Fumaramidine - Compound Card

Fumaramidine

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Fumaramidine

Structure
Zoomed Structure
  • Family: Plantae - Papaveraceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Phthalideisoquinoline Alkaloid
Canonical Smiles COc1cc(/C=C/2\NC(=O)c3c2ccc2c3OCO2)c(cc1OC)CCN(C)C
InChI InChI=1S/C22H24N2O5/c1-24(2)8-7-13-10-18(26-3)19(27-4)11-14(13)9-16-15-5-6-17-21(29-12-28-17)20(15)22(25)23-16/h5-6,9-11H,7-8,12H2,1-4H3,(H,23,25)/b16-9-
InChIKey HAJRBXQNVTZIIF-SXGWCWSVSA-N
Formula C22H24N2O5
HBA 6
HBD 1
MW 396.44
Rotatable Bonds 6
TPSA 69.26
LogP 2.78
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.32
Exact Mass 396.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Fumaria parviflora Fumariaceae Plantae 1464625
2 Fumaria parviflora Papaveraceae Plantae 1464625

Showing of synonyms

  • Elsaid M.B, Elnaggar D.M, et al. (2022). Production of isoquinoline alkaloids from the in vitro conserved Fumaria parviflora and their in vitro wound healing activity. Natural product research, 2022, 36(10), 2575-2579. [View] [PubMed]
Pubchem: 11596387

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C=C(NC2=O)c(c23)ccc4c3OCO4

Level: 1

Mol. Weight: 396.44 g/mol

Structure

SMILES: O=C1NC(=C)c(c12)ccc3c2OCO3

Level: 0

Mol. Weight: 396.44 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 396.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.03
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.950
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.66

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.630
Plasma Protein Binding
51.8
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-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
15.000
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.600
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.090
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
9.720
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
-29.460
Rat (Acute)
2.410
Rat (Chronic Oral)
1.600
Fathead Minnow
4.900
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
456.360
Hydration Free Energy
-5.310
Log(D) at pH=7.4
3.010
Log(P)
2.63
Log S
-3.18
Log(Vapor Pressure)
-9.26
Melting Point
133.75
pKa Acid
8.28
pKa Basic
9.24
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.9478
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9260
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.9235
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9100
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9095
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9051
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8875
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 3 0.8813
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8812
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8747
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8707
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8701
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8692
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.8682
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8669
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8655
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8648
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8627
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8597
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8516
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8505
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8503
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8472
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8349
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8294
Beta-secretase 2 Q9Y5Z0 BACE2_HUMAN Homo sapiens 3 0.8198
Troponin C, slow skeletal and cardiac muscles P63316 TNNC1_HUMAN Homo sapiens 3 0.8029
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7979
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7976
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.7969
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7957
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7954
Putative snRNP Sm-like protein Q8ZYG5 Q8ZYG5_PYRAE Pyrobaculum aerophilum 3 0.7947
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.7903
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7807
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7799
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7799
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7784
Calmodulin-domain protein kinase 1, putative A3FQ16 A3FQ16_CRYPI Cryptosporidium parvum 3 0.7771
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7762
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7718
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7699
TGF-beta-activated kinase 1 and MAP3K7-binding protein 1 Q15750 TAB1_HUMAN Homo sapiens 3 0.7690
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7628
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7555
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7546
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7542
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 3 0.7502
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7491
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7482
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7469
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7451
Nitric oxide synthase 3 P29474 NOS3_HUMAN Homo sapiens 3 0.7451
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7450
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7435
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7431
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7417
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7401
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7399
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7399
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7389
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7367
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7366
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7360
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7353
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7335
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7334
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7325
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7322
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7297
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7294
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7285
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7282
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7278
Interstitial collagenase P03956 MMP1_HUMAN Homo sapiens 3 0.7271
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7262
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7253
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7239
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7235
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 4 0.7235
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7230
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7230
(R)-S-adenosyl-L-methionine hydrolase O58212 O58212_PYRHO Pyrococcus horikoshii OT3 3 0.7208
Inorganic pyrophosphatase Q3JUV5 Q3JUV5_BURP1 Burkholderia pseudomallei 3 0.7197
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7197
4-hydroxyphenylacetate 3-monooxygenase, reductase component Q5SJP7 HPAC_THET8 Thermus thermophilus 3 0.7189
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7186
Mitogen-activated protein kinase kinase kinase 7 O43318 M3K7_HUMAN Homo sapiens 3 0.7179
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 3 0.7179
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7170
L-methionine gamma-lyase P13254 MEGL_PSEPU Pseudomonas putida 3 0.7164
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7159
Capsid protein VP1 O56137 O56137_9VIRU Adeno-associated virus - 6 3 0.7149
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.7147
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 2 0.7137
16S rRNA (guanine(1405)-N(7))-methyltransferase Q763K9 Q763K9_ECOLX Escherichia coli 3 0.7136
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7124
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 3 0.7123
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7119
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7114
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7110
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7110
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7107
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7104
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7102
Acidic mammalian chitinase Q9BZP6 CHIA_HUMAN Homo sapiens 3 0.7093
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7082
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7073
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7073
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 2 0.7062
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7057
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7028
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7016
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7015
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7015
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7005
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7004
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7003

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