ANPDB

Select a section from the left sidebar

Ealapasamine A

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

Canonical Smiles	COc1c2[C@@H](C)N[C@@H](Cc2cc(c1c1cc(c2cc(c3c(O)cc(c4c3C[C@@H](C)N[C@H]4C)OC)c3c(c2O)c(OC)cc(c3)C)c(c2c1cc(C)cc2OC)O)O)C
InChI	InChI=1S/C48H52N2O8/c1-21-11-28-30(42-34-16-24(4)50-26(6)41(34)39(57-9)20-36(42)52)18-32(46(53)44(28)37(13-21)55-7)33-19-31(29-12-22(2)14-38(56-8)45(29)47(33)54)43-35(51)17-27-15-23(3)49-25(5)40(27)48(43)58-10/h11-14,17-20,23-26,49-54H,15-16H2,1-10H3/t23-,24-,25-,26+/m1/s1
InChIKey	YMWBNESVKMRLPF-POTDNYQPSA-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

Showing of synonyms

Tshitenge DT, Feineis D, et al. (2017). Antiplasmodial ealapasamines A-C,‘mixed’ naphthylisoquinoline dimers from the Central African liana Ancistrocladus ealaensis.. Scientific reports,2017, 7(1), 5767. [View] [PubMed]

Pubchem: 171351450

No compound-protein relationship available.

SMILES: C1NCCc(c12)ccc(c2)-c3cc(cc(c34)cccc4)-c(cc(c56)cccc6)cc5-c7cccc(c78)CNCC8

Level: 3

Mol. Weight: 784.95 g/mol

SMILES: c1cccc(c12)ccc(c2)-c(cc(c34)cccc4)cc3-c5cccc(c56)CNCC6

Level: 2

Mol. Weight: 784.95 g/mol

SMILES: c1cccc(c12)ccc(c2)-c(cc(c34)cccc4)cc3-c(c5)ccc(c56)CCNC6

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)CCNC4

Level: 1

Mol. Weight: 784.95 g/mol

SMILES: c1cccc(c12)ccc(c2)-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

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.77
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 130.65
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 17860.43

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.34
Plasma Protein Binding: 74.22
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: 6.88
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Toxic
Bioconcentration Factor: -416.67
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.24
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 6.1
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: -32411187.36
Rat (Acute): 2.24
Rat (Chronic Oral): 3.08
Fathead Minnow: 40917.63
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: 3640161.64
Hydration Free Energy: -2.92
Log(D) at pH=7.4: 6.18
Log(P): 7.94
Log S: -7.45
Log(Vapor Pressure): -119815.5
Melting Point: 230.58
pKa Acid: -834.85
pKa Basic: 9.5

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.9145
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.9145
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.9108
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.9108
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.8497
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.8497
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.8425
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.8425
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8347
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8347
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8297
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8297
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7915
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7915
DNA ligase	P43813	DNLJ_HAEIN	Haemophilus influenzae	3	0.7897
DNA ligase	P43813	DNLJ_HAEIN	Haemophilus influenzae	3	0.7897
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7614
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7614
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7548
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7548
Dihydrofolate reductase type 1 from Tn4003	P13955	DYRA_STAAU	Staphylococcus aureus	4	0.7530
Dihydrofolate reductase type 1 from Tn4003	P13955	DYRA_STAAU	Staphylococcus aureus	4	0.7530
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7506
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7506
Bifunctional dihydrofolate reductase-thymidylate synthase	Q27552	Q27552_CRYPV	Cryptosporidium parvum	3	0.7469
Bifunctional dihydrofolate reductase-thymidylate synthase	Q27552	Q27552_CRYPV	Cryptosporidium parvum	3	0.7469
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.7435
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.7435
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7383
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7383
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	4	0.7309
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	4	0.7309
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	4	0.7302
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	4	0.7302
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7261
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7261
DNA polymerase theta	O75417	DPOLQ_HUMAN	Homo sapiens	4	0.7194
DNA polymerase theta	O75417	DPOLQ_HUMAN	Homo sapiens	4	0.7194
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7166
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7166
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7160
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7160
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7095
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7095
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7092
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7092
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7056
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7056
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7055
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7055
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7016
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7016
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7009
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7009

Download SDF