2-[(3S)-9-hydroxy-1-methyl-10-oxo-3H,4H,10H-naphtho[2,3-c]pyran-3-yl]acetic acid

• ChemBase ID: 6151
• Molecular Formular: C16H14O5
• Molecular Mass: 286.27936
• Monoisotopic Mass: 286.08412355
• SMILES: Oc1c2C(=O)C3=C(O[C@@H](CC3=Cc2ccc1)CC(=O)O)C
• Canonical SMILES: OC(=O)C[C@H]1OC(=C2C(=Cc3c(C2=O)c(O)ccc3)C1)C
• InChI: InChI=1S/C16H14O5/c1-8-14-10(6-11(21-8)7-13(18)19)5-9-3-2-4-12(17)15(9)16(14)20/h2-5,11,17H,6-7H2,1H3,(H,18,19)/t11-/m0/s1
• InChIKey: HHXSOTFPYPQSBU-NSHDSACASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(3S)-9-hydroxy-1-methyl-10-oxo-3H,4H,10H-naphtho[2,3-c]pyran-3-yl]acetic acid
• IUPAC Traditional name: (S)-dnpa
• Synonyms: [(3S)-9-hydroxy-1-methyl-10-oxo-4,10-dihydro-3H-benzo[g]isochromen-3-yl]acetic acid

Database IDs

• PubChem SID: 99445012; 160969576
• PubChem CID: 443833

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.734721
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.17371148
• LogD (pH = 7.4): -1.3536973
• Log P: 1.9389912
• Molar Refractivity: 77.3547 cm^3
• Polarizability: 28.775229 Å^3
• Polar Surface Area: 83.83 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.01
• LOG S: -3.34
• Solubility (Water): 1.30e-01 g/l

DETAILS

DrugBank - DB08541

Drug information: experimental