NP-MRD: Showing NP-Card for Lupinalbin A (NP0057057)

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Record Information

Version

2.0

Created at

2022-04-28 02:36:56 UTC

Updated at

2022-04-28 02:36:57 UTC

NP-MRD ID

NP0057057

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lupinalbin A

Description

Lupinalbin a belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom. Thus, lupinalbin a is considered to be a flavonoid lipid molecule. Lupinalbin A is found in Flemingia macrophylla, Moghania philippinensis, Iris pseudacorus, Lotus creticus, Lupinus albus , Lupinus luteus and Vigna angularis. Lupinalbin a is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 32  0  0  0  0  0  0  0  0999 V2000
   -0.0428    0.4194   -2.0211 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4382    0.0804   -0.9001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7798   -0.0971   -0.6003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7360    0.1051   -1.5707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4862    0.4791   -2.8547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0521   -0.0956   -1.1811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4012   -0.4729    0.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7349   -0.6639    0.4401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4161   -0.6655    1.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0785   -0.4754    0.6870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1591   -0.6722    1.6286 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1347   -0.5046    1.3524 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2318   -0.6222    2.0539 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2928   -0.3552    1.3606 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6604   -0.3303    1.6173 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5651    0.0004    0.6550 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9503    0.0378    0.8708 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1437    0.3233   -0.6151 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8150    0.3093   -0.9011 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8918   -0.0304    0.0889 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5129   -0.1275    0.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7005    0.6819   -3.3867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8364    0.0522   -1.9119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3144    0.0822    0.8050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6571   -0.9627    2.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0327   -0.5797    2.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3057   -0.1923    1.7898 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8733    0.5923   -1.3995 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4231    0.5514   -1.8723 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 20 14  1  0
 14 13  1  0
 13 12  1  0
 12 21  2  0
 21  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 14 15  2  0
 15 16  1  0
 21 20  1  0
 10  3  1  0
 11 12  1  0
 17 27  1  0
 18 28  1  0
 19 29  1  0
  5 22  1  0
  6 23  1  0
  8 24  1  0
  9 25  1  0
 15 26  1  0
M  END


  Mrv1533004231522062D          

 21 24  0  0  0  0            999 V2000
    0.2933   -3.3650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1146   -3.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4585   -2.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2799   -2.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7574   -3.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5769   -3.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1960   -2.6835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0334   -1.8747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9778   -2.9471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5969   -2.4018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4343   -1.5930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3787   -2.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5413   -3.4742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3231   -3.7378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9222   -4.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1404   -3.7559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5213   -4.3011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7395   -4.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0205   -4.4422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4136   -3.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5922   -3.9606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  6 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  5 20  1  0  0  0  0
 20 21  2  0  0  0  0
  2 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0057057

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C2C(OC3=C2C(=O)C2=C(O)C=C(O)C=C2O3)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H8O6/c16-6-1-2-8-10(4-6)20-15-12(8)14(19)13-9(18)3-7(17)5-11(13)21-15/h1-5,16-18H

> <INCHI_KEY>
BBBAWACESCACAP-UHFFFAOYSA-N

> <FORMULA>
C15H8O6

> <MOLECULAR_WEIGHT>
284.223

> <EXACT_MASS>
284.032087978

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
27.354613714065984

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7,14-trihydroxy-2,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-1(10),3,5,7,11,13,15-heptaen-9-one

> <ALOGPS_LOGP>
2.86

> <JCHEM_LOGP>
2.947358664666666

> <ALOGPS_LOGS>
-2.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.78971573075722

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.450813443245314

> <JCHEM_PKA_STRONGEST_BASIC>
-3.030891276224961

> <JCHEM_POLAR_SURFACE_AREA>
100.13000000000001

> <JCHEM_REFRACTIVITY>
70.85340000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.85e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lupinalbin A

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  O   UNK     0       0.547  -6.281   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.081  -6.137   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.723  -4.737   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.256  -4.593   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.147  -5.849   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.677  -6.027   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.833  -5.009   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.529  -3.499   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.292  -5.501   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.448  -4.483   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.144  -2.974   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      11.907  -4.975   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.210  -6.485   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      13.670  -6.977   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      11.055  -7.503   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.595  -7.011   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.440  -8.029   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.980  -7.537   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.638  -8.292   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.505  -7.249   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.972  -7.393   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   20                                                  
CONECT    6    5    7   18                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   16                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15    9   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17    6   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19    5   21                                                  
CONECT   21   20    2                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₈O₆

Average Mass

284.2230 Da

Monoisotopic Mass

284.03209 Da

IUPAC Name

5,7,14-trihydroxy-2,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-1(10),3,5,7,11,13,15-heptaen-9-one

Traditional Name

lupinalbin A

CAS Registry Number

Not Available

SMILES

OC1=CC=C2C(OC3=C2C(=O)C2=C(O)C=C(O)C=C2O3)=C1

InChI Identifier

InChI=1S/C15H8O6/c16-6-1-2-8-10(4-6)20-15-12(8)14(19)13-9(18)3-7(17)5-11(13)21-15/h1-5,16-18H

InChI Key

BBBAWACESCACAP-UHFFFAOYSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Flemingia macrophylla	LOTUS Database	35616633
Flemingia philippinensis	-	KNApSAcK
Iris pseudacorus	LOTUS Database	35616633
Lotus creticus	LOTUS Database	35616633
Lupinus albus	Plant	KNApSAcK
Lupinus luteus	LOTUS Database	35616633
Vigna angularis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflav-2-enes

Direct Parent

Isoflavones

Alternative Parents

Substituents

Isoflavone
Coumaronochromene
Chromone
Coumarin
Benzopyran
1-benzopyran
Benzofuran
Furopyran
Pyranone
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Furan
Polyol
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Other Flavonoids (LMPK12160012 )

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	2.86	ALOGPS
logP	2.95	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	7.45	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	100.13 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	70.85 m³·mol⁻¹	ChemAxon
Polarizability	27.35 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5324349

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Lupinalbin A (NP0057057)

MOL for NP0057057 (Lupinalbin A)

3D MOL for NP0057057 (Lupinalbin A)

3D SDF for NP0057057 (Lupinalbin A)

3D-SDF for NP0057057 (Lupinalbin A)

PDB for NP0057057 (Lupinalbin A)

3D PDB for NP0057057 (Lupinalbin A)

SMILES for NP0057057 (Lupinalbin A)

INCHI for NP0057057 (Lupinalbin A)

Structure for NP0057057 (Lupinalbin A)

3D Structure for NP0057057 (Lupinalbin A)