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3’,4’,5,5’,7-pentahydroxyflavanone

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

Canonical Smiles	Oc1cc2O[C@@H](CC(=O)c2c(c1)O)c1cc(O)c(c(c1)O)O
InChI	InChI=1S/C15H12O7/c16-7-3-8(17)14-9(18)5-12(22-13(14)4-7)6-1-10(19)15(21)11(20)2-6/h1-4,12,16-17,19-21H,5H2/t12-/m0/s1
InChIKey	USQXPEWRYWRRJD-LBPRGKRZSA-N
Formula	C₁₅H₁₂O₇
HBA	7
HBD	5
MW	304.25
Rotatable Bonds	1
TPSA	127.45
LogP	1.92
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	22
Formal Charge	0
Fraction CSP3	0.13
Exact Mass	304.06
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ficus thonningii	Moraceae	Plantae	309310
2	Imperata cylindrica	Gramineae	Plantae	80369

Showing of synonyms

Nago RDT, Nayim P, et al. (2021). Prenylated Flavonoids and C-15 Isoprenoid Analogues with Antibacterial Properties from the Whole Plant of Imperata cylindrica (L.) Raeusch (Gramineae). Molecules. 2021, 26(16), 4717. [View] [PubMed]
Ango PY, Kapche DW, et al. (2016). Thonningiiflavanonol A and thonningiiflavanonol B, two novel flavonoids, and other constituents of Ficus thonningii Blume (Moraceae).. Zeitschrift fur Naturforschung. C, Journal of biosciences,2016, 71(3-4), 65-71. [View] [PubMed]

Pubchem: 440836

Cas: 81398-31-4

Zinc: ZINC000004096948

Kegg Ligand: C05911

Chebi: 48026

No compound-protein relationship available.

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

Level: 1

Mol. Weight: 304.25 g/mol

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 304.25 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 304.25 g/mol

Antioxidant

Absorption

Caco-2 (logPapp): -6.45
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.270
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.68

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.760
Plasma Protein Binding: 89.92
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-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: 14.040
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.540
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.880
Liver Injury II: Safe
hERG Blockers: Toxic
Daphnia Maga: 4.870
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: 2.720
Rat (Acute): 2.310
Rat (Chronic Oral): 3.330
Fathead Minnow: 4.100
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 486.730
Hydration Free Energy: -10.880
Log(D) at pH=7.4: 1.220
Log(P): 1.61
Log S: -3.13
Log(Vapor Pressure): -8.59
Melting Point: 246.14
pKa Acid: 6.32
pKa Basic: 7.93

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.9102
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.8675
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8566
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.8514
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8482
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.8411
Dihydroflavonol 4-reductase	P51110	DFRA_VITVI	Vitis vinifera	7	0.8390
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8386
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8344
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.8322
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8316
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.8303
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8245
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.8183
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.8168
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8157
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	4	0.8087
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	4	0.8084
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8071
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8021
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.8013
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	6	0.7980
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7973
DNA topoisomerase 4 subunit B	H7C794	PARE_ENTFA	Enterococcus faecalis	3	0.7960
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7946
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.7910
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7909
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7891
Purine nucleoside phosphorylase	B9JYS2	B9JYS2_AGRVS	Agrobacterium vitis	4	0.7880
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	4	0.7875
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7853
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7830
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7816
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.7805
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	6	0.7786
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7742
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7736
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7725
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7703
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7694
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7680
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	4	0.7665
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7662
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7648
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7643
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7635
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	6	0.7601
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7586
Major strawberry allergen Fra a 1-3	D0E0C7	FRA13_FRAAN	Fragaria ananassa	4	0.7578
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7578
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase	Q8DNV6	Q8DNV6_STRR6	Streptococcus pneumoniae	3	0.7568
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7546
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7540
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	4	0.7535
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7503
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7498
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7497
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7481
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7479
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7473
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.7432
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7419
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7387
Chalcone synthase 2	P30074	CHS2_MEDSA	Medicago sativa	5	0.7353
Tubulin--tyrosine ligase	F6Z895	A9ULH4_XENTR	Xenopus tropicalis	4	0.7350
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7331
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7329
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7328
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7317
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7308
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	5	0.7285
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7281
FMN-dependent NAD(P)H:quinone oxidoreductase 1	Q9I5F3	AZOR1_PSEAE	Pseudomonas aeruginosa	2	0.7280
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7232
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7225
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7202
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7194
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7193
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7174
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7169
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7167
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	2	0.7131
Pyridoxal kinase	P82197	PDXK_SHEEP	Ovis aries	3	0.7128
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7123
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	3	0.7119
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7119
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7116
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7114
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7106
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7089
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7085
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7082
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7065
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7064
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7061
Dihydrofolate reductase	P00381	DYR_LACCA	Lacticaseibacillus casei	4	0.7060
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7052
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	3	0.7047
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7041
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7038
Dihydroflavonol 4-reductase	P51110	DFRA_VITVI	Vitis vinifera	5	0.7034
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7025
Purine nucleoside phosphorylase	P9WP00	PUNA_MYCTO	Mycobacterium tuberculosis	4	0.7017

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