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Human Metabolome Database Version 3.5

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Showing metabocard for Estriol 3-sulfate 16-glucuronide (HMDB10356)

Record Information
Version 3.5
Creation Date 2008-09-16 02:28:35 -0600
Update Date 2013-06-10 11:16:40 -0600
HMDB ID HMDB10356
Secondary Accession Numbers None
Metabolite Identification
Common Name Estriol 3-sulfate 16-glucuronide
Description Estriol 3-sulfate 16-glucuronide is a natural human metabolite of Estriol 3-sulfate 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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (16alpha,17beta)-17-hydroxy-3-(sulfooxy)estra-1,3,5(10)-trien-16-yl-beta-D-Glucopyranosiduronic acid
  2. (16alpha,17beta)-17-hydroxy-3-(sulfooxy)estra-1,3,5(10)-trien-16-yl-beta-delta-Glucopyranosiduronic acid
  3. Estriol 3-sulfate 16-glucuronide
  4. Estriol 3-sulfate 16-glucuronoside
  5. Estriol 3-sulfate 16alpha-glucuronide
  6. Estriol 3-sulfate 16alpha-glucuronoside
  7. Estriol 3-sulphate 16-glucuronide
  8. Estriol 3-sulphate 16-glucuronoside
  9. Estriol 3-sulphate 16alpha-glucuronide
  10. Estriol 3-sulphate 16alpha-glucuronoside
Chemical Formula C24H32O12S
Average Molecular Weight 544.569
Monoisotopic Molecular Weight 544.161447178
IUPAC Name (2S,3S,4S,5R)-3,4,5-trihydroxy-6-{[(1S,10R,11S,13R,14R,15S)-14-hydroxy-15-methyl-5-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-13-yl]oxy}oxane-2-carboxylic acid
Traditional IUPAC Name (2S,3S,4S,5R)-3,4,5-trihydroxy-6-{[(1S,10R,11S,13R,14R,15S)-14-hydroxy-15-methyl-5-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-13-yl]oxy}oxane-2-carboxylic acid
CAS Registry Number 4661-65-8
SMILES [H][C@@]12C[C@@H](OC3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(OS(O)(=O)=O)C=C3
InChI Identifier InChI=1S/C24H32O12S/c1-24-7-6-13-12-5-3-11(36-37(31,32)33)8-10(12)2-4-14(13)15(24)9-16(21(24)28)34-23-19(27)17(25)18(26)20(35-23)22(29)30/h3,5,8,13-21,23,25-28H,2,4,6-7,9H2,1H3,(H,29,30)(H,31,32,33)/t13-,14-,15+,16-,17+,18+,19-,20+,21+,23?,24+/m1/s1
InChI Key ATNWFRGUDKUYOG-SUPAOECSSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Steroidal Glycosides
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Sesquiterpene Glycosides
Substituents
  • 1,2 Diol
  • 17 Hydroxy Steroid
  • Acetal
  • Beta Hydroxy Acid
  • Carboxylic Acid
  • Cyclic Alcohol
  • Cyclohexane
  • Cyclohexene
  • Estrogen Skeleton
  • Glucuronic Acid Or Derivative
  • Glucuronide
  • Glycosyl Compound
  • Hexose Monosaccharide
  • O Glycosyl Compound
  • Organic Sulfuric Acid Monoester
  • Oxane
  • Phenanthrene
  • Saccharide
  • Secondary Alcohol
  • Sesquiterpene Backbone
  • Sugar Acid
  • Sulfate Ester
  • Sulfated Steroid Skeleton
  • Terpene Glycoside
  • Tetralin
Direct Parent Steroidal Glycosides
Ontology
Status Detected and 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
State Solid
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
Water Solubility 1.83 g/L ALOGPS
LogP 0.01 ALOGPS
LogP -0.92 ChemAxon
LogS -2.47 ALOGPS
pKa (strongest acidic) -1.7 ChemAxon
pKa (strongest basic) -3.3 ChemAxon
Hydrogen Acceptor Count 11 ChemAxon
Hydrogen Donor Count 6 ChemAxon
Polar Surface Area 200.28 A2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 123.54 ChemAxon
Polarizability 54.16 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Amniotic Fluid
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Amniotic Fluid Detected and Quantified 0.046 +/- 0.036 uM Adult (>18 years old) Both Comment Ambulant pregnancy
Blood Detected and Quantified 0.11 +/- 0.08 uM Adult (>18 years old) Female Comment Ambulant pregnancy
Urine Detected and Quantified 0.49 +/- 0.25 umol/mmol creatinine Adult (>18 years old) Both Comment Ambulant pregnancy
Associated Disorders and Diseases
Disease References
Pregnancy
  • Andreolini F, Borra C, Caccamo F, Di Corcia A, Nicoletti I, Samperi R, Improta F: Estriol and its conjugates in late pregnancy determined by extraction with Carbopack B and liquid chromatography with fluorometric detection. Clin Chem. 1985 Oct;31(10):1698-702. Pubmed: 2994907 Link_out
    Associated OMIM IDs None
    DrugBank ID Not Available
    DrugBank Metabolite ID Not Available
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID Not Available
    FoodDB ID FDB027508
    KNApSAcK ID Not Available
    Chemspider ID 133283 Link_out
    KEGG Compound ID C03033 Link_out
    BioCyc ID Beta-D-Glucuronides Link_out
    BiGG ID Not Available
    Wikipedia Link Not Available
    NuGOwiki Link HMDB10356 Link_out
    Metagene Link HMDB10356 Link_out
    METLIN ID Not Available
    PubChem Compound 151223 Link_out
    PDB ID Not Available
    ChEBI ID Not Available
    References
    Synthesis Reference Not Available
    Material Safety Data Sheet (MSDS) Not Available
    General References Not Available
    Enzymes
    Name: UDP-glucuronosyltransferase 2B28
    Reactions: Not Available
    Gene Name: UGT2B28
    Uniprot ID: Q9BY64 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 2B4
    Reactions: Not Available
    Gene Name: UGT2B4
    Uniprot ID: P06133 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 1-4
    Reactions: Not Available
    Gene Name: UGT1A4
    Uniprot ID: P22310 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 2B7
    Reactions: Not Available
    Gene Name: UGT2B7
    Uniprot ID: P16662 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 2B15
    Reactions: Not Available
    Gene Name: UGT2B15
    Uniprot ID: P54855 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 2A1
    Reactions: Not Available
    Gene Name: UGT2A1
    Uniprot ID: Q9Y4X1 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 1-1
    Reactions: Not Available
    Gene Name: UGT1A1
    Uniprot ID: P22309 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 1-9
    Reactions: Not Available
    Gene Name: UGT1A9
    Uniprot ID: O60656 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 1-8
    Reactions: Not Available
    Gene Name: UGT1A8
    Uniprot ID: Q9HAW9 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 1-3
    Reactions: Not Available
    Gene Name: UGT1A3
    Uniprot ID: P35503 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 1-10
    Reactions: Not Available
    Gene Name: UGT1A10
    Uniprot ID: Q9HAW8 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 2B17
    Reactions: Not Available
    Gene Name: UGT2B17
    Uniprot ID: O75795 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 1-6
    Reactions: Not Available
    Gene Name: UGT1A6
    Uniprot ID: P19224 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 1-5
    Reactions: Not Available
    Gene Name: UGT1A5
    Uniprot ID: P35504 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 2B11
    Reactions: Not Available
    Gene Name: UGT2B11
    Uniprot ID: O75310 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 1-7
    Reactions: Not Available
    Gene Name: UGT1A7
    Uniprot ID: Q9HAW7 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Beta-glucuronidase
    Reactions: Not Available
    Gene Name: GUSB
    Uniprot ID: P08236 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 2A3
    Reactions: Not Available
    Gene Name: UGT2A3
    Uniprot ID: Q6UWM9 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: HCG2039726, isoform CRA_f
    Reactions: Not Available
    Gene Name: UGT1A10
    Uniprot ID: Q5DT02 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: HCG2039726, isoform CRA_e
    Reactions: Not Available
    Gene Name: UGT1A8
    Uniprot ID: Q5DSZ6 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP glycosyltransferase 1 family polypeptide A7
    Reactions: Not Available
    Gene Name: UGT1A7
    Uniprot ID: Q5DSZ7 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA