NP-MRD: Showing NP-Card for lespedin (NP0240969)

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Record Information

Version

2.0

Created at

2022-09-07 00:55:04 UTC

Updated at

2022-09-07 00:55:04 UTC

NP-MRD ID

NP0240969

Secondary Accession Numbers

None

Natural Product Identification

Common Name

lespedin

Description

Kaempferitrin, also known as lespenefril or lespedin, belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Kaempferitrin is an extremely weak basic (essentially neutral) compound (based on its pKa). lespedin is found in Aconitum lycoctonum, Agrimonia pilosa, Androsace umbellata, Arabidopsis thaliana, Bauhinia forficata, Cardamine leucantha, Celastrus orbiculatus, Chenopodiastrum murale, Chenopodium album, Cinnamomum burmannii, Cinnamomum osmophloeum, Cinnamomum yabunikkei, Colocasia antiquorum, Dryopteris crassirhizoma, Farsetia aegyptia, Ficus septica, Garcinia dulcis, Humulus lupulus, Annulohypoxylon bovei, Ixora coccinea, Justicia spicigera, Lespedeza virgata, Ligustrum vulgare, Dorycnium hirsutum, Macrothelypteris torresiana, Pterogyne nitens, Raphanus sativus, Sedum dendroideum, Hylotelephium telephium, Tilia tomentosa, Trichosanthes cucumeroides and Vicia faba. lespedin was first documented in 1951 (PMID: 14882347). A glycosyloxyflavone that is kaempferol attached to alpha-L-rhamnopyranosyl residues at positions 3 and 7 respectively via glycosidic linkages (PMID: 15501431) (PMID: 16268506) (PMID: 16423486) (PMID: 17497804).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309272007372D          

 41 45  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309272007372D          

 41 45  0  0  0  0            999 V2000
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10013.797010006.3670    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10013.080710005.9523    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10012.359610006.3632    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10011.644610005.9428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.626410008.4322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.349010008.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.628610007.6046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13  8  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 19 20  1  0  0  0  0
 18 19  1  0  0  0  0
 18 21  1  0  0  0  0
 21 11  1  0  0  0  0
 19 14  2  0  0  0  0
 17 20  2  0  0  0  0
  8  1  1  0  0  0  0
 15  3  1  0  0  0  0
 17  2  1  0  0  0  0
 22 23  1  0  0  0  0
 22 27  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27  3  1  6  0  0  0
 22  4  1  1  0  0  0
 23  5  1  1  0  0  0
 24  7  1  6  0  0  0
 25  6  1  1  0  0  0
 33 29  1  1  0  0  0
 34 28  1  6  0  0  0
 35 30  1  6  0  0  0
 36 31  1  1  0  0  0
 39 40  1  0  0  0  0
 39 41  2  0  0  0  0
 37 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 40 29  1  0  0  0  0
 37 38  1  6  0  0  0
 40 21  2  0  0  0  0
 20 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0240969

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](OC2=CC(O)=C3C(=O)C(O[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)=C(OC3=C2)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H30O14/c1-9-17(30)20(33)22(35)26(37-9)39-13-7-14(29)16-15(8-13)40-24(11-3-5-12(28)6-4-11)25(19(16)32)41-27-23(36)21(34)18(31)10(2)38-27/h3-10,17-18,20-23,26-31,33-36H,1-2H3/t9-,10-,17-,18-,20+,21+,22+,23+,26-,27-/m0/s1

> <INCHI_KEY>
PUPKKEQDLNREIM-QNSQPKOQSA-N

> <FORMULA>
C27H30O14

> <MOLECULAR_WEIGHT>
578.523

> <EXACT_MASS>
578.163555646

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
55.37917525387238

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-hydroxy-2-(4-hydroxyphenyl)-3,7-bis({[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy})-4H-chromen-4-one

> <ALOGPS_LOGP>
0.45

> <JCHEM_LOGP>
-0.015518134333332045

> <ALOGPS_LOGS>
-2.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.556778906358883

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.083350053109648

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6122003587144

> <JCHEM_POLAR_SURFACE_AREA>
225.05999999999995

> <JCHEM_REFRACTIVITY>
136.35159999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.82e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
kaempferitrin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8695.0448687.809   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8685.7188680.865   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8683.0558685.504   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8680.3928687.044   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8677.7228685.504   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8680.3928680.884   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8677.7228682.424   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8693.7138687.044   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8692.3808687.813   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8691.0468687.043   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8691.0468685.504   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8692.3808684.734   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8693.7138685.504   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8685.7188685.495   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8684.3848684.726   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8684.3848683.185   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8685.7178682.415   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0    8688.3808685.495   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0    8687.0468684.725   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8687.0468683.185   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8689.7148684.725   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8680.3908685.502   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8679.0568684.732   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8679.0568683.192   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8680.3908682.422   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0    8681.7238683.192   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0    8681.7238684.732   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0    8693.7508680.885   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0    8691.0588682.419   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0    8693.7688677.785   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0    8691.0968676.226   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0    8689.7298680.086   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0    8691.0678680.878   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0    8692.4138680.111   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0    8692.4218678.552   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0    8691.0848677.778   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0    8689.7388678.545   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0    8688.4038677.760   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0    8688.3698682.407   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0    8689.7188683.188   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0    8688.3738680.862   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2   17                                                            
CONECT    3   15   27                                                       
CONECT    4   22                                                            
CONECT    5   23                                                            
CONECT    6   25                                                            
CONECT    7   24                                                            
CONECT    8    9   13    1                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   21                                                  
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14   15   19                                                       
CONECT   15   14   16    3                                                  
CONECT   16   15   17                                                       
CONECT   17   16   20    2                                                  
CONECT   18   19   21                                                       
CONECT   19   20   18   14                                                  
CONECT   20   19   17   39                                                  
CONECT   21   18   11   40                                                  
CONECT   22   23   27    4                                                  
CONECT   23   22   24    5                                                  
CONECT   24   23   25    7                                                  
CONECT   25   24   26    6                                                  
CONECT   26   25   27                                                       
CONECT   27   22   26    3                                                  
CONECT   28   34                                                            
CONECT   29   33   40                                                       
CONECT   30   35                                                            
CONECT   31   36                                                            
CONECT   32   37   33                                                       
CONECT   33   29   32   34                                                  
CONECT   34   28   33   35                                                  
CONECT   35   30   34   36                                                  
CONECT   36   31   35   37                                                  
CONECT   37   32   36   38                                                  
CONECT   38   37                                                            
CONECT   39   40   41   20                                                  
CONECT   40   39   29   21                                                  
CONECT   41   39                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

View in JSmol

Synonyms

Value	Source
3,7-Bis((6-deoxy-alpha-L-mannopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	ChEBI
Kaempferol 3,7-bisrhamnoside	ChEBI
Kaempferol 3,7-dirhamnoside	ChEBI
Kaempferol 3-O-alpha-L-rhamnopyranosyl-7-O-alpha-L-rhamnopyranoside	ChEBI
Kaempferol-3,7-O-alpha-L-dirhamnoside	ChEBI
Kaempferol-dirhamnoside	ChEBI
Lespedin	ChEBI
Lespenefril	ChEBI
Lespenephril	ChEBI
Lespenephryl	ChEBI
3,7-Bis((6-deoxy-a-L-mannopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	Generator
3,7-Bis((6-deoxy-α-L-mannopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	Generator
Kaempferol 3-O-a-L-rhamnopyranosyl-7-O-a-L-rhamnopyranoside	Generator
Kaempferol 3-O-α-L-rhamnopyranosyl-7-O-α-L-rhamnopyranoside	Generator
Kaempferol-3,7-O-a-L-dirhamnoside	Generator
Kaempferol-3,7-O-α-L-dirhamnoside	Generator
3,7-Bis-(alpha-6-deoxymannopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one	HMDB
Kaempferitrin	ChEBI
Kaempferol 3,7-di-O-a-L-rhamnoside	Generator
Kaempferol 3,7-di-O-α-L-rhamnoside	Generator
3,4',5,7-Tetrahydroxyflavone 3,7-dirhamnoside	PhytoBank
3,4’,5,7-Tetrahydroxyflavone 3,7-dirhamnoside	PhytoBank
Grosvenorine II	PhytoBank
Kaempferol 3-O-alpha-L-rhamnopyranoside 7-O-alpha-L-rhamnopyranoside	PhytoBank
Kaempferol 3-O-α-L-rhamnopyranoside 7-O-α-L-rhamnopyranoside	PhytoBank
Kaempferol 3,7-di-alpha-L-rhamnoside	PhytoBank
Kaempferol 3,7-di-α-L-rhamnoside	PhytoBank
Kaempferol 3,7-di-alpha-L-rhamnopyranoside	PhytoBank
Kaempferol 3,7-di-α-L-rhamnopyranoside	PhytoBank
Kaempferol 3,7-di-O-alpha-L-rhamnopyranoside	PhytoBank
Kaempferol 3,7-di-O-α-L-rhamnopyranoside	PhytoBank
Kaempferol 3,7-O-alpha-L-dirhamnoside	PhytoBank
Kaempferol 3,7-O-α-L-dirhamnoside	PhytoBank
Kaempferol 3,7-di-O-rhamnopyranoside	PhytoBank
Kaempferol 3,7-di-O-rhamnoside	PhytoBank
Kaempferol 3-O-rhamnoside 7-O-rhamnoside	PhytoBank
Kaempferol-3,7-O-dirhamnose	PhytoBank

Chemical Formula

C₂₇H₃₀O₁₄

Average Mass

578.5230 Da

Monoisotopic Mass

578.16356 Da

IUPAC Name

5-hydroxy-2-(4-hydroxyphenyl)-3,7-bis({[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy})-4H-chromen-4-one

Traditional Name

kaempferitrin

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](OC2=CC(O)=C3C(=O)C(O[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)=C(OC3=C2)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C27H30O14/c1-9-17(30)20(33)22(35)26(37-9)39-13-7-14(29)16-15(8-13)40-24(11-3-5-12(28)6-4-11)25(19(16)32)41-27-23(36)21(34)18(31)10(2)38-27/h3-10,17-18,20-23,26-31,33-36H,1-2H3/t9-,10-,17-,18-,20+,21+,22+,23+,26-,27-/m0/s1

InChI Key

PUPKKEQDLNREIM-QNSQPKOQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aconitum lycoctonum	LOTUS Database	35616633
Agrimonia pilosa	LOTUS Database	35616633
Androsace umbellata	LOTUS Database	35616633
Arabidopsis thaliana	LOTUS Database	35616633
Bauhinia forficata	LOTUS Database	35616633
Cardamine leucantha	LOTUS Database	35616633
Celastrus orbiculatus	LOTUS Database	35616633
Chenopodiastrum murale	LOTUS Database	35616633
Chenopodium album	LOTUS Database	35616633
Cinnamomum burmanni	LOTUS Database	35616633
Cinnamomum osmophloeum	LOTUS Database	35616633
Cinnamomum yabunikkei	LOTUS Database	35616633
Colocasia antiquorum	LOTUS Database	35616633
Dryopteris crassirhizoma	LOTUS Database	35616633
Farsetia aegyptia	LOTUS Database	35616633
Ficus septica	LOTUS Database	35616633
Garcinia dulcis	LOTUS Database	35616633
Humulus lupulus	LOTUS Database	35616633
Hypoxylon bovei	LOTUS Database	35616633
Ixora coccinea	LOTUS Database	35616633
Justicia spicigera	LOTUS Database	35616633
Lespedeza virgata	LOTUS Database	35616633
Ligustrum vulgare	LOTUS Database	35616633
Lotus hirsutus	LOTUS Database	35616633
Macrothelypteris torresiana	LOTUS Database	35616633
Pterogyne nitens	LOTUS Database	35616633
Raphanus sativus	LOTUS Database	35616633
Sedum dendroideum	LOTUS Database	35616633
Sedum telephium	LOTUS Database	35616633
Tilia tomentosa	LOTUS Database	35616633
Trichosanthes cucumeroides	LOTUS Database	35616633
Vicia faba	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dihydroxyflavone (CHEBI:68883 )
glycosyloxyflavone (CHEBI:68883 )
alpha-L-rhamnoside (CHEBI:68883 )
Flavones and Flavonols (C16981 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.45	ALOGPS
logP	-0.016	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	7.08	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	225.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	136.35 m³·mol⁻¹	ChemAxon
Polarizability	55.38 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0037438

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00005189

Chemspider ID

4588900

KEGG Compound ID

C16981

BioCyc ID

kaempferol-3-rhamnoside-7-rhamnoside

BiGG ID

Not Available

Wikipedia Link

Kaempferitrin

METLIN ID

Not Available

PubChem Compound

5486199

PDB ID

Not Available

ChEBI ID

68883

Good Scents ID

Not Available

References

General References

HATTORI S: Identity of lespedin with kaempferitrin. Nature. 1951 Nov 3;168(4279):788. doi: 10.1038/168788a0. [PubMed:14882347 ]
Jorge AP, Horst H, de Sousa E, Pizzolatti MG, Silva FR: Insulinomimetic effects of kaempferitrin on glycaemia and on 14C-glucose uptake in rat soleus muscle. Chem Biol Interact. 2004 Oct 15;149(2-3):89-96. doi: 10.1016/j.cbi.2004.07.001. [PubMed:15501431 ]
Yang XW, Zhang JY, Xu W, Li J, Zhang WQ: [The biotransformation of kaempferitrin by human intestinal flora]. Yao Xue Xue Bao. 2005 Aug;40(8):717-21. [PubMed:16268506 ]
Pinheiro TS, Johansson LA, Pizzolatti MG, Biavatti MW: Comparative assessment of kaempferitrin from medicinal extracts of Bauhinia forficata link. J Pharm Biomed Anal. 2006 May 3;41(2):431-6. doi: 10.1016/j.jpba.2005.12.010. Epub 2006 Jan 19. [PubMed:16423486 ]
Urgaonkar S, Shaw JT: Synthesis of kaempferitrin. J Org Chem. 2007 Jun 8;72(12):4582-5. doi: 10.1021/jo070502w. Epub 2007 May 11. [PubMed:17497804 ]
LOTUS database [Link]

Showing NP-Card for lespedin (NP0240969)

MOL for NP0240969 (lespedin)

3D MOL for NP0240969 (lespedin)

3D SDF for NP0240969 (lespedin)

3D-SDF for NP0240969 (lespedin)

PDB for NP0240969 (lespedin)

3D PDB for NP0240969 (lespedin)

SMILES for NP0240969 (lespedin)

INCHI for NP0240969 (lespedin)

Structure for NP0240969 (lespedin)

3D Structure for NP0240969 (lespedin)