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Quercetin 3-O-neohesperidoside

Family: Plantae - Apiaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavone Glycoside

Canonical Smiles	OC[C@H]1O[C@@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O)c2ccc(c(c2)O)O)[C@@H]([C@H]([C@H]1O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O
InChI	InChI=1S/C27H30O16/c1-8-17(33)20(36)22(38)26(39-8)43-25-21(37)18(34)15(7-28)41-27(25)42-24-19(35)16-13(32)5-10(29)6-14(16)40-23(24)9-2-3-11(30)12(31)4-9/h2-6,8,15,17-18,20-22,25-34,36-38H,7H2,1H3/t8-,15+,17-,18-,20+,21-,22+,25+,26-,27-/m0/s1
InChIKey	FYBMGZSDYDNBFX-KLUVJTJFSA-N
Formula	C₂₇H₃₀O₁₆
HBA	16
HBD	10
MW	610.52
Rotatable Bonds	6
TPSA	269.43
LogP	-1.69
Number Rings	5
Number Aromatic Rings	3
Heavy Atom Count	43
Formal Charge	0
Fraction CSP3	0.44
Exact Mass	610.15
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Pituranthos scoparius	Apiaceae	Plantae	489362

Showing of synonyms

Dahia M, Siracusa L, et al. (2009). Constituents of the polar extracts from Algerian Pituranthos scoparius. Natural Product Communications,2009,4(12),1691-1692. [View] [PubMed]

Pubchem: 5748416

Cas: 117611-67-3

Gnps: CCMSLIB00006126958

Zinc: ZINC000049889474

Nmrshiftdb2: 60030668

Chembl: CHEMBL499824

Comptox: DTXSID60151840

CPRiL: 458369

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC(OCCC4)C4OC5CCCCO5

Level: 3

Mol. Weight: 610.52 g/mol

SMILES: c1cccc(c12)occ(c2=O)OC(OCCC3)C3OC4CCCCO4

Level: 2

Mol. Weight: 610.52 g/mol

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCCO4

Level: 2

Mol. Weight: 610.52 g/mol

SMILES: c1cccc(c12)occ(c2=O)OC3CCCCO3

Level: 1

Mol. Weight: 610.52 g/mol

SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3

Level: 1

Mol. Weight: 610.52 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 610.52 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 610.52 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 610.52 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 610.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.62
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.450
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 9.63

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.740
Plasma Protein Binding: 67.96
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: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 13.500
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -3.440
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.950
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.580
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: -13509.690
Rat (Acute): 2.260
Rat (Chronic Oral): 4.270
Fathead Minnow: 29.960
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 506.830
Hydration Free Energy: -3.120
Log(D) at pH=7.4: -0.870
Log(P): -0.14
Log S: -4.46
Log(Vapor Pressure): -14.78
Melting Point: 189.99
pKa Acid: 3.71
pKa Basic: 7.83

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8915
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8915
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8786
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8786
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8660
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8660
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.8584
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.8584
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.8386
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.8386
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.8245
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.8245
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8223
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8223
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8219
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8219
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8173
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8173
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8164
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8164
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8156
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8156
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.8144
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.8144
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8015
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8015
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7990
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7990
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7966
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7966
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7889
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7889
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7845
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7845
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7767
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7767
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7748
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7748
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7687
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7687
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7605
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7605
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7588
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7588
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7422
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7422
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7349
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7349
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7279
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7279
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7154
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7154
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7092
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7092
14-3-3 protein gamma	P61981	1433G_HUMAN	Homo sapiens	3	0.7050
14-3-3 protein gamma	P61981	1433G_HUMAN	Homo sapiens	3	0.7050

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