Record Information
Version3.6
Creation Date2008-09-16 08:41:15 UTC
Update Date2013-06-10 17:21:04 UTC
HMDB IDHMDB10364
Secondary Accession NumbersNone
Metabolite Identification
Common Name11-Hydroxyprogesterone 11-glucuronide
Description11-hydroxyprogesterone 11-glucuronide is a natural human metabolite of 11-hydroxyprogesterone generated in the liver by UDP glucuonyltransferase. Glucuronidation is used to assist in the excretion of toxic substances, drugs or other substances that cannot be used as an energy source. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher water solubility than the original substance, is eventually excreted by the kidneys.
Structure
Thumb
Synonyms
  1. 11-Hpg
  2. 11-Hydroxyprogesterone 11-glucuronoside
  3. 11alpha-Glucuronylprogesterone
  4. 11alpha-Hydroxyprogesterone 11-glucuronide
  5. 11alpha-Hydroxyprogesterone 11-glucuronoside
Chemical FormulaC27H38O9
Average Molecular Weight506.5852
Monoisotopic Molecular Weight506.251582814
IUPAC Name(2S,3S,4S,5R,6R)-6-{[(2R,14S,15S)-14-acetyl-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-17-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional IUPAC Name(2S,3S,4S,5R,6R)-6-{[(2R,14S,15S)-14-acetyl-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-17-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry Number77710-64-6
SMILES
CC(=O)[C@H]1CCC2C3CCC4=CC(=O)CC[C@]4(C)C3C(C[C@]12C)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O
InChI Identifier
InChI=1S/C27H38O9/c1-12(28)16-6-7-17-15-5-4-13-10-14(29)8-9-26(13,2)19(15)18(11-27(16,17)3)35-25-22(32)20(30)21(31)23(36-25)24(33)34/h10,15-23,25,30-32H,4-9,11H2,1-3H3,(H,33,34)/t15?,16-,17?,18?,19?,20+,21+,22-,23+,25-,26+,27-/m1/s1
InChI KeyWVTMNZAPPOMZST-UCMXSJKRSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassSteroids and Steroid Derivatives
Sub ClassSteroidal Glycosides
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
  • Glucuronides(Lipidmaps)
  • Steroids and Steroid Derivatives
Substituents
  • 1,2 Diol
  • 20 Keto Steroid
  • 3 Keto Steroid
  • Acetal
  • Beta Hydroxy Acid
  • Carboxylic Acid
  • Cyclohexane
  • Cyclohexene
  • Decaline
  • Glucuronic Acid Or Derivative
  • Glucuronide
  • Glycosyl Compound
  • Hexose Monosaccharide
  • Ketone
  • O Glycosyl Compound
  • Oxane
  • Progestogin Skeleton
  • Saccharide
  • Secondary Alcohol
  • Sesterterpene
  • Sugar Acid
  • Terpene Glycoside
Direct ParentSteroid Glucuronide Conjugates
Ontology
StatusExpected and Not Quantified
Origin
  • Drug or steroid metabolite
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Waste products
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility0.38 g/LALOGPS
logP1.63ALOGPS
logP1.39ChemAxon
logS-3.1ALOGPS
pKa (strongest acidic)3.59ChemAxon
pKa (strongest basic)-3.7ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count9ChemAxon
hydrogen donor count4ChemAxon
polar surface area150.59ChemAxon
rotatable bond count4ChemAxon
refractivity126.58ChemAxon
polarizability52.56ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00610
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB027516
KNApSAcK IDNot Available
Chemspider ID24850122
KEGG Compound IDNot Available
BioCyc IDBeta-D-Glucuronides
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB10364
Metagene LinkHMDB10364
METLIN IDNot Available
PubChem Compound42621273
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Gene Name:
UGT2B28
Uniprot ID:
Q9BY64
Gene Name:
UGT2B4
Uniprot ID:
P06133
Gene Name:
UGT1A4
Uniprot ID:
P22310
Gene Name:
UGT2B7
Uniprot ID:
P16662
Gene Name:
UGT2B15
Uniprot ID:
P54855
Gene Name:
UGT2A1
Uniprot ID:
Q9Y4X1
Gene Name:
UGT1A1
Uniprot ID:
P22309
Gene Name:
UGT1A9
Uniprot ID:
O60656
Gene Name:
UGT1A8
Uniprot ID:
Q9HAW9
Gene Name:
UGT1A3
Uniprot ID:
P35503
Gene Name:
UGT1A10
Uniprot ID:
Q9HAW8
Gene Name:
UGT2B17
Uniprot ID:
O75795
Gene Name:
UGT1A6
Uniprot ID:
P19224
Gene Name:
UGT1A5
Uniprot ID:
P35504
Gene Name:
UGT2B11
Uniprot ID:
O75310
Gene Name:
UGT1A7
Uniprot ID:
Q9HAW7
Gene Name:
GUSB
Uniprot ID:
P08236
Gene Name:
UGT2A3
Uniprot ID:
Q6UWM9
Gene Name:
UGT1A10
Uniprot ID:
Q5DT02
Gene Name:
UGT1A8
Uniprot ID:
Q5DSZ6