Fumarofine - Compound Card

Fumarofine

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Fumarofine

Structure
Zoomed Structure
  • Family: Plantae - Fumariaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Isoquinoline Alkaloid
Canonical Smiles COc1cc2CCN(C3C(c2cc1O)(O)C(=O)c1c3ccc2c1OCO2)C
InChI InChI=1S/C20H19NO6/c1-21-6-5-10-7-15(25-2)13(22)8-12(10)20(24)18(21)11-3-4-14-17(27-9-26-14)16(11)19(20)23/h3-4,7-8,18,22,24H,5-6,9H2,1-2H3
InChIKey BJGPRDJBNLOGMI-UHFFFAOYSA-N
Formula C20H19NO6
HBA 7
HBD 2
MW 369.37
Rotatable Bonds 1
TPSA 88.46
LogP 1.74
Number Rings 5
Number Aromatic Rings 2
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.35
Exact Mass 369.12
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: 632772
Nmrshiftdb2: 60069868

No compound-protein relationship available.

Structure

SMILES: O1COc(c1c23)ccc2C4C(C3=O)c5c(CCN4)cccc5

Level: 0

Mol. Weight: 369.37 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.88
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.770
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.0

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.960
Plasma Protein Binding
38.13
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
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.830
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.400
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.280
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
9.140
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
-12.130
Rat (Acute)
2.340
Rat (Chronic Oral)
1.630
Fathead Minnow
4.800
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
448.350
Hydration Free Energy
-7.160
Log(D) at pH=7.4
2.610
Log(P)
1.31
Log S
-2.61
Log(Vapor Pressure)
-9.05
Melting Point
213.3
pKa Acid
6.87
pKa Basic
5.38
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9178
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9178
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.9041
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.9041
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8670
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8670
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8561
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8561
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8538
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8538
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8514
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8514
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8368
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8368
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.8324
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.8324
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8301
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8301
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8214
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8214
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 4 0.8124
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 4 0.8124
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.8037
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.8037
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.7935
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.7935
Pyruvate kinase PKM P14618 KPYM_HUMAN Homo sapiens 3 0.7856
Pyruvate kinase PKM P14618 KPYM_HUMAN Homo sapiens 3 0.7856
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 4 0.7836
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 4 0.7836
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7828
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7828
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7825
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7825
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7763
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7763
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 4 0.7743
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 4 0.7743
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7661
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7661
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7637
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7637
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7616
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7616
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7611
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7611
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7578
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7578
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7576
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7576
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7542
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7542
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7446
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7446
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7431
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7431
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7401
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7401
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7328
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7328
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7303
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7303
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7277
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7277
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7275
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7275
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7270
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7270
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7231
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7231
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7202
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7202
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7183
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7183
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7181
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7181
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7179
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7179
Nucleoside diphosphate kinase P15266 NDK_MYXXA Myxococcus xanthus 3 0.7169
Nucleoside diphosphate kinase P15266 NDK_MYXXA Myxococcus xanthus 3 0.7169
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7137
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7137
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7060
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7060
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7060
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7060
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7012
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7012
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7008
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7008
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7007
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7007
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7006
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7006

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