(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-(13C,2H3)methyl-6,11-diazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),9,12,14-tetraene-4-carboxamide

• ChemBase ID: 170472
• Molecular Formular: C33H37N5O6
• Molecular Mass: 600.66943484
• Monoisotopic Mass: 600.27773877
• SMILES: c1cc2[nH]cc3C[C@@H]4C(c(c1)c23)C[C@H](CN4[13CH3])C(=O)N[C@@]1(O[C@@]2(N([C@H](C(=O)N3[C@H]2CCC3O)Cc2ccccc2)C1=O)O)C
• Canonical SMILES: [13CH3]N1C[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/i2+1
• InChIKey: AHRNWGXNCFKOII-JHEZGXLCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (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-(^1^3C,^2H₃)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 Traditional name: (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-(^1^3C,^2H₃)methyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(16),9,12,14-tetraene-4-carboxamide
• Synonyms: (5'α,10α)-9,10-Dihydro-8',12'-dihydroxy-2'-methyl-5'-(phenylmethyl)ergotaman-3',6',18-trione-13C,d3; 8'-Hydroxy Dihydro Ergotamine-13C,d3

Database IDs

• PubChem SID: 164226382
• PubChem CID: 71748986

CALCULATED PROPERTIES

• Acid pKa: 9.707389
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -0.5172511
• LogD (pH = 7.4): 1.2420721
• Log P: 2.1177254
• Molar Refractivity: 160.5351 cm^3
• Polarizability: 63.491394 Å^3
• Polar Surface Area: 138.44 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H941352

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

REFERENCES

• 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)