(3S,6S,9R,13S,17R,18S,18aR)-17,18-dichloro-3-ethyl-6,13-bis(hydroxymethyl)-9-phenyl-octadecahydropyrrolo[1,2-d]1,4,7,10,13-pentaazacyclohexadecane-1,4,7,11,14-pentone

• ChemBase ID: 126798
• Molecular Formular: C24H31Cl2N5O7
• Molecular Mass: 572.43824
• Monoisotopic Mass: 571.16005372
• SMILES: O=C1[C@H](CO)NC(=O)[C@H](NC(=O)[C@H]2N(C(=O)[C@H](NC(=O)C[C@@H](N1)c1ccccc1)CO)C[C@H]([C@H]2Cl)Cl)CC
• Canonical SMILES: OC[C@@H]1NC(=O)[C@@H](CC)NC(=O)[C@@H]2[C@H](Cl)[C@@H](CN2C(=O)[C@H](NC(=O)C[C@@H](NC1=O)c1ccccc1)CO)Cl
• InChI: InChI=1S/C24H31Cl2N5O7/c1-2-14-21(35)30-16(10-32)22(36)29-15(12-6-4-3-5-7-12)8-18(34)27-17(11-33)24(38)31-9-13(25)19(26)20(31)23(37)28-14/h3-7,13-17,19-20,32-33H,2,8-11H2,1H3,(H,27,34)(H,28,37)(H,29,36)(H,30,35)/t13-,14+,15-,16+,17+,19-,20+/m1/s1
• InChIKey: PMBVHCCVEPYDSN-BADCMNFISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,6S,9R,13S,17R,18S,18aR)-17,18-dichloro-3-ethyl-6,13-bis(hydroxymethyl)-9-phenyl-octadecahydropyrrolo[1,2-d]1,4,7,10,13-pentaazacyclohexadecane-1,4,7,11,14-pentone
• IUPAC Traditional name: cyclochlorotine
• Synonyms: Cyclo[(R)-3-phenyl-β-alanyl-L-seryl-(2α,3α,4α)-3,4-dichloro-L-prolyl-L-2-aminobutanoyl-L-seryl]; Yellowed rice toxin; Cyclochlorotine

Database IDs

• CAS Number: 12663-46-6
• PubChem SID: 162221126
• PubChem CID: 25565; 57134655
• Chemspider ID: 28426727
• KEGG ID: C19379
• Wikipedia Title: Cyclochlorotine

CALCULATED PROPERTIES

• Acid pKa: 8.84773
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): -1.6577196
• LogD (pH = 7.4): -1.6710542
• Log P: -1.6575469
• Molar Refractivity: 134.7928 cm^3
• Polarizability: 53.26394 Å^3
• Polar Surface Area: 177.17 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false