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Fumaramine

Family: Plantae - Papaveraceae
Kingdom: Plantae
Class: Alkaloid
- Subclass: Isoquinoline Alkaloid

Canonical Smiles	CN(CCc1cc2OCOc2cc1/C=C\1/NC(=O)c2c1ccc1c2OCO1)C
InChI	InChI=1S/C21H20N2O5/c1-23(2)6-5-12-8-17-18(27-10-26-17)9-13(12)7-15-14-3-4-16-20(28-11-25-16)19(14)21(24)22-15/h3-4,7-9H,5-6,10-11H2,1-2H3,(H,22,24)/b15-7+
InChIKey	ZURFNKDWDFKHSG-VIZOYTHASA-N
Formula	C₂₁H₂₀N₂O₅
HBA	6
HBD	1
MW	380.4
Rotatable Bonds	4
TPSA	69.26
LogP	2.49
Number Rings	5
Number Aromatic Rings	2
Heavy Atom Count	28
Formal Charge	0
Fraction CSP3	0.29
Exact Mass	380.14
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: 6450006

Cas: 30341-99-2

Nmrshiftdb2: 60059207

No compound-protein relationship available.

SMILES: O1COc(c12)ccc(c2)C=C(NC3=O)c(c34)ccc5c4OCO5

Level: 1

Mol. Weight: 380.4 g/mol

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

Level: 0

Mol. Weight: 380.4 g/mol

SMILES: O1COc(c12)cccc2

Level: 0

Mol. Weight: 380.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.95
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.86
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -2.7

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.84
Plasma Protein Binding: 59.78
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: 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: 18.22
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.41
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.45
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 6.06
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: -23.27
Rat (Acute): 2.36
Rat (Chronic Oral): 1.41
Fathead Minnow: 4.9
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: 474.96
Hydration Free Energy: -4.92
Log(D) at pH=7.4: 2.47
Log(P): 2.94
Log S: -4.44
Log(Vapor Pressure): -11.39
Melting Point: 175.79
pKa Acid: 8.04
pKa Basic: 8.46

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9275
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.9204
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9099
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9060
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9019
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.8849
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8835
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8781
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.8769
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.8709
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.8707
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8679
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.8623
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8613
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8584
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8583
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8493
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8482
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.8452
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8410
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	3	0.8371
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8362
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.8292
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8285
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.8234
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8230
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.8218
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.8154
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8146
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8145
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8004
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	3	0.7896
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7883
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7882
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7867
Protein LlR18A	P52778	L18A_LUPLU	Lupinus luteus	3	0.7860
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640	Q9CCZ4	Y2640_MYCLE	Mycobacterium leprae	3	0.7791
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.7778
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7764
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7762
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7760
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7740
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7735
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7725
Serine/threonine-protein kinase toxin HipA	P23874	HIPA_ECOLI	Escherichia coli	3	0.7708
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7693
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7664
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7643
Activin receptor type-1	Q04771	ACVR1_HUMAN	Homo sapiens	3	0.7638
Tubulin alpha chain	D0VWZ0	D0VWZ0_SHEEP	Ovis aries	3	0.7629
Class 10 plant pathogenesis-related protein 2B	Q9LLQ2	P102B_LUPLU	Lupinus luteus	2	0.7607
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7596
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7572
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7550
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7544
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7531
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7513
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.7490
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7461
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7411
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7403
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7376
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7375
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7366
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7349
Endoplasmin	P14625	ENPL_HUMAN	Homo sapiens	3	0.7346
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7332
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	2	0.7313
Dipeptidyl peptidase 4	P22411	DPP4_PIG	Sus scrofa	3	0.7290
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7290
RNA polymerase sigma factor SigA	Q5SKW1	Q5SKW1_THET8	Thermus thermophilus	3	0.7290
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7289
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7285
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7275
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7270
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7263
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	2	0.7257
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7235
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7231
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7201
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7195
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7187
Protein S100-A4	P26447	S10A4_HUMAN	Homo sapiens	3	0.7171
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	3	0.7167
Ephrin type-B receptor 4	P54760	EPHB4_HUMAN	Homo sapiens	3	0.7157
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	4	0.7137
4-hydroxyphenylacetate 3-monooxygenase, reductase component	Q5SJP7	HPAC_THET8	Thermus thermophilus	3	0.7132
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7119
Dihydrofolate reductase	P00374	DYR_HUMAN	Homo sapiens	3	0.7118
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7116
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.7115
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7102
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7093
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7089
Pyridoxal kinase	P82197	PDXK_SHEEP	Ovis aries	3	0.7084
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7075
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7074
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.7064
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.7062
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7060
Enoyl-ACP reductase	Q9BH77	Q9BH77_PLAFA	Plasmodium falciparum	3	0.7057
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7051
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7050
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	2	0.7048
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7042
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7039
Bifunctional purine biosynthesis protein ATIC	P31335	PUR9_CHICK	Gallus gallus	3	0.7033
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7031
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7028
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7021
Enoyl-ACP reductase	Q9BJJ9	Q9BJJ9_PLAFA	Plasmodium falciparum	3	0.7012
Tryptophan synthase alpha chain	P16608	TRPA_THET2	Thermus thermophilus	2	0.7005
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7003

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