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Mbandakamine A

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

Canonical Smiles	COc1ccc(c2c1c(O)cc(c2c1cc(c2c(O)cc(c3c2C[C@@H](C)N[C@@H]3C)OC)c2c(c1O)c(OC)cc(c2)C)C)c1c(O)cc(c2c1C[C@@H](C)N[C@@H]2C)OC
InChI	InChI=1S/C48H52N2O8/c1-21-13-28-29(44-31-17-24(4)50-26(6)42(31)39(58-10)20-35(44)53)18-32(48(54)45(28)37(14-21)56-8)40-22(2)15-33(51)47-36(55-7)12-11-27(46(40)47)43-30-16-23(3)49-25(5)41(30)38(57-9)19-34(43)52/h11-15,18-20,23-26,49-54H,16-17H2,1-10H3/t23-,24-,25-,26-/m1/s1
InChIKey	BLJJDDGPLGZUPD-VEYUFSJPSA-N
Formula	C₄₈H₅₂N₂O₈
HBA	10
HBD	6
MW	784.95
Rotatable Bonds	7
TPSA	141.9
LogP	9.66
Number Rings	8
Number Aromatic Rings	6
Heavy Atom Count	58
Formal Charge	0
Fraction CSP3	0.33
Exact Mass	784.37
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ancistrocladus ealaensis	Ancistrocladaceae	Plantae	714098
2	Ancistrocladus ealaensis	Ancistrocladaceae	Plantae	714098
3	Ancistrocladus sp.	Ancistrocladaceae	Plantae	300538
4	Ancistrocladus liana	Ancistrocladaceae	Plantae	63071

Showing of synonyms

Tshitenge DT, Bruhn T, et al. (2019). An Unusually Broad Series of Seven Cyclombandakamines, Bridged Dimeric Naphthylisoquinoline Alkaloids from the Congolese Liana Ancistrocladus ealaensis.. Scientific reports,2019, 9(1), 9812. [View] [PubMed]
Tshitenge DT, Feineis D, et al. (2018). Mbandakamine-Type Naphthylisoquinoline Dimers and Related Alkaloids from the Central African Liana Ancistrocladus ealaensis with Antiparasitic and Antileukemic Activities.. Journal of natural products,2018, 81(4), 918-933. [View] [PubMed]
Bringmann G, Lombe BK, et al. (2013). Mbandakamines A and B, unsymmetrically coupled dimeric naphthylisoquinoline alkaloids, from a Congolese Ancistrocladus species.. Organic letters,2013, 15(11), 2590-2593. [View] [PubMed]
Lombe BK, Feineis D, et al. (2021). Spirombandakamine A3 and Cyclombandakamines A8 and A9, polycyclic naphthylisoquinoline dimers, with antiprotozoal activity, from a congolese ancistrocladus plant. Journal of natural products,2021, 84(4), 1335-1344. [View] [PubMed]

Pubchem: 71723153

Zinc: ZINC000205903174

Chembl: CHEMBL4285508

No compound-protein relationship available.

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

Level: 3

Mol. Weight: 784.95 g/mol

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

Level: 2

Mol. Weight: 784.95 g/mol

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

Level: 2

Mol. Weight: 784.95 g/mol

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

Level: 1

Mol. Weight: 784.95 g/mol

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

Level: 1

Mol. Weight: 784.95 g/mol

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 784.95 g/mol

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 784.95 g/mol

Antileukemia

Antimalarial

Antiparasitic

Antiprotozoal

Absorption

Caco-2 (logPapp): -5.75
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 133.850
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 18277.5

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.340
Plasma Protein Binding: 74.98
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: 7.210
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Toxic
Bioconcentration Factor: -427.060
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.010
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 6.080
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Toxic
NR-AR-LBD: Toxic
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: -33169342.750
Rat (Acute): 2.340
Rat (Chronic Oral): 2.760
Fathead Minnow: 41874.980
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: 3725559.510
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 6.350
Log(P): 7.7
Log S: -7.52
Log(Vapor Pressure): -122622.21
Melting Point: 236.82
pKa Acid: -855.12
pKa Basic: 9.43

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8589
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8589
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8389
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8389
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.8159
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.8159
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8144
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8144
Caspase-6	P55212	CASP6_HUMAN	Homo sapiens	3	0.8097
Caspase-6	P55212	CASP6_HUMAN	Homo sapiens	3	0.8097
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7964
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7964
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.7911
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.7911
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7325
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7325
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7247
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7247
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7156
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7156
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.7126
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.7126
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7115
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7115
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7113
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7113
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.7078
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.7078

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