3-[(2R,5S,8S,8aS)-5-benzyl-8a-hydroxy-2-methyl-2-[(4R,7R)-6-methyl-6,11-diazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),9,12,14-tetraene-4-amido]-3,6-dioxo-hexahydro-2H-[1,3]oxazolo[3,2-a]piperazin-8-yl]propanoic acid

• ChemBase ID: 167719
• Molecular Formular: C33H37N5O7
• Molecular Mass: 615.67618
• Monoisotopic Mass: 615.26929855
• SMILES: c1cc2[nH]cc3C[C@@H]4C(c(c1)c23)C[C@H](CN4C)C(=O)N[C@@]1(O[C@@]2(N([C@H](C(=O)N[C@H]2CCC(=O)O)Cc2ccccc2)C1=O)O)C
• Canonical SMILES: OC(=O)CC[C@@H]1NC(=O)[C@@H](N2[C@@]1(O)O[C@@](C2=O)(C)NC(=O)[C@H]1CN(C)[C@H]2C(C1)c1cccc3c1c(C2)c[nH]3)Cc1ccccc1
• InChI: InChI=1S/C33H37N5O7/c1-32(36-29(41)20-14-22-21-9-6-10-23-28(21)19(16-34-23)15-24(22)37(2)17-20)31(43)38-25(13-18-7-4-3-5-8-18)30(42)35-26(11-12-27(39)40)33(38,44)45-32/h3-10,16,20,22,24-26,34,44H,11-15,17H2,1-2H3,(H,35,42)(H,36,41)(H,39,40)/t20-,22?,24-,25+,26+,32-,33+/m1/s1
• InChIKey: CXZPBEVCAUGOGC-PANVYSLLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(2R,5S,8S,8aS)-5-benzyl-8a-hydroxy-2-methyl-2-[(4R,7R)-6-methyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(16),9,12,14-tetraene-4-amido]-3,6-dioxo-hexahydro-2H-[1,3]oxazolo[3,2-a]piperazin-8-yl]propanoic acid
• IUPAC Traditional name: 3-[(2R,5S,8S,8aS)-5-benzyl-8a-hydroxy-2-methyl-2-[(4R,7R)-6-methyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(16),9,12,14-tetraene-4-amido]-3,6-dioxo-dihydro-5H-[1,3]oxazolo[3,2-a]piperazin-8-yl]propanoic acid
• Synonyms: (5'α,10α)-9,10-Dihydro-12'-hydroxy-2'-methyl-3',6',18-trioxo-5'-(phenylmethyl)-7',8'-secoergotaman-8'-oic Acid; Dihydro Ergotamine Ring-opened Acid

Database IDs

• CAS Number: 91653-37-1
• PubChem SID: 162261852
• PubChem CID: 71316200

CALCULATED PROPERTIES

• Acid pKa: 3.539327
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -0.465021
• LogD (pH = 7.4): -0.49626747
• Log P: -0.46335647
• Molar Refractivity: 162.4961 cm^3
• Polarizability: 64.13183 Å^3
• Polar Surface Area: 164.3 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D449580

Dihydro Ergotamine Ring-opened Acid is a metabolite of Dihydroergotamine (6190-39-2).

REFERENCES

• Maurer, G. et al.: Eur. J. Clin. Pharmacol., 26, 463 (1984)