(1'S,2R,2'R,3R,3aS,5'S,6S,7aR,10'S,11'S)-2',3,6,15'-tetramethyl-3a,4,5,6,7,7a-hexahydro-3H-spiro[furo[3,2-b]pyridine-2,14'-tetracyclo[8.7.0.02,7.011,16]heptadecane]-7',15'-dien-5'-ol hydrate

• ChemBase ID: 155005
• Molecular Formular: C27H43NO3
• Molecular Mass: 429.63522
• Monoisotopic Mass: 429.32429424
• SMILES: C[C@H]1C[C@@H]2[C@H]([C@H]([C@]3(O2)CC[C@H]2[C@@H]4CC=C5C[C@H](CC[C@@]5([C@H]4CC2=C3C)C)O)C)NC1.O
• Canonical SMILES: O[C@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2CC2=C(C)[C@]4(CC[C@@H]32)O[C@H]2[C@H]([C@H]4C)NC[C@H](C2)C)C1)C.O
• InChI: InChI=1S/C27H41NO2.H2O/c1-15-11-24-25(28-14-15)17(3)27(30-24)10-8-20-21-6-5-18-12-19(29)7-9-26(18,4)23(21)13-22(20)16(27)2;/h5,15,17,19-21,23-25,28-29H,6-14H2,1-4H3;1H2/t15-,17+,19-,20-,21-,23-,24+,25-,26-,27-;/m0./s1
• InChIKey: KDAGJRDPNXDDSB-HBYCUIHISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1'S,2R,2'R,3R,3aS,5'S,6S,7aR,10'S,11'S)-2',3,6,15'-tetramethyl-3a,4,5,6,7,7a-hexahydro-3H-spiro[furo[3,2-b]pyridine-2,14'-tetracyclo[8.7.0.0^2,^7.0^1^1,^1^6]heptadecane]-7',15'-dien-5'-ol hydrate
• IUPAC Traditional name: cyclopamine hydrate
• Synonyms: 11-deoxojervine hydrate; Cyclopamine hydrate; 去氧芥芬胺 水合物; 环巴胺 水合物

Database IDs

• PubChem SID: 24724439; 162249143
• PubChem CID: 71312049

CALCULATED PROPERTIES

• Acid pKa: 18.204288
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.5760557
• LogD (pH = 7.4): 1.2571619
• Log P: 3.7964666
• Molar Refractivity: 122.1691 cm^3
• Polarizability: 48.454803 Å^3
• Polar Surface Area: 41.49 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble ≥5 mg/mL; H2O: insoluble
• Apperance: white solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... EBP(10682)

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C27H41NO2 · xH2O

DETAILS

Sigma Aldrich - C4116

Biochem/physiol Actions
Cyclopamine is a Hedgehog signaling pathway inhibitor; inhibits the growth of medulloblastoma cells.