(1S,5R,13R,17S)-10,17-dihydroxy-4-(3-methylbut-2-en-1-yl)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7,9,11(18)-trien-14-one

• ChemBase ID: 128537
• Molecular Formular: C21H25NO4
• Molecular Mass: 355.4275
• Monoisotopic Mass: 355.17835829
• SMILES: O=C1[C@@H]2Oc3c4c(ccc3O)C[C@H]3N(CC[C@@]24[C@@]3(O)CC1)CC=C(C)C
• Canonical SMILES: CC(=CCN1CC[C@@]23[C@@]4([C@H]1Cc1c3c(O[C@H]2C(=O)CC4)c(cc1)O)O)C
• InChI: InChI=1S/C21H25NO4/c1-12(2)6-9-22-10-8-20-17-13-3-4-14(23)18(17)26-19(20)15(24)5-7-21(20,25)16(22)11-13/h3-4,6,16,19,23,25H,5,7-11H2,1-2H3/t16-,19+,20+,21-/m1/s1
• InChIKey: OHKCLOQPSLQCQR-MBPVOVBZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,17S)-10,17-dihydroxy-4-(3-methylbut-2-en-1-yl)-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7,9,11(18)-trien-14-one
• IUPAC Traditional name: (1S,5R,13R,17S)-10,17-dihydroxy-4-(3-methylbut-2-en-1-yl)-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7,9,11(18)-trien-14-one
• Synonyms: Nalmexone

Database IDs

• CAS Number: 16676-26-9
• PubChem SID: 162222844
• PubChem CID: 5360516
• Chemspider ID: 4514525
• Wikipedia Title: Nalmexone

CALCULATED PROPERTIES

• Acid pKa: 7.346695
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.3410362
• LogD (pH = 7.4): 1.1811553
• Log P: 1.4416004
• Molar Refractivity: 98.6777 cm^3
• Polarizability: 38.218487 Å^3
• Polar Surface Area: 70.0 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true