(2S,3S,4S,5R,6R)-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),2,4,6,8,10,15(20)-heptaen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 177800
• Molecular Formular: C28H28N2O11
• Molecular Mass: 568.52872
• Monoisotopic Mass: 568.16930973
• SMILES: c1(ccc2c(c1)c(c1c(n2)c2n(C1)c(=O)c1c(c2)[C@@](C(=O)OC1)(O)CC)CC)O[C@@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O
• Canonical SMILES: CC[C@@]1(O)C(=O)OCc2c1cc1c3nc4ccc(cc4c(c3Cn1c2=O)CC)O[C@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: 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
• InChIKey: SSJQVDUAKDRWTA-TUPTZLRNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-{[(19S)-10,19-diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0^2,^1^1.0^4,^9.0^1^5,^2^0]henicosa-1(21),2,4,6,8,10,15(20)-heptaen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-{[(19S)-10,19-diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0^2,^1^1.0^4,^9.0^1^5,^2^0]henicosa-1(21),2,4,6,8,10,15(20)-heptaen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 4,11-Diethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl β-D-Glucopyranosiduronic Acid; (4S)-4,11-Diethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl β-D-Glucopyranosiduronic Acid; SN-38 Glucuronide

Database IDs

• CAS Number: 121080-63-5
• PubChem SID: 164233710
• PubChem CID: 71752211

CALCULATED PROPERTIES

• Acid pKa: 3.1032526
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): -2.3577626
• LogD (pH = 7.4): -3.5182335
• Log P: -1.1698077
• Molar Refractivity: 138.1274 cm^3
• Polarizability: 55.03203 Å^3
• Polar Surface Area: 196.18 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: Pale Yellow Solid
• Melting Point: >250°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - S589980

A metabolite of Irinotecan

REFERENCES

• Fujita, K., et al.: Biol. Pharm. Bull., 31, 2137 (2008)
• Sandanaraj, E., et al.: Pharmacogen. J., 8, 174 (2008)
• Chen, K., et al.: Chem. Biol., 15, 1277 (2008)
• Prijovich, Z., et al.: Mol. Canc. Ther., 8, 940 (2008)