U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C37H40N2O6.ClH
Molecular Weight 645.184
Optical Activity ( + )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BERBAMINE MONOHYDROCHLORIDE

SMILES

Cl.[H][C@@]12CC3=CC=C(OC4=CC(C[C@@]5([H])N(C)CCC6=C5C(OC7=C(OC)C=C(CCN1C)C2=C7)=C(OC)C(OC)=C6)=CC=C4O)C=C3

InChI

InChIKey=SFPGJACKHKXGBH-QBYKQQEBSA-N
InChI=1S/C37H40N2O6.ClH/c1-38-14-12-24-19-32(41-3)33-21-27(24)28(38)16-22-6-9-26(10-7-22)44-31-18-23(8-11-30(31)40)17-29-35-25(13-15-39(29)2)20-34(42-4)36(43-5)37(35)45-33;/h6-11,18-21,28-29,40H,12-17H2,1-5H3;1H/t28-,29+;/m0./s1

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C37H40N2O6
Molecular Weight 608.7233
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

Targets

Targets

PubMed

PubMed

TitleDatePubMed
Protection of T cells from radiation-induced apoptosis by Cepharanthin.
2001 Nov
In vitro effect of alkaloids on bloodstream forms of Trypanosoma brucei and T. congolense.
2001 Oct
A comparative study on the anti-inflammatory, antinociceptive and antipyretic effects of isoquinoline alkaloids from the roots of Turkish Berberis species.
2002 Dec 27
Effect of Mahonia aquifolium active compounds on interleukin-8 production in the human monocytic cell line THP-1.
2002 Mar
The effect of calmodulin antagonist berbaminederivative-EBB on hepatoma in vitro and in vivo.
2002 May
Interaction of multidrug resistance reversal agents with P-glycoprotein ATPase activity on blood-brain barrier.
2002 May
Inhibition of Na(+),K(+)-ATPase by the extract of Stephania cephararantha HAYATA and bisbenzylisoquinoline alkaloid cycleanine, a major constituent.
2003 Aug 1
[Reversal effect of berbamine on multidrug resistance of K562/A02 cells and its mechanism].
2003 Dec
[Detection of P-170 and treatment with berbamine in primary acute leukemia].
2003 Feb
Integrity of actin-network is involved in uridine 5'-triphosphate evoked store-operated Ca2+ entry in bovine adrenocortical fasciculata cells.
2003 Jan
Effect of E6, a novel calmodulin inhibitor, on activity of P-glycoprotein in purified primary cultured rat brain microvessel endothelial cells.
2003 Nov
[Distribution of four alkaloids in plants of Berberis].
2004 Feb
[Comparison of the anti-arrhythmic effects of matrine and berbamine with amiodarone and RP58866].
2004 Sep
[Effects of berbamine on K562 cells and its mechanisms in vitro and in vivo].
2005 Jun
[The mechanism of apoptosis of chronic myeloid leukemia cells induced by the novel p210 bcr/abl inhibitor berbamine].
2006 Aug 29
Berbamine: a novel inhibitor of bcr/abl fusion gene with potent anti-leukemia activity.
2006 Jan
[Effects of berbamine on growth of leukemia cell line NB4 and its mechanism].
2006 Mar
Regulatory T cells, a potent immunoregulatory target for CAM researchers: modulating tumor immunity, autoimmunity and alloreactive immunity (III).
2006 Sep
Berbamine induces apoptosis in human hepatoma cell line SMMC7721 by loss in mitochondrial transmembrane potential and caspase activation.
2007 Apr
Free radical scavenging activity and lipoxygenase inhibition of Mahonia aquifolium extract and isoquinoline alkaloids.
2007 Jul 16
Berbamine selectively induces apoptosis of human acute promyelocytic leukemia cells via survivin-mediated pathway.
2007 May 5
Pharmacological and therapeutic effects of Berberis vulgaris and its active constituent, berberine.
2008 Aug
Novel immunomodulatory properties of berbamine through selective down-regulation of STAT4 and action of IFN-gamma in experimental autoimmune encephalomyelitis.
2008 Jul 15
Studies on alkaloids binding to GC-rich human survivin promoter DNA using positive and negative ion electrospray ionization mass spectrometry.
2008 Mar
Harnessing gene expression to identify the genetic basis of drug resistance.
2009
Berbamine induces Fas-mediated apoptosis in human hepatocellular carcinoma HepG2 cells and inhibits its tumor growth in nude mice.
2009
Effects of theanine on growth of human lung cancer and leukemia cells as well as migration and invasion of human lung cancer cells.
2009 Apr
Berbamine exhibits potent antitumor effects on imatinib-resistant CML cells in vitro and in vivo.
2009 Apr
Berbamine derivatives: a novel class of compounds for anti-leukemia activity.
2009 Aug
Berbamine, a novel nuclear factor kappaB inhibitor, inhibits growth and induces apoptosis in human myeloma cells.
2009 Dec
The antiproliferation effect of berbamine on k562 resistant cells by inhibiting NF-kappaB pathway.
2009 Jul
Probing the binding sites and the effect of berbamine on the structure of bovine serum albumin.
2009 Jun
A new dawn for the use of traditional Chinese medicine in cancer therapy.
2009 Mar 20
Antihyperglycemic and antioxidant effect of Berberis aristata root extract and its role in regulating carbohydrate metabolism in diabetic rats.
2009 May 4
Suppression of growth, migration and invasion of highly-metastatic human breast cancer cells by berbamine and its molecular mechanisms of action.
2009 Oct 1
[Berbamine induces apoptosis of multiple myeloma RPMI 8226 cells by activating GADD45/JNK pathway].
2009 Sep
Suppression of human lung cancer cell growth and migration by berbamine.
2010 Aug
Traditional herbal medicine in far-west Nepal: a pharmacological appraisal.
2010 Dec 13
A novel calmodulin antagonist O-(4-ethoxyl-butyl)-berbamine overcomes multidrug resistance in drug-resistant MCF-7/ADR breast carcinoma cells.
2010 Jul
Degradation of HER2/neu by ANT2 shRNA suppresses migration and invasiveness of breast cancer cells.
2010 Jul 23
Circumvention of multi-drug resistance of cancer cells by Chinese herbal medicines.
2010 Jul 25
4-Chlorobenzoyl berbamine induces apoptosis and G2/M cell cycle arrest through the PI3K/Akt and NF-kappaB signal pathway in lymphoma cells.
2010 Mar
Tissue culture and generation of autotetraploid plants of Sophora flavescens Aiton.
2010 Oct
Substance Class Chemical
Created
by admin
on Sat Dec 16 19:33:36 GMT 2023
Edited
by admin
on Sat Dec 16 19:33:36 GMT 2023
Record UNII
2FAW2F3Q2Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BERBAMINE MONOHYDROCHLORIDE
Common Name English
Berbaman-12-ol, 6,6′,7-trimethoxy-2,2′-dimethyl-, monohydrochloride
Common Name English
16H-1,24:6,9-Dietheno-11,15-metheno-2H-pyrido[2′,3′:17,18][1,11]dioxacycloeicosino[2,3,4-ij]isoquinolin-12-ol, 3,4,4a,5,16a,17,18,19-octahydro-21,22,26-trimethoxy-4,17-dimethyl-, monohydrochloride, (4aS,16aR)-
Systematic Name English
16H-1,24:6,9-Dietheno-11,15-metheno-2H-pyrido[2′,3′:17,18][1,11]dioxacycloeicosino[2,3,4-ij]isoquinolin-12-ol, 3,4,4a,5,16a,17,18,19-octahydro-21,22,26-trimethoxy-4,17-dimethyl-, hydrochloride (1:1), (4aS,16aR)-
Systematic Name English
Code System Code Type Description
CAS
69475-26-9
Created by admin on Sat Dec 16 19:33:37 GMT 2023 , Edited by admin on Sat Dec 16 19:33:37 GMT 2023
PRIMARY
FDA UNII
2FAW2F3Q2Z
Created by admin on Sat Dec 16 19:33:37 GMT 2023 , Edited by admin on Sat Dec 16 19:33:37 GMT 2023
PRIMARY
PUBCHEM
56845155
Created by admin on Sat Dec 16 19:33:37 GMT 2023 , Edited by admin on Sat Dec 16 19:33:37 GMT 2023
PRIMARY
Related Record Type Details
SOLVATE->ANHYDROUS
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY