NP-MRD: Showing NP-Card for Lanceolarin (NP0138482)

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Record Information

Version

2.0

Created at

2022-06-29 17:31:32 UTC

Updated at

2022-06-29 17:31:32 UTC

NP-MRD ID

NP0138482

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lanceolarin

Description

Biochanin a 7-o-apiosyl-(1->6)-glucoside belongs to the class of organic compounds known as isoflavonoid o-glycosides. These are o-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one. Thus, biochanin a 7-O-apiosyl-(1->6)-glucoside is considered to be a flavonoid. Lanceolarin is found in Alstonia scholaris, Andira inermis and Dalbergia sissoo. Based on a literature review very few articles have been published on Biochanin a 7-o-apiosyl-(1->6)-glucoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652306292219312D          

 41 45  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END

  Mrv1652306292219312D          

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    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  2  0  0  0  0
 16 20  1  0  0  0  0
 14 21  1  0  0  0  0
 22 21  1  1  0  0  0
 22 23  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
 22 27  1  0  0  0  0
 26 28  1  1  0  0  0
 28 29  1  0  0  0  0
 30 29  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 30 34  1  0  0  0  0
 32 35  1  1  0  0  0
 35 36  1  0  0  0  0
 32 37  1  6  0  0  0
 31 38  1  6  0  0  0
 25 39  1  6  0  0  0
 24 40  1  1  0  0  0
 23 41  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0138482

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1)C1=COC2=CC(O[C@@H]3O[C@H](CO[C@@H]4OC[C@](O)(CO)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)=CC(O)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H30O14/c1-36-13-4-2-12(3-5-13)15-8-37-17-7-14(6-16(29)19(17)20(15)30)40-25-23(33)22(32)21(31)18(41-25)9-38-26-24(34)27(35,10-28)11-39-26/h2-8,18,21-26,28-29,31-35H,9-11H2,1H3/t18-,21-,22+,23-,24+,25-,26-,27-/m1/s1

> <INCHI_KEY>
VGKGODYADVWBQB-NRIIMPDMSA-N

> <FORMULA>
C27H30O14

> <MOLECULAR_WEIGHT>
578.523

> <EXACT_MASS>
578.163555646

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
56.870376390147015

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7-{[(2S,3R,4S,5S,6R)-6-({[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-5-hydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
0.10

> <JCHEM_LOGP>
-0.3218007076666664

> <ALOGPS_LOGS>
-2.84

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.70175290556784

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.282039706503151

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1423790163389214

> <JCHEM_POLAR_SURFACE_AREA>
214.05999999999997

> <JCHEM_REFRACTIVITY>
134.97979999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.39e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lanceolarin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      10.669   6.160   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      12.003   6.930   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.164   8.462   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      13.670   8.782   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      14.440   7.448   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      13.410   6.304   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      13.526  10.315   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      12.125  10.956   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      14.907   9.700   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      11.020   9.492   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3                                                       
CONECT    9    6   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   12   18                                                  
CONECT   18   17    9   19                                                  
CONECT   19   18                                                            
CONECT   20   16                                                            
CONECT   21   14   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24   41                                                  
CONECT   24   23   25   40                                                  
CONECT   25   24   26   39                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26   22                                                       
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   34                                                  
CONECT   31   30   32   38                                                  
CONECT   32   31   33   35   37                                             
CONECT   33   32   34                                                       
CONECT   34   33   30                                                       
CONECT   35   32   36                                                       
CONECT   36   35                                                            
CONECT   37   32                                                            
CONECT   38   31                                                            
CONECT   39   25                                                            
CONECT   40   24                                                            
CONECT   41   23                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

View in JSmol

Synonyms

Value	Source
Biochanin-a-7-apiosyl(1-2)glucoside	MeSH

Chemical Formula

C₂₇H₃₀O₁₄

Average Mass

578.5230 Da

Monoisotopic Mass

578.16356 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

15914-68-8

SMILES

COC1=CC=C(C=C1)C1=COC2=CC(O[C@@H]3O[C@H](CO[C@@H]4OC[C@](O)(CO)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)=CC(O)=C2C1=O

InChI Identifier

InChI=1S/C27H30O14/c1-36-13-4-2-12(3-5-13)15-8-37-17-7-14(6-16(29)19(17)20(15)30)40-25-23(33)22(32)21(31)18(41-25)9-38-26-24(34)27(35,10-28)11-39-26/h2-8,18,21-26,28-29,31-35H,9-11H2,1H3/t18-,21-,22+,23-,24+,25-,26-,27-/m1/s1

InChI Key

VGKGODYADVWBQB-NRIIMPDMSA-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
Alstonia Alstonia scholaris	LOTUS Database	35616633
Andira inermis	LOTUS Database	35616633
Dalbergia sissoo	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavonoid o-glycosides. These are o-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavonoid O-glycosides

Direct Parent

Isoflavonoid O-glycosides

Alternative Parents

Substituents

Isoflavonoid o-glycoside
Isoflavonoid-7-o-glycoside
4p-o-methylisoflavone
Isoflavone
Hydroxyisoflavonoid
Phenolic glycoside
O-glycosyl compound
Glycosyl compound
Disaccharide
Chromone
1-benzopyran
Benzopyran
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Pyranone
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Pyran
Monocyclic benzene moiety
Oxane
Benzenoid
Heteroaromatic compound
Oxolane
Tertiary alcohol
Vinylogous acid
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Organic oxygen compound
Alcohol
Primary alcohol
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Isoflavonoids (LMPK12050223 )

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00010116

Chemspider ID

4590913

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5492234

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Lanceolarin (NP0138482)

MOL for NP0138482 (Lanceolarin)

3D MOL for NP0138482 (Lanceolarin)

3D SDF for NP0138482 (Lanceolarin)

3D-SDF for NP0138482 (Lanceolarin)

PDB for NP0138482 (Lanceolarin)

3D PDB for NP0138482 (Lanceolarin)

SMILES for NP0138482 (Lanceolarin)

INCHI for NP0138482 (Lanceolarin)

Structure for NP0138482 (Lanceolarin)

3D Structure for NP0138482 (Lanceolarin)