(4R,7R)-N-[(1S,2S,4R,7S)-7-benzyl-2,10-dihydroxy-4-methyl-5,8-dioxo-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),9,12,14-tetraene-4-carboxamide

• ChemBase编号: 170471
• 分子式: C33H37N5O6
• 平均质量: 599.67678
• 单一同位素质量: 599.27438393
• 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)N3[C@H]2CCC3O)Cc2ccccc2)C1=O)O)C
• Canonical SMILES: CN1C[C@@H](CC2[C@H]1Cc1c[nH]c3c1c2ccc3)C(=O)N[C@]1(C)O[C@@]2(N(C1=O)[C@@H](Cc1ccccc1)C(=O)N1[C@H]2CCC1O)O
• InChI: InChI=1S/C33H37N5O6/c1-32(35-29(40)20-14-22-21-9-6-10-23-28(21)19(16-34-23)15-24(22)36(2)17-20)31(42)38-25(13-18-7-4-3-5-8-18)30(41)37-26(11-12-27(37)39)33(38,43)44-32/h3-10,16,20,22,24-27,34,39,43H,11-15,17H2,1-2H3,(H,35,40)/t20-,22?,24-,25+,26+,27?,32-,33+/m1/s1
• InChIKey: AHRNWGXNCFKOII-UYPVSMPXSA-N

名称和登记号

名称

• IUPAC标准名: (4R,7R)-N-[(1S,2S,4R,7S)-7-benzyl-2,10-dihydroxy-4-methyl-5,8-dioxo-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),9,12,14-tetraene-4-carboxamide
• IUPAC传统名: (4R,7R)-N-[(1S,2S,4R,7S)-7-benzyl-2,10-dihydroxy-4-methyl-5,8-dioxo-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),9,12,14-tetraene-4-carboxamide
• 别名: (5'α,10α)-9,10-Dihydro-8',12'-dihydroxy-2'-methyl-5'-(phenylmethyl)ergotaman-3',6',18-trione; 8'-Hydroxy Dihydro Ergotamine(Mixture of Diastereomers)

登记号

• CAS号: 90650-44-5
• PubChem SID: 164226381
• PubChem CID: 146217

理论计算性质

• 可自由旋转的化学键: 4
• 里宾斯基五规则: false
• Acid pKa: 9.707389
• 质子受体: 7
• 质子供体: 4
• LogD (pH = 5.5): -0.5172511
• LogD (pH = 7.4): 1.2420721
• Log P: 2.1177254
• 摩尔折射率: 160.5351 cm^3
• 极化性: 63.491394 Å^3
• 极化表面积: 138.44 Å^2

详细说明

Toronto Research Chemicals - H941350

The main metabolite of Dihydroergotamine, as 5-HT1A receptor agonist in the brain.

参考文献

• File, S., et al.: J. Neurosci., 16, 4810 (1996)
• Assie, M., et al.: Eur. J. Pharmacol., 386, 97 (1996)
• Fabre, V., et al.: Eur. J. Neurosci., 12, 2299 (1996)
• Akerman, S., et al.: Eur. J. Pharmacol., 424, 53 (1996)