NP-MRD: Showing NP-Card for Dalbergioidin (NP0047440)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-03-17 20:40:14 UTC

Updated at

2022-03-17 20:40:15 UTC

NP-MRD ID

NP0047440

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dalbergioidin

Description

Dalbergioidin belongs to the class of organic compounds known as isoflavanones. These are polycyclic compounds containing an isoflavan skeleton which bears a ketone at position C4. Thus, dalbergioidin is considered to be a flavonoid lipid molecule. Dalbergioidin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Dalbergioidin has been detected, but not quantified in, several different foods, such as green beans, hyacinth beans, lima beans, scarlet beans, and mung beans. Dalbergioidin is found in Desmodium gangeticum , Desmodium oojeinense, Desmodium uncinatum, Dipogon lignosus, Gynerium sagittatum , Lablab niger, Lespedeza cyrtobotrya, Macroptilium atropurpureum, Macroptilium bracteatum, Macroptilium lathyroides, Macroptilium martii, Macrotyloma axillare, Mucuna pruriens , Ormosia monosperma, Sphenostylis angustifolia, Sphenostylis stenocarpa , Strongylodon macrobotrys, Strophostyles helvola, Swartzia polyphylla, Uraria picta, Vigna mungo, Vigna subterranea and Dolichos biflorus . This could make dalbergioidin a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI

  Mrv0541 05061306392D          

 21 23  0  0  0  0            999 V2000
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  7  1  1  0  0  0  0
  7  3  2  0  0  0  0
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  2  1  0  0  0  0
 10  6  1  0  0  0  0
 10  9  1  0  0  0  0
 11  3  1  0  0  0  0
 11  9  2  0  0  0  0
 12  4  1  0  0  0  0
 13  5  2  0  0  0  0
 14 12  2  0  0  0  0
 14 13  1  0  0  0  0
 15 10  1  0  0  0  0
 15 14  1  0  0  0  0
 16  7  1  0  0  0  0
 17  8  1  0  0  0  0
 18 11  1  0  0  0  0
 19 12  1  0  0  0  0
 20 15  2  0  0  0  0
 21  6  1  0  0  0  0
 21 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047440

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(O)=C(C=C1)C1COC2=CC(O)=CC(O)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O6/c16-7-1-2-9(11(18)3-7)10-6-21-13-5-8(17)4-12(19)14(13)15(10)20/h1-5,10,16-19H,6H2

> <INCHI_KEY>
WNHXBLZBOWXNQO-UHFFFAOYSA-N

> <FORMULA>
C15H12O6

> <MOLECULAR_WEIGHT>
288.2522

> <EXACT_MASS>
288.063388116

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
27.429864365980315

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(2,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
2.06

> <JCHEM_LOGP>
2.424092792333333

> <ALOGPS_LOGS>
-2.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.095767983554266

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.877494855455804

> <JCHEM_PKA_STRONGEST_BASIC>
-3.864899029874036

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
73.65740000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.76e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+-)-dalbergioidin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      12.003   6.930   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1    9                                                       
CONECT    3    7   11                                                       
CONECT    4    8   12                                                       
CONECT    5    8   13                                                       
CONECT    6   10   21                                                       
CONECT    7    1    3   16                                                  
CONECT    8    4    5   17                                                  
CONECT    9    2   10   11                                                  
CONECT   10    6    9   15                                                  
CONECT   11    3    9   18                                                  
CONECT   12    4   14   19                                                  
CONECT   13    5   14   21                                                  
CONECT   14   12   13   15                                                  
CONECT   15   10   14   20                                                  
CONECT   16    7                                                            
CONECT   17    8                                                            
CONECT   18   11                                                            
CONECT   19   12                                                            
CONECT   20   15                                                            
CONECT   21    6   13                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
(+-)-Dalbergioidin	HMDB
2,3-Dihydro-5,7-dihydroxy-3-(2,4-dihydroxyphenyl)-4H-1-benzopyran-4-one, 9ci	HMDB
5,7,2',4'-Tetrahydroxyisoflavanone	HMDB
Dalbergioidin	MeSH

Chemical Formula

C₁₅H₁₂O₆

Average Mass

288.2522 Da

Monoisotopic Mass

288.06339 Da

IUPAC Name

3-(2,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(+-)-dalbergioidin

CAS Registry Number

30368-42-4

SMILES

OC1=CC(O)=C(C=C1)C1COC2=CC(O)=CC(O)=C2C1=O

InChI Identifier

InChI=1S/C15H12O6/c16-7-1-2-9(11(18)3-7)10-6-21-13-5-8(17)4-12(19)14(13)15(10)20/h1-5,10,16-19H,6H2

InChI Key

WNHXBLZBOWXNQO-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Desmodium gangeticum	Plant	KNApSAcK
Desmodium oojeinense	LOTUS Database	35616633
Desmodium uncinatum	LOTUS Database	35616633
Dipogon lignosus	Plant	KNApSAcK
Gynerium sagittatum	Plant	KNApSAcK
Lablab niger	Plant	KNApSAcK
Lablab purpureus	FooDB	KNAPSACK
Lespedeza cyrtobotrya	Plant	KNApSAcK
Macroptilium atropurpureum	Plant	KNApSAcK
Macroptilium bracteatum	Plant	KNApSAcK
Macroptilium lathyroides	Plant	KNApSAcK
Macroptilium martii	Plant	KNApSAcK
Macrotyloma axillare	Plant	KNApSAcK
Mucuna pruriens	Plant	KNApSAcK
Ormosia monosperma	Plant	KNApSAcK
Phaseolus coccineus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Phaseolus lunatus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Phaseolus vulgaris	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sphenostylis angustifolia	Plant	KNApSAcK
Sphenostylis stenocarpa	Plant	KNApSAcK
Strongylodon macrobotrys	Plant	KNApSAcK
Strophostyles helvola	Plant	KNApSAcK
Swartzia polyphylla	Plant	KNApSAcK
Uraria picta	LOTUS Database	35616633
Vigna angularis	FooDB	KNAPSACK
Vigna mungo	LOTUS Database	35616633
Vigna radiata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vigna subterranea	Plant	KNApSAcK
Vigna umbellata	FooDB	KNAPSACK
Vigna unguiculata ssp. cylindrica	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavanones. These are polycyclic compounds containing an isoflavan skeleton which bears a ketone at position C4.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavans

Direct Parent

Isoflavanones

Alternative Parents

Substituents

Isoflavanone
Isoflavanol
Hydroxyisoflavonoid
Chromone
1-benzopyran
Chromane
Benzopyran
Resorcinol
Aryl ketone
Aryl alkyl ketone
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

isoflavanones (CHEBI:65 )
isoflavanones (C10415 )
Isoflavonoids (C10415 )
Isoflavonoids (LMPK12050500 )

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	2.06	ALOGPS
logP	2.42	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	7.88	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	73.66 m³·mol⁻¹	ChemAxon
Polarizability	27.43 Å³	ChemAxon
Number of Rings	3	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

HMDB0032707

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

181994

PDB ID

Not Available

ChEBI ID

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Dalbergioidin (NP0047440)

MOL for NP0047440 (Dalbergioidin)

3D MOL for NP0047440 (Dalbergioidin)

3D SDF for NP0047440 (Dalbergioidin)

3D-SDF for NP0047440 (Dalbergioidin)

PDB for NP0047440 (Dalbergioidin)

3D PDB for NP0047440 (Dalbergioidin)

SMILES for NP0047440 (Dalbergioidin)

INCHI for NP0047440 (Dalbergioidin)

Structure for NP0047440 (Dalbergioidin)

3D Structure for NP0047440 (Dalbergioidin)