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Naringenin-8-sulfonate

Family: Plantae - Cistaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavanone Sulfonate

Canonical Smiles	Oc1ccc(cc1)[C@@H]1CC(=O)c2c(O1)c(c(cc2O)O)S(=O)(=O)[O-]
InChI	InChI=1S/C15H12O8S/c16-8-3-1-7(2-4-8)12-6-10(18)13-9(17)5-11(19)15(14(13)23-12)24(20,21)22/h1-5,12,16-17,19H,6H2,(H,20,21,22)/p-1/t12-/m0/s1
InChIKey	LCPZLQSYAGXVKZ-LBPRGKRZSA-M
Formula	C₁₅H₁₁O₈S-
HBA	8
HBD	3
MW	351.31
Rotatable Bonds	2
TPSA	144.19
LogP	1.41
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	24
Formal Charge	-1
Fraction CSP3	0.13
Exact Mass	351.02
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Fumana montana	Cistaceae	Plantae	441235

Showing of synonyms

Laraoui H, Haba H, et al. (2019). A new flavanone sulfonate and other phenolic compounds from Fumana montana. Biochemical Systematics and Ecology, 2019, 86, 103927. [View]

No compound-protein relationship available.

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

Level: 1

Mol. Weight: 351.31 g/mol

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 351.31 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 351.31 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.77
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.140
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -5.19

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.010
Plasma Protein Binding: 82.84
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-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: 6.460
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: 0.160
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.160
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.680
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: Toxic
T. Pyriformis: 6.180
Rat (Acute): 2.050
Rat (Chronic Oral): 1.820
Fathead Minnow: 3.970
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 492.850
Hydration Free Energy: -7.750
Log(D) at pH=7.4: 0.920
Log(P): 1.23
Log S: -2.22
Log(Vapor Pressure): -12.25
Melting Point: 294.3
pKa Acid: 5.94
pKa Basic: 3.27

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9212
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9169
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.9112
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.8893
Heat shock protein HSP 90-beta	P08238	HS90B_HUMAN	Homo sapiens	3	0.8857
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.8789
FMN-dependent NAD(P)H:quinone oxidoreductase 1	Q9I5F3	AZOR1_PSEAE	Pseudomonas aeruginosa	3	0.8770
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	3	0.8755
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8744
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.8690
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	4	0.8640
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.8378
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.8266
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	3	0.8202
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.8123
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.8109
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.8098
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.8039
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7956
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.7911
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7905
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	3	0.7901
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7870
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	3	0.7836
DNA topoisomerase 4 subunit B	H7C794	PARE_ENTFA	Enterococcus faecalis	3	0.7780
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7776
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7739
Polymerase acidic protein	Q5EP34	Q5EP34_9INFA	Influenza A virus	3	0.7726
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	3	0.7687
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7631
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7618
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7548
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	3	0.7475
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.7472
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7427
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7416
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7409
Lysozyme C II	P11941	LYSC2_ONCMY	Oncorhynchus mykiss	3	0.7409
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7353
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7348
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7345
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.7343
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7326
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7324
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7311
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	3	0.7307
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7299
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7299
Isoleucine--tRNA ligase	P56690	SYI_THET8	Thermus thermophilus	3	0.7298
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	3	0.7293
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7291
UDP-N-acetylglucosamine 1-carboxyvinyltransferase	P33038	MURA_ENTCC	Enterobacter cloacae subsp. cloacae	3	0.7282
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7268
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.7219
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7194
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7191
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7191
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7190
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7186
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7184
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7168
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	4	0.7162
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7146
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7133
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	4	0.7132
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.7127
Activin receptor type-1	Q04771	ACVR1_HUMAN	Homo sapiens	3	0.7127
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7106
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7088
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	4	0.7071
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	4	0.7068
Hepatocyte growth factor receptor	P08581	MET_HUMAN	Homo sapiens	4	0.7055
YbaK/aminoacyl-tRNA synthetase-associated domain-containing protein	Q5SHN1	Q5SHN1_THET8	Thermus thermophilus	3	0.7034
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.7025
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7019
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7007

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