Quercetin-3-O-alpha-L-rhamnopyranoside - Compound Card

Quercetin-3-O-alpha-L-rhamnopyranoside

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Quercetin-3-O-alpha-L-rhamnopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonoid Glycoside
Canonical Smiles Oc1cc(O)c2c(c1)oc(c(c2=O)O[C@@H]1O[C@@H](C)[C@H]([C@H]([C@H]1O)O)O)c1ccc(c(c1)O)O
InChI InChI=1S/C21H20O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-18,21-26,28-29H,1H3/t7-,15+,17+,18+,21-/m0/s1
InChIKey OXGUCUVFOIWWQJ-OQCXDQQJSA-N
Formula C21H20O11
HBA 11
HBD 7
MW 448.38
Rotatable Bonds 3
TPSA 190.28
LogP 0.49
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.29
Exact Mass 448.1
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Inga edulis Mart Leguminosae/Fabaceae Plantae 690231
2 Albizia zygia Mimosaceae Plantae 1179219
3 Agelanthus brunneus Loranthaceae Plantae 48922
4 Ixora coccinea Rubiaceae Plantae 43503

Showing of synonyms

  • Thomas Wieland MK, Pantaleon A, et al. (2021). (‒)-Brunneusine, a new phenolic compound with antibacterial properties in aqueous medium from the leaves of Agelanthus brunneus (Engl.) Tiegh (LORANTHACEAE). Naturforsch C J Biosci, 2021,77(3-4),157-165. [View]
  • Koagne RR, Annang F, et al. (2020). Cytotoxycity and antiplasmodial activity of phenolic derivatives from Albizia zygia (DC.) J.F. Macbr. (Mimosaceae).. BMC complementary medicine and therapies,2020, 20(1), 8. [View] [PubMed]
  • Idowu TO, Ogundaini AO, et al. (2010). Doubly linked, A-type proanthocyanidin trimer and other constituents of Ixora coccinea leaves and their antioxidant and antibacterial properties. Phytochemistry,2010,71(17–18),2092-2098. [View]
  • Tchuenmogne AMT, Donfack EV, et al. (2013). Ingacamerounol, A New Flavonol and Other Chemical Constituents from Leaves and Stem Bark of Inga edulis Mart. Bulletin of the Korean Chemical Society, 2013, 34(12), 3859–3862. [View]
Pubchem: 6325794
Nmrshiftdb2: 60024834
CPRiL: 105901
Structure

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

Level: 2

Mol. Weight: 448.38 g/mol

Structure

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

Level: 1

Mol. Weight: 448.38 g/mol

Structure

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

Level: 1

Mol. Weight: 448.38 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 448.38 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 448.38 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 448.38 g/mol

Antibacterial

Absorption

Caco-2 (logPapp)
-6.68
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.61
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
0.9

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.89
Plasma Protein Binding
85.04
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
14.35
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.72
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.21
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.63
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
-62.15
Rat (Acute)
2.36
Rat (Chronic Oral)
3.97
Fathead Minnow
3.71
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
626.06
Hydration Free Energy
-6.04
Log(D) at pH=7.4
0.58
Log(P)
1.27
Log S
-4.14
Log(Vapor Pressure)
-11.42
Melting Point
206.82
pKa Acid
4.67
pKa Basic
7.48
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9757
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9287
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 8 0.9062
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.9015
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8969
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8921
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 4 0.8837
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8777
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8667
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8535
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8511
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8445
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8418
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8417
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8324
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8286
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8228
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8192
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 6 0.8184
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8153
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8127
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8098
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8059
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8035
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7948
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7924
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7876
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7812
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7799
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7769
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7761
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7760
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7722
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7714
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 6 0.7702
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7695
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7678
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7652
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7644
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7644
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7633
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7619
Multidrug efflux pump subunit AcrB P31224 ACRB_ECOLI Escherichia coli 4 0.7595
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7571
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7556
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7534
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7518
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7508
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7507
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7412
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.7410
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7362
DNA polymerase theta O75417 DPOLQ_HUMAN Homo sapiens 4 0.7351
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7348
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7329
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7181
Beta-hexosaminidase Q9KU37 NAGZ_VIBCH Vibrio cholerae serotype O1 3 0.7180
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 4 0.7179
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7176
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7167
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7139
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7111
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 4 0.7107
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7028
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7026
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7006

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