(19S)-19-ethyl-19-hydroxy-8-nitro-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: 154370
• Molecular Formular: C20H15N3O6
• Molecular Mass: 393.3496
• Monoisotopic Mass: 393.09608522
• SMILES: CC[C@@]1(c2cc3n(c(=O)c2COC1=O)Cc1c3nc2cccc(c2c1)[N+](=O)[O-])O
• Canonical SMILES: CC[C@@]1(O)C(=O)OCc2c1cc1c3nc4cccc(c4cc3Cn1c2=O)[N+](=O)[O-]
• InChI: InChI=1S/C20H15N3O6/c1-2-20(26)13-7-16-17-10(8-22(16)18(24)12(13)9-29-19(20)25)6-11-14(21-17)4-3-5-15(11)23(27)28/h3-7,26H,2,8-9H2,1H3/t20-/m0/s1
• InChIKey: VHXNKPBCCMUMSW-FQEVSTJZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (19S)-19-ethyl-19-hydroxy-8-nitro-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; (19S)-19-ethyl-19-hydroxy-8-nitro-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)-heptaene-14,18-dione
• IUPAC Traditional name: 9-nitrocamptothecin; (19S)-19-ethyl-19-hydroxy-8-nitro-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)-heptaene-14,18-dione
• Synonyms: 9-nitrocamptothecin; Rubitecan; (9S)-9-[(Dimethylamino)methyl]-6,7,10,11-tetrahydro-9H,18H-5,21:12,17-Dimethenodibenzo[e,k]pyrrolo[3,4-h][1,4,13]oxadiazacyclohexadecine-18,20(19H)-dione Hydrochloride; LY 333531; Ruboxistaurin Hydrochloride

Database IDs

• CAS Number: 169939-93-9; 91421-42-0
• MDL Number: MFCD06656294
• PubChem SID: 162248509
• PubChem CID: 472335

CALCULATED PROPERTIES

• Acid pKa: 11.706159
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 1.1602228
• LogD (pH = 7.4): 1.160206
• Log P: 1.1602274
• Molar Refractivity: 101.8172 cm^3
• Polarizability: 39.110985 Å^3
• Polar Surface Area: 125.55 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• RTECS: UQ0493300
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: room temp

Product Information

• Empirical Formula (Hill Notation): C20H15N3O6

DETAILS

Sigma Aldrich - R3655

Biochem/physiol Actions
Topoisomerase I inhibitor. Rubitecan induces protein- linked DNA single strand breaks, blocking DNA and RNA synthesis in dividing cells. This mode of action makes rubitecan a potential chemotherapeutic agent, and it has been used with some success against refractory pancreatic cancer.1

Toronto Research Chemicals - R701525

Ruboxistaurin is a protein kinase C (PKC) β inhibitor, exhibits significant anti-angiogenic activity that reduces the response of vascular endothelial cells to stimulation by vascular endothelial growth factor (VEGF). Ruboxistaurin is used in treatment of

REFERENCES

• Miller, J., et al.: Diabetes Metab. Rev., 13, 37 (1997)
• Suzuma, I., et al.: J. Biol. Chem., 277, 1047 (1997)
• Ali, N., et al.: J. Pharmacol. Sci., 98, 130 (1997)