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Quercetin 3-O-[alpha-rhamnosyl (1→6)] [beta-glucosyl (1→2)]-beta-glucoside-7-O-alpha-rhamnoside

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

Canonical Smiles	OC[C@H]1OC(O[C@@H]2[C@@H](O)C(O[C@@H]([C@H]2O)COC2O[C@H](C)[C@H]([C@@H]([C@@H]2O)O)O)Oc2c(oc3c(c2=O)c(O)cc(c3)OC2O[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)O
InChI	InChI=1S/C39H50O25/c1-10-21(44)26(49)29(52)36(57-10)56-9-19-24(47)34(63-38-31(54)28(51)23(46)18(8-40)61-38)32(55)39(62-19)64-35-25(48)20-16(43)6-13(59-37-30(53)27(50)22(45)11(2)58-37)7-17(20)60-33(35)12-3-4-14(41)15(42)5-12/h3-7,10-11,18-19,21-24,26-32,34,36-47,49-55H,8-9H2,1-2H3/t10-,11-,18-,19-,21-,22-,23-,24-,26+,27+,28+,29+,30+,31-,32-,34+,36?,37?,38?,39?/m1/s1
InChIKey	JOXXHKHYJZQZDC-BISWWVLVSA-N
Formula	C₃₉H₅₀O₂₅
HBA	25
HBD	15
MW	918.8
Rotatable Bonds	11
TPSA	407.5
LogP	-5.36
Number Rings	7
Number Aromatic Rings	3
Heavy Atom Count	64
Formal Charge	0
Fraction CSP3	0.62
Exact Mass	918.26
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Warburgia ugandensis	Canellaceae	Plantae	549619

Showing of synonyms

Manguro LO, Ugi I, et al. (2003). Flavonol glycosides of Warburgia ugandensis leaves. Phytochemistry,2003,64(4),891-896. [View] [PubMed]

No compound-protein relationship available.

SMILES: O1CCCCC1OCC2CC(OC3CCCCO3)CC(O2)Oc(c4=O)c(-c5ccccc5)oc(c46)cc(cc6)OC7CCCCO7

Level: 5

Mol. Weight: 918.8 g/mol

SMILES: O1CCCCC1OCC2CC(OC3CCCCO3)CC(O2)Oc(c4=O)coc(c45)cc(cc5)OC6CCCCO6

Level: 4

Mol. Weight: 918.8 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)c(-c4ccccc4)oc(c35)cc(cc5)OC6CCCCO6

Level: 4

Mol. Weight: 918.8 g/mol

SMILES: O1CCCCC1OCC2CC(OC3CCCCO3)CC(O2)Oc(c4=O)c(-c5ccccc5)oc(c46)cccc6

Level: 4

Mol. Weight: 918.8 g/mol

SMILES: O1CCCCC1Oc(cc2)cc(c23)oc(-c4ccccc4)c(c3=O)OC(OCC5)CC5OC6CCCCO6

Level: 4

Mol. Weight: 918.8 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)coc(c34)cc(cc4)OC5CCCCO5

Level: 3

Mol. Weight: 918.8 g/mol

SMILES: O1CCCCC1OCC2CC(OC3CCCCO3)CC(O2)Oc(c4=O)coc(c45)cccc5

Level: 3

Mol. Weight: 918.8 g/mol

SMILES: O1CCCCC1Oc(cc2)cc(c23)occ(c3=O)OC(OCC4)CC4OC5CCCCO5

Level: 3

Mol. Weight: 918.8 g/mol

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

Level: 3

Mol. Weight: 918.8 g/mol

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC(OCC4)CC4OC5CCCCO5

Level: 3

Mol. Weight: 918.8 g/mol

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

Level: 3

Mol. Weight: 918.8 g/mol

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

Level: 2

Mol. Weight: 918.8 g/mol

SMILES: c1cccc(c12)occ(c2=O)OC(OCC3)CC3OC4CCCCO4

Level: 2

Mol. Weight: 918.8 g/mol

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

Level: 2

Mol. Weight: 918.8 g/mol

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

Level: 2

Mol. Weight: 918.8 g/mol

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

Level: 2

Mol. Weight: 918.8 g/mol

SMILES: O1CCCCC1OCC2CC(CCO2)OC3CCCCO3

Level: 2

Mol. Weight: 918.8 g/mol

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

Level: 1

Mol. Weight: 918.8 g/mol

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

Level: 1

Mol. Weight: 918.8 g/mol

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

Level: 1

Mol. Weight: 918.8 g/mol

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 918.8 g/mol

SMILES: C1COCCC1OC2CCCCO2

Level: 1

Mol. Weight: 918.8 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 918.8 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 918.8 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 918.8 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.59
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 1407.84
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 184893.98

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.59
Plasma Protein Binding: 34.03
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: 6.01
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -4290.47
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.65
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.05
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: -335567340.54
Rat (Acute): 2.46
Rat (Chronic Oral): 5.67
Fathead Minnow: 423590.94
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: 37734155.74
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -11.05
Log(P): -2.99
Log S: -4.18
Log(Vapor Pressure): -1242479.75
Melting Point: 247.15
pKa Acid: -8987.61
pKa Basic: -45.84

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8924
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8924
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8165
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8165
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7958
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7958
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7708
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7708
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7645
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7645
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7585
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7585
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	3	0.7578
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	3	0.7578
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7438
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7438
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7405
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7405
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	3	0.7261
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	3	0.7261
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.7248
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.7248
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7165
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7165
Small heat shock protein StHsp14.0	Q970D9	Q970D9_SULTO	Sulfurisphaera tokodaii	3	0.7003
Small heat shock protein StHsp14.0	Q970D9	Q970D9_SULTO	Sulfurisphaera tokodaii	3	0.7003

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