methyl 23-(dimethylamino)-4,8,12,22,24-pentahydroxy-1,12-dimethyl-6,17-dioxo-10-[(3,4,5-trimethoxy-4,6-dimethyloxan-2-yl)oxy]-20,25-dioxahexacyclo[19.3.1.02,19.05,18.07,16.09,14]pentacosa-2(19),3,5(18),7,9(14),15-hexaene-13-carboxylate

• ChemBase ID: 132488
• Molecular Formular: C39H49NO16
• Molecular Mass: 787.80346
• Monoisotopic Mass: 787.30513449
• SMILES: CC1C(C(C(C(O1)OC1CC(C(c2c1c(c1c(c2)C(=O)c2c(c(cc3c2OC2C(C(C(C3(O2)C)O)N(C)C)O)O)C1=O)O)C(=O)OC)(C)O)OC)(C)OC)OC
• Canonical SMILES: COC(=O)C1c2cc3c(c(c2C(CC1(C)O)OC1OC(C)C(C(C1OC)(C)OC)OC)O)C(=O)c1c(C3=O)c2OC3OC(c2cc1O)(C)C(C(C3O)N(C)C)O
• InChI: InChI=1S/C39H49NO16/c1-14-32(49-7)39(4,52-10)33(50-8)36(53-14)54-19-13-37(2,48)24(34(47)51-9)15-11-16-21(27(43)20(15)19)28(44)22-18(41)12-17-30(23(22)26(16)42)55-35-29(45)25(40(5)6)31(46)38(17,3)56-35/h11-12,14,19,24-25,29,31-33,35-36,41,43,45-46,48H,13H2,1-10H3
• InChIKey: KGTDRFCXGRULNK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 23-(dimethylamino)-4,8,12,22,24-pentahydroxy-1,12-dimethyl-6,17-dioxo-10-[(3,4,5-trimethoxy-4,6-dimethyloxan-2-yl)oxy]-20,25-dioxahexacyclo[19.3.1.0^2,^1^9.0^5,^1^8.0^7,^1^6.0^9,^1^4]pentacosa-2(19),3,5(18),7,9(14),15-hexaene-13-carboxylate
• IUPAC Traditional name: methyl 23-(dimethylamino)-4,8,12,22,24-pentahydroxy-1,12-dimethyl-6,17-dioxo-10-[(3,4,5-trimethoxy-4,6-dimethyloxan-2-yl)oxy]-20,25-dioxahexacyclo[19.3.1.0^2,^1^9.0^5,^1^8.0^7,^1^6.0^9,^1^4]pentacosa-2(19),3,5(18),7,9(14),15-hexaene-13-carboxylate
• Synonyms: Nogalamycin

Database IDs

• CAS Number: 1404-15-5
• MDL Number: MFCD00083442
• PubChem SID: 162226765; 24897545
• PubChem CID: 4526

CALCULATED PROPERTIES

• Acid pKa: 8.765459
• H Acceptors: 16
• H Donor: 5
• LogD (pH = 5.5): 1.2316054
• LogD (pH = 7.4): 2.4136612
• Log P: 2.5236783
• Molar Refractivity: 193.7436 cm^3
• Polarizability: 76.878784 Å^3
• Polar Surface Area: 229.44 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: RA4550000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 45-46-61-20/21/22
• Safety Statements: 53-22-36/37/39-45
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H312-H332-H350-H360
• GHS Precautionary statements: P201-P280-P308 + P313
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95%
• Biological Source: from Streptomyces nogalater

DETAILS

Sigma Aldrich - N2019

Biochem/physiol Actions
Anthracyclic antitumor antibiotic. It is used as a sequence specific DNA binding (intercalation) reagent, binds d(CGTACG), d(ATGCAT).
Anthracyclic antitumor antibiotic.