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Ancistrocongoline A

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

Canonical Smiles	COc1cc(C)cc2c1c(O)ccc2c1c(O)cc(c2c1C[C@@H](C)N([C@@H]2C)C)O
InChI	InChI=1S/C24H27NO4/c1-12-8-16-15(6-7-18(26)24(16)21(9-12)29-5)23-17-10-13(2)25(4)14(3)22(17)19(27)11-20(23)28/h6-9,11,13-14,26-28H,10H2,1-5H3/t13-,14-/m1/s1
InChIKey	GWJJRDKEDFSIDL-ZIAGYGMSSA-N
Formula	C₂₄H₂₇NO₄
HBA	5
HBD	3
MW	393.48
Rotatable Bonds	2
TPSA	73.16
LogP	4.88
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	29
Formal Charge	0
Fraction CSP3	0.33
Exact Mass	393.19
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ancistrocladus likoko	Ancistrocladaceae	Plantae	714102
2	Ancistrocladus likoko	Ancistrocladaceae	Plantae	714102
3	Ancistrocladus congolensis	Ancistrocladaceae	Plantae	714097

Showing of synonyms

Bringmann G, Messer K, et al. (2002). Ancistrocongolines A-D, new naphthylisoquinoline alkaloids from Ancistrocladus congolensis. Journal of natural products,2002, 65(8), 1096-1101. [View] [PubMed]
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]
Fayez S, Feineis D, et al. (2017). Ancistrolikokines E-H and related 5,8'-coupled naphthylisoquinoline alkaloids from the Congolese liana Ancistrocladus likoko with antiausterity activities against PANC-1 human pancreatic cancer cells.. RSC Adv., 2017,7, 53740-53751. [View]

Pubchem: 392424

Cas: 455255-21-7

Zinc: ZINC000005849005

Nmrshiftdb2: 70059385

Chembl: CHEMBL520005

No compound-protein relationship available.

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

Level: 1

Mol. Weight: 393.48 g/mol

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 393.48 g/mol

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 393.48 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.19
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.020
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.26

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.920
Plasma Protein Binding: 80.34
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: 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: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 7.540
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 2.240
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.580
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 8.210
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Toxic
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: -17.530
Rat (Acute): 2.320
Rat (Chronic Oral): 2.240
Fathead Minnow: 4.710
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 482.060
Hydration Free Energy: -8.530
Log(D) at pH=7.4: 3.660
Log(P): 4.27
Log S: -4.3
Log(Vapor Pressure): -8.67
Melting Point: 180.63
pKa Acid: 8.54
pKa Basic: 8.43

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	0.9366
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.9366
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9365
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9365
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.9278
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.9278
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.9164
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.9164
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9140
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9140
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.9128
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.9128
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.9014
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.9014
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.8554
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.8554
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	4	0.8548
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	4	0.8548
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8527
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8527
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8512
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8512
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8319
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8319
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8279
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.8279
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8279
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.8279
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8278
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8278
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.8191
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.8191
Endolysin	P00720	ENLYS_BPT4	Enterobacteria phage T4	3	0.8165
Endolysin	P00720	ENLYS_BPT4	Enterobacteria phage T4	3	0.8165
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8024
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8024
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8005
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8005
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7946
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7946
Transthyretin	Q9PTT3	Q9PTT3_SPAAU	Sparus aurata	3	0.7937
Transthyretin	Q9PTT3	Q9PTT3_SPAAU	Sparus aurata	3	0.7937
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7895
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7895
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.7875
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.7875
11-beta-hydroxysteroid dehydrogenase 1	Q6QLL4	DHI1_CAVPO	Cavia porcellus	3	0.7866
11-beta-hydroxysteroid dehydrogenase 1	Q6QLL4	DHI1_CAVPO	Cavia porcellus	3	0.7866
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7783
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7783
UDP-glycosyltransferase 72B1	Q9M156	U72B1_ARATH	Arabidopsis thaliana	4	0.7630
UDP-glycosyltransferase 72B1	Q9M156	U72B1_ARATH	Arabidopsis thaliana	4	0.7630
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7610
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7610
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7609
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7609
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	4	0.7603
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	4	0.7603
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7555
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7555
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7522
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7522
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.7507
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.7507
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7466
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7466
Alcohol dehydrogenase E chain	P00327	ADH1E_HORSE	Equus caballus	4	0.7436
Alcohol dehydrogenase E chain	P00327	ADH1E_HORSE	Equus caballus	4	0.7436
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7422
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7422
Endoplasmin	P14625	ENPL_HUMAN	Homo sapiens	3	0.7400
Endoplasmin	P14625	ENPL_HUMAN	Homo sapiens	3	0.7400
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	4	0.7391
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	4	0.7391
ADP compounds hydrolase NudE	P45799	NUDE_ECOLI	Escherichia coli	3	0.7388
ADP compounds hydrolase NudE	P45799	NUDE_ECOLI	Escherichia coli	3	0.7388
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7376
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7376
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7345
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7345
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.7277
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.7277
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640	Q9CCZ4	Y2640_MYCLE	Mycobacterium leprae	3	0.7272
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640	Q9CCZ4	Y2640_MYCLE	Mycobacterium leprae	3	0.7272
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7269
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7269
Thyroxine-binding globulin	P05543	THBG_HUMAN	Homo sapiens	3	0.7259
Thyroxine-binding globulin	P05543	THBG_HUMAN	Homo sapiens	3	0.7259
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7243
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7243
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7214
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7214
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7213
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7213
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7206
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7206
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7203
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7203
Genome polyprotein	A0EKU1	A0EKU1_9FLAV	Meaban virus	3	0.7196
Genome polyprotein	A0EKU1	A0EKU1_9FLAV	Meaban virus	3	0.7196
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7188
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7188
Histamine N-methyltransferase	P50135	HNMT_HUMAN	Homo sapiens	4	0.7187
Histamine N-methyltransferase	P50135	HNMT_HUMAN	Homo sapiens	4	0.7187
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7127
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7127
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7124
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7124
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7107
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7107
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7102
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7102
Diphtheria toxin	P00588	DTX_CORBE	Corynephage beta	3	0.7092
Diphtheria toxin	P00588	DTX_CORBE	Corynephage beta	3	0.7092
Thiamine-monophosphate kinase	O67883	THIL_AQUAE	Aquifex aeolicus	3	0.7088
Thiamine-monophosphate kinase	O67883	THIL_AQUAE	Aquifex aeolicus	3	0.7088
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7084
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7084
Bifunctional dihydrofolate reductase-thymidylate synthase	Q27552	Q27552_CRYPV	Cryptosporidium parvum	3	0.7080
Bifunctional dihydrofolate reductase-thymidylate synthase	Q27552	Q27552_CRYPV	Cryptosporidium parvum	3	0.7080
Genome polyprotein	P12823	POLG_DEN2P	Dengue virus type 2	3	0.7068
Genome polyprotein	P12823	POLG_DEN2P	Dengue virus type 2	3	0.7068
Hepatocyte growth factor receptor	P08581	MET_HUMAN	Homo sapiens	4	0.7064
Hepatocyte growth factor receptor	P08581	MET_HUMAN	Homo sapiens	4	0.7064
Gag-Pol polyprotein	P03366	POL_HV1B1	Human immunodeficiency virus type 1 group M subtype B	4	0.7049
Gag-Pol polyprotein	P03366	POL_HV1B1	Human immunodeficiency virus type 1 group M subtype B	4	0.7049
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7016
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7016
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7008
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7008
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7007
Dihydrofolate reductase	P22906	DYR_CANAX	Candida albicans	4	0.7007
Dihydrofolate reductase	P22906	DYR_CANAX	Candida albicans	4	0.7007
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7007

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