Berbamine

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	55d34313-d44e-4b45-8ea6-da1663a62afc
Taxonomy	Lignans, neolignans and related compounds
IUPAC Name	(1S,14R)-20,21,25-trimethoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.23,6.18,12.114,18.027,31.022,33]hexatriaconta-3(36),4,6(35),8,10,12(34),18,20,22(33),24,26,31-dodecaen-9-ol
SMILES (Canonical)	CN1CCC2=CC(=C3C=C2C1CC4=CC=C(C=C4)OC5=C(C=CC(=C5)CC6C7=C(O3)C(=C(C=C7CCN6C)OC)OC)O)OC
SMILES (Isomeric)	CN1CCC2=CC(=C3C=C2[C@@H]1CC4=CC=C(C=C4)OC5=C(C=CC(=C5)C[C@@H]6C7=C(O3)C(=C(C=C7CCN6C)OC)OC)O)OC
InChI	InChI=1S/C37H40N2O6/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/t28-,29+/m0/s1
InChI Key	DFOCUWZXJBAUSQ-URLMMPGGSA-N
Popularity	390 references in papers

Physical and Chemical Properties

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Molecular Formula	C₃₇H₄₀N₂O₆
Molecular Weight	608.70 g/mol
Exact Mass	608.28863700 g/mol
Topological Polar Surface Area (TPSA)	72.90 Å²
XlogP	6.10
Atomic LogP (AlogP)	6.86
H-Bond Acceptor	8
H-Bond Donor	1
Rotatable Bonds	3

Synonyms

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(+)-Berbamine

d-Berbamine

478-61-5

Berbenine

UNII-V5KM4XJ0WM

V5KM4XJ0WM

CHEBI:3063

CHEMBL504323

NSC-121842

2-27-00-00891 (Beilstein Handbook Reference)

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8474	84.74%
Caco-2	+	0.6950	69.50%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.4795	47.95%
OATP2B1 inhibitior	-	0.8588	85.88%
OATP1B1 inhibitior	+	0.9452	94.52%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.9968	99.68%
P-glycoprotein inhibitior	+	0.9482	94.82%
P-glycoprotein substrate	+	0.5471	54.71%
CYP3A4 substrate	+	0.6763	67.63%
CYP2C9 substrate	+	0.7890	78.90%
CYP2D6 substrate	+	0.7253	72.53%
CYP3A4 inhibition	-	0.8481	84.81%
CYP2C9 inhibition	-	0.9517	95.17%
CYP2C19 inhibition	-	0.9248	92.48%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9157	91.57%
CYP2C8 inhibition	+	0.5918	59.18%
CYP inhibitory promiscuity	-	0.9706	97.06%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6360	63.60%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9443	94.43%
Skin irritation	-	0.7831	78.31%
Skin corrosion	-	0.9539	95.39%
Ames mutagenesis	+	0.8300	83.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8737	87.37%
Micronuclear	+	0.5900	59.00%
Hepatotoxicity	-	0.9375	93.75%
skin sensitisation	-	0.8898	88.98%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.8264	82.64%
Acute Oral Toxicity (c)	III	0.7616	76.16%
Estrogen receptor binding	+	0.7723	77.23%
Androgen receptor binding	+	0.7396	73.96%
Thyroid receptor binding	+	0.6478	64.78%
Glucocorticoid receptor binding	+	0.8607	86.07%
Aromatase binding	+	0.6161	61.61%
PPAR gamma	+	0.5994	59.94%
Honey bee toxicity	-	0.7604	76.04%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.6800	68.00%
Fish aquatic toxicity	+	0.7947	79.47%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL340	P08684	Cytochrome P450 3A4	19952.6 nM 19952.6 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	31622.8 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.44%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.17%	91.11%
CHEMBL217	P14416	Dopamine D2 receptor	95.68%	95.62%
CHEMBL2056	P21728	Dopamine D1 receptor	94.82%	91.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	93.37%	93.99%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.21%	95.56%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	90.72%	93.40%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.74%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.85%	85.14%
CHEMBL261	P00915	Carbonic anhydrase I	88.82%	96.76%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	88.57%	89.62%
CHEMBL2535	P11166	Glucose transporter	87.49%	98.75%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	87.36%	82.38%
CHEMBL2581	P07339	Cathepsin D	86.64%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.52%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.06%	95.89%
CHEMBL4208	P20618	Proteasome component C5	84.85%	90.00%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	84.73%	91.03%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	83.45%	82.67%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.31%	92.94%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.25%	99.17%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	83.24%	100.00%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	83.10%	80.78%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.00%	90.71%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.65%	89.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.25%	94.00%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	80.56%	95.78%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.48%	86.33%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Ardisia crispa

Atherosperma moschatum

Berberis empetrifolia