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5'-O-demethylhamatine

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

Canonical Smiles	COc1cc(O)c(c2c1[C@H](C)N[C@H](C2)C)c1c(C)cc(c2c1cccc2O)OC
InChI	InChI=1S/C24H27NO4/c1-12-9-19(28-4)23-15(7-6-8-17(23)26)21(12)24-16-10-13(2)25-14(3)22(16)20(29-5)11-18(24)27/h6-9,11,13-14,25-27H,10H2,1-5H3/t13-,14-/m0/s1
InChIKey	CFUJKOWBPQAPSW-KBPBESRZSA-N
Formula	C₂₄H₂₇NO₄
HBA	5
HBD	3
MW	393.48
Rotatable Bonds	3
TPSA	70.95
LogP	4.84
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 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: 24814587

Zinc: ZINC000140180791

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): -5.1
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.930
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -1.52

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.160
Plasma Protein Binding: 77.27
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: Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 8.350
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.520
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.190
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 9.140
Micronucleos: Toxic
NR-AhR: Safe
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: -20.770
Rat (Acute): 2.310
Rat (Chronic Oral): 2.160
Fathead Minnow: 4.990
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: 462.070
Hydration Free Energy: -7.960
Log(D) at pH=7.4: 4.510
Log(P): 4.06
Log S: -4.93
Log(Vapor Pressure): -8.66
Melting Point: 155.72
pKa Acid: 9.52
pKa Basic: 9.08

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.9245
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.9245
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9226
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9226
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.9008
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.9008
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8977
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8977
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8972
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8972
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8918
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8918
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8829
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8829
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8689
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8689
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8615
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8615
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8568
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8568
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8475
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8475
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.8434
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.8434
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8389
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8389
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8332
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8332
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8217
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8217
Renin	P00797	RENI_HUMAN	Homo sapiens	3	0.8185
Renin	P00797	RENI_HUMAN	Homo sapiens	3	0.8185
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.8177
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.8177
Endolysin	P00720	ENLYS_BPT4	Enterobacteria phage T4	3	0.8153
Endolysin	P00720	ENLYS_BPT4	Enterobacteria phage T4	3	0.8153
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8149
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8149
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7971
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7971
Transthyretin	Q9PTT3	Q9PTT3_SPAAU	Sparus aurata	3	0.7956
Transthyretin	Q9PTT3	Q9PTT3_SPAAU	Sparus aurata	3	0.7956
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7890
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7890
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7773
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7773
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.7749
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.7749
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7734
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7734
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7648
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7648
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	3	0.7577
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	3	0.7577
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7560
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7560
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7516
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7516
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.7497
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.7497
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7485
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7485
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7424
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7424
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7410
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7410
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7397
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7397
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7357
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7357
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7321
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7321
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7219
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7219
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7215
Thyroxine-binding globulin	P05543	THBG_HUMAN	Homo sapiens	3	0.7215
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7215
Thyroxine-binding globulin	P05543	THBG_HUMAN	Homo sapiens	3	0.7215
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7196
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7196
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7176
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7176
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7173
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7173
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7166
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7166
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7165
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7165
Beta-lactamase	P00811	AMPC_ECOLI	Escherichia coli	3	0.7137
Beta-lactamase	P00811	AMPC_ECOLI	Escherichia coli	3	0.7137
Thymidylate synthase ThyA	P9WFR9	TYSY_MYCTU	Mycobacterium tuberculosis	3	0.7135
Thymidylate synthase ThyA	P9WFR9	TYSY_MYCTU	Mycobacterium tuberculosis	3	0.7135
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7124
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7124
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.7060
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.7060
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7057
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7057
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7031
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7031
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7025
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7025
Endoplasmin	P14625	ENPL_HUMAN	Homo sapiens	3	0.7015
Endoplasmin	P14625	ENPL_HUMAN	Homo sapiens	3	0.7015

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