CAS 4449-51-8

Cyclopamine

Description:

Cyclopamine is a naturally occurring alkaloid derived from the plant Veratrum californicum, known for its role as a potent inhibitor of the Hedgehog signaling pathway, which is crucial in embryonic development and cell differentiation. It has a molecular formula of C15H21NO2 and features a complex structure characterized by a cyclopentane ring fused to a steroid-like framework. Cyclopamine is recognized for its teratogenic effects, particularly in disrupting normal limb and organ development when exposure occurs during critical periods of embryogenesis. This compound has garnered interest in medicinal chemistry and developmental biology due to its implications in cancer research, particularly in tumors associated with aberrant Hedgehog signaling. Cyclopamine is typically studied in laboratory settings, where its effects on cellular processes are examined, contributing to a better understanding of developmental disorders and potential therapeutic strategies. However, due to its biological activity, handling cyclopamine requires caution, and its use is regulated in many jurisdictions.

Formula: C₂₇H₄₁NO₂

InChI: InChI=1/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,6-14H2,1-4H3/t15-,17+,19-,20-,21-,23-,24+,25-,26-,27-/m0/s1

InChI key: InChIKey=QASFUMOKHFSJGL-LAFRSMQTSA-N

SMILES: CC=1[C@]2([C@H](C)[C@]3([C@](O2)(C[C@H](C)CN3)[H])[H])CC[C@@]4(C1C[C@]5([C@]4(CC=C6[C@]5(C)CC[C@H](O)C6)[H])[H])[H]

Synonyms:

• (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
• (3beta,22S,23R)-17,23-epoxyveratraman-3-ol
• 11-Deoxojervine
• 11-Deoxyjervine
• Hsdb 3505
• Jervine, 11-deoxo-
• Jervine, 11-deoxo- (7CI)
• 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)-
• 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)-
• Veratraman-3-ol, 17,23-epoxy-, (3-beta,23-beta)- (9CI)
• Veratraman-3-ol, 17,23-epoxy-, (3beta,23beta)-
• Veratraman-3-ol, 17,23-epoxy-, (3β,23β)-
• Cyclopamine
• (2'R,3S,3'R,3'aS,6'S,6aS,6bS,7'aR,11aS,11bR)-
• (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
• (3S,6AS,6bS,8aR,10S,12aS,13S,13aS,15aS,15bR)-10,13,14,15b-tetramethyl-1,2,3,4,6,6a,6b,7,7a,8a
• alkaloidv
• Cyclopamine hydrate,11-deoxojervine hydrate
• Cyclopamine, >=98%
• (3b,23b)-17,23-Epoxy-11-deoxoveratraman-3-ol
• CyclopaMine (11-deoxojervine)
• (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
• CyclopaMine, froM VeratruM californiciM
• CYCLOPAMINE(RG)
• Cyclopamine 11-Deoxojervine (3b,23b)-17,23-Epoxy-11-deoxoveratraman-3-ol
• 11-deoxo-jervin
• 17β,23β-Epoxyveratraman-3β-ol
• 17,23β-Epoxyveratraman-3β-ol

Cyclopamine, 99%

CAS: 4449-51-8

Cyclopamine, is used as a hedgehog [Hh] signaling pathway and Smo inhibitor. It depletes stem-like cancer cells in glioblastoma and blocks tumor engraftment. Can also be used to induce differentiation of human embryonic stem cells (hESCs) into hormone-expressing endocrine cells. This Thermo Scienti

Formula: C₂₇H₄₁NO₂

Purity: 99%

Molecular weight: 411.62

Ref: 02-J61528

Cyclopamine

CAS: 4449-51-8

Cyclopamine

Formula: C₂₇H₄₁NO₂

Color and Shape: White Solid-Powder

Molecular weight: 411.61994

Ref: 54-BIC1011

Cyclopamine

CAS: 4449-51-8

Formula: C₂₇H₄₁NO₂

Purity: 98%

Color and Shape: Solid

Molecular weight: 411.6199

Ref: IN-DA00D80O

Cyclopamine

CAS: 4449-51-8

Cyclopamine

Formula: C₂₇H₄₁NO₂

Purity: ≥98%

Molecular weight: 411.62

Ref: 54-BUP10569

Cyclopamine

CAS: 4449-51-8

Formula: C₂₇H₄₁NO₂

Purity: >99%

Molecular weight: 411.63

Ref: BP-BP0437

Cyclopamine

CAS: 4449-51-8

Formula: C₂₇H₄₁NO₂

Purity: ≥ 98.0%

Color and Shape: White to off-white solid

Molecular weight: 411.6

Ref: 7W-GL2803

Cyclopamine

CAS: 4449-51-8

Cyclopamine (11-Deoxojervine), a Smoothened (Smo) antagonist (IC50: 46 nM in TM3Hh12 cells), belongs to the group of steroidal jerveratrum alkaloids.

Formula: C₂₇H₄₁NO₂

Purity: 98.31% - 99.66%

Color and Shape: White Solid

Molecular weight: 411.62

Ref: TM-T2825

Cyclopamine

CAS: 4449-51-8

Formula: C₂₇H₄₁NO₂

Molecular weight: 411.63

Ref: 4Z-C-224001

Cyclopamine

CAS: 4449-51-8

(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

Formula: C₂₇H₄₁NO₂

Purity: 98%

Molecular weight: 411.62

Ref: IN-DG122875

Cyclopamine

CAS: 4449-51-8

Natural alkaloid

Formula: C₂₇H₄₁NO₂

Purity: ≥ 95.0 % (HPLC)

Color and Shape: Powder

Molecular weight: 411.63

Ref: 5G-82510

Cyclopamine

Controlled Product

CAS: 4449-51-8

Formula: C₂₇H₄₁NO₂

Color and Shape: Neat

Molecular weight: 411.62

Ref: TR-C988400

Cyclopamine

CAS: 4449-51-8

Inhibitor of the Smoothened receptor and Hedgehog signalling pathway. Cyclopamine is a steroidal alkaloid that binds to the heptahelical bundle of Smoothened and negatively regulates transcription of downstream genes. In prostate cancer cells, cyclopamine inhibited cell growth, arrested cell cycle and in glioblastoma, it depleted stem cell-like cancer cells.

Formula: C₂₇H₄₁NO₂

Purity: Min. 95%

Color and Shape: White Solid

Molecular weight: 411.62 g/mol

Ref: 3D-FC20718

Cyclopamine

CAS: 4449-51-8

M01634 - Cyclopamine

Formula: C₂₇H₄₁NO₂

Purity: 98%

Color and Shape: Solid

Molecular weight: 411.63

Ref: 10-M01634