Quercitrin

  • GreenMolBD CID : 587
  • Molecular Formula : C21H20O11
  • Molecular Weight : 448.38
  • Exact Molecular Mass : 448.101
  • IUPAC Name : 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
  • 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
  • InChI Key : OXGUCUVFOIWWQJ-HQBVPOQASA-N
  • Canonical SMILES : CC1C(C(C(C(O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C=C4)O)O)O)O)O
  • Isomeric SMILES : CC1C(C(C(C(O1)Oc2c(=O)c3c(cc(cc3oc2c4ccc(c(c4)O)O)O)O)O)O)O
  • Cross Reference  Pubchem

1. Classification

1.1. Description

This compound belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.

1.2. Taxonomy Tree

1.3. Alternative Parent

3'-hydroxyflavonoids; 4'-hydroxyflavonoids; 5-hydroxyflavonoids; 7-hydroxyflavonoids; Flavones; Hexoses; O-glycosyl compounds; Chromones; Catechols; 1-hydroxy-2-unsubstituted benzenoids; 1-hydroxy-4-unsubstituted benzenoids; Pyranones and derivatives; Oxanes; Benzene and substituted derivatives; Vinylogous acids; Heteroaromatic compounds; Secondary alcohols; Oxacyclic compounds; Polyols; Acetals; Hydrocarbon derivatives; Organic oxides;

1.4. Molecular Framework

Aromatic heteropolycyclic compounds

1.5. Substituents

Flavonoid-3-o-glycoside; Hydroxyflavonoid; 3'-hydroxyflavonoid; 4'-hydroxyflavonoid; 5-hydroxyflavonoid; 7-hydroxyflavonoid; Flavone; Hexose monosaccharide; Chromone; Glycosyl compound; O-glycosyl compound; Benzopyran; 1-benzopyran; Catechol; 1-hydroxy-2-unsubstituted benzenoid; Pyranone; 1-hydroxy-4-unsubstituted benzenoid; Phenol; Monocyclic benzene moiety; Benzenoid; Pyran; Monosaccharide; Oxane; Vinylogous acid; Heteroaromatic compound; Secondary alcohol; Organoheterocyclic compound; Oxacycle; Polyol; Acetal; Organic oxide; Organic oxygen compound; Alcohol; Hydrocarbon derivative; Organooxygen compound; Aromatic heteropolycyclic compound

2. Physical Properties

SlogP TPSA HBD HBA nHA nRB nAA nAB SMR vdw_vol vdw_area Density
0.297 186.37 7 11 32 3 12 12 10.4862 522.831 386.052 0.8576

3. Quantum Information

Heat of Formation Dipole Moment Electronegativity Homo Lumo Hardness
-406.248355 3.26 -4.628 -8.7121 -0.54425 4.084

4. Compound Reactivity

DLP nRFG nLMR
1 1 7

5. Topkat Properties

WOE Prediction Ames Prediction DTP Prediction Rat Oral LD50 (g/kg body weight) Rat Inhalational LC50 (mg/m3/h) Chronic LOAEL (g/kg body weight) Skin Irritancy Skin Sensitization Ocular Irritancy Aerobic Biodegradability Prediction Fathead Minnow LC50 (g/l) Daphnia EC50 (mg/l)
Non-Carcinogen Non-Mutagen Toxic 0.960093 216.493 0.134166 None Weak Mild Degradable 0.640513 2.53329

6. Drug-Likeliness Test

Lipinski's rule of five Jorgensen's rule of three Goshe filter Veber filter PAINS1 PAINS2 PAINS3
No No Yes No Yes No Yes

7. Synonyms

Name
quercitrin
522-12-3
Quercetrin
Quercetin 3-rhamnoside
Quercitroside
Quercimelin
Thujin
Quercetin 3-L-rhamnoside
Quercitronic acid
Quercetin 3-O-rhamnoside
UNII-2Y8906LC5P
CHEBI:17558
Quercetin 3-O-alpha-L-rhamnoside
Quercetin-3-L-rhamnoside
3,3',4',5,7-Pentahydroxyflavone-3-L-rhamnoside
Quercetin-3-rhamnoside
NSC9221
Quercetin, 3-(6-deoxy-alpha-L-mannopyranoside)
QUERCETIN 3-A-L-RHAMNOSIDE
Mannopyranoside, quercetin-3 6-deoxy-, alpha-L-
Quercetin 3-O-alpha-rhamnopyranoside
Usaf cf-2
MFCD00016932
Quercetrin-3-O-rham
Rhamnosyl-3-quercitin
Quercitin-3-rhamnoside
luteolin 6-deoxy-alpha-L-mannopyranoside
Rhamnoside, quercetin-3
Quercetin-3-O-rhamnoside
C.I. 75720
HSDB 4339
NCI-C60102
EINECS 208-322-5
Quercetin 3-O-alpha-L-rhamnopyranoside
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl 6-deoxy-alpha-L-mannopyranoside
BRN 0068135
CI 75720
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-chromen-4-one
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
AI3-36095
Quercetin 3-O-L-rhamnoside
CHEMBL82242
Quercetin 3-O-rhamnopyranoside
Flavone, 3,3',4',5,7-pentahydroxy-, 3-rhamnoside
Flavone, 3,3',4',5,7-pentahydroxy-, 3-(6-deoxy-alpha-L-mannopyranoside)
4gue
3-((6-Deoxy-alpha-L-mannopyranosyl)-oxy)-2-(3,4-dihydr oxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one
4H-1-Benzopyran-4-one, 3-((6-deoxy-.alpha.-L-mannopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-
4H-1-Benzopyran-4-one, 3-((6-deoxy-alpha-L-mannopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-
4H-1-Benzopyran-4-one, 3-[(6-deoxy-.alpha.-L-mannopyranosyl)oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-
QCT
D07DJS
AC1NQX24
BIDD:PXR0076
5-18-05-00514 (Beilstein Handbook Reference)
MLS002472998
SCHEMBL147092
MEGxp0_000185
ACon1_000189
BDBM84978
cid_5280459
DTXSID50200230
MolPort-000-882-121
OXGUCUVFOIWWQJ-HQBVPOQASA-N
2Y8906LC5P
HMS2219D24
3-((6-Deoxy-alpha-L-mannopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-benzopyran-4-one
HY-N0418
ZINC4175638
BDBM50056315
AKOS000278033
API0004008
CS-5408
MCULE-7562123660
SMP1_000253
AC-20295
AN-45535
BC216298
BT000794
CA002591
CA010210
CC-34149
O981
SC-26573
SMR001397103
AB0016764
KB-180086
NP-000463
F0013
FT-0603445
N1840
C01750
522Q123
C-22454
I07-0264
Q-100588
Q-100945
Quercitrin, primary pharmaceutical reference standard
BRD-K98601533-001-01-7
Flavone, 3,3',4',5, 7-pentahydroxy-, 3-rhamnoside
3-O-a-L-Rhamnopyranosyloxy-3',4',5,7-tetrahydroxyflavone
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-4H-chromen-4-one
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl 6-deoxy-.alpha.-L-mannopyranoside
3-((6-Deoxy-alpha-L-mannopyranosyl)-oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one
3-[(6-deoxy-a-l-mannopyranosyl)oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4h-benzopyran-4-one
4H-1-Benzopyran-4-one, 3-((6-deoxy-alpha-L-mannopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy- (9CI)
4H-1-Benzopyran-4-one,3-[(6-deoxy-a-L-mannopyranosyl)oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-
Quercetin-3-O-alpha-L-rhamnoside
BG01739212
BG01739213

8. Compound in Different Plants

Compound Name Plant Name Compound in Plant Parts Ref
Quercitrin
Achras sapota L. Fruit 2
Ammannia baccifera L. Whole Plant 4
Argemone maxicana L. Aerial 1
Bauhinia variegate 1
Ficus elastica Leaf 2
Ixora coccinea L.  Root; Leaf 2 , 5 , 8 , 11
Juglans regia Leaf 7 , 9 , 17
Lumnitzera racemosa Twig 2 , 4
Mangifera indica Peel; Pulp; Seed 2 , 3
Melastoma malabathricum Leaf 2 , 3 , 4
Rosa damascena Flower 17

9. Targets

ID Target Name Gene Symbol Organism Protein Crystal Complex Activity Values Reference
Potency (nM) Ki (nM) IC50 (nM) Kd (nM) EC50 (nM) kon (M-1-s-1) koff (s-1) Biological Assay DOI Article PMID PubChem AID
2 aldo-keto reductase family 1 member B Akr1b1 Rattus norvegicus 0.16 385353
2 aldo-keto reductase family 1 member B AKR1B1 Homo sapiens 0.15 322413
2 aldo-keto reductase family 1 member B AKR1B1 Homo sapiens 2 639825
477 aldo-keto reductase family 1, member B1 (aldose reductase) AKR1B1 Bos taurus 10 34503
222 aldo-keto reductase family 1, member C21 Akr1c21 Mus musculus 33.3 322409
249 DNA polymerase eta POLH Homo sapiens 39.8107 588591
65 DNA polymerase iota POLI Homo sapiens 35.4813 588590
197 DNA polymerase kappa POLK Homo sapiens 44.6684 588579
256 flap structure-specific endonuclease 1 FEN1 Homo sapiens 39.8107 588795
43 glutaminase GLS Homo sapiens 35.4813 624170
259 glycogen synthase kinase 3 alpha GSK3A Homo sapiens 29.77 463203
90 karyopherin subunit beta 1 KPNB1 Homo sapiens 50.1187 540263
123 L3MBTL1, histone methyl-lysine binding protein L3MBTL1 Homo sapiens 19.9526 485360
670 Neuraminidase 4GUE 121200 10.1016/j.bmcl.2014.07.010 25096296
670 Neuraminidase 4GUE 109000 10.1016/j.bmcl.2014.07.010 25096296
280 PC4 and SFRS1 interacting protein 1 PSIP1 Homo sapiens 2.606 1053172
280 PC4 and SFRS1 interacting protein 1 PSIP1 Homo sapiens 13.938 1053171
1107 prolyl 4-hydroxylase subunit beta P4HB Homo sapiens 2.48 602350
1107 prolyl 4-hydroxylase subunit beta P4HB Homo sapiens 2.48 624274
151 prostaglandin-endoperoxide synthase 1 PTGS1 Bos taurus 2000 399401
151 prostaglandin-endoperoxide synthase 1 PTGS1 Bos taurus 2000 399404
152 prostaglandin-endoperoxide synthase 2 PTGS2 Ovis aries 2000 399402
152 prostaglandin-endoperoxide synthase 2 PTGS2 Ovis aries 2000 399405
19 Protein-tyrosine phosphatase 1B (PTP1B) Homo sapiens 4GUE 17 10.1016/j.bmcl.2015.04.003 25891102
91 snurportin 1 SNUPN Homo sapiens 50.1187 540263

10. Chemical Vendors

SID Source Name Source URL Source Detail Registry ID Source Record URL
92718097Hangzhou APIChem TechnologySource URLSource DetailAC-20295Source Record URL
88530110MolPortSource URLSource DetailMolPort-000-882-121Source Record URL
3570884811717 CheMall CorporationSource URLSource DetailBG01739212Source Record URL
3570884821717 CheMall CorporationSource URLSource DetailBG01739213Source Record URL
3611157221717 CheMall CorporationSource URLSource DetailBG02570463Source Record URL
3615608091717 CheMall CorporationSource URLSource DetailBG04717156Source Record URL
3599312101717 CheMall CorporationSource URLSource DetailBG06775389Source Record URL
310279517Glentham Life Sciences Ltd.Source URLSource DetailGC2615Source Record URL
322078641Pi ChemicalsSource URLSource DetailPI-20425Source Record URL
163614410ApexBio TechnologySource URLSource DetailN1840Source Record URL
319554505AbovChem LLCSource URLSource DetailHY-N0418Source Record URL
316429980abcr GmbHSource URLSource DetailAB171855Source Record URL
316469758abcr GmbHSource URLSource DetailAB253941Source Record URL
254778366Boc SciencesSource URLSource Detail522-12-3Source Record URL
252949525MculeSource URLSource DetailMCULE-7562123660Source Record URL
104225321ISpharmSource URLSource DetailI07-0264Source Record URL
255345174BiosynthSource URLSource DetailQ-100588Source Record URL
255345526BiosynthSource URLSource DetailQ-100945Source Record URL
162251569Chembase.cnSource URLSource Detail157432Source Record URL
126628588ChemMolSource URLSource Detail30107903Source Record URL
126653521ChemMolSource URLSource Detail44005536Source Record URL
126688969ChemMolSource URLSource Detail49427619Source Record URL
113853303ABI ChemSource URLSource DetailAC1NQX24Source Record URL
252406474MolepediaSource URLSource DetailM90013039PSource Record URL
251888140labseekerSource URLSource DetailSC-26573Source Record URL
350089586DC ChemicalsSource URLSource DetailDCH-011Source Record URL
318356350CambridgeChemSource URLSource DetailCB20526Source Record URL
104826456AKos Consulting & SolutionsSource URLSource DetailAKOS000278033Source Record URL
164788624Finetech Industry LimitedSource URLSource DetailFT-0603445Source Record URL
312694926TargetMolSource URLSource DetailT2871Source Record URL
373567748AmbinterSource URLSource DetailAmb22167885Source Record URL
196105948BoerchemSource URLSource DetailBC216298Source Record URL
329978005Acorn PharmaTech Product ListSource URLSource DetailACN-035424Source Record URL
257173840ZINCSource URLSource DetailZINC4175638Source Record URL
172835740Nanjing KaimuboSource URLSource DetailKB-180086Source Record URL
355037073MuseChemSource URLSource DetailI003900Source Record URL
274951655ChemFacesSource URLSource DetailCFN98850Source Record URL
349097575Chemieliva Pharmaceutical Co., LtdSource URLSource DetailPBCM0615721Source Record URL
223398378Assembly Blocks Pvt. Ltd.Source URLSource DetailAB0016764Source Record URL
251911816AvaChem ScientificSource URLSource Detail1131Source Record URL
251914893AvaChem ScientificSource URLSource Detail522-12-3Source Record URL
348354478AbMole BioscienceSource URLSource DetailM4384Source Record URL
310132596Aurora Fine Chemicals LLCSource URLSource DetailA17.904.881Source Record URL
290041519Aurora Fine Chemicals LLCSource URLSource DetailK05.568.265Source Record URL
329747128Sigma-AldrichSource URLSource Detail00740580_SIALSource Record URL
341835190OChemSource URLSource Detail5037Source Record URL
313035923AbaChemSceneSource URLSource DetailCS-5408Source Record URL
29204521R&D ChemicalsSource URLSource Detail1236Source Record URL
347260574LabNetwork, a WuXi AppTec CompanySource URLSource DetailLN01345120Source Record URL
313035806MedChemexpress MCESource URLSource DetailHY-N0418Source Record URL
318267089Chem-Space.com DatabaseSource URLSource DetailCSC000051329Source Record URL
57357747NovoSeekSource URLSource Detail5280459Source Record URL
318238562Yuhao ChemicalSource URLSource DetailLQ0919Source Record URL
252359117AHH Chemical co.,ltdSource URLSource DetailAPI-1448Source Record URL
223672383AN PharmaTechSource URLSource DetailAN-45535Source Record URL
252216149Race ChemicalSource URLSource DetailRV022504779Source Record URL
162183065AK Scientific, Inc. (AKSCI)Source URLSource DetailO981Source Record URL