(2R,3R,4S)-2-{[(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-dihydroxy-3,4-dihydro-2H-pyran-6-carboxylic acid

• ChemBase ID: 177799
• Molecular Formular: C28H26N2O10
• Molecular Mass: 550.51344
• Monoisotopic Mass: 550.15874504
• 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=C(O1)C(=O)O)O)O
• Canonical SMILES: CC[C@@]1(O)C(=O)OCc2c1cc1c3nc4ccc(cc4c(c3Cn1c2=O)CC)O[C@@H]1OC(=C[C@@H]([C@@H]1O)O)C(=O)O
• InChI: InChI=1S/C28H26N2O10/c1-3-13-14-7-12(39-26-23(32)20(31)9-21(40-26)25(34)35)5-6-18(14)29-22-15(13)10-30-19(22)8-17-16(24(30)33)11-38-27(36)28(17,37)4-2/h5-9,20,23,26,31-32,37H,3-4,10-11H2,1-2H3,(H,34,35)/t20-,23+,26+,28-/m0/s1
• InChIKey: KMHNKMBQOGMTMU-NZIYMESCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S)-2-{[(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-dihydroxy-3,4-dihydro-2H-pyran-6-carboxylic acid
• IUPAC Traditional name: (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}-4,5-dihydroxy-5,6-dihydro-4H-pyran-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 4-Deoxy-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 4-Deoxy-β-D-glucopyranosiduronic Acid; SN-38 4-Deoxy-glucuronide

Database IDs

• PubChem SID: 164233709
• PubChem CID: 71752210

CALCULATED PROPERTIES

• LogD (pH = 5.5): -1.623711
• LogD (pH = 7.4): -2.7802184
• Log P: -0.43518266
• Molar Refractivity: 138.4884 cm^3
• Polarizability: 54.115273 Å^3
• Polar Surface Area: 175.95 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false
• Acid pKa: 3.0986626
• H Acceptors: 10
• H Donor: 4

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: Yellow Foam

DETAILS

Toronto Research Chemicals - S589970

Byproduct formed during the preparation of SN-38 Glucuronide.