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6-prenylpinocembrin

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

Canonical Smiles	CC(=CCc1c(O)cc2c(c1O)C(=O)CC(O2)c1ccccc1)C
InChI	InChI=1S/C20H20O4/c1-12(2)8-9-14-15(21)10-18-19(20(14)23)16(22)11-17(24-18)13-6-4-3-5-7-13/h3-8,10,17,21,23H,9,11H2,1-2H3
InChIKey	UOWOIGNEFLTNAW-UHFFFAOYSA-N
Formula	C₂₀H₂₀O₄
HBA	4
HBD	2
MW	324.38
Rotatable Bonds	3
TPSA	66.76
LogP	4.31
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	24
Formal Charge	0
Fraction CSP3	0.25
Exact Mass	324.14
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Pseudarthria hookeri	Leguminosae/Fabaceae	Plantae	992776

Showing of synonyms

Tchamgoue J, Hafizur R, et al. (2016). Flavonoids and other constituents with insulin secretion activity from Pseudarthria hookeri. Phytochemistry Letters, 2016, 17, 181-186. [View]

Pubchem: 480763

Cas: 55051-77-9

Nmrshiftdb2: 70086882

Chembl: CHEMBL2143430

Bindingdb: 69607

No compound-protein relationship available.

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

Level: 1

Mol. Weight: 324.38 g/mol

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 324.38 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 324.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.63
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.61
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.77

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.06
Plasma Protein Binding: 63.13
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: 4.9
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.02
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.8
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.6
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: 3.35
Rat (Acute): 2.07
Rat (Chronic Oral): 2.5
Fathead Minnow: 4.81
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 407.7
Hydration Free Energy: -9.42
Log(D) at pH=7.4: 3.53
Log(P): 5.36
Log S: -5.07
Log(Vapor Pressure): -8.32
Melting Point: 142.16
pKa Acid: 7.32
pKa Basic: 6.67

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.9357
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.9282
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.9172
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.9112
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.8781
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.8678
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.8646
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8642
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8633
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8619
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.8530
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.8524
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8414
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8344
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8319
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8306
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8226
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	4	0.8154
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.8136
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8134
Purine nucleoside phosphorylase	Q8I3X4	Q8I3X4_PLAF7	Plasmodium falciparum	3	0.8119
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8107
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	4	0.8068
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.8051
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	3	0.8041
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7990
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7971
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.7962
Dipeptidyl peptidase 4	P22411	DPP4_PIG	Sus scrofa	3	0.7942
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7871
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7778
Cyclic dipeptide N-prenyltransferase	D1D8L6	D1D8L6_ASPFM	Neosartorya fumigata	3	0.7713
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7678
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7653
Glutathione S-transferase F2	P46422	GSTF2_ARATH	Arabidopsis thaliana	3	0.7631
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.7621
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7601
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	3	0.7574
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.7567
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	3	0.7551
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.7546
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7543
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7533
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7532
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7524
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.7519
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	3	0.7492
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7465
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7464
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.7457
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7456
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7445
Lanosterol 14-alpha-demethylase	Q385E8	Q385E8_TRYB2	Trypanosoma brucei brucei	3	0.7444
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7427
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7423
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7417
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7385
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7384
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7340
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7335
Inorganic pyrophosphatase	Q3JUV5	Q3JUV5_BURP1	Burkholderia pseudomallei	2	0.7327
Plasma membrane ATPase	Q42932	Q42932_NICPL	Nicotiana plumbaginifolia	2	0.7324
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7317
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7315
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7309
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7300
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	2	0.7295
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7288
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7273
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7271
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7259
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7246
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	2	0.7226
Reductase homolog	Q9ZGC1	Q9ZGC1_STRCY	Streptomyces cyanogenus	4	0.7220
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7209
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7209
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7200
C-1-tetrahydrofolate synthase, cytoplasmic	P11586	C1TC_HUMAN	Homo sapiens	3	0.7196
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.7183
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7176
Chalcone synthase 2	P30074	CHS2_MEDSA	Medicago sativa	4	0.7173
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7170
1-deoxy-D-xylulose 5-phosphate reductoisomerase	P45568	DXR_ECOLI	Escherichia coli	2	0.7166
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7163
Nuclear receptor ROR-gamma	P51449	RORG_HUMAN	Homo sapiens	3	0.7152
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7141
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A	Q13946	PDE7A_HUMAN	Homo sapiens	3	0.7131
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7102
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	4	0.7086
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7078
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase	Q3JRA0	ISPF_BURP1	Burkholderia pseudomallei	3	0.7077
F420-dependent methylenetetrahydromethanopterin dehydrogenase	P94951	MTD_METKA	Methanopyrus kandleri	2	0.7070
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7059
Glycylpeptide N-tetradecanoyltransferase	A5K1A2	A5K1A2_PLAVS	Plasmodium vivax	3	0.7057
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.7056
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	2	0.7056
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7053
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7046
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7044
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	3	0.7042
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7035
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7034
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7003

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