You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:26:11 UTC
Update Date2019-07-23 07:14:30 UTC
HMDB IDHMDB0060511
Secondary Accession Numbers
  • HMDB60511
Metabolite Identification
Common NameSN38 glucuronide
DescriptionSN38 glucuronide is a metabolite of irinotecan. Irinotecan is a drug used for the treatment of cancer. Irinotecan prevents DNA from unwinding by inhibition of topoisomerase 1. In chemical terms, it is a semisynthetic analogue of the natural alkaloid camptothecin. Its main use is in colon cancer, in particular, in combination with other chemotherapy agents. This includes the regimen FOLFIRI, which consists of infusional 5-fluorouracil, leucovorin, and irinotecan. Irinotecan received accelerated approval by the U.S. (Wikipedia)
Structure
Data?1563866070
Synonyms
ValueSource
sn-38gKegg
7-Ethyl-10-hydroxycamptothecin beta-glucuronideHMDB
sn 38gHMDB
7-Ethyl-10-hydroxycamptothecin glucuronideHMDB
Chemical FormulaC28H28N2O11
Average Molecular Weight568.5287
Monoisotopic Molecular Weight568.169309748
IUPAC Name(2S,3S,4S,5R,6S)-6-{[(19S)-10,19-diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional NameSN38 glucuronide
CAS Registry NumberNot Available
SMILES
CCC1=C2C=C(O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)C=CC2=NC2=C1CN1C2=CC2=C(COC(=O)[C@]2(O)CC)C1=O
InChI Identifier
InChI=1S/C28H28N2O11/c1-3-12-13-7-11(40-26-22(33)20(31)21(32)23(41-26)25(35)36)5-6-17(13)29-19-14(12)9-30-18(19)8-16-15(24(30)34)10-39-27(37)28(16,38)4-2/h5-8,20-23,26,31-33,38H,3-4,9-10H2,1-2H3,(H,35,36)/t20-,21-,22+,23-,26+,28-/m0/s1
InChI KeySSJQVDUAKDRWTA-CAYKMONMSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as camptothecins. These are heterocyclic compounds comprising a planar pentacyclic ring structure, that includes a pyrrolo[3,4-beta]-quinoline moiety (rings A, B and C), conjugated pyridone moiety (ring D) and one chiral center at position 20 within the alpha-hydroxy lactone ring with (S) configuration (the E-ring).
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassCamptothecins
Sub ClassNot Available
Direct ParentCamptothecins
Alternative Parents
Substituents
  • Camptothecin
  • Phenolic glycoside
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Pyranopyridine
  • Quinoline
  • Beta-hydroxy acid
  • Pyridinone
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • Monosaccharide
  • Oxane
  • Pyran
  • Pyridine
  • Benzenoid
  • Tertiary alcohol
  • Heteroaromatic compound
  • Secondary alcohol
  • Lactone
  • Lactam
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Azacycle
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid
  • Acetal
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

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
Water Solubility1.25 g/LALOGPS
logP0.62ALOGPS
logP-1.2ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)3.1ChemAxon
pKa (Strongest Basic)3.96ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area196.18 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity138.13 m³·mol⁻¹ChemAxon
Polarizability57.46 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fkl-5100390000-1ec43087b83f26748d87Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0092-9311277000-c1c07e9db55581211f9eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fr6-0009080000-5f1a65f43e213c62eeebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0039010000-2585cc0e99f4ba0dc2b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-1195000000-be2f080bb0e154f9465bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01bc-0103090000-b768445c1a809e7a7461Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0007-1109040000-c2cdd95f3d8b534e6630Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0536-2029000000-490976843fd8c2f8cbeeSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC11376
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound443154
PDB IDNot Available
ChEBI ID8990
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Only showing the first 10 proteins. There are 19 proteins in total.

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme has glucuronidating capacity with steroid substrates such as 5-beta-androstane 3-alpha,17-beta-diol, estradiol, ADT, eugenol and bile acids. Only isoform 1 seems to be active.
Gene Name:
UGT2B28
Uniprot ID:
Q9BY64
Molecular weight:
38742.9
Reactions
SN-38 + Uridine diphosphate glucuronic acid → SN38 glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
Gene Name:
UGT2B4
Uniprot ID:
P06133
Molecular weight:
60512.035
Reactions
SN-38 + Uridine diphosphate glucuronic acid → SN38 glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
Gene Name:
UGT1A4
Uniprot ID:
P22310
Molecular weight:
60024.535
Reactions
SN-38 + Uridine diphosphate glucuronic acid → SN38 glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:
UGT2B10
Uniprot ID:
P36537
Molecular weight:
60773.485
Reactions
SN-38 + Uridine diphosphate glucuronic acid → SN38 glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:
UGT2B7
Uniprot ID:
P16662
Molecular weight:
60720.15
Reactions
SN-38 + Uridine diphosphate glucuronic acid → SN38 glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xenobiotic substrates, including simple phenolic compounds, 7-hydroxylated coumarins, flavonoids, anthraquinones, and certain drugs and their hydroxylated metabolites. It also catalyzes the glucuronidation of endogenous estrogens and androgens.
Gene Name:
UGT2B15
Uniprot ID:
P54855
Molecular weight:
61035.815
Reactions
SN-38 + Uridine diphosphate glucuronic acid → SN38 glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Active on odorants and seems to be involved in olfaction; it could help clear lipophilic odorant molecules from the sensory epithelium.
Gene Name:
UGT2A1
Uniprot ID:
Q9Y4X1
Molecular weight:
60771.605
Reactions
SN-38 + Uridine diphosphate glucuronic acid → SN38 glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
SN-38 + Uridine diphosphate glucuronic acid → SN38 glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:
UGT1A9
Uniprot ID:
O60656
Molecular weight:
59940.495
Reactions
SN-38 + Uridine diphosphate glucuronic acid → SN38 glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:
UGT1A8
Uniprot ID:
Q9HAW9
Molecular weight:
59741.035
Reactions
SN-38 + Uridine diphosphate glucuronic acid → SN38 glucuronide + Uridine 5'-diphosphatedetails

Only showing the first 10 proteins. There are 19 proteins in total.