(19Z,21Z,23Z,25Z,27Z,29Z,31Z)-33-{[(3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-17-[7-(4-aminophenyl)-5-hydroxy-4-methyl-7-oxoheptan-2-yl]-1,3,5,7,37-pentahydroxy-18-methyl-9,13,15-trioxo-16,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid

• ChemBase ID: 1023
• Molecular Formular: C59H84N2O18
• Molecular Mass: 1109.30086
• Monoisotopic Mass: 1108.57191386
• SMILES: O1C2(O)CC(O)C(C1CC(OC1O[C@@H]([C@@H](O)[C@H](N)[C@@H]1O)C)/C=C\C=C/C=C\C=C/C=C\C=C/C=C\C(C(OC(=O)CC(=O)CCCC(=O)CC(O)CC(O)CC(O)C2)C(CC(C(O)CC(=O)c1ccc(N)cc1)C)C)C)C(=O)O
• Canonical SMILES: OC1CC(O)CC(=O)CCCC(=O)CC(=O)OC(C(CC(C(CC(=O)c2ccc(cc2)N)O)C)C)C(C)/C=C\C=C/C=C\C=C/C=C\C=C/C=C\C(CC2OC(CC(C1)O)(O)CC(O)C2C(=O)O)OC1O[C@H](C)[C@H]([C@@H]([C@@H]1O)N)O
• InChI: InChI=1S/C59H84N2O18/c1-35-18-15-13-11-9-7-5-6-8-10-12-14-16-21-46(77-58-55(72)53(61)54(71)38(4)76-58)31-50-52(57(73)74)49(69)34-59(75,79-50)33-45(66)29-44(65)28-43(64)27-41(62)19-17-20-42(63)30-51(70)78-56(35)37(3)26-36(2)47(67)32-48(68)39-22-24-40(60)25-23-39/h5-16,18,21-25,35-38,43-47,49-50,52-56,58,64-67,69,71-72,75H,17,19-20,26-34,60-61H2,1-4H3,(H,73,74)/b6-5-,9-7-,10-8-,13-11-,14-12-,18-15-,21-16-/t35?,36?,37?,38-,43?,44?,45?,46?,47?,49?,50?,52?,53+,54-,55+,56?,58?,59?/m1/s1
• InChIKey: YKSVGLFNJPQDJE-WDANKXQLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (19Z,21Z,23Z,25Z,27Z,29Z,31Z)-33-{[(3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-17-[7-(4-aminophenyl)-5-hydroxy-4-methyl-7-oxoheptan-2-yl]-1,3,5,7,37-pentahydroxy-18-methyl-9,13,15-trioxo-16,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid
• IUPAC Traditional name: candicidin
• Brand Name: Candicidin A; Candicidin D; FR-008-III; Vanobid
• Synonyms: Candicidin

Database IDs

• CAS Number: 1403-17-4
• PubChem SID: 46504812; 160964486
• PubChem CID: 441142

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.6770744
• H Acceptors: 19
• H Donor: 11
• LogD (pH = 5.5): 0.9276812
• LogD (pH = 7.4): 0.80546075
• Log P: 0.92744017
• Molar Refractivity: 300.5014 cm^3
• Polarizability: 115.361824 Å^3
• Polar Surface Area: 356.38 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.94
• LOG S: -5.07
• Solubility (Water): 9.34e-03 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 1.7

DETAILS

DrugBank - DB01152

• Drug Groups: approved
• Description: Candicidin is an antibiotic obtained from a streptomyces (Streptomyces griseus) and active against some fungi of the genus Candida (C. albicans). Candicidin is administered intravaginally in the treatment of vulvovaginal candidiasis.
• Indication: Used in the topical treatment of vulvovaginal candidiasis.
• Pharmacology: Candicidin is a polyene antifungal antibiotic produced by a strain of Streptomyces griseus. It is especially effective against Candida albicans (more effective than amphotericin B), and is administered intravaginally in the treatment of vulvovaginal candidiasis.
• Affected Organisms: Various Fungus Species
• External Links: Wikipedia