(3R,4S,7S,8R,11S,12R)-8-ethynyl-3,7-dimethyl-18,20,27-triazaheptacyclo[15.11.0.03,15.04,12.07,11.019,27.021,26]octacosa-1(28),15,17,19,21,23,25-heptaen-8-ol

• ChemBase ID: 133480
• Molecular Formular: C29H31N3O
• Molecular Mass: 437.57594
• Monoisotopic Mass: 437.24671263
• SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC1=Cc2c(cn4c5ccccc5nc4n2)C[C@]31C
• Canonical SMILES: C#C[C@]1(O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=Cc3c(C[C@]12C)cn1c(n3)nc2c1cccc2
• InChI: InChI=1S/C29H31N3O/c1-4-29(33)14-12-22-20-10-9-19-15-24-18(16-27(19,2)21(20)11-13-28(22,29)3)17-32-25-8-6-5-7-23(25)30-26(32)31-24/h1,5-8,15,17,20-22,33H,9-14,16H2,2-3H3/t20-,21+,22+,27+,28+,29+/m1/s1
• InChIKey: YBCYJDNOPAFFOW-XOAARHKISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S,7S,8R,11S,12R)-8-ethynyl-3,7-dimethyl-18,20,27-triazaheptacyclo[15.11.0.0^3,^1^5.0^4,^1^2.0^7,^1^1.0^1^9,^2^7.0^2^1,^2^6]octacosa-1(28),15,17,19,21,23,25-heptaen-8-ol
• IUPAC Traditional name: (3R,4S,7S,8R,11S,12R)-8-ethynyl-3,7-dimethyl-18,20,27-triazaheptacyclo[15.11.0.0^3,^1^5.0^4,^1^2.0^7,^1^1.0^1^9,^2^7.0^2^1,^2^6]octacosa-1(28),15,17,19,21,23,25-heptaen-8-ol
• Synonyms: 17-β-Hydroxy-17-α-ethynyl-δ-4-androstano[3,2-b]pyrimido[1,2-a]benzimidazole; WIN 62,577

Database IDs

• CAS Number: 138091-43-7
• MDL Number: MFCD00153883
• PubChem SID: 24278780; 162227757
• PubChem CID: 15118529

CALCULATED PROPERTIES

• Acid pKa: 17.594933
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.6446667
• LogD (pH = 7.4): 4.6499066
• Log P: 4.649974
• Molar Refractivity: 131.4559 cm^3
• Polarizability: 51.30718 Å^3
• Polar Surface Area: 50.42 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble4 mg/mL; ethanol: soluble1.4 mg/mL; H2O: insoluble
• Apperance: yellow solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... TACR1(6869)rat ... Tacr1(24807)

DETAILS

Sigma Aldrich - W104

Biochem/physiol Actions
Non-peptide NK1 tachykinin receptor antagonist.