5'-O-demethylhamatinine - Compound Card

5'-O-demethylhamatinine

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5'-O-demethylhamatinine

Structure
Zoomed Structure
  • 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(c2c1cccc2O)OC
InChI InChI=1S/C24H25NO4/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/h6-9,11,13,26-27H,10H2,1-5H3/t13-/m0/s1
InChIKey GPWAEBFQEPWECQ-ZDUSSCGKSA-N
Formula C24H25NO4
HBA 5
HBD 2
MW 391.47
Rotatable Bonds 3
TPSA 71.28
LogP 5.0
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.29
Exact Mass 391.18
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: 135550838

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 391.47 g/mol

Structure

SMILES: C1=NCCc(c12)cccc2

Level: 0

Mol. Weight: 391.47 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 391.47 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.85
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.770
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.67

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.400
Plasma Protein Binding
88.29
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
Non-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
6.020
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.460
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.230
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.170
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
-14.650
Rat (Acute)
2.240
Rat (Chronic Oral)
2.420
Fathead Minnow
5.220
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
478.140
Hydration Free Energy
-6.620
Log(D) at pH=7.4
4.220
Log(P)
4.9
Log S
-6.56
Log(Vapor Pressure)
-8.19
Melting Point
176.51
pKa Acid
9.26
pKa Basic
7.46
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 0.9260
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9260
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9259
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9259
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 0.9006
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9006
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8960
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8960
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8948
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8948
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8889
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8889
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8790
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8790
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8733
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8733
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8701
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8701
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8643
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8643
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8631
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8631
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8466
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.8466
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8466
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8466
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.8466
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8466
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8420
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8420
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.8405
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.8405
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8363
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8363
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8350
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8350
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8246
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8246
Renin P00797 RENI_HUMAN Homo sapiens 3 0.8085
Renin P00797 RENI_HUMAN Homo sapiens 3 0.8085
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7911
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7911
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7911
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7911
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7849
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7849
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7837
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7837
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7823
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7823
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7782
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7782
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7714
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7714
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 4 0.7711
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 4 0.7711
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 3 0.7676
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 3 0.7676
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7643
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7643
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7618
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7618
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7588
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7588
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7584
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7584
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7573
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7573
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7518
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7518
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7477
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7477
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7427
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7427
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7426
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7426
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7418
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7418
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7410
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7410
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7408
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7408
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7340
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7340
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7328
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7328
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7294
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7294
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7253
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7253
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7246
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7246
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7246
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7246
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7245
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7245
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7214
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7214
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7194
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7194
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7191
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7191
Thymidylate synthase ThyA P9WFR9 TYSY_MYCTU Mycobacterium tuberculosis 3 0.7191
Thymidylate synthase ThyA P9WFR9 TYSY_MYCTU Mycobacterium tuberculosis 3 0.7191
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7188
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7188
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7184
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7184
Beta-lactamase P00811 AMPC_ECOLI Escherichia coli 3 0.7173
Beta-lactamase P00811 AMPC_ECOLI Escherichia coli 3 0.7173
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7164
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7164
Nicotinamide riboside kinase 1 Q9NWW6 NRK1_HUMAN Homo sapiens 4 0.7162
Nicotinamide riboside kinase 1 Q9NWW6 NRK1_HUMAN Homo sapiens 4 0.7162
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7149
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7149
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7142
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7142
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7092
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7092
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7087
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7087
Thymidylate synthase Q4JQW2 TYSY_VZVO Varicella-zoster virus 3 0.7075
Thymidylate synthase Q4JQW2 TYSY_VZVO Varicella-zoster virus 3 0.7075
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7057
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7057
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7033
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7033
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7016
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7016
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7012
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7012
Rifampin ADP-ribosyl transferase A0QRS5 A0QRS5_MYCS2 Mycolicibacterium smegmatis155) 3 0.7004
Rifampin ADP-ribosyl transferase A0QRS5 A0QRS5_MYCS2 Mycolicibacterium smegmatis155) 3 0.7004

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