Nicotiflorin

  • GreenMolBD CID : 562
  • Molecular Formula : C27H30O15
  • Molecular Weight : 594.522
  • Exact Molecular Mass : 594.158
  • IUPAC Name : 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
  • InChI : InChI=1S/C27H30O15/c1-9-17(31)20(34)22(36)26(39-9)38-8-15-18(32)21(35)23(37)27(41-15)42-25-19(33)16-13(30)6-12(29)7-14(16)40-24(25)10-2-4-11(28)5-3-10/h2-7,9,15,17-18,20-23,26-32,34-37H,8H2,1H3/t9-,15+,17-,18+,20+,21-,22+,23+,26+,27-/m0/s1
  • InChI Key : RTATXGUCZHCSNG-QHWHWDPRSA-N
  • Canonical SMILES : CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC=C(C=C5)O)O)O)O)O)O)O
  • Isomeric SMILES : CC1C(C(C(C(O1)OCC2C(C(C(C(O2)Oc3c(=O)c4c(cc(cc4oc3c5ccc(cc5)O)O)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

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

1.4. Molecular Framework

Aromatic heteropolycyclic compounds

1.5. Substituents

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

2. Physical Properties

SlogP TPSA HBD HBA nHA nRB nAA nAB SMR vdw_vol vdw_area Density
-1.5844 245.29 9 15 42 6 12 12 13.5831 693.877 510.889 0.856811

3. Quantum Information

Heat of Formation Dipole Moment Electronegativity Homo Lumo Hardness
-589.492675 7.96 -4.559 -8.73182 -0.3859 4.173

4. Compound Reactivity

DLP nRFG nLMR
8 2 9

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 1.661 24.5626 0.073456 None Weak Moderate Degradable 3.57481 1.54146

6. Drug-Likeliness Test

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

7. Synonyms

Name
Nicotiflorin
Kaempferol-3-O-rutinoside
17650-84-9
NICOTIFLOROSIDE
Kaempferol-3-O-beta-rutinoside
UNII-4056D20K3H
Kaempferol 3-Rutinoside
CHEBI:69657
MFCD03427292
4056D20K3H
Nictoflorin
kaempferol 3-O-(6''-O-alpha-L-rhamnopyranosyl)-beta-D-glucopyranoside
3-rutinosylkaempferol
Kaempferol 3-O-rutinose
AC1NSXA1
MLS000563045
SCHEMBL240355
CHEMBL498879
Kaempferol 3-O-beta-rutinoside
MEGxp0_000024
Kaempferol 3-O-|A -rutinoside
ACon1_002178
MolPort-001-740-194
RTATXGUCZHCSNG-QHWHWDPRSA-N
HMS2268M08
ZINC4349478
BDBM50378581
MCULE-3239674829
4H-1-Benzopyran-4-one, 3-((6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-
BT000970
CA001278
SMR001215820
NP-000047
FT-0697835
W1678
3,4',5,7-Tetrahydroxyflavone 3-rhamnoglucoside
Flavone, 3,4',5,7-tetrahydroxy-, 3-rhamnoglucoside
Kaempferol 3-O-beta -rutinoside, >=98.0% (HPLC)
3,4 inverted exclamation marka,5,7-Tetrahydroxyflavone 3-rhamnoglucoside
3-((6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
4H-1-Benzopyran-4-one,3-[[6-O-(6-deoxy-a-L-mannopyranosyl)-b-D-glucopyranosyl]oxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-
5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-3-{[(2S,3R,4S,5S,6R)-3,4,5-TRIHYDROXY-6-({[(2R,3R,4R,5R,6S)-3,4,5-TRIHYDROXY-6-METHYLOXAN-2-YL]OXY}METHYL)OXAN-2-YL]OXY}CHROMEN-4-ONE
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside
Kaempferol-3-rutinoside
Kaempferol 3-O-rutinoside
AKOS032962209

8. Compound in Different Plants

Compound Name Plant Name Compound in Plant Parts Ref
Nicotiflorin
Acalypha indica L. Flower; Leaf 8
Coriandrum sativum Linn. Vegetative; Fruit 22
Crocus sativus L. Stigma 16
Impatiens balsamina L.  Flower 4 , 14
Ixora coccinea L.  Flower 8
Jasminum graniflorum Flower 9 , 20
Manihot esculenta
Microcos paniculata Leaf 8
Ricinus communis Leaf 7
Rosa damascena Flower 17
Sesbania grandiflora Flower 1
Viola odorata Flower 1

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 11.3 654333
667 dual specificity tyrosine phosphorylation regulated kinase 1A Dyrk1a Rattus norvegicus 7.779 588345

10. Chemical Vendors

SID Source Name Source URL Source Detail Registry ID Source Record URL
318356343CambridgeChemSource URLSource DetailCB21133Source Record URL
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350090077DC ChemicalsSource URLSource DetailDCS-065Source Record URL
310133465Aurora Fine Chemicals LLCSource URLSource DetailA17.905.755Source Record URL
290041418Aurora Fine Chemicals LLCSource URLSource DetailK05.568.132Source Record URL
347757321Alfa ChemistrySource URLSource Detail17650-84-9Source Record URL
310275600Glentham Life Sciences Ltd.Source URLSource DetailGK4486Source Record URL
355397626AKos Consulting & SolutionsSource URLSource DetailAKOS032962209Source Record URL
254768828Boc SciencesSource URLSource Detail17650-84-9Source Record URL
252551009AK Scientific, Inc. (AKSCI)Source URLSource DetailW1678Source Record URL
29204308R&D ChemicalsSource URLSource Detail1053Source Record URL
273221857Finetech Industry LimitedSource URLSource DetailFT-0697835Source Record URL
252416664MolepediaSource URLSource DetailM90150749PSource Record URL
316469711abcr GmbHSource URLSource DetailAB253888Source Record URL
88783179MolPortSource URLSource DetailMolPort-001-740-194Source Record URL
355175271MuseChemSource URLSource DetailM084355Source Record URL
374100675Combi-BlocksSource URLSource DetailQW-8272Source Record URL
373988051MedChemexpress MCESource URLSource DetailHY-N1475Source Record URL
251916357AvaChem ScientificSource URLSource Detail17650-84-9Source Record URL
251917704AvaChem ScientificSource URLSource Detail2913Source Record URL
114172481ABI ChemSource URLSource DetailAC1NSXA1Source Record URL
347639655LabNetwork, a WuXi AppTec CompanySource URLSource DetailLN01871763Source Record URL
374243365Key Organics/BIONETSource URLSource DetailAS-35049Source Record URL
348840903Chemieliva Pharmaceutical Co., LtdSource URLSource DetailPBCM0359054Source Record URL
319474457eNovation ChemicalsSource URLSource DetailD511490Source Record URL
340124450Acorn PharmaTech Product ListSource URLSource DetailACN-047244Source Record URL
354307166iChemical Technology USA IncSource URLSource DetailEBD2197887Source Record URL
257249226ZINCSource URLSource DetailZINC4349478Source Record URL
348354329AbMole BioscienceSource URLSource DetailM4235Source Record URL
162248869Chembase.cnSource URLSource Detail154731Source Record URL
274951124ChemFacesSource URLSource DetailCFN99830Source Record URL
329769863Sigma-AldrichSource URLSource Detail90242_SIGMASource Record URL
318465243Herbest Bio-TechSource URLSource DetailHK210623Source Record URL
3599856821717 CheMall CorporationSource URLSource DetailBG06826970Source Record URL