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Quercetin 3-O-[alpha-rhamnosyl (1→2)][alpha-rhamnosyl (1→4)]-alpha-rhamnoside

Family: Plantae - Myrsinaceae
Kingdom: Plantae
Class: Flavonoid

Canonical Smiles	Oc1cc(O)c2c(c1)oc(c(c2=O)OC1O[C@H](C)[C@H]([C@@H]([C@@H]1OC1O[C@H](C)[C@H]([C@@H]([C@@H]1O)O)O)O)OC1O[C@H](C)[C@H]([C@@H]([C@@H]1O)O)O)c1ccc(c(c1)O)O
InChI	InChI=1S/C33H40O19/c1-9-19(38)22(41)24(43)31(46-9)50-27-11(3)48-33(30(26(27)45)52-32-25(44)23(42)20(39)10(2)47-32)51-29-21(40)18-16(37)7-13(34)8-17(18)49-28(29)12-4-5-14(35)15(36)6-12/h4-11,19-20,22-27,30-39,41-45H,1-3H3/t9-,10-,11-,19-,20-,22+,23+,24+,25+,26+,27-,30+,31?,32?,33?/m1/s1
InChIKey	VWEVUYZRDHPINN-LDBNZQTHSA-N
Formula	C₃₃H₄₀O₁₉
HBA	19
HBD	11
MW	740.66
Rotatable Bonds	7
TPSA	308.12
LogP	-1.81
Number Rings	6
Number Aromatic Rings	3
Heavy Atom Count	52
Formal Charge	0
Fraction CSP3	0.55
Exact Mass	740.22
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Embelia schimperi	Myrsinaceae	Plantae	2595069

Showing of synonyms

Manguro LO, Ugi I, et al. (2004). Further flavonol glycosides of Embelia schimperi leaves.. Bulletin of the Chemical Society of Ethiopia,2004,18(1),51-57. [View] [PubMed]

No compound-protein relationship available.

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC(C4OC5CCCCO5)OCC(C4)OC6CCCCO6

Level: 4

Mol. Weight: 740.66 g/mol

SMILES: c1cccc(c12)occ(c2=O)OC(C3OC4CCCCO4)OCC(C3)OC5CCCCO5

Level: 3

Mol. Weight: 740.66 g/mol

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

Level: 3

Mol. Weight: 740.66 g/mol

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC(OC4)CCC4OC5CCCCO5

Level: 3

Mol. Weight: 740.66 g/mol

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

Level: 2

Mol. Weight: 740.66 g/mol

SMILES: c1cccc(c12)occ(c2=O)OC(OC3)CCC3OC4CCCCO4

Level: 2

Mol. Weight: 740.66 g/mol

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

Level: 2

Mol. Weight: 740.66 g/mol

SMILES: O1CCCCC1OC2CC(COC2)OC3CCCCO3

Level: 2

Mol. Weight: 740.66 g/mol

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

Level: 1

Mol. Weight: 740.66 g/mol

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

Level: 1

Mol. Weight: 740.66 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 740.66 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 740.66 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 740.66 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 740.66 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.56
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -1.91
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 535.05

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.74
Plasma Protein Binding: 53.23
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: 11.04
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -9.23
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.7
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.74
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: -967347.49
Rat (Acute): 2.38
Rat (Chronic Oral): 4.54
Fathead Minnow: 1231.92
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: 101615.91
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -0.63
Log(P): 0.17
Log S: -4.94
Log(Vapor Pressure): -3344.22
Melting Point: 227.82
pKa Acid: -3.07
pKa Basic: 4.87

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9649
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9649
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8987
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8987
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.8917
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.8917
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8851
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8851
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8313
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8313
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8100
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8100
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.7938
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.7938
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	4	0.7877
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	4	0.7877
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7838
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7838
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7764
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7764
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7738
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7738
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7737
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7737
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.7735
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.7735
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7695
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7695
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7678
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7678
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7616
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7616
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7609
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7609
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7376
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7376
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7327
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7327
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7149
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7149
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7125
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7125
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7065
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7065
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7044
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7044
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.7044
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.7044

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