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5′-(3-methylbut-2-enyl)pratensein

Family: Leguminosae/Fabaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Isoflavone

Canonical Smiles	COc1c(O)cc(cc1CC=C(C)C)c1coc2c(c1=O)c(O)cc(c2)O
InChI	InChI=1S/C21H20O6/c1-11(2)4-5-12-6-13(7-17(24)21(12)26-3)15-10-27-18-9-14(22)8-16(23)19(18)20(15)25/h4,6-10,22-24H,5H2,1-3H3
InChIKey	ONLZHAOKMQJPIC-UHFFFAOYSA-N
Formula	C₂₁H₂₀O₆
HBA	6
HBD	3
MW	368.39
Rotatable Bonds	4
TPSA	100.13
LogP	4.09
Number Rings	3
Number Aromatic Rings	3
Heavy Atom Count	27
Formal Charge	0
Fraction CSP3	0.19
Exact Mass	368.13
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Erythrina schliebenii	Leguminosae/Fabaceae	Plantae	2590720

Showing of synonyms

Nyandoro SS, Munissi JJ, et al. (2017). Flavonoids from Erythrina schliebenii.. Journal of Natural Products,2017,80(2),377-383. [View] [PubMed]

Pubchem: 5481243

Gnps: CCMSLIB00000845302

Zinc: ZINC000014762997

Nmrshiftdb2: 60056944

Chembl: CHEMBL4088424

No compound-protein relationship available.

SMILES: c1cccc(c12)occ(c2=O)-c3ccccc3

Level: 1

Mol. Weight: 222.24 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 146.14 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.11
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.890
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.72

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.220
Plasma Protein Binding: 87.02
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 5.770
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.600
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.060
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.230
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -1.070
Rat (Acute): 2.260
Rat (Chronic Oral): 3.060
Fathead Minnow: 5.170
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 477.890
Hydration Free Energy: -9.790
Log(D) at pH=7.4: 3.740
Log(P): 4.93
Log S: -6.11
Log(Vapor Pressure): -8.59
Melting Point: 221.16
pKa Acid: 8.94
pKa Basic: 6.23

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
IOMT 3	Q06YR3	Q06YR3_MEDTR	Medicago truncatula	4	0.9510
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9391
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.9359
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.9208
Transthyretin	P02766	TTHY_HUMAN	Homo sapiens	4	0.9105
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.9089
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.8964
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.8908
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.8896
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	3	0.8860
Dihydrofolate reductase	P22906	DYR_CANAX	Candida albicans	4	0.8848
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.8844
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8839
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8790
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8772
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8760
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.8713
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8711
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.8690
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8686
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8648
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.8637
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8614
Phosphodiesterase	Q53I60	Q53I60_TRYCR	Trypanosoma cruzi	4	0.8587
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.8568
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8535
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8523
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.8517
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8490
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.8485
Biotin carboxylase	P24182	ACCC_ECOLI	Escherichia coli	4	0.8461
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.8456
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8455
Nucleoside diphosphate kinase A 2	P52175	NDKA2_BOVIN	Bos taurus	4	0.8398
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	4	0.8389
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8387
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase	Q8DNV6	Q8DNV6_STRR6	Streptococcus pneumoniae	3	0.8362
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8321
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8321
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8313
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8285
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8264
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8234
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8202
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	4	0.8136
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.8121
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8113
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8104
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.8096
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.8055
Tau-tubulin kinase 1	Q5TCY1	TTBK1_HUMAN	Homo sapiens	4	0.8030
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.8026
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7995
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7976
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7974
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.7954
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7947
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.7922
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7917
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7853
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	3	0.7849
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	3	0.7843
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7836
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7832
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7818
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7786
Pteridine reductase	O76290	O76290_TRYBB	Trypanosoma brucei brucei	3	0.7773
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7760
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	4	0.7747
Biotin carboxylase	P24182	ACCC_ECOLI	Escherichia coli	4	0.7678
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7673
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7662
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7647
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7611
Dihydropteroate synthase	Q81VW8	Q81VW8_BACAN	Bacillus anthracis	4	0.7608
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7601
Cyclic dipeptide N-prenyltransferase	D1D8L6	D1D8L6_ASPFM	Neosartorya fumigata	3	0.7597
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7590
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.7576
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	3	0.7575
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7565
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7564
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7563
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.7559
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7536
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.7534
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7506
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	3	0.7503
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7466
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7437
Aminoglycoside N(3)-acetyltransferase	A0A3P1UCA6	Q81P86_BACAN	Bacillus anthracis	3	0.7426
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7416
Bromodomain protein, putative	Q8I240	Q8I240_PLAF7	Plasmodium falciparum	4	0.7414
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.7413
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	5	0.7390
Sepiapterin reductase	Q64105	SPRE_MOUSE	Mus musculus	3	0.7387
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7384
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7375
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7371
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7365
Multidrug efflux pump subunit AcrB	P31224	ACRB_ECOLI	Escherichia coli	4	0.7360
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7358
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7354
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7354
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.7352
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7321
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7319
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7307
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7300
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7289
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7283
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7274
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7269
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7268
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7263
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7262
Aldehyde dehydrogenase, mitochondrial	P05091	ALDH2_HUMAN	Homo sapiens	4	0.7258
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7255
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7254
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7247
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7244
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7233
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	4	0.7217
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7215
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7206
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	4	0.7204
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7192
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	3	0.7164
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7155
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7154
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7152
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	4	0.7142
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7142
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7141
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7128
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7118
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7117
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7114
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7107
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	3	0.7100
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7092
Chalcone synthase 2	P30074	CHS2_MEDSA	Medicago sativa	4	0.7088
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7080
Estrogen receptor	P03372	ESR1_HUMAN	Homo sapiens	3	0.7072
Thiosulfate reductase	Q72LA4	Q72LA4_THET2	Thermus thermophilus	4	0.7050
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7043
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7038
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7030
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7028
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7025
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7006
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7004
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7001

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