(6S)-3,5,6-trihydroxy-4,6-bis(3-methylbut-2-en-1-yl)-2-(3-methylbutanoyl)cyclohexa-2,4-dien-1-one

• ChemBase ID: 127733
• Molecular Formular: C21H30O5
• Molecular Mass: 362.4599
• Monoisotopic Mass: 362.20932406
• SMILES: O=C(C1=C(O)C(=C(O)[C@](O)(C1=O)CC=C(C)C)CC=C(C)C)CC(C)C
• Canonical SMILES: CC(=CCC1=C(O)[C@@](C(=O)C(=C1O)C(=O)CC(C)C)(O)CC=C(C)C)C
• InChI: InChI=1S/C21H30O5/c1-12(2)7-8-15-18(23)17(16(22)11-14(5)6)20(25)21(26,19(15)24)10-9-13(3)4/h7,9,14,23-24,26H,8,10-11H2,1-6H3/t21-/m0/s1
• InChIKey: VMSLCPKYRPDHLN-NRFANRHFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6S)-3,5,6-trihydroxy-4,6-bis(3-methylbut-2-en-1-yl)-2-(3-methylbutanoyl)cyclohexa-2,4-dien-1-one
• IUPAC Traditional name: humulone
• Synonyms: α-Lupulic acid; α-Bitter acid; Humulone

Database IDs

• CAS Number: 26472-41-3
• PubChem SID: 162222051
• PubChem CID: 442911; 72625
• Chemspider ID: 391214
• Unique Ingredient Identifier: KHB4767H3K
• Wikipedia Title: Humulone

CALCULATED PROPERTIES

• Acid pKa: 2.9490097
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.0168525
• LogD (pH = 7.4): -1.082198
• Log P: 3.600608
• Molar Refractivity: 106.3035 cm^3
• Polarizability: 39.718803 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true