(4R,7R)-N-[(1S,2S,4R,7S)-2-hydroxy-4-methyl-5,8-dioxo-7-(propan-2-yl)-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide

• ChemBase ID: 127290
• Molecular Formular: C29H35N5O5
• Molecular Mass: 533.6187
• Monoisotopic Mass: 533.26381925
• SMILES: O=C1N2CCC[C@H]2[C@]2(O)O[C@](C(=O)N2[C@H]1C(C)C)(NC(=O)[C@@H]1C=C2c3cccc4c3c(c[nH]4)C[C@H]2N(C)C1)C
• Canonical SMILES: O=C([C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)c[nH]3)N[C@]1(C)O[C@@]2(N(C1=O)[C@@H](C(C)C)C(=O)N1[C@H]2CCC1)O
• InChI: InChI=1S/C29H35N5O5/c1-15(2)24-26(36)33-10-6-9-22(33)29(38)34(24)27(37)28(3,39-29)31-25(35)17-11-19-18-7-5-8-20-23(18)16(13-30-20)12-21(19)32(4)14-17/h5,7-8,11,13,15,17,21-22,24,30,38H,6,9-10,12,14H2,1-4H3,(H,31,35)/t17-,21-,22+,24+,28-,29+/m1/s1
• InChIKey: BGHDUTQZGWOQIA-VQSKNWBGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,7R)-N-[(1S,2S,4R,7S)-2-hydroxy-4-methyl-5,8-dioxo-7-(propan-2-yl)-3-oxa-6,9-diazatricyclo[7.3.0.0^2,^6]dodecan-4-yl]-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-carboxamide
• IUPAC Traditional name: ergovaline
• Synonyms: Ergovaline

Database IDs

• CAS Number: 2873-38-3
• PubChem SID: 162221611
• PubChem CID: 104843
• Chemspider ID: 94635
• Wikipedia Title: Ergovaline

CALCULATED PROPERTIES

• Acid pKa: 9.695486
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -0.3272176
• LogD (pH = 7.4): 1.397892
• Log P: 1.8289045
• Molar Refractivity: 144.5444 cm^3
• Polarizability: 56.78957 Å^3
• Polar Surface Area: 118.21 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Pregnancy Category: 4 months (US)