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Ancistroealaine E

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

Canonical Smiles	COc1cc(OC)c2c(c1c1ccc(c3c1cc(C)cc3OC)O)C[C@@H](N=C2C)C
InChI	InChI=1S/C25H27NO4/c1-13-9-17-16(7-8-19(27)25(17)20(10-13)28-4)24-18-11-14(2)26-15(3)23(18)21(29-5)12-22(24)30-6/h7-10,12,14,27H,11H2,1-6H3/t14-/m0/s1
InChIKey	GVGRYGWGGUHNJH-AWEZNQCLSA-N
Formula	C₂₅H₂₇NO₄
HBA	5
HBD	1
MW	405.49
Rotatable Bonds	4
TPSA	60.28
LogP	5.3
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	30
Formal Charge	0
Fraction CSP3	0.32
Exact Mass	405.19
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ancistrocladus ealaensis	Ancistrocladaceae	Plantae	714098

Showing of synonyms

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]

Pubchem: 145986997

Chembl: CHEMBL4293488

No compound-protein relationship available.

SMILES: c1cccc(c12)cccc2-c3cccc(c34)C=NCC4

Level: 1

Mol. Weight: 405.49 g/mol

SMILES: C1=NCCc(c12)cccc2

Level: 0

Mol. Weight: 405.49 g/mol

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 405.49 g/mol

Antileukemia

Antiparasitic

Absorption

Caco-2 (logPapp): -4.87
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.750
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.02

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.620
Plasma Protein Binding: 86.67
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 6.330
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.760
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.000
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 6.500
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: -27.790
Rat (Acute): 2.580
Rat (Chronic Oral): 2.340
Fathead Minnow: 5.570
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: 500.670
Hydration Free Energy: -5.280
Log(D) at pH=7.4: 3.940
Log(P): 5.34
Log S: -6.78
Log(Vapor Pressure): -7.94
Melting Point: 163.76
pKa Acid: 10.09
pKa Basic: 7.7

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9558
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.9167
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.9163
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.9133
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9081
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8791
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.8743
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	4	0.8687
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8660
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.8617
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.8609
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8516
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8479
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.8290
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8275
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.8202
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8116
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.8069
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.8054
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7964
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7918
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7909
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7806
UDP-glycosyltransferase 72B1	Q9M156	U72B1_ARATH	Arabidopsis thaliana	4	0.7789
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.7779
Actin-related protein 3	P61157	ARP3_BOVIN	Bos taurus	4	0.7724
Hepatocyte growth factor receptor	P08581	MET_HUMAN	Homo sapiens	4	0.7709
Endolysin	P00720	ENLYS_BPT4	Enterobacteria phage T4	3	0.7705
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.7702
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	4	0.7698
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7624
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7573
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7557
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7549
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7511
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7474
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	3	0.7469
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7432
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7422
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7416
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	4	0.7395
Bifunctional dihydrofolate reductase-thymidylate synthase	Q27552	Q27552_CRYPV	Cryptosporidium parvum	3	0.7392
Thyroxine-binding globulin	P05543	THBG_HUMAN	Homo sapiens	3	0.7381
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase	O67060	ISPE_AQUAE	Aquifex aeolicus	3	0.7372
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7367
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7365
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7359
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7355
Gag-Pol polyprotein	P03366	POL_HV1B1	Human immunodeficiency virus type 1 group M subtype B	4	0.7354
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.7351
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7351
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7343
Sterol 14alpha-demethylase	P9WPP9	CP51_MYCTU	Mycobacterium tuberculosis	4	0.7339
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640	Q9CCZ4	Y2640_MYCLE	Mycobacterium leprae	3	0.7321
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7312
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7285
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7284
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7262
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7244
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7229
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.7218
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7181
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7173
Genome polyprotein	A0EKU1	A0EKU1_9FLAV	Meaban virus	3	0.7171
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7140
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7136
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7135
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7127
Dihydrofolate reductase	Q83AB2	Q83AB2_COXBU	Coxiella burnetii	3	0.7116
Hematopoietic prostaglandin D synthase	O60760	HPGDS_HUMAN	Homo sapiens	3	0.7110
ADP compounds hydrolase NudE	P45799	NUDE_ECOLI	Escherichia coli	3	0.7096
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.7057
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7055
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.7052
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7048
Aminoglycoside 3'-phosphotransferase AphA1-IAB	B0VD92	B0VD92_ACIBY	Acinetobacter baumannii	4	0.7046
Dihydropteroate synthase	Q81VW8	Q81VW8_BACAN	Bacillus anthracis	3	0.7041
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7041
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7024
Transthyretin	Q9PTT3	Q9PTT3_SPAAU	Sparus aurata	3	0.7019
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	3	0.7012
Endoplasmin	P14625	ENPL_HUMAN	Homo sapiens	3	0.7009
Aminoglycoside 3'-phosphotransferase AphA1-IAB	B0VD92	B0VD92_ACIBY	Acinetobacter baumannii	4	0.7005

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