(4R,7R)-6-methyl-6,11-diazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),2,9,12,14-pentaene-4-carboxylic acid

• ChemBase ID: 128154
• Molecular Formular: C16H16N2O2
• Molecular Mass: 268.31044
• Monoisotopic Mass: 268.12117776
• SMILES: O=C(O)[C@@H]1C=C2c3cccc4c3c(c[nH]4)C[C@H]2N(C1)C
• Canonical SMILES: CN1C[C@@H](C=C2[C@H]1Cc1c[nH]c3c1c2ccc3)C(=O)O
• InChI: InChI=1S/C16H16N2O2/c1-18-8-10(16(19)20)5-12-11-3-2-4-13-15(11)9(7-17-13)6-14(12)18/h2-5,7,10,14,17H,6,8H2,1H3,(H,19,20)/t10-,14-/m1/s1
• InChIKey: ZAGRKAFMISFKIO-QMTHXVAHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,7R)-6-methyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(16),2,9,12,14-pentaene-4-carboxylic acid
• IUPAC Traditional name: lysergic acid
• Synonyms: 6-Methyl- 9,10- didehydroergoline- 8-carboxylic acid; Lysergic acid

Database IDs

• CAS Number: 82-58-6
• PubChem SID: 162222468
• PubChem CID: 6717
• CHEBI ID: 6604
• Chemspider ID: 6461
• Wikipedia Title: Lysergic_acid

CALCULATED PROPERTIES

• Acid pKa: 3.6504738
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.7862347
• LogD (pH = 7.4): -0.8272867
• Log P: -0.7841139
• Molar Refractivity: 77.6219 cm^3
• Polarizability: 30.602657 Å^3
• Polar Surface Area: 56.33 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 238 - 240 °C