Dihydrofumariline - Compound Card

Dihydrofumariline

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Dihydrofumariline

Structure
Zoomed Structure
  • Family: Fumariaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Isoquinoline Alkaloid
Canonical Smiles CN1CCc2c([C@@]31Cc1c([C@H]3O)c3OCOc3cc1)cc1c(c2)OCO1
InChI InChI=1S/C20H19NO5/c1-21-5-4-11-6-15-16(25-9-24-15)7-13(11)20(21)8-12-2-3-14-18(26-10-23-14)17(12)19(20)22/h2-3,6-7,19,22H,4-5,8-10H2,1H3/t19-,20+/m1/s1
InChIKey AKCAVBOVRWGORC-UXHICEINSA-N
Formula C20H19NO5
HBA 6
HBD 1
MW 353.37
Rotatable Bonds 0
TPSA 60.39
LogP 2.12
Number Rings 6
Number Aromatic Rings 2
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.4
Exact Mass 353.13
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: 102118431

No compound-protein relationship available.

Structure

SMILES: C1c2ccc(OCO3)c3c2CC14c5c(CCN4)cc6c(c5)OCO6

Level: 0

Mol. Weight: 323.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.88
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.68
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.21

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.84
Plasma Protein Binding
66.66
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
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-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
16.13
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.66
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.84
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.43
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
Toxic
T. Pyriformis
-11.29
Rat (Acute)
2.27
Rat (Chronic Oral)
1.22
Fathead Minnow
4.23
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
441.77
Hydration Free Energy
-6.02
Log(D) at pH=7.4
2.55
Log(P)
2.75
Log S
-3.43
Log(Vapor Pressure)
-11.26
Melting Point
196.55
pKa Acid
10.64
pKa Basic
6.67
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9656
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9656
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9344
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9344
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9205
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9205
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8973
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8973
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8646
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8646
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8507
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8507
Rifampin ADP-ribosyl transferase A0QRS5 A0QRS5_MYCS2 Mycolicibacterium smegmatis155) 4 0.8225
Rifampin ADP-ribosyl transferase A0QRS5 A0QRS5_MYCS2 Mycolicibacterium smegmatis155) 4 0.8225
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8207
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8207
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.7988
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.7988
Calmodulin-domain protein kinase 1, putative A3FQ16 A3FQ16_CRYPI Cryptosporidium parvum 3 0.7893
Calmodulin-domain protein kinase 1, putative A3FQ16 A3FQ16_CRYPI Cryptosporidium parvum 3 0.7893
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7820
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7820
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7776
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7776
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7758
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7758
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7756
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7756
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7752
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7752
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7728
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7728
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7715
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7715
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7682
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7682
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7676
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7676
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7675
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7675
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7654
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7654
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7654
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7654
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7647
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7647
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7594
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7594
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7573
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7573
Nitric oxide synthase, inducible P35228 NOS2_HUMAN Homo sapiens 3 0.7548
Nitric oxide synthase, inducible P35228 NOS2_HUMAN Homo sapiens 3 0.7548
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7471
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7471
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 4 0.7465
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 4 0.7465
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 2 0.7464
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 2 0.7464
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7421
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7421
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7419
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7419
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7406
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7406
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7379
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7379
Putative cytochrome P450 Q70AS3 Q70AS3_STRPE Streptomyces peucetius 3 0.7360
Putative cytochrome P450 Q70AS3 Q70AS3_STRPE Streptomyces peucetius 3 0.7360
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7359
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7359
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7265
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7265
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7250
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7250
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7227
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7227
Beta-lactamase P00811 AMPC_ECOLI Escherichia coli 3 0.7214
Beta-lactamase P00811 AMPC_ECOLI Escherichia coli 3 0.7214
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7210
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7210
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7208
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7208
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7163
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7163
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7155
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7155
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7141
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7141
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7137
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7137
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7129
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7129
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7121
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7121
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7105
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7105
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7100
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7100
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7099
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7099
Diamine acetyltransferase 1 P21673 SAT1_HUMAN Homo sapiens 2 0.7096
Diamine acetyltransferase 1 P21673 SAT1_HUMAN Homo sapiens 2 0.7096
Heat shock protein 75 kDa, mitochondrial Q12931 TRAP1_HUMAN Homo sapiens 3 0.7088
Heat shock protein 75 kDa, mitochondrial Q12931 TRAP1_HUMAN Homo sapiens 3 0.7088
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7075
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7075
Beta-lactamase P00811 AMPC_ECOLI Escherichia coli 3 0.7069
Beta-lactamase P00811 AMPC_ECOLI Escherichia coli 3 0.7069
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.7062
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.7062
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7046
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7046
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7033
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7033
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7033
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7033
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7031
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7031
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 3 0.7029
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 3 0.7029
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7006
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7006

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