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6-prenylnaringenin

Family: Plantae - Cruciferae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavanone

Canonical Smiles	CC(=CCc1c(O)cc2c(c1O)C(=O)C[C@H](O2)c1ccc(cc1)O)C
InChI	InChI=1S/C20H20O5/c1-11(2)3-8-14-15(22)9-18-19(20(14)24)16(23)10-17(25-18)12-4-6-13(21)7-5-12/h3-7,9,17,21-22,24H,8,10H2,1-2H3/t17-/m0/s1
InChIKey	YHWNASRGLKJRJJ-KRWDZBQOSA-N
Formula	C₂₀H₂₀O₅
HBA	5
HBD	3
MW	340.38
Rotatable Bonds	3
TPSA	86.99
LogP	4.02
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	25
Formal Charge	0
Fraction CSP3	0.25
Exact Mass	340.13
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Lepidium sativum	Cruciferae	Plantae	33125

Showing of synonyms

El-Haggar M, El-Hosseiny L, et al. (2021). Phytochemical investigation, antimicrobial and cytotoxic activities of suspension cultures of Lepidium sativum L.. South African Journal of Botany, 2021, 138, 500-505. [View]

Pubchem: 155094

Cas: 68236-13-5

Gnps: CCMSLIB00006443565

Zinc: ZINC000004098363

Kegg Ligand: C09832

Chebi: 27566

Nmrshiftdb2: 60024546

Comptox: DTXSID80218409

CPRiL: 79422

SMILES: c1cccc(c12)OC(CC2=O)c3ccccc3

Level: 1

Mol. Weight: 340.38 g/mol

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 340.38 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 340.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.65
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.77
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.62

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.04
Plasma Protein Binding: 78.75
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: Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 6.45
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.77
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.78
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 6.2
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Toxic
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: 1.8
Rat (Acute): 2.03
Rat (Chronic Oral): 2.75
Fathead Minnow: 4.67
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 443.71
Hydration Free Energy: -10.4
Log(D) at pH=7.4: 3.15
Log(P): 4.64
Log S: -5.1
Log(Vapor Pressure): -8.83
Melting Point: 186.25
pKa Acid: 7.25
pKa Basic: 6.42

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9453
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.9433
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.9186
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.9100
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9029
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	4	0.9022
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.9019
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.8951
Chalcone synthase 2	P30074	CHS2_MEDSA	Medicago sativa	5	0.8842
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.8837
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8816
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.8787
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.8736
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.8717
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.8717
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8688
Caspase-6	P55212	CASP6_HUMAN	Homo sapiens	3	0.8681
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.8657
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8645
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.8530
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.8516
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8513
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	4	0.8505
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.8494
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.8417
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.8389
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.8326
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8319
RNA polymerase sigma factor SigA	Q5SKW1	Q5SKW1_THET8	Thermus thermophilus	3	0.8292
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8290
GTPase KRas	P01116	RASK_HUMAN	Homo sapiens	3	0.8287
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.8251
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8250
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8223
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8175
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.8123
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	3	0.8121
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	4	0.8074
Major strawberry allergen Fra a 1-3	D0E0C7	FRA13_FRAAN	Fragaria ananassa	4	0.8062
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8026
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase	Q8DNV6	Q8DNV6_STRR6	Streptococcus pneumoniae	3	0.7943
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	4	0.7916
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7901
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	5	0.7898
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7876
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7874
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7873
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7848
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7824
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.7791
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7785
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.7771
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7767
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7757
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	3	0.7737
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7679
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.7577
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.7542
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.7539
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7534
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7515
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	3	0.7508
Cyclic dipeptide N-prenyltransferase	D1D8L6	D1D8L6_ASPFM	Neosartorya fumigata	3	0.7409
Threonine--tRNA ligase	P0A8M3	SYT_ECOLI	Escherichia coli	3	0.7387
Beta-glucuronidase	P05804	BGLR_ECOLI	Escherichia coli	3	0.7365
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7349
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7336
TetR family transcriptional regulator	Q58L87	Q58L87_MYCSM	Mycolicibacterium smegmatis	3	0.7333
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.7330
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7326
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7325
Reductase homolog	Q9ZGC1	Q9ZGC1_STRCY	Streptomyces cyanogenus	4	0.7319
Phenolphthiocerol/phthiocerol polyketide synthase subunit C	P96202	PPSC_MYCTU	Mycobacterium tuberculosis	3	0.7311
Dihydrofolate reductase	P0ABQ4	DYR_ECOLI	Escherichia coli	3	0.7309
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.7303
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7295
C-1-tetrahydrofolate synthase, cytoplasmic	P11586	C1TC_HUMAN	Homo sapiens	3	0.7295
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.7243
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	4	0.7240
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7230
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7204
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7203
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7190
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7184
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7178
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7176
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7158
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.7150
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7148
Isoleucine--tRNA ligase	P56690	SYI_THET8	Thermus thermophilus	3	0.7110
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	2	0.7100
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7093
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7093
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.7091
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7082
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7072
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7067
23S rRNA (guanine(745)-N(1))-methyltransferase	P36999	RLMA_ECOLI	Escherichia coli	3	0.7046
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7045
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7036
Matrix metalloproteinase-9	P14780	MMP9_HUMAN	Homo sapiens	3	0.7030
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	2	0.7030
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7023
ABC-type polar amino acid transport system, ATPase component	Q8RCC2	Q8RCC2_CALS4	Caldanaerobacter subterraneus subsp. tengcongensis	2	0.7022
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7013
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7012

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