Fumaricine - Compound Card

Fumaricine

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Fumaricine

Structure
Zoomed Structure
  • Family: Plantae - Fumariaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Isoquinoline Alkaloid
Canonical Smiles COc1cc2c(cc1OC)CCN([C@@]12Cc2c([C@@H]1O)c1OCOc1cc2)C
InChI InChI=1S/C21H23NO5/c1-22-7-6-12-8-16(24-2)17(25-3)9-14(12)21(22)10-13-4-5-15-19(27-11-26-15)18(13)20(21)23/h4-5,8-9,20,23H,6-7,10-11H2,1-3H3/t20-,21+/m0/s1
InChIKey QDNMFIYGVRUVCE-LEWJYISDSA-N
Formula C21H23NO5
HBA 6
HBD 1
MW 369.42
Rotatable Bonds 2
TPSA 60.39
LogP 2.41
Number Rings 5
Number Aromatic Rings 2
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.43
Exact Mass 369.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Fumaria capreolata Fumariaceae Plantae 1053349
2 Fumaria bastardii Fumariaceae Plantae 1155334

Showing of synonyms

  • Maiza-Benabdesselam F, Khentache S, et al. (2007). Antioxidant activities of alkaloid extracts of two Algerian species of Fumaria : Fumaria capreolata and Fumaria bastardii. Records of Natural Products,2007,1(2-3),28-35. [View]
Pubchem: 442236
Kegg Ligand: C09444
Chebi: 5191
Nmrshiftdb2: 60032692

No compound-protein relationship available.

Structure

SMILES: C1c2ccc(OCO3)c3c2CC14c5c(CCN4)cccc5

Level: 0

Mol. Weight: 369.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.94
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.640
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.9

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.920
Plasma Protein Binding
62.33
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
13.580
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.510
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.840
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
9.620
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
-15.830
Rat (Acute)
2.330
Rat (Chronic Oral)
1.390
Fathead Minnow
4.400
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
422.820
Hydration Free Energy
-6.990
Log(D) at pH=7.4
2.260
Log(P)
2.13
Log S
-2.65
Log(Vapor Pressure)
-8.8
Melting Point
177.96
pKa Acid
10.3
pKa Basic
6.61
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8996
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8996
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8621
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8621
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8617
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8617
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8613
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8613
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8545
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8545
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.8526
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.8526
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8282
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8282
Cytochrome P450 2C5 P00179 CP2C5_RABIT Oryctolagus cuniculus 3 0.8210
Cytochrome P450 2C5 P00179 CP2C5_RABIT Oryctolagus cuniculus 3 0.8210
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8109
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8109
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7945
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7945
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7921
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7921
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7908
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7908
Inorganic pyrophosphatase Q3JUV5 Q3JUV5_BURP1 Burkholderia pseudomallei 3 0.7876
Inorganic pyrophosphatase Q3JUV5 Q3JUV5_BURP1 Burkholderia pseudomallei 3 0.7876
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7819
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7819
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7771
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7771
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7739
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7739
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7734
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7734
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 4 0.7697
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 4 0.7697
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7670
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7670
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7665
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7665
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7653
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7653
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7614
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7614
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7582
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7582
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7582
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7582
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.7565
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.7565
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7564
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7564
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7552
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7552
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7530
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7530
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7517
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7517
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7491
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7491
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 2 0.7478
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 2 0.7478
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7420
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7420
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7408
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7408
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7376
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7376
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 4 0.7372
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 4 0.7372
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7371
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7371
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7369
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7369
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7346
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7346
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7333
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7333
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7328
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7328
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7297
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7297
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7290
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7290
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7228
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7228
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7211
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7211
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7191
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7191
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7181
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7181
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7170
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7170
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7163
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7163
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7161
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7161
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7158
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7158
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7158
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7158
RNA polymerase sigma factor SigA Q5SKW1 Q5SKW1_THET8 Thermus thermophilus 3 0.7151
RNA polymerase sigma factor SigA Q5SKW1 Q5SKW1_THET8 Thermus thermophilus 3 0.7151
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7117
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7117
Heat shock protein 75 kDa, mitochondrial Q12931 TRAP1_HUMAN Homo sapiens 3 0.7082
Heat shock protein 75 kDa, mitochondrial Q12931 TRAP1_HUMAN Homo sapiens 3 0.7082
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.7075
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.7075
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7071
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7071
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.7046
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.7046
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7031
Orotidine 5'-phosphate decarboxylase O26232 PYRF_METTH Methanothermobacter thermautotrophicus 3 0.7031
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7031
Orotidine 5'-phosphate decarboxylase O26232 PYRF_METTH Methanothermobacter thermautotrophicus 3 0.7031
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7007
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7007
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7006
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7006
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7005
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7005

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