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Mbandakamine B4

Family: Plantae - Ancistrocladaceae
Kingdom: Plantae
Class: Alkaloid
- Subclass: Naphthylisoquinoline Alkaloid

Canonical Smiles	COc1cc(O)c(c2c1[C@@H](C)N[C@@H](C2)C)c1cc(c2c(C)cc(c3c2c(ccc3OC)c2c(O)cc(c3c2C[C@@H](C)N([C@@H]3C)C)OC)O)c(c2c1cc(C)cc2OC)O
InChI	InChI=1S/C49H54N2O8/c1-22-14-29-30(45-31-17-24(3)50-26(5)42(31)39(58-10)20-36(45)54)19-33(49(55)46(29)38(15-22)57-9)41-23(2)16-34(52)48-37(56-8)13-12-28(47(41)48)44-32-18-25(4)51(7)27(6)43(32)40(59-11)21-35(44)53/h12-16,19-21,24-27,50,52-55H,17-18H2,1-11H3/t24-,25-,26-,27-/m1/s1
InChIKey	MPLQOMZYFMFMIU-FPCALVHFSA-N
Formula	C₄₉H₅₄N₂O₈
HBA	10
HBD	5
MW	798.98
Rotatable Bonds	7
TPSA	133.11
LogP	10.0
Number Rings	8
Number Aromatic Rings	6
Heavy Atom Count	59
Formal Charge	0
Fraction CSP3	0.35
Exact Mass	798.39
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ancistrocladus sp.	Ancistrocladaceae	Plantae	300538

Showing of synonyms

Mufusama JP, Feineis D, et al. (2019). Antiprotozoal dimeric naphthylisoquinolines, mbandakamines B3 and B4 , and related 5,8'-coupled monomeric alkaloids, ikelacongolines A – D, from a Congolese. Ancistrocladus liana.. RSC advances,2019, 9(21), 12034-12046. [View] [PubMed]

Pubchem: 132608470

No compound-protein relationship available.

SMILES: C1CNCc(c12)cccc2-c3cccc(c34)cccc4-c(cc(c56)cccc6)cc5-c7cccc(c78)CNCC8

Level: 3

Mol. Weight: 798.98 g/mol

SMILES: c1cccc(c12)cccc2-c(cc(c34)cccc4)cc3-c5cccc(c56)CNCC6

Level: 2

Mol. Weight: 798.98 g/mol

SMILES: c1cccc(c12)ccc(c2)-c3cccc(c34)cccc4-c5cccc(c56)CNCC6

Level: 2

Mol. Weight: 798.98 g/mol

SMILES: c1cccc(c12)cccc2-c3cccc(c34)CNCC4

Level: 1

Mol. Weight: 798.98 g/mol

SMILES: c1cccc(c12)cccc2-c(c3)ccc(c34)cccc4

Level: 1

Mol. Weight: 798.98 g/mol

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 798.98 g/mol

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 798.98 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.78
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 211.510
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 28422.01

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.330
Plasma Protein Binding: 73.67
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Inhibitor

Excretion

Clearance: 7.450
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Toxic
Bioconcentration Factor: -661.070
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.210
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 4.580
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Toxic
NR-AR-LBD: Toxic
NR-Aromatase: Toxic
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: -51579807.260
Rat (Acute): 2.390
Rat (Chronic Oral): 2.620
Fathead Minnow: 65114.590
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 5796178.280
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 6.080
Log(P): 8.21
Log S: -7.46
Log(Vapor Pressure): -190809.35
Melting Point: 211.77
pKa Acid: -1350.47
pKa Basic: 10.7

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8957
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8957
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8897
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8897
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.8772
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.8772
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8731
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8731
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8619
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8619
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8402
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8402
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.8383
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.8383
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.8262
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.8262
Caspase-6	P55212	CASP6_HUMAN	Homo sapiens	3	0.8204
Caspase-6	P55212	CASP6_HUMAN	Homo sapiens	3	0.8204
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8076
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8076
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.7982
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.7982
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.7819
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.7819
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7526
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7526
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7474
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7474
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7371
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7371
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7346
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7346
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7249
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7249
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7132
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7132

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