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5,7,4’,5’-tetrahydroxy-8,3’-diprenylfavanone

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

Canonical Smiles	CC(=CCc1cc(cc(c1O)O)C1CC(=O)c2c(O1)c(CC=C(C)C)c(cc2O)O)C
InChI	InChI=1S/C25H28O6/c1-13(2)5-7-15-9-16(10-21(29)24(15)30)22-12-20(28)23-19(27)11-18(26)17(25(23)31-22)8-6-14(3)4/h5-6,9-11,22,26-27,29-30H,7-8,12H2,1-4H3
InChIKey	HCBKENVWCDLQOA-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: 480770

Cas: 124596-89-0

Chebi: 175410

Nmrshiftdb2: 70072292

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): -5.69
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.97
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.58

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.0
Plasma Protein Binding: 62.41
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: 8.82
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.05
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.64
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.09
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: -22.88
Rat (Acute): 2.11
Rat (Chronic Oral): 3.25
Fathead Minnow: 5.18
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: 501.36
Hydration Free Energy: -6.06
Log(D) at pH=7.4: 3.28
Log(P): 5.8
Log S: -6.29
Log(Vapor Pressure): -8.9
Melting Point: 187.98
pKa Acid: 7.2
pKa Basic: 6.97

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9127
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.9088
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.9067
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.8952
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8922
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8921
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.8789
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.8783
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8738
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8690
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.8578
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.8448
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.8430
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8376
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8373
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.8268
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8162
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8160
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8129
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8110
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8090
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8089
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8050
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8023
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7981
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7976
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7974
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7948
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7931
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7918
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7894
Dihydrofolate reductase	Q81R22	Q81R22_BACAN	Bacillus anthracis	4	0.7868
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7859
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7831
Dihydrofolate reductase	Q81R22	Q81R22_BACAN	Bacillus anthracis	4	0.7824
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.7816
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.7805
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7740
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	3	0.7720
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.7635
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7605
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7596
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7558
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	3	0.7549
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7541
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7533
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7533
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7527
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7527
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	3	0.7526
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7521
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7505
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7502
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7501
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase	Q8DNV6	Q8DNV6_STRR6	Streptococcus pneumoniae	3	0.7493
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7487
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7460
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7438
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7408
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.7405
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7393
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	4	0.7392
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7385
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7376
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7361
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7350
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7347
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	4	0.7345
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.7343
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7323
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7313
Nitric oxide synthase 3	P29474	NOS3_HUMAN	Homo sapiens	3	0.7293
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7272
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7259
C-1-tetrahydrofolate synthase, cytoplasmic	P11586	C1TC_HUMAN	Homo sapiens	3	0.7247
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7247
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7241
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7225
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7223
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7222
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7212
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	5	0.7194
ADP compounds hydrolase NudE	P45799	NUDE_ECOLI	Escherichia coli	2	0.7193
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7176
Purine nucleoside phosphorylase DeoD-type	Q5EEL8	DEOD_BACCE	Bacillus cereus	3	0.7175
Avidin	P02701	AVID_CHICK	Gallus gallus	5	0.7138
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	3	0.7138
Sepiapterin reductase	Q64105	SPRE_MOUSE	Mus musculus	3	0.7136
RNA-dependent RNA polymerase	Q6A562	Q6A562_9VIRU	Thosea asigna virus	2	0.7128
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7126
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7104
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7103
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7099
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7097
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7079
Uridine kinase	Q5SKR5	URK_THET8	Thermus thermophilus	5	0.7070
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	2	0.7068
Vitamin D(3) 25-hydroxylase	C4B644	CPVDH_PSEAH	Pseudonocardia autotrophica	3	0.7065
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	3	0.7064
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7062
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7061
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7061
Tyrosine-protein kinase HCK	P08631	HCK_HUMAN	Homo sapiens	5	0.7056
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7052
Sodium-dependent dopamine transporter	Q7K4Y6	DAT_DROME	Drosophila melanogaster	2	0.7051
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7043
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7041
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7024
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7015
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7013
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	4	0.7010
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.7010
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7003
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7000

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