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(S)-lupinifolin 4'-methyl ether

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

Canonical Smiles	COc1ccc(cc1)[C@@H]1CC(=O)c2c(O1)c(CC=C(C)C)c1c(c2O)C=CC(O1)(C)C
InChI	InChI=1S/C26H28O5/c1-15(2)6-11-19-24-18(12-13-26(3,4)31-24)23(28)22-20(27)14-21(30-25(19)22)16-7-9-17(29-5)10-8-16/h6-10,12-13,21,28H,11,14H2,1-5H3/t21-/m0/s1
InChIKey	FVIRUWAOHVUWTO-NRFANRHFSA-N
Formula	C₂₆H₂₈O₅
HBA	5
HBD	1
MW	420.51
Rotatable Bonds	4
TPSA	64.99
LogP	5.8
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	31
Formal Charge	0
Fraction CSP3	0.35
Exact Mass	420.19
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Derris trifoliata	Leguminosae/Fabaceae	Plantae	185716

Showing of synonyms

Yenesew AB, Twinomuhwezi H, et al. (2009). Antiplasmodial and larvicidal flavonoids from Derris trifoliata.. Bulletin of the Chemical Society of Ethiopia,2009,23(3),409-414. [View] [PubMed]

Pubchem: 44178660

Zinc: ZINC000144135700

Nmrshiftdb2: 70024452

No compound-protein relationship available.

SMILES: O1CC=Cc(c2)c1cc(c23)OC(CC3=O)c4ccccc4

Level: 1

Mol. Weight: 420.51 g/mol

SMILES: O=C1CCOc(c12)cc3c(c2)C=CCO3

Level: 0

Mol. Weight: 420.51 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 420.51 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.71
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.640
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.27

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.380
Plasma Protein Binding: 79.18
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: Substrate
CYP 2C9 Inhibitor: Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 8.180
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.080
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.020
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 7.850
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: Toxic
T. Pyriformis: -39.640
Rat (Acute): 2.600
Rat (Chronic Oral): 2.430
Fathead Minnow: 5.340
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 468.850
Hydration Free Energy: -4.070
Log(D) at pH=7.4: 4.520
Log(P): 6.53
Log S: -6.93
Log(Vapor Pressure): -8.38
Melting Point: 148.07
pKa Acid: 8.15
pKa Basic: 5.62

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.9435
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.9435
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.9128
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.9128
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.8649
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.8649
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.8346
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.8346
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.8150
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.8150
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.8141
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.8141
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.8130
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.8130
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8002
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8002
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.8001
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.8001
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7996
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7996
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7887
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7887
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7885
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7885
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.7841
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.7841
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.7799
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.7799
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7760
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7760
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7759
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7759
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	2	0.7676
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	2	0.7676
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	2	0.7641
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	2	0.7641
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.7628
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.7628
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7612
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7612
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7598
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7598
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7586
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7586
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7585
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7585
FMN-dependent NAD(P)H:quinone oxidoreductase 1	Q9I5F3	AZOR1_PSEAE	Pseudomonas aeruginosa	2	0.7575
FMN-dependent NAD(P)H:quinone oxidoreductase 1	Q9I5F3	AZOR1_PSEAE	Pseudomonas aeruginosa	2	0.7575
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7574
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7574
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	4	0.7548
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	4	0.7548
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	2	0.7517
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	2	0.7517
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7506
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7506
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.7500
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.7500
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7496
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7496
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	3	0.7475
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	3	0.7475
Caspase-3	P42574	CASP3_HUMAN	Homo sapiens	2	0.7431
Caspase-3	P42574	CASP3_HUMAN	Homo sapiens	2	0.7431
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7419
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7419
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7400
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7400
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7399
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7399
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7393
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7393
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7387
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7387
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7296
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7296
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7292
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7292
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7291
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7291
Vitamin D3 dihydroxylase	P18326	CPXE_STRGO	Streptomyces griseolus	3	0.7257
Vitamin D3 dihydroxylase	P18326	CPXE_STRGO	Streptomyces griseolus	3	0.7257
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7244
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7244
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7244
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7244
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7195
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7195
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7145
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7145
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7145
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7145
Mitogen-activated protein kinase 10	P53779	MK10_HUMAN	Homo sapiens	4	0.7120
Mitogen-activated protein kinase 10	P53779	MK10_HUMAN	Homo sapiens	4	0.7120
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7111
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7111
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.7105
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.7105
RNA-dependent RNA polymerase	Q6A562	Q6A562_9VIRU	Thosea asigna virus	2	0.7104
RNA-dependent RNA polymerase	Q6A562	Q6A562_9VIRU	Thosea asigna virus	2	0.7104
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7090
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7090
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7080
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7080
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7065
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7065
Vitamin D3 dihydroxylase	P18326	CPXE_STRGO	Streptomyces griseolus	3	0.7065
Vitamin D3 dihydroxylase	P18326	CPXE_STRGO	Streptomyces griseolus	3	0.7065
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7030
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7030
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7027
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7027
RNA polymerase sigma factor SigA	Q5SKW1	Q5SKW1_THET8	Thermus thermophilus	3	0.7024
RNA polymerase sigma factor SigA	Q5SKW1	Q5SKW1_THET8	Thermus thermophilus	3	0.7024
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7013
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7013

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