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6-O-methylancistrocladinine

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

Canonical Smiles	COc1cc(OC)c2c(c1c1c(C)cc(c3c1cccc3OC)OC)C[C@@H](N=C2C)C
InChI	InChI=1S/C26H29NO4/c1-14-11-20(29-5)25-17(9-8-10-19(25)28-4)23(14)26-18-12-15(2)27-16(3)24(18)21(30-6)13-22(26)31-7/h8-11,13,15H,12H2,1-7H3/t15-/m0/s1
InChIKey	XSHYHGPIMCKDFK-HNNXBMFYSA-N
Formula	C₂₆H₂₉NO₄
HBA	5
HBD	0
MW	419.52
Rotatable Bonds	5
TPSA	49.28
LogP	5.6
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	31
Formal Charge	0
Fraction CSP3	0.35
Exact Mass	419.21
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ancistrocladus tanzaniensis	Ancistrocladaceae	Plantae	714107
2	Ancistrocladus congolensis	Ancistrocladaceae	Plantae	714097
3	Ancistrocladus abbreviatus	Ancistrocladaceae	Plantae	122295

Showing of synonyms

Fayez S, Cacciatore A, et al. (2021). Ancistrobrevidines A-C and related naphthylisoquinoline alkaloids with cytotoxic activities against heLa and pancreatic cancer cells, from the liana Ancistrocladus abbreviatus. Bioorganic & Medicinal Chemistry,2021, 30,115950. [View]
Bringmann G, Dreyer M, et al. (2004). Ancistrotanzanine C and related 5,1'- and 7,3'-coupled naphthylisoquinoline alkaloids from Ancistrocladus tanzaniensis. Journal of Natural Products,2004,67(5),743-748. [View] [PubMed]
Bringmann G, Spuziak J, et al. (2008). Six naphthylisoquinoline alkaloids and a related benzopyranone from a Congolese Ancistrocladus species related to Ancistrocladus congolensis. Phytochemistry,2008, 69(4), 1065-1075. [View] [PubMed]

Pubchem: 11212280

Cas: 134984-06-8

Zinc: ZINC000013359242

Nmrshiftdb2: 70054307

Chembl: CHEMBL464727

No compound-protein relationship available.

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

Level: 1

Mol. Weight: 419.52 g/mol

SMILES: C1=NCCc(c12)cccc2

Level: 0

Mol. Weight: 419.52 g/mol

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 419.52 g/mol

Antiprotozoal

Absorption

Caco-2 (logPapp): -5.06
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.760
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.4

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.730
Plasma Protein Binding: 83.47
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 7.450
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 2.030
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.060
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 7.810
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: Toxic
T. Pyriformis: -52.390
Rat (Acute): 2.990
Rat (Chronic Oral): 2.220
Fathead Minnow: 5.910
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 509.520
Hydration Free Energy: -3.850
Log(D) at pH=7.4: 3.870
Log(P): 5.66
Log S: -6.41
Log(Vapor Pressure): -7.33
Melting Point: 144.72
pKa Acid: 12.05
pKa Basic: 8.18

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	0.9706
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9706
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9328
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9328
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.9114
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.9114
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.9069
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.9069
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8805
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8805
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8639
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8639
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8630
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8630
Endolysin	P00720	ENLYS_BPT4	Enterobacteria phage T4	3	0.8521
Endolysin	P00720	ENLYS_BPT4	Enterobacteria phage T4	3	0.8521
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8157
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8157
Actin-related protein 3	P61157	ARP3_BOVIN	Bos taurus	4	0.8096
Actin-related protein 3	P61157	ARP3_BOVIN	Bos taurus	4	0.8096
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8076
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8076
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8075
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8075
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8004
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8004
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7998
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7998
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7955
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7955
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7941
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7941
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.7808
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.7808
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7753
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7753
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.7747
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.7747
Squalene synthase	P37268	FDFT_HUMAN	Homo sapiens	4	0.7678
Squalene synthase	P37268	FDFT_HUMAN	Homo sapiens	4	0.7678
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7640
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7640
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7633
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7633
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.7606
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.7606
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7600
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7600
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7578
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7578
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.7558
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.7558
Thyroxine-binding globulin	P05543	THBG_HUMAN	Homo sapiens	3	0.7548
Thyroxine-binding globulin	P05543	THBG_HUMAN	Homo sapiens	3	0.7548
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7507
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7507
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7493
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7493
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7492
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7492
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.7449
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.7449
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7429
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7429
Thymidylate synthase ThyA	P9WFR9	TYSY_MYCTU	Mycobacterium tuberculosis	3	0.7426
Thymidylate synthase ThyA	P9WFR9	TYSY_MYCTU	Mycobacterium tuberculosis	3	0.7426
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7376
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7376
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7338
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7338
Endoplasmin	P14625	ENPL_HUMAN	Homo sapiens	3	0.7324
Endoplasmin	P14625	ENPL_HUMAN	Homo sapiens	3	0.7324
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7317
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7317
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7308
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7308
Thymidylate synthase	Q4JQW2	TYSY_VZVO	Varicella-zoster virus	3	0.7297
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7297
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7297
Thymidylate synthase	Q4JQW2	TYSY_VZVO	Varicella-zoster virus	3	0.7297
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7295
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7295
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7268
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7268
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7206
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7206
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7200
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7200
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	3	0.7183
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	3	0.7183
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7148
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7148
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7125
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7125
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	3	0.7087
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	3	0.7087
Albumin	P02768	ALBU_HUMAN	Homo sapiens	4	0.7081
Albumin	P02768	ALBU_HUMAN	Homo sapiens	4	0.7081
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7069
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7069
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7015
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7015

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