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5,7,4’,5’-tetrahydroxy-6,3’-diprenylflavanone

Family: Plantae - Cyperaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Prenylflavone

Canonical Smiles	CC(=CCc1c(O)cc2c(c1O)C(=O)CC(O2)c1cc(O)c(c(c1)CC=C(C)C)O)C
InChI	InChI=1S/C25H28O6/c1-13(2)5-7-15-9-16(10-20(28)24(15)29)21-12-19(27)23-22(31-21)11-18(26)17(25(23)30)8-6-14(3)4/h5-6,9-11,21,26,28-30H,7-8,12H2,1-4H3
InChIKey	LCRYGWPAHFISLY-UHFFFAOYSA-N
Formula	C₂₅H₂₈O₆
HBA	6
HBD	4
MW	424.49
Rotatable Bonds	5
TPSA	107.22
LogP	5.23
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	31
Formal Charge	0
Fraction CSP3	0.32
Exact Mass	424.19
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Schoenus nigricans	Cyperaceae	Plantae	76506

Showing of synonyms

Dawidar A, Jakupovic J, et al. (1994). Prenylstilbenes and prenylflavanones from Schoenus nigricans.. Phytochemistry, 1994, 36(3), 803-806. [View]

Pubchem: 42607994

No compound-protein relationship available.

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

Level: 1

Mol. Weight: 424.49 g/mol

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 424.49 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 424.49 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.65
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.95
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.06

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.06
Plasma Protein Binding: 61.57
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 8.01
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.16
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.07
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.73
Micronucleos: Toxic
NR-AhR: Safe
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: -23.01
Rat (Acute): 2.1
Rat (Chronic Oral): 3.06
Fathead Minnow: 5.2
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: 510.2
Hydration Free Energy: -6.28
Log(D) at pH=7.4: 3.33
Log(P): 6.01
Log S: -6.13
Log(Vapor Pressure): -9.34
Melting Point: 188.43
pKa Acid: 6.49
pKa Basic: 6.82

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	0.9305
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9273
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8921
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.8903
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8745
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8737
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8515
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.8481
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8423
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8418
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8411
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8356
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.8330
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8324
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8319
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8316
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8308
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8272
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.8271
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.8257
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8244
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8240
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.8239
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.8088
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.8040
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.8032
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.8005
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	3	0.7989
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7926
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7898
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7842
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7820
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7815
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7783
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7735
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.7704
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	4	0.7637
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7629
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7626
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7593
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.7591
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7538
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	6	0.7534
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7521
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7500
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7496
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7472
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.7455
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7435
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7422
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7419
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7411
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7383
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7368
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7366
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7363
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7332
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7328
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7328
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7327
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7326
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	2	0.7325
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7325
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7318
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7316
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7313
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7310
Cyclic dipeptide N-prenyltransferase	D1D8L6	D1D8L6_ASPFM	Neosartorya fumigata	3	0.7284
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.7282
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7281
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7270
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7252
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7247
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7231
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7223
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7221
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7193
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7189
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.7166
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7163
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	3	0.7160
Sepiapterin reductase	Q64105	SPRE_MOUSE	Mus musculus	3	0.7157
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7139
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	3	0.7136
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7130
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7122
NTPase P4	Q94M05	Q94M05_9VIRU	Pseudomonas phage phi12	3	0.7121
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7097
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7093
Ferrichrome outer membrane transporter/phage receptor	P06971	FHUA_ECOLI	Escherichia coli	3	0.7090
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7068
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7061
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7059
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7048
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7033
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7030
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	3	0.7027
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7009
C-1-tetrahydrofolate synthase, cytoplasmic	P11586	C1TC_HUMAN	Homo sapiens	3	0.7004

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