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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:26:04 UTC
Update Date2019-07-23 07:14:30 UTC
HMDB IDHMDB0060510
Secondary Accession Numbers
  • HMDB60510
Metabolite Identification
Common NameSN-38
DescriptionSN-38, also known as sn 38 or irrinotecan, 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). SN-38 is a drug. SN-38 is a strong basic compound (based on its pKa). Click on genes, proteins and metabolites below to link to respective articles. In vitro cytotoxicity assays show that the potency of SN-38 relative to irinotecan varies from 2- to 2000-fold. SN-38 exists in all living organisms, ranging from bacteria to humans. Within humans, SN-38 participates in a number of enzymatic reactions. In particular, SN-38 can be biosynthesized from irinotecan through the action of the enzymes liver carboxylesterase 1 and cocaine esterase. In addition, SN-38 and uridine diphosphate glucuronic acid can be converted into sn-38 glucuronide and uridine 5'-diphosphate; which is catalyzed by the enzymes UDP-glucuronosyltransferase 1-10 and UDP-glucuronosyltransferase 1-1. In humans, SN-38 is involved in irinotecan action pathway. It can cause the symptoms of diarrhoea and myelosuppression experienced by ~25% of the patients administered irinotecan. It is the active metabolite of irinotecan (an analog of camptothecin - a topoisomerase I inhibitor) but has 1000 times more activity than irinotecan itself. The variant of UGT1A1 in ~10% of Caucasians which leads to poor metabolism of SN-38 predicts irinotecan toxicity, as it is then less easily excreted from the body in its SN-38 glucuronide form. SN38 is formed via hydrolysis of irinotecan by carboxylesterases and metabolized via glucuronidation by UGT1A1. SN-38 and its glucuronide are lost into the bile and intestines. SN-38 is an antineoplastic drug.
Structure
Data?1563866070
Synonyms
ValueSource
10-Hydroxy-7-ethylcamptothecinChEBI
7-Ethyl-10-hydroxy-20(S)-camptothecinChEBI
7-Ethyl-10-hydroxycamptothecinChEBI
sn 38ChEBI
sn 38 LactoneChEBI
CPT 11HMDB
CamptosarHMDB
IrrinotecanHMDB
Camptothecin-11HMDB
Irinotecan hydrochlorideHMDB
CPT-11HMDB
sn38 CPDHMDB
IrinotecanHMDB
NK012 CompoundHMDB
Chemical FormulaC22H20N2O5
Average Molecular Weight392.4046
Monoisotopic Molecular Weight392.13722176
IUPAC Name(19S)-10,19-diethyl-7,19-dihydroxy-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)-heptaene-14,18-dione
Traditional Name7-ethyl-10-hydroxycamptothecin
CAS Registry NumberNot Available
SMILES
CCC1=C2C=C(O)C=CC2=NC2=C1CN1C2=CC2=C(COC(=O)[C@]2(O)CC)C1=O
InChI Identifier
InChI=1S/C22H20N2O5/c1-3-12-13-7-11(25)5-6-17(13)23-19-14(12)9-24-18(19)8-16-15(20(24)26)10-29-21(27)22(16,28)4-2/h5-8,25,28H,3-4,9-10H2,1-2H3/t22-/m0/s1
InChI KeyFJHBVJOVLFPMQE-QFIPXVFZSA-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
  • Hydroxyquinoline
  • Pyranopyridine
  • Quinoline
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyridinone
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Tertiary alcohol
  • Carboxylic acid ester
  • Lactam
  • Lactone
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

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 Solubility0.29 g/LALOGPS
logP2.73ALOGPS
logP1.87ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)9.68ChemAxon
pKa (Strongest Basic)3.91ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area99.96 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity106.12 m³·mol⁻¹ChemAxon
Polarizability41.43 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0cds-0019000000-79b6acd0ac5020e4fdaeSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0200-4001940000-c0a3b0dcc77abbfdfa52Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0019000000-953c13d44f1f753e244dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000f-0049000000-3bc00f235d1656474ceaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0090000000-0c561151ab4c396125a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-1a6f7a9c5371b8ce6492Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0005-0009000000-2782aeafd6952cc625f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004r-1092000000-87d95d0b42a2bf62be7eSpectrum
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 IDDB05482
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID94634
KEGG Compound IDC11173
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSN-38
METLIN IDNot Available
PubChem Compound104842
PDB IDNot Available
ChEBI ID8988
Food Biomarker OntologyNot Available
VMH IDNot Available
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 ]
  2. Sostelly A, Payen L, Guitton J, Di Pietro A, Falson P, Honorat M, Boumendjel A, Geze A, Freyer G, Tod M: Quantitative evaluation of the combination between cytotoxic drug and efflux transporter inhibitors based on a tumour growth inhibition model. Fundam Clin Pharmacol. 2014 Apr;28(2):161-9. doi: 10.1111/fcp.12005. Epub 2013 Feb 6. [PubMed:23384250 ]
  3. Yao Y, Su X, Xie Y, Wang Y, Kang T, Gou L, Yi C, Yang J: Synthesis, characterization, and antitumor evaluation of the albumin-SN38 conjugate. Anticancer Drugs. 2013 Mar;24(3):270-7. doi: 10.1097/CAD.0b013e32835c3543. [PubMed:23233044 ]
  4. Sostelly A, Payen L, Guitton J, Di Pietro A, Falson P, Honorat M, Valdameri G, Geze A, Boumendjel A, Freyer G, Tod M: A template model for studying anticancer drug efflux transporter inhibitors in vitro. Fundam Clin Pharmacol. 2013 Oct;27(5):544-56. doi: 10.1111/j.1472-8206.2012.01054.x. Epub 2012 Aug 8. [PubMed:22882086 ]
  5. Shimo T, Kurebayashi J, Kanomata N, Yamashita T, Kozuka Y, Moriya T, Sonoo H: Antitumor and anticancer stem cell activity of a poly ADP-ribose polymerase inhibitor olaparib in breast cancer cells. Breast Cancer. 2014 Jan;21(1):75-85. doi: 10.1007/s12282-012-0356-z. Epub 2012 Mar 28. [PubMed:22454224 ]
  6. Al-Kasspooles MF, Williamson SK, Henry D, Howell J, Niu F, Decedue CJ, Roby KF: Preclinical antitumor activity of a nanoparticulate SN38. Invest New Drugs. 2013 Aug;31(4):871-80. doi: 10.1007/s10637-012-9919-2. Epub 2013 Jan 9. [PubMed:23299391 ]

Only showing the first 10 proteins. There are 21 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 21 proteins in total.