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Quercetin-3-gentiotrioside

Family: Plantae - Tribulaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavonoid Glycoside

Canonical Smiles	OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](OC[C@H]3O[C@@H](Oc4c(oc5c(c4=O)c(O)cc(c5)O)c4ccc(c(c4)O)O)[C@@H]([C@H]([C@@H]3O)O)O)[C@@H]([C@H]([C@@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C33H40O22/c34-6-15-19(39)23(43)26(46)31(52-15)49-7-16-20(40)24(44)27(47)32(53-16)50-8-17-21(41)25(45)28(48)33(54-17)55-30-22(42)18-13(38)4-10(35)5-14(18)51-29(30)9-1-2-11(36)12(37)3-9/h1-5,15-17,19-21,23-28,31-41,43-48H,6-8H2/t15-,16-,17-,19-,20-,21-,23+,24+,25+,26-,27-,28-,31-,32-,33+/m1/s1
InChIKey	XXHSUYNZCSBPBG-GZIDCZEMSA-N
Formula	C₃₃H₄₀O₂₂
HBA	22
HBD	14
MW	788.66
Rotatable Bonds	10
TPSA	368.81
LogP	-4.89
Number Rings	6
Number Aromatic Rings	3
Heavy Atom Count	55
Formal Charge	0
Fraction CSP3	0.55
Exact Mass	788.2
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Tribulus pentandrus	Tribulaceae	Plantae	1965241
2	Tribulus terrestris	Tribulaceae	Plantae	210369

Showing of synonyms

Saleh NAM, Ahmed AA, et al. (1982). Flavonoid glycosides of Tribulus pentandrus and T. terrestris. Phytochemistry,1982,21(8),1995-2000. [View]

Pubchem: 5319886

Cas: 61474-16-6

Zinc: ZINC000085530903

Chebi: 136780

Nmrshiftdb2: 70038901

Metabolights: MTBLC136780

No compound-protein relationship available.

SMILES: O1CCCCC1OCC2CCCC(O2)OCC3CCCC(O3)Oc(c4=O)c(-c5ccccc5)oc(c46)cccc6

Level: 4

Mol. Weight: 788.66 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)OCC3CCCC(O3)Oc(c4=O)coc(c45)cccc5

Level: 3

Mol. Weight: 788.66 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5

Level: 3

Mol. Weight: 788.66 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)coc(c34)cccc4

Level: 2

Mol. Weight: 788.66 g/mol

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

Level: 2

Mol. Weight: 788.66 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)OCC3CCCCO3

Level: 2

Mol. Weight: 788.66 g/mol

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

Level: 1

Mol. Weight: 788.66 g/mol

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

Level: 1

Mol. Weight: 788.66 g/mol

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 788.66 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 788.66 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 788.66 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 788.66 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.54
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 12.320
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 2486.99

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.570
Plasma Protein Binding: 48.68
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: 7.430
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -56.480
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.850
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.810
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: -4506927.800
Rat (Acute): 2.340
Rat (Chronic Oral): 4.450
Fathead Minnow: 5698.020
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 499556.740
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -2.420
Log(P): -2.58
Log S: -4.59
Log(Vapor Pressure): -16387.89
Melting Point: 222.22
pKa Acid: -83.81
pKa Basic: 10.4

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.9028
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.9028
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.9024
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.9024
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8893
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8893
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8883
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8883
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8722
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8722
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8638
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8638
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.8604
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.8604
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8455
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8455
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8416
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8416
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.8395
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.8395
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8285
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8285
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8245
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8245
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8145
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8145
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8122
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8122
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8090
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8090
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7970
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7970
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7930
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7930
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7824
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7824
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7774
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7774
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7717
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7717
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	4	0.7695
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	4	0.7695
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7673
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7673
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7478
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7478
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7419
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7419
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	3	0.7408
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	3	0.7408
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7324
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7324
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.7315
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.7315
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase	P62617	ISPF_ECOLI	Escherichia coli	3	0.7302
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase	P62617	ISPF_ECOLI	Escherichia coli	3	0.7302
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7224
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7224
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7179
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7179
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7162
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7162
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7139
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7139
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.7114
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.7114
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7069
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7069
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7054
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7054
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7039
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7039
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7037
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7037
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7012
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7012
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7005
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7005
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7004
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7004

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