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Ent-ealaine D

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

Canonical Smiles	COc1cc(O)cc2c1C(=N[C@@H](C2)C)C
InChI	InChI=1S/C12H15NO2/c1-7-4-9-5-10(14)6-11(15-3)12(9)8(2)13-7/h5-7,14H,4H2,1-3H3/t7-/m1/s1
InChIKey	RZNYTVOTEIMHNS-SSDOTTSWSA-N
Formula	C₁₂H₁₅NO₂
HBA	3
HBD	1
MW	205.26
Rotatable Bonds	1
TPSA	41.82
LogP	2.15
Number Rings	2
Number Aromatic Rings	1
Heavy Atom Count	15
Formal Charge	0
Fraction CSP3	0.42
Exact Mass	205.11
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ancistrocladus likoko	Ancistrocladaceae	Plantae	714102

Showing of synonyms

Fayez S, Feineis D, et al. (2018). Ancistrolikokine I and further 5,8′-coupled naphthylisoquinoline alkaloids from the Congolese liana Ancistrocladus likoko and their cytotoxic activities against drug-sensitive and multidrug resistant human leukemia cells.. Fitoterapia,2018, 129, 114-125. [View] [PubMed]

No compound-protein relationship available.

SMILES: C1=NCCc(c12)cccc2

Level: 0

Mol. Weight: 205.26 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.9
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.340
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.75

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.370
Plasma Protein Binding: 46.3
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 9.270
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.000
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: -0.540
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 5.140
Micronucleos: Safe
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: Safe
T. Pyriformis: 2.540
Rat (Acute): 2.120
Rat (Chronic Oral): 2.010
Fathead Minnow: 4.020
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 317.060
Hydration Free Energy: -8.280
Log(D) at pH=7.4: 1.790
Log(P): 2.34
Log S: -2.9
Log(Vapor Pressure): -4.11
Melting Point: 124.72
pKa Acid: 10.39
pKa Basic: 7.86

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.9735
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9550
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.9520
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9511
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9461
Dihydropteroate synthase	Q81VW8	Q81VW8_BACAN	Bacillus anthracis	3	0.9441
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9421
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9408
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.9400
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.9396
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9346
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.9335
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.9334
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9306
NADPH-dependent 7-cyano-7-deazaguanine reductase	Q9KTK0	QUEF_VIBCH	Vibrio cholerae serotype O1	3	0.9283
Repressor protein	Q7X0D9	Q7X0D9_ACIAD	Acinetobacter baylyi	3	0.9279
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.9276
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.9229
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.9225
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.9014
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.8989
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.8969
tRNA-guanine(15) transglycosylase	O58843	ATGT_PYRHO	Pyrococcus horikoshii	3	0.8759
Sulfotransferase 1A1	P50225	ST1A1_HUMAN	Homo sapiens	3	0.8727
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.8681
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8511
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase	P62617	ISPF_ECOLI	Escherichia coli	3	0.8485
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.8463
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	3	0.8462
S-norcoclaurine synthase	Q67A25	NCS_THLFG	Thalictrum flavum subsp. glaucum	3	0.8428
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.8386
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8358
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.8239
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.8193
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.8094
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7899
orotidine-5'-phosphate decarboxylase	Q8T6J6	Q8T6J6_PLAFA	Plasmodium falciparum	4	0.7894
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7759
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7742
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7706
Pteridine reductase	O76290	O76290_TRYBB	Trypanosoma brucei brucei	3	0.7698
Dihydropteroate synthase	Q81VW8	Q81VW8_BACAN	Bacillus anthracis	3	0.7654
O-GlcNAcase NagJ	Q0TR53	OGA_CLOP1	Clostridium perfringens	3	0.7632
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7625
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7615
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7602
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	3	0.7598
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7583
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7563
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase	Q8ZMF7	ISPF_SALTY	Salmonella typhimurium	3	0.7541
RNA-dependent RNA polymerase	Q6A562	Q6A562_9VIRU	Thosea asigna virus	2	0.7538
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7534
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7522
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7515
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7514
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7452
Dihydropteroate synthase	Q81VW8	Q81VW8_BACAN	Bacillus anthracis	3	0.7432
Rac-like GTP-binding protein ARAC7	O82480	RAC7_ARATH	Arabidopsis thaliana	3	0.7430
rRNA methylase	Q8DSS3	Q8DSS3_STRMU	Streptococcus mutans serotype c	2	0.7416
chitinase	B0Y2Y2	B0Y2Y2_ASPFC	Aspergillus fumigatus	3	0.7415
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	3	0.7408
Dihydropteroate synthase	Q81VW8	Q81VW8_BACAN	Bacillus anthracis	3	0.7396
Poly(A) polymerase	P29468	PAP_YEAST	Saccharomyces cerevisiae	3	0.7377
Putative N-acetyl glucosaminyl transferase	Q6U8B0	Q6U8B0_RAOTE	Raoultella terrigena	3	0.7358
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	3	0.7352
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7337
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7331
Dihydropteroate synthase	Q81VW8	Q81VW8_BACAN	Bacillus anthracis	3	0.7309
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7300
3',5'-cyclic-AMP phosphodiesterase 4B	Q07343	PDE4B_HUMAN	Homo sapiens	3	0.7286
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	2	0.7271
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7270
N-acetyltransferase domain-containing protein	Q9HV14	Q9HV14_PSEAE	Pseudomonas aeruginosa	3	0.7268
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7267
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7263
Metallo-beta-lactamase type 2	P26918	BLAB_AERHY	Aeromonas hydrophila	2	0.7259
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase	Q8RQP5	ISPF_THET8	Thermus thermophilus	3	0.7244
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7238
Thymidylate kinase	Q9KQI2	KTHY_VIBCH	Vibrio cholerae serotype O1	3	0.7238
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7233
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7232
Capsid protein VP1	O56137	O56137_9VIRU	Adeno-associated virus - 6	3	0.7227
Beta-galactoside alpha-2,6-sialyltransferase 1	P15907	SIAT1_HUMAN	Homo sapiens	3	0.7223
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	4	0.7194
Uridine phosphorylase	Q5XA29	Q5XA29_STRP6	Streptococcus pyogenes serotype M6	3	0.7193
Cytochrome b-c1 complex subunit 1, mitochondrial	P31800	QCR1_BOVIN	Bos taurus	3	0.7175
Cytidylate kinase	Q5SL35	KCY_THET8	Thermus thermophilus	3	0.7162
Chloramphenicol 3-O phosphotransferase	Q56148	CPT_STRVP	Streptomyces venezuelae	3	0.7139
DNA topoisomerase 1	P06612	TOP1_ECOLI	Escherichia coli	3	0.7137
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7128
tRNA-guanine(15) transglycosylase	O58843	ATGT_PYRHO	Pyrococcus horikoshii	3	0.7121
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7119
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7114
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7105
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7098
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7080
GTPase IMAP family member 2	Q9UG22	GIMA2_HUMAN	Homo sapiens	3	0.7080
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	3	0.7053
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.7042
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1	O50008	METE1_ARATH	Arabidopsis thaliana	2	0.7041
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	2	0.7033
Purine nucleoside phosphorylase 2	P45563	XAPA_ECOLI	Escherichia coli	3	0.7025
Ceramide transfer protein	Q9Y5P4	CERT_HUMAN	Homo sapiens	2	0.7013
Cytosolic IMP-GMP specific 5'-nucleotidase	Q5ZZB6	Q5ZZB6_LEGPH	Legionella pneumophila subsp. pneumophila	3	0.7008
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	3	0.7002

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