(1'S,2R,2'R,3R,3aS,5'S,6S,7aR,10'S,11'S)-5'-hydroxy-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-17'-one

• ChemBase ID: 127931
• Molecular Formular: C27H39NO3
• Molecular Mass: 425.60346
• Monoisotopic Mass: 425.29299411
• SMILES: O=C1C2=C([C@@]3(O[C@@H]4C[C@@H](CN[C@H]4[C@H]3C)C)CC[C@H]2[C@@H]2CC=C3C[C@@H](O)CC[C@]3(C)[C@@H]12)C
• Canonical SMILES: O[C@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2C(=O)C2=C(C)[C@]4(CC[C@@H]32)O[C@H]2[C@H]([C@H]4C)NC[C@H](C2)C)C1)C
• InChI: InChI=1S/C27H39NO3/c1-14-11-21-24(28-13-14)16(3)27(31-21)10-8-19-20-6-5-17-12-18(29)7-9-26(17,4)23(20)25(30)22(19)15(27)2/h5,14,16,18-21,23-24,28-29H,6-13H2,1-4H3/t14-,16+,18-,19-,20-,21+,23+,24-,26-,27-/m0/s1
• InChIKey: CLEXYFLHGFJONT-DNMILWOZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1'S,2R,2'R,3R,3aS,5'S,6S,7aR,10'S,11'S)-5'-hydroxy-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-17'-one
• IUPAC Traditional name: jervine
• Synonyms: (3β, 23β)-17,23-Epoxy-3-hydroxyveratraman-11-one; 11-Ketocyclopamine; Jervine; (3β,23β)- 17,23- Epoxy- 3-hydroxyveratraman- 11-one; Jervine

Database IDs

• CAS Number: 469-59-0
• EC Number: 207-417-9
• MDL Number: MFCD01684066
• PubChem SID: 162222247; 24896194
• PubChem CID: 10098
• CHEMBL: 186779
• Chemspider ID: 9694
• Wikipedia Title: Jervine

CALCULATED PROPERTIES

• LogD (pH = 7.4): 0.927553
• Log P: 3.3851504
• Molar Refractivity: 122.8882 cm^3
• Polarizability: 48.51331 Å^3
• Polar Surface Area: 58.56 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true
• Acid pKa: 18.204275
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.1701644

PROPERTIES

Physical Property

• Solubility: 10 mg/mL in EtOH; 6 mg/mL in DMF; H2O: insoluble; methanol: >2 mg/mL
• Apperance: powder

Safety Information

• RTECS: WG9700000
• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: -20°C

Pharmacology Properties

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

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C27H39NO3

DETAILS

Sigma Aldrich - J4145

Biochem/physiol Actions
Jervine is a sonic hedgehog (Shh) pathway inhibitor.