Compound: CYCLOPAMINE
SMILES: O1[C@@]2(C(=C3[C@H]([C@@H]4CC=C5[C@@]([C@H]4C3)(CC[C@@H](C5)O)C)CC2)C)[C@H](C)[C@H]6[C@H]1C[C@H](C)CN6
InChIKey: QASFUMOKHFSJGL-LAFRSMQTSA-N
Synonyms: CYCLOPAMINE, 4449-51-8, 11-Deoxojervine, 11-Deoxyjervine, DTXSID6043709, Alkaloid V, ZH658AJ192, NSC-734950, DTXCID4023709, Veratraman-3-ol, 17,23-epoxy-, (3beta,23beta)-, (3beta23R)-17,23-Epoxyveratraman-3-ol, (3S,3'R,3'aS,6'S,6aS,6bS,7'aR,9R,11aS,11bR)-3',6',10,11b-tetramethylspiro[2,3,4,6,6a,6b,7,8,11,11a-decahydro-1H-benzo[a]fluorene-9,2'-3a,4,5,6,7,7a-hexahydro-3H-furo[3,2-b]pyridine]-3-ol, (3S,3'R,3'aS,6'S,6aS,6bS,7'aR,9R,11aS,11bR)-3',6',10,11b-tetramethylspiro(2,3,4,6,6a,6b,7,8,11,11a-decahydro-1H-benzo(a)fluorene-9,2'-3a,4,5,6,7,7a-hexahydro-3H-furo(3,2-b)pyridine)-3-ol, 3,4'-Dinitroflavone, RefChem:129819, (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, (2'R,3S,3'R,3'aS,6'S,6aS,6bS,7'aR,11aS,11bR)-1,2,3,3'a,4,4',5',6,6',6a,6b,7,7',7'a,8,11,11a,11b-Octadecahydro-3',6',10,11b-tetramethylspiro(9H-benzo(a)fluorene-9,2'(3'H)-furo(3,2-b)pyridin)-3-ol, 628-058-8, MFCD09878269, Jervine, 11-deoxo-, CHEMBL254129, (2'R,3S,3'R,3a'S,6aS,6bS,6'S,7a'R,11aS,11bR)-3',6',10,11b-tetramethyl-1,2,3,3a',4,4',5',6,6a,6b,6',7,7',7a',8,11,11a,11b-octadecahydro-3'H-spiro[benzo[a]fluorene-9,2'-furo[3,2-b]pyridin]-3-ol, Spiro[9H-benzo[a]fluorene-9,2'(3'H)-furo[3,2-b]pyridin]-3-ol, 1,2,3,3'a,4,4',5',6,6',6a,6b,7,7',7'a,8,11,11a,11b-octadecahydro-3',6',10,11b-tetramethyl-, (2'R,3S,3'R,3'aS,6'S,6aS,6bS,7'aR,11aS,11bR)- (9CI), UNII-ZH658AJ192, HSDB 3505, CY8, CYCLOPAMINE?, Cyclopamine (Standard), CYCLOPAMINE [MI], 1178510-81-0, CYCLOPAMINE [HSDB], SCHEMBL29153, BSPBio_001032, MLS006010945, CHEBI:4021, GTPL10328, EX-A952, GLXC-02575, HMS1792D13, HMS1990D13, HMS3403D13, Tox21_300632, BDBM50232973, HB2965, HY-17024R, MSK001551, NSC734950, s1146, AKOS024456709, CCG-208181, CS-0633, EBC-373054, FC20718, NSC 734950, NCGC00163474-03, NCGC00163474-04, NCGC00163474-07, NCGC00254431-01, AC-34305, HY-17024, SMR001822854, CAS-4449-51-8, F16272, Cyclopamine11-Deoxyjervine; Jervine, 11-deoxo-, SR-05000002357, Veratraman-3-ol,23-epoxy-, (3-beta,23-beta)-, Q3271319, SR-05000002357-2, (22S,23R)-17beta-17,23-Epoxyveratraman-3beta-ol, BRD-K58938839-001-03-8, Veratraman-3-ol, 17,23-epoxy-, (3-beta,23-beta)-, Z3243808232, (3alpha,8alpha,14beta,22S,23R)-17,23-epoxyveratraman-3-ol, (2?R,3S,3?R,3?aS,6?S,6aS,6bS,7?aR,11aS,11bR)-1,2,3,3?a,4,4?,5?,6,6?,6a,6b,7,7?,7?a,8,11,11a,11b-Octadecahydro-3?,6?,10,11b-tetrameth ylspiro[9H-benzo[a]fluorene-9,2?(3?H)-furo[3,2-b]pyridin]-3-ol, (3S,3'R,3'aS,6'S,6aS,6bS,7'aR,9R,11aS,11bR)-3',6',10,11b-tetramethyl-1,2,3,3'a,4,4',5',6,6',6a,6b,7,7',7'a,8,11,11a,11b-octadecahydro-3'H-spiro[cyclohexa[a]fluorene-9,2'-furo[3,2-b]pyridin]-3-ol, 11051-96-0, Spiro(9H-benzo(a)fluorene-9,2-b)pyridin)-3-o l, 1,2,3,3'a,4,4',5',6,6',6a,6b,7,7',7'a,8,11,11a,11b-octa deca hydro-3',6',10,11b-tetramethyl-, (2'R,3S,3'R,3'aS,6'S,6aS,6bS,7'aR,11aS,11bR)-, Spiro[9H-benzo[a]fluorene-9,2'(3'H)-furo[3,2-b]pyridin]-3-ol, 1,2,3,3'a,4,4',5',6,6',6a,6b,7,7',7'a,8,11,11a,11b-octadecahydro-3',6',10,11b-tetramethyl-, (3S,3'R,3a'S,6'S,6aS,6bS,7a'R,9R,11aS,11bR)-
Theoretical properties:
molecular_formula: C27H41NO2
molecular_weight: 411.6 g/mol
exact_mass: 411.313729551 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 0
heavy_atom_count: 30
topological_polar_surface_area: 41.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Cyclopamine is a member of piperidines. It has a role as a glioma-associated oncogene inhibitor.
chembl: CYCLOPAMINE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Cyclopamine (11-deoxojervine) is a naturally occurring steroidal alkaloid. It is a teratogenic component of corn lily (Veratrum californicum), which when consumed during gestation has been demonstrated to induce birth defects, including the development of a single eye (cyclopia) in offspring. The molecule was named after this effect, which was originally observed by Idaho lamb farmers in 1957 after their herds gave birth to cycloptic lambs. It then took more than a decade to identify corn lily as the culprit. Later work suggested that differing rain patterns had changed grazing behaviours, which led to a greater quantity of corn lily to be ingested by pregnant sheep. Cyclopamine interrupts the sonic hedgehog signalling pathway, instrumental in early development, ultimately causing birth defects.