(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),2,9,12,14-pentaene-4-carboxamide; 2,3-dihydroxybutanedioic acid

• ChemBase ID: 168159
• Molecular Formular: C37H41N5O11
• Molecular Mass: 732.74099484
• Monoisotopic Mass: 732.283612
• SMILES: C(C(O)C(=O)O)(O)C(=O)O.c1cc2[nH]cc3C[C@@H]4C(=C[C@H](CN4[13CH3])C(=O)N[C@@]4(O[C@@]5(N([C@H](C(=O)N6[C@H]5CCC6)Cc5ccccc5)C4=O)O)C)c(c1)c23
• Canonical SMILES: O=C([C@H]1CN([13CH3])[C@H]2C(=C1)c1cccc3c1c(C2)c[nH]3)N[C@]1(C)O[C@@]2(N(C1=O)[C@@H](Cc1ccccc1)C(=O)N1[C@H]2CCC1)O.OC(=O)C(C(C(=O)O)O)O
• InChI: InChI=1S/C33H35N5O5.C4H6O6/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;5-1(3(7)8)2(6)4(9)10/h3-6,8-11,15,17,21,25-27,34,42H,7,12-14,16,18H2,1-2H3,(H,35,39);1-2,5-6H,(H,7,8)(H,9,10)/t21-,25-,26+,27+,32-,33+;/m1./s1/i2+1
• InChIKey: NMTWKEWYQXZGCI-VFSAYZOFSA-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),2,9,12,14-pentaene-4-carboxamide; 2,3-dihydroxybutanedioic acid
• IUPAC Traditional name: (.+-.)-tartaric acid; (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),2,9,12,14-pentaene-4-carboxamide
• Synonyms: (5α)-12'-Hydroxy-2'-methyl-5'-(phenylmethyl)-ergotaman-3',6',18-trione-13C,d3 (2R,3R)-2,3-Dihydroxybutanedioate; Ergam-13C,d3; Ergate-13C,d3; Ergomar-13C,d3; Gynergen-13C,d3; Lingraine-13C,d3; Lingran-13C,d3; NSC 41869-13C,d3; Neo-Ergotin-13C,d3; Rigetamin-13C,d3; Secagyn-13C,d3; Secupan-13C,d3; Ergotamine-13C,d3 Tartrate

Database IDs

• PubChem SID: 162262291
• PubChem CID: 71316402

CALCULATED PROPERTIES

• Acid pKa: 9.695263
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 0.44161355
• LogD (pH = 7.4): 2.1667228
• Log P: 2.5976973
• Molar Refractivity: 160.1678 cm^3
• Polarizability: 62.6887 Å^3
• Polar Surface Area: 118.21 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - E599502

Labelled Ergotamine. Antimigraine.

REFERENCES

• Hofmann, et al.: Experientia, 17, 206 (1961)
• Kreilgard, B., et al.: Anal. Profiles Drug Subs., 6, 113 (1961)
• Perrin, V.L., et al.: Clin. Pharmacokinet., 10, 334 (1961)