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Hamatinine

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

Canonical Smiles	COc1cc(O)c(c2c1C(=N[C@H](C2)C)C)c1c(C)cc(c2c1cccc2OC)OC
InChI	InChI=1S/C25H27NO4/c1-13-10-20(29-5)25-16(8-7-9-19(25)28-4)22(13)24-17-11-14(2)26-15(3)23(17)21(30-6)12-18(24)27/h7-10,12,14,27H,11H2,1-6H3/t14-/m0/s1
InChIKey	NXPYZSTXOUQQLT-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 congolensis	Ancistrocladaceae	Plantae	714097

Showing of synonyms

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: 136676242

Zinc: ZINC000013359236

Nmrshiftdb2: 70054305

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

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.84
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.720
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.07

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.600
Plasma Protein Binding: 87.61
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: Non-Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 6.710
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.540
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.140
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 6.420
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: -28.690
Rat (Acute): 2.590
Rat (Chronic Oral): 2.350
Fathead Minnow: 5.530
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: 494.130
Hydration Free Energy: -5.250
Log(D) at pH=7.4: 4.120
Log(P): 5.03
Log S: -6.63
Log(Vapor Pressure): -7.94
Melting Point: 161.81
pKa Acid: 9.81
pKa Basic: 7.78

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	0.9652
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9652
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9208
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9208
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.9109
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.9109
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.8993
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.8993
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8785
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8785
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8680
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8680
Endolysin	P00720	ENLYS_BPT4	Enterobacteria phage T4	3	0.8553
Endolysin	P00720	ENLYS_BPT4	Enterobacteria phage T4	3	0.8553
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8521
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8521
Renin	P00797	RENI_HUMAN	Homo sapiens	3	0.8103
Renin	P00797	RENI_HUMAN	Homo sapiens	3	0.8103
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8097
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8097
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8087
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8087
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8070
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8070
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7987
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7987
Actin-related protein 3	P61157	ARP3_BOVIN	Bos taurus	4	0.7981
Actin-related protein 3	P61157	ARP3_BOVIN	Bos taurus	4	0.7981
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7906
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7906
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7836
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7836
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.7833
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.7833
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.7749
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.7749
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7687
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7687
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7628
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7628
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7595
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7595
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7591
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7591
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7577
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7577
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7575
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7575
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.7573
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.7573
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.7486
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.7486
Thyroxine-binding globulin	P05543	THBG_HUMAN	Homo sapiens	3	0.7465
Thyroxine-binding globulin	P05543	THBG_HUMAN	Homo sapiens	3	0.7465
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7444
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7444
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7434
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7434
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7425
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7425
Thymidylate synthase ThyA	P9WFR9	TYSY_MYCTU	Mycobacterium tuberculosis	3	0.7410
Thymidylate synthase ThyA	P9WFR9	TYSY_MYCTU	Mycobacterium tuberculosis	3	0.7410
Endoplasmin	P14625	ENPL_HUMAN	Homo sapiens	3	0.7357
Endoplasmin	P14625	ENPL_HUMAN	Homo sapiens	3	0.7357
Thymidylate synthase	Q4JQW2	TYSY_VZVO	Varicella-zoster virus	3	0.7308
Thymidylate synthase	Q4JQW2	TYSY_VZVO	Varicella-zoster virus	3	0.7308
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
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7290
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7290
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7280
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7280
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.7254
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.7254
Squalene synthase	P37268	FDFT_HUMAN	Homo sapiens	4	0.7223
Squalene synthase	P37268	FDFT_HUMAN	Homo sapiens	4	0.7223
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7217
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7217
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7191
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7191
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	3	0.7181
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	3	0.7181
Beta-lactamase	P00811	AMPC_ECOLI	Escherichia coli	3	0.7180
Beta-lactamase	P00811	AMPC_ECOLI	Escherichia coli	3	0.7180
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7160
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7160
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7138
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7138
Albumin	P02768	ALBU_HUMAN	Homo sapiens	4	0.7068
Albumin	P02768	ALBU_HUMAN	Homo sapiens	4	0.7068

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