N-methyldioncophylline A - Compound Card

N-methyldioncophylline A

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N-methyldioncophylline A

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1cccc2c1c(OC)cc(c2c1ccc2c(c1O)[C@@H](C)N([C@@H](C2)C)C)C
InChI InChI=1S/C25H29NO3/c1-14-12-21(29-6)24-18(8-7-9-20(24)28-5)22(14)19-11-10-17-13-15(2)26(4)16(3)23(17)25(19)27/h7-12,15-16,27H,13H2,1-6H3/t15-,16-/m1/s1
InChIKey ZSYADESMHZOJRK-HZPDHXFCSA-N
Formula C25H29NO3
HBA 4
HBD 1
MW 391.51
Rotatable Bonds 3
TPSA 41.93
LogP 5.48
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.36
Exact Mass 391.21
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Ancistrocladus abbreviatus Ancistrocladaceae Plantae 122295

Showing of synonyms

  • François G, Bringmann G, et al. (1995). Activities of extracts and naphthylisoquinoline alkaloids from Triphyophyllum peltatum, Ancistrocladus abbreviatus and Ancistrocladus barteri against Plasmodium berghei (Anka strain) in vitro. Journal of Ethnopharmacology, 1995, 46(2), 115-120. [View]
Pubchem: 14844756
Nmrshiftdb2: 70016116

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)cccc2-c(c3)ccc(c34)CCNC4

Level: 1

Mol. Weight: 391.51 g/mol

Structure

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 391.51 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 391.51 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.08
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
-0.81

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.130
Plasma Protein Binding
83.07
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
7.760
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.520
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.740
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.570
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
Safe
T. Pyriformis
-20.850
Rat (Acute)
2.860
Rat (Chronic Oral)
1.910
Fathead Minnow
5.090
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
454.240
Hydration Free Energy
-6.560
Log(D) at pH=7.4
3.850
Log(P)
4.65
Log S
-4.23
Log(Vapor Pressure)
-9.07
Melting Point
137.26
pKa Acid
9.76
pKa Basic
9.38
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 0.9511
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9446
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9221
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8970
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8861
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8784
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.8739
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8621
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8480
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8468
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8431
Bromodomain testis-specific protein Q58F21 BRDT_HUMAN Homo sapiens 3 0.8394
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.8345
GTPase KRas P01116 RASK_HUMAN Homo sapiens 3 0.8328
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8315
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8294
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8288
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8276
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.8171
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8138
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.8055
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8046
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8018
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8005
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7956
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7944
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7936
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7917
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7814
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7811
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7786
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.7775
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7747
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7745
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7717
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7716
Alpha-1-acid glycoprotein 2 P19652 A1AG2_HUMAN Homo sapiens 3 0.7714
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7707
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7704
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7664
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7657
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7639
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7624
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7609
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7595
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7568
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7561
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7555
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7487
Glycylpeptide N-tetradecanoyltransferase Q4Q5S8 Q4Q5S8_LEIMA Leishmania major 3 0.7481
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7476
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7476
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7459
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7458
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7447
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7434
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7426
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7388
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7357
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7347
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7313
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7284
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7249
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7248
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7215
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7179
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7167
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7161
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7150
Prostaglandin F2a synthase Q8I6L9 Q8I6L9_TRYCR Trypanosoma cruzi 2 0.7076
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7067
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7057
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7057
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7053
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7045
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7042
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 4 0.7032
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7023
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.7018
Dihydrofolate reductase P9WNX1 DYR_MYCTU Mycobacterium tuberculosis 3 0.7010
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7004
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7004
Mitomycin-binding protein O05205 O05205_STRLA Streptomyces lavendulae 2 0.7003

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