Mass449.6320 Da
Monoisotopic Mass449.31412 Da
IUPAC Name2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]acetic acid
Traditional Nameglycodeoxycholic acid
CAS Registry NumberNot 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])C[C@H](O)[C@]12C)[C@H](C)CCC(=O)NCC(O)=O
InChI Identifier
InChI=1S/C26H43NO5/c1-15(4-9-23(30)27-14-24(31)32)19-7-8-20-18-6-5-16-12-17(28)10-11-25(16,2)21(18)13-22(29)26(19,20)3/h15-22,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16-,17-,18+,19-,20+,21+,22+,25+,26-/m1/s1
InChI KeyWVULKSPCQVQLCU-BUXLTGKBSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 400 MHz, methanol, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, methanol, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, methanol, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Streptomyces nigraLOTUS Database
Trypanosoma bruceiLOTUS Database
Species Where Detected
Species NameSourceReference
Penicillium sp. SA29KNApSAcK Database
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as glycinated bile acids and derivatives. These are compounds with a structure characterized by the presence of a glycine linked to a bile acid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentGlycinated bile acids and derivatives
Alternative Parents
Substituents
  • Glycinated bile acid
  • Dihydroxy bile acid, alcohol, or derivatives
  • Hydroxy bile acid, alcohol, or derivatives
  • 3-hydroxysteroid
  • 12-hydroxysteroid
  • Hydroxysteroid
  • 3-alpha-hydroxysteroid
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Fatty amide
  • Fatty acyl
  • N-acyl-amine
  • Cyclic alcohol
  • Carboxamide group
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organic nitrogen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.69ALOGPS
logP2.69ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)3.77ChemAxon
pKa (Strongest Basic)-0.32ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area106.86 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity122 m³·mol⁻¹ChemAxon
Polarizability52.15 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00030411
Chemspider ID2299354
KEGG Compound IDC05464
BioCyc IDGLYCODEOXYCHOLIC_ACID
BiGG IDNot Available
Wikipedia LinkGlycodeoxycholic_acid
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID27471
Good Scents IDNot Available
References
General References
  1. Bloch CA, Watkins JB: Determination of conjugated bile acids in human bile and duodenal fluid by reverse-phase high-performance liquid chromatography. J Lipid Res. 1978 May;19(4):510-3. [PubMed:659989 ]
  2. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
  3. Khurana S, Raina H, Pappas V, Raufman JP, Pallone TL: Effects of deoxycholylglycine, a conjugated secondary bile acid, on myogenic tone and agonist-induced contraction in rat resistance arteries. PLoS One. 2012;7(2):e32006. doi: 10.1371/journal.pone.0032006. Epub 2012 Feb 16. [PubMed:22359652 ]
  4. Cekic AB, Alhan E, Usta A, Turkyilmaz S, Kural BV, Ercin C: Effects of clotrimazol on the acute necrotizing pancreatitis in rats. Inflammation. 2013 Dec;36(6):1576-83. doi: 10.1007/s10753-013-9702-3. [PubMed:23892997 ]