(2S)-3-[(1S,3S,4R)-3,4-dihydroxy-1-methoxy-2-oxopentyl]-2-{[(2S,4R,5R,6R)-4-{[(2S,4R,5R,6R)-4-{[(2S,4S,5R,6R)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy}-5-hydroxy-6-methyloxan-2-yl]oxy}-5-hydroxy-6-methyloxan-2-yl]oxy}-6-{[(2S,4R,5S,6R)-4-{[(2S,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-5-hydroxy-6-methyloxan-2-yl]oxy}-8,9-dihydroxy-7-methyl-1,2,3,4-tetrahydroanthracen-1-one

• ChemBase ID: 130482
• Molecular Formular: C52H76O24
• Molecular Mass: 1085.14544
• Monoisotopic Mass: 1084.47265331
• SMILES: Cc1c(cc2cc3CC([C@@H](C(=O)[C@H]([C@@H](C)O)O)OC)[C@@H](C(=O)c3c(c2c1O)O)O[C@H]1C[C@H]([C@@H]([C@@H](C)O1)O)O[C@H]1C[C@H]([C@@H]([C@@H](C)O1)O)O[C@H]1C[C@@](C)([C@@H]([C@@H](C)O1)O)O)O[C@H]1C[C@H]([C@H]([C@@H](C)O1)O)O[C@H]1C[C@H]([C@@H]([C@@H](C)O1)O)O
• Canonical SMILES: CO[C@@H](C1Cc2cc3cc(O[C@@H]4O[C@H](C)[C@@H]([C@@H](C4)O[C@H]4C[C@@H](O)[C@@H]([C@H](O4)C)O)O)c(c(c3c(c2C(=O)[C@H]1O[C@@H]1O[C@H](C)[C@H]([C@@H](C1)O[C@@H]1O[C@H](C)[C@H]([C@@H](C1)O[C@@H]1O[C@H](C)[C@H]([C@@](C1)(C)O)O)O)O)O)O)C)C(=O)[C@H]([C@H](O)C)O
• InChI: InChI=1S/C52H76O24/c1-18-29(72-34-14-30(43(58)21(4)68-34)73-33-13-28(54)42(57)20(3)67-33)12-26-10-25-11-27(49(66-9)48(63)41(56)19(2)53)50(47(62)39(25)46(61)38(26)40(18)55)76-36-16-31(44(59)23(6)70-36)74-35-15-32(45(60)22(5)69-35)75-37-17-52(8,65)51(64)24(7)71-37/h10,12,19-24,27-28,30-37,41-45,49-51,53-61,64-65H,11,13-17H2,1-9H3/t19-,20-,21-,22-,23-,24-,27?,28-,30-,31-,32-,33+,34+,35+,36+,37+,41+,42-,43+,44-,45-,49+,50+,51-,52+/m1/s1
• InChIKey: CFCUWKMKBJTWLW-GWRQQDNDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-3-[(1S,3S,4R)-3,4-dihydroxy-1-methoxy-2-oxopentyl]-2-{[(2S,4R,5R,6R)-4-{[(2S,4R,5R,6R)-4-{[(2S,4S,5R,6R)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy}-5-hydroxy-6-methyloxan-2-yl]oxy}-5-hydroxy-6-methyloxan-2-yl]oxy}-6-{[(2S,4R,5S,6R)-4-{[(2S,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-5-hydroxy-6-methyloxan-2-yl]oxy}-8,9-dihydroxy-7-methyl-1,2,3,4-tetrahydroanthracen-1-one
• IUPAC Traditional name: plicamycin
• Synonyms: Aureolic acid; Mithracin; Antibiotic LA 7017; Mithramycin A; Mitramycin; Plicatomycin; Plicamycin

Database IDs

• CAS Number: 18378-89-7
• PubChem SID: 162224761
• PubChem CID: 5284610
• ATC CODE: L01DC02
• CHEMBL: 509846
• Chemspider ID: 4447655
• DrugBank ID: DB06810
• KEGG ID: D00468
• Unique Ingredient Identifier: NIJ123W41V
• Wikipedia Title: Plicamycin

CALCULATED PROPERTIES

• Acid pKa: 8.491704
• H Acceptors: 24
• H Donor: 11
• LogD (pH = 5.5): 2.0724516
• LogD (pH = 7.4): 2.0391889
• Log P: 2.072891
• Molar Refractivity: 257.0091 cm^3
• Polarizability: 105.68714 Å^3
• Polar Surface Area: 358.2 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Admin Routes: Intravenous
• Legal Status: discontinued; Rx-only (US)
• Pregnancy Category: X (US)