Jerveratrum-type alkaloids

Description:

Steroidal alkaloids with a structure that is based on the jervane ring system. Jerveratrum alkaloids have alkamines with 1-3 oxygen atoms, and occur as such or as monoglycosides.

Ancestors:

Organic compounds ⮕ Lipids and lipid-like molecules ⮕ Steroids and steroid derivatives ⮕ Steroidal alkaloids ⮕ Jerveratrum-type alkaloids

Jervine
- ≥98%
Cas Number: 469-59-0 EC Number: 207-417-9

Formula: C₂₇H₃₉NO₃ Molecular Weight: 425.6

IUPAC Name: (3S,3'R,3'aS,6'S,6aS,6bS,7'aR,9R,11aS,11bR)-3-hydroxy-3',6',10,11b-tetramethylspiro[1,2,3,4,6,6a,6b,7,8,11a-decahydrobenzo[a]fluorene-9,2'-3a,4,5,6,7,show more

SMILES: CC1CC2C(C(C3(O2)CCC4C5CC=C6CC(CCC6(C5C(=O)C4=C3C)C)O)C)NC1

InChIKey: CLEXYFLHGFJONT-DNMILWOZSA-N

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,show more
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cyclopamine
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

InChIKey: QASFUMOKHFSJGL-LAFRSMQTSA-N

InChI: InChI=1S/C27H41NO2/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,6-1show more

Synonyms: (3beta,22S,23R)-17,23-epoxyveratraman-3-ol | A881419 | HMS3403D13 | GAMMA CYCLODEXTRIN [MART.] | BRD-K58938839-001-03...
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cyclopamine-KAAD
IUPAC Name: N-[2-(3',6',10,11b-tetramethyl-3-oxospiro[1,2,4,6,6a,6b,7,8,11,11a-decahydrobenzo[a]fluorene-9,2'-3,3a,5,6,7,7a-hexahydrofuro[3,2-b]pyridine]-4'-yl)etshow more

SMILES: CC1CN(CCNC(=O)CCCCCNC(=O)CCc2ccccc2)C2C(C1)OC1(C2C)CCC2C(=C1C)CC1C2CC=C2C1(C)CCC(=O)C2

InChIKey: WDHRPWOAMDJICD-UHFFFAOYSA-N

InChI: InChI=1S/C44H63N3O4/c1-29-25-39-42(47(28-29)24-23-46-40(49)13-9-6-10-22-45-41(50)17-14-32-11-7-5-8-12-32)31(3)44(51-39)21-19-35-36-16-15-33-26-34(48)1show more

Synonyms: 3-keto, N-aminoethyl aminocaproyl dihydrocinnamoyl cyclopamine | KAAD-cyclopamine
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Jervine
- 10mM in DMSO
Cas Number: 469-59-0 EC Number: 207-417-9

Formula: C₂₇H₃₉NO₃ Molecular Weight: 425.6

IUPAC Name: (3S,3'R,3'aS,6'S,6aS,6bS,7'aR,9R,11aS,11bR)-3-hydroxy-3',6',10,11b-tetramethylspiro[1,2,3,4,6,6a,6b,7,8,11a-decahydrobenzo[a]fluorene-9,2'-3a,4,5,6,7,show more

SMILES: CC1CC2C(C(C3(O2)CCC4C5CC=C6CC(CCC6(C5C(=O)C4=C3C)C)O)C)NC1

InChIKey: CLEXYFLHGFJONT-DNMILWOZSA-N

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,show more

Synonyms: JERVINE|469-59-0|Iervin|11-Ketocyclopamine|Jerwiny|Jerwiny [Polish]|CHEBI:6088|CHEMBL186779|(3S,3'R,3'aS,6'S,6aS,6bS,...
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Cyclopamine (ethanol solution)
- ≥99%
Cas Number: 4449-51-8 EC Number: 628-058-8

Formula: C₂₇H₄₁NO₂ Molecular Weight: 411.62

IUPAC Name: (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-heshow more

SMILES: CC1CC2C(C(C3(O2)CCC4C5CC=C6CC(CCC6(C5CC4=C3C)C)O)C)NC1

InChIKey: QASFUMOKHFSJGL-LAFRSMQTSA-N

InChI: InChI=1S/C27H41NO2/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,6-1show more

Synonyms: (3beta,22S,23R)-17,23-epoxyveratraman-3-ol | A881419 | HMS3403D13 | GAMMA CYCLODEXTRIN [MART.] | BRD-K58938839-001-03...
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Peimisine
- ≥98%
Cas Number: 19773-24-1

Formula: C₂₇H₄₁NO₃ Molecular Weight: 427.625

IUPAC Name: (3S,3'R,3'aS,4aS,6'S,6aR,6bS,7'aR,9R,11aS,11bR)-3-hydroxy-3',6',10,11b-tetramethylspiro[1,2,3,4,4a,6,6a,6b,7,8,11,11a-dodecahydrobenzo[a]fluorene-9,2'show more

SMILES: CC1CC2C(C(C3(O2)CCC4C5CC(=O)C6CC(CCC6(C5CC4=C3C)C)O)C)NC1

InChIKey: KYELXPJVGNZIGC-GKFGJCLESA-N

InChI: InChI=1S/C27H41NO3/c1-14-9-24-25(28-13-14)16(3)27(31-24)8-6-18-19(15(27)2)11-21-20(18)12-23(30)22-10-17(29)5-7-26(21,22)4/h14,16-18,20-22,24-25,28-29Hshow more

Synonyms: Ebeiensine | AKOS015888866 | AC-34008 | (3S,3'R,3'aS,4aS,6'S,6aR,6bS,7'aR,9R,11aS,11bR)-3-hydroxy-3',6',10,11b-tetram...
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Cyclopamine
- ≥99%
Cas Number: 4449-51-8 EC Number: 628-058-8

Formula: C₂₇H₄₁NO₂ Molecular Weight: 411.62

IUPAC Name: (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-heshow more

SMILES: CC1CC2C(C(C3(O2)CCC4C5CC=C6CC(CCC6(C5CC4=C3C)C)O)C)NC1

InChIKey: QASFUMOKHFSJGL-LAFRSMQTSA-N

InChI: InChI=1S/C27H41NO2/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,6-1show more

Synonyms: (3beta,22S,23R)-17,23-epoxyveratraman-3-ol | A881419 | HMS3403D13 | GAMMA CYCLODEXTRIN [MART.] | BRD-K58938839-001-03...
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Jervine
- ≥97%(HPLC)
Cas Number: 469-59-0 EC Number: 207-417-9

Formula: C₂₇H₃₉NO₃ Molecular Weight: 425.6

IUPAC Name: (3S,3'R,3'aS,6'S,6aS,6bS,7'aR,9R,11aS,11bR)-3-hydroxy-3',6',10,11b-tetramethylspiro[1,2,3,4,6,6a,6b,7,8,11a-decahydrobenzo[a]fluorene-9,2'-3a,4,5,6,7,show more

SMILES: CC1CC2C(C(C3(O2)CCC4C5CC=C6CC(CCC6(C5C(=O)C4=C3C)C)O)C)NC1

InChIKey: CLEXYFLHGFJONT-DNMILWOZSA-N

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,show more

Synonyms: NSC7520 | NSC-7520 | CCG-208226 | Spiro[9H-benzo[a]fluorene-9,2-b]-pyridin]-11(1H)-one,2,3,3'a,4,4',5',6,6',6a,6b,7,7...
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