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Quercetin-3-O-alpha-L-rhamnopyranoside-7-O-[2-O-caffeoyl]-beta-D-glucopyranoside

Family: Plantae - Umbelliferae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavonol Glycoside

Canonical Smiles	OC[C@H]1O[C@@H](Oc2cc(O)c3c(c2)oc(c(c3=O)O[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)c2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1O)O)OC(=O)/C=C/c1ccc(c(c1)O)O
InChI	InChI=1S/C36H36O19/c1-13-26(44)29(47)31(49)35(50-13)55-33-28(46)25-21(42)10-16(11-22(25)52-32(33)15-4-6-18(39)20(41)9-15)51-36-34(30(48)27(45)23(12-37)53-36)54-24(43)7-3-14-2-5-17(38)19(40)8-14/h2-11,13,23,26-27,29-31,34-42,44-45,47-49H,12H2,1H3/b7-3+/t13-,23+,26-,27+,29+,30-,31+,34+,35-,36+/m0/s1
InChIKey	CNEVIJJOMGHIOS-GYAACDNMSA-N
Formula	C₃₆H₃₆O₁₉
HBA	19
HBD	11
MW	772.67
Rotatable Bonds	9
TPSA	315.96
LogP	-0.36
Number Rings	6
Number Aromatic Rings	4
Heavy Atom Count	55
Formal Charge	0
Fraction CSP3	0.33
Exact Mass	772.19
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ferula longipes	Umbelliferae	Plantae	1514033

Showing of synonyms

Bouratoua A, Khalfallah A, et al. (2018). Chemical composition and antioxidant activity of aerial parts of Ferula longipes Coss. ex Bonnier and Maury. Nat Prod Res,2018,32(16),1873-1880. [View] [PubMed]

No compound-protein relationship available.

SMILES: c1ccccc1C=CC(=O)OC2C(OCCC2)Oc(cc3)cc(c34)oc(-c5ccccc5)c(c4=O)OC6CCCCO6

Level: 4

Mol. Weight: 772.67 g/mol

SMILES: c1ccccc1C=CC(=O)OC2C(OCCC2)Oc(cc3)cc(c34)occ(c4=O)OC5CCCCO5

Level: 3

Mol. Weight: 772.67 g/mol

SMILES: c1ccccc1C=CC(=O)OC2C(OCCC2)Oc(cc3)cc(c34)oc(cc4=O)-c5ccccc5

Level: 3

Mol. Weight: 772.67 g/mol

SMILES: O1CCCCC1Oc(cc2)cc(c23)oc(-c4ccccc4)c(c3=O)OC5CCCCO5

Level: 3

Mol. Weight: 772.67 g/mol

SMILES: c1ccccc1C=CC(=O)OC2C(OCCC2)Oc(cc3)cc(c34)occc4=O

Level: 2

Mol. Weight: 772.67 g/mol

SMILES: O1CCCCC1Oc(cc2)cc(c23)occ(c3=O)OC4CCCCO4

Level: 2

Mol. Weight: 772.67 g/mol

SMILES: c1ccccc1-c(cc2=O)oc(c23)cc(cc3)OC4CCCCO4

Level: 2

Mol. Weight: 772.67 g/mol

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

Level: 2

Mol. Weight: 772.67 g/mol

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

Level: 1

Mol. Weight: 772.67 g/mol

SMILES: O=c1ccoc(c12)cc(cc2)OC3CCCCO3

Level: 1

Mol. Weight: 772.67 g/mol

SMILES: C1OCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 772.67 g/mol

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

Level: 1

Mol. Weight: 772.67 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 772.67 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 772.67 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 772.67 g/mol

Antioxidant

Absorption

Caco-2 (logPapp): -6.55
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 13.780
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 2596.88

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.780
Plasma Protein Binding: 67.99
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: 11.340
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -59.970
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.150
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 8.120
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: -4709766.510
Rat (Acute): 2.460
Rat (Chronic Oral): 4.840
Fathead Minnow: 5953.140
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 521937.310
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 0.050
Log(P): 1.17
Log S: -5.58
Log(Vapor Pressure): -17171.23
Melting Point: 254.58
pKa Acid: -89.33
pKa Basic: 5.35

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	0.9361
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.9171
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8997
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8276
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.8108
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7984
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.7914
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7911
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7891
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7863
Serine/threonine-protein kinase N1	Q16512	PKN1_HUMAN	Homo sapiens	3	0.7793
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7766
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7738
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.7593
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7575
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7504
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7500
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	3	0.7482
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7457
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7355
Eukaryotic translation initiation factor 4E-1	P29557	IF4E1_WHEAT	Triticum aestivum	4	0.7325
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7301
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7257
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.7236
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7191
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7188
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.7176
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7170
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7134
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7116
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7092
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7089
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7068
Probable bifunctional SAT/APS kinase	O67174	SATC_AQUAE	Aquifex aeolicus	3	0.7061
DNA ligase	P43813	DNLJ_HAEIN	Haemophilus influenzae	3	0.7053
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7042
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4	Q8GZB6	SUVH4_ARATH	Arabidopsis thaliana	3	0.7030
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7020
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	3	0.7007

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