6-O-methylhamatine - Compound Card

6-O-methylhamatine

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6-O-methylhamatine

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1cc(OC)c2c(c1c1c(C)cc(c3c1cccc3OC)OC)C[C@@H](N[C@H]2C)C
InChI InChI=1S/C26H31NO4/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/h8-11,13,15-16,27H,12H2,1-7H3/t15-,16-/m0/s1
InChIKey RVMRJGIRKITWGW-HOTGVXAUSA-N
Formula C26H31NO4
HBA 5
HBD 1
MW 421.54
Rotatable Bonds 5
TPSA 48.95
LogP 5.44
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.38
Exact Mass 421.23
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: 11058911
Nmrshiftdb2: 70106363

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 421.54 g/mol

Structure

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 421.54 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 421.54 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.17
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.810
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.43

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.230
Plasma Protein Binding
73.36
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.860
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.930
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.050
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
9.470
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
-58.320
Rat (Acute)
2.950
Rat (Chronic Oral)
1.890
Fathead Minnow
5.800
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
476.330
Hydration Free Energy
-4.470
Log(D) at pH=7.4
3.970
Log(P)
4.87
Log S
-4.39
Log(Vapor Pressure)
-8.4
Melting Point
142.9
pKa Acid
12.31
pKa Basic
10.39
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 0.9694
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9694
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9304
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9304
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9023
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9023
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9010
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9010
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8586
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8586
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8443
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8443
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.8186
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.8186
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8169
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8169
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8156
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8156
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8081
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8081
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8065
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8065
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7993
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7993
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7960
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7960
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7910
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7910
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7879
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7879
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7859
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7859
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7690
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7690
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7620
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7620
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7579
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7579
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7574
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7574
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7554
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7554
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7536
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7536
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7532
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7532
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7478
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7478
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7455
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7455
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7381
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7381
Thymidylate synthase ThyA P9WFR9 TYSY_MYCTU Mycobacterium tuberculosis 3 0.7374
Thymidylate synthase ThyA P9WFR9 TYSY_MYCTU Mycobacterium tuberculosis 3 0.7374
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7356
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7356
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7355
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7355
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7347
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7347
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7339
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7339
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7332
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7332
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.7317
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.7317
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7271
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7271
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7261
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7261
Albumin P02768 ALBU_HUMAN Homo sapiens 4 0.7080
Albumin P02768 ALBU_HUMAN Homo sapiens 4 0.7080
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7038
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7038
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7023
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7023
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7003
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7003

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