(4R,7R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-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; methanesulfonic acid

• ChemBase ID: 167610
• Molecular Formular: C34H41N5O8S
• Molecular Mass: 680.77569484
• Monoisotopic Mass: 680.27093914
• 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]2CCC3)Cc2ccccc2)C1=O)O)C.CS(=O)(=O)O
• Canonical SMILES: CS(=O)(=O)O.[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]2CCC1)O
• InChI: InChI=1S/C33H37N5O5.CH4O3S/c1-32(35-29(39)21-15-23-22-10-6-11-24-28(22)20(17-34-24)16-25(23)36(2)18-21)31(41)38-26(14-19-8-4-3-5-9-19)30(40)37-13-7-12-27(37)33(38,42)43-32;1-5(2,3)4/h3-6,8-11,17,21,23,25-27,34,42H,7,12-16,18H2,1-2H3,(H,35,39);1H3,(H,2,3,4)/t21-,23?,25-,26+,27+,32-,33+;/m1./s1/i2+1
• InChIKey: ADYPXRFPBQGGAH-ZYPLPAQJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,7R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-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; methanesulfonic acid
• IUPAC Traditional name: (4R,7R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-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; methanesulfonic acid
• Synonyms: 5'α,10α)-9,10-Dihydro-12'-hydroxy-2'-methyl-5'-(phenylmethyl)ergotaman-3',6',18-trione-13C,d3 Methanesulfonate; 9,10-Dihydroergotamine-13C,d3 Monomethanesulfonate; (+)-Dihydroergotamine-13C,d3 Mesylate; Dihytamine-13C,d3; Dirgotarl-13C,d3; Endophleban-13C,d3; Ergomimet-13C,d3; Ergont-13C,d3; Ergotonin-13C,d3; Ikaran-13C,d3; Migranal-13C,d3; Morena-13C,d3; Tonopres-13C,d3; Verladyn-13C,d3; Dihydro Ergotamine-13C,d3 Mesylate

Database IDs

• PubChem SID: 162261743
• PubChem CID: 71316167

CALCULATED PROPERTIES

• Acid pKa: 9.712761
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 0.07567159
• LogD (pH = 7.4): 1.835023
• Log P: 2.7116222
• Molar Refractivity: 159.3948 cm^3
• Polarizability: 62.85823 Å^3
• Polar Surface Area: 118.21 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D449082

A labelled α-androgenic blocker with selective venoconstrictor properties. Also binds to serotonin 5HT1-receptors. Antimigraine.

REFERENCES

• de Marees, et al.: Eur. J. Clin. Pharmacol., 30, 685 (1986)
• McCarthy, B.G., et al.: Headache, 29, 420 (1986)
• Ziegler, D., et al.: Neurology, 44, 447 (1986)