19-ethyl-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

• ChemBase ID: 156499
• Molecular Formular: C20H16N2O5
• Molecular Mass: 364.35144
• Monoisotopic Mass: 364.10592162
• SMILES: CCC1(c2cc3n(c(=O)c2COC1=O)Cc1c3nc2ccc(cc2c1)O)O
• Canonical SMILES: CCC1(O)C(=O)OCc2c1cc1c3nc4ccc(cc4cc3Cn1c2=O)O
• InChI: InChI=1S/C20H16N2O5/c1-2-20(26)14-7-16-17-11(5-10-6-12(23)3-4-15(10)21-17)8-22(16)18(24)13(14)9-27-19(20)25/h3-7,23,26H,2,8-9H2,1H3
• InChIKey: HAWSQZCWOQZXHI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 19-ethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0^2,^1^1.0^4,^9.0^1^5,^2^0]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione
• IUPAC Traditional name: 19-ethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0^2,^1^1.0^4,^9.0^1^5,^2^0]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione
• Synonyms: 10-Hydroxycamptothecin; Camptothecin; 10-羟基喜树碱

Database IDs

• CAS Number: 19685-09-7; 64439-81-2
• MDL Number: MFCD00274425
• PubChem SID: 162250637; 24895558
• PubChem CID: 4330531

CALCULATED PROPERTIES

• Acid pKa: 9.6547575
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.9146374
• LogD (pH = 7.4): 0.9142486
• Log P: 0.9166779
• Molar Refractivity: 96.4734 cm^3
• Polarizability: 37.803802 Å^3
• Polar Surface Area: 99.96 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Pharmacology Properties

• Mechanism of Action: Inhibitor of DNA enzyme topoisomerase I

Product Information

• Grade: analytical standard, for drug analysis
• Biological Source: Minor alkaloid from Camptotheca acuminata (Nyssaceae)
• Application(s): Used in cancer chemotherapy
• Empirical Formula (Hill Notation): C20H16N2O5

REFERENCES

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