NP-MRD: Showing NP-Card for (±)-3',7-Dihydroxy-2',4'-dimethoxyisoflavan (NP0045994)

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Record Information

Version

2.0

Created at

2022-03-17 19:46:39 UTC

Updated at

2022-03-17 19:46:39 UTC

NP-MRD ID

NP0045994

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(±)-3',7-Dihydroxy-2',4'-dimethoxyisoflavan

Description

(R)-3',7-Dihydroxy-2',4'-dimethoxyisoflavan, also known as (+/-)-mucronulatol, belongs to the class of organic compounds known as 3'-hydroxy,4'-methoxyisoflavonoids. These are isoflavonoids carrying a methoxy group attached to the C4' atom, as well as a hydroxyl group at the C3'-position of the isoflavonoid backbone (R)-3',7-Dihydroxy-2',4'-dimethoxyisoflavan is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (R)-3',7-Dihydroxy-2',4'-dimethoxyisoflavan has been detected, but not quantified in, a few different foods, such as common beans, green beans, and yellow wax beans. (±)-3',7-Dihydroxy-2',4'-dimethoxyisoflavan is found in Astragalus adsurgens, Astragalus cicer, Dalbergia candenatensis, Dalbergia ecastaphyllum, Dalbergia odorifera, Dalbergia parviflora, Dalbergia variabilis, Indigofera aspalathoides, Machaerium mucronulatum, Oxytropis falcata and Pterocarpus soyauxii. This could make (R)-3',7-dihydroxy-2',4'-dimethoxyisoflavan a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241208022D          

 22 24  0  0  0  0            999 V2000
   -2.1445   -1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4846   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4846   -0.0004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7421    0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0004   -0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0004   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7421   -1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7421   -2.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4846   -2.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1445   -2.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8870   -2.4745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4021   -0.8246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0620   -1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8045    2.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8045    1.6495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1445    1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4021    1.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6596    1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6596    0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4021   -0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1445    0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8870   -0.0004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1 10  1  0  0  0  0
  2  3  1  0  0  0  0
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 19  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
 12 20  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 21  2  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045994

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C(OC)=C(C=C1)C1COC2=CC(O)=CC=C2C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H18O5/c1-20-14-6-5-13(17(21-2)16(14)19)11-7-10-3-4-12(18)8-15(10)22-9-11/h3-6,8,11,18-19H,7,9H2,1-2H3

> <INCHI_KEY>
NUNFZNIXYWTZMW-UHFFFAOYSA-N

> <FORMULA>
C17H18O5

> <MOLECULAR_WEIGHT>
302.3218

> <EXACT_MASS>
302.115423686

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
31.735353635999903

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(3-hydroxy-2,4-dimethoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol

> <ALOGPS_LOGP>
2.76

> <JCHEM_LOGP>
2.8763353459999994

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.932811730625065

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.249227754479632

> <JCHEM_PKA_STRONGEST_BASIC>
-4.408625702418465

> <JCHEM_POLAR_SURFACE_AREA>
68.15

> <JCHEM_REFRACTIVITY>
81.8866

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.76e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(3-hydroxy-2,4-dimethoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -4.003  -2.309   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.771  -1.539   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.771  -0.001   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.385   0.769   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.001  -0.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.001  -1.539   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.385  -2.309   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.385  -3.849   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.771  -4.619   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.003  -3.849   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -5.389  -4.619   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.617  -1.539   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.849  -2.309   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.235   4.619   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.235   3.079   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.003   2.309   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.617   3.079   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.231   2.309   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.231   0.769   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.617  -0.001   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.003   0.769   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.389  -0.001   0.000  0.00  0.00           O+0
CONECT    1    2   10                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   19                                                  
CONECT    6    5    7                                                       
CONECT    7    2    6    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    1    9   11                                                  
CONECT   11   10                                                            
CONECT   12   13   20                                                       
CONECT   13   12                                                            
CONECT   14   15                                                            
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19    5   18   20                                                  
CONECT   20   12   19   21                                                  
CONECT   21   16   20   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
(+/-)-mucronulatol	HMDB
(+)-Mucronulatol	HMDB
(R)-Mucronulatol	HMDB
3',7-Dihydroxy-2',4'-dimethoxyisoflavan	HMDB
Mucronulatol	MeSH

Chemical Formula

C₁₇H₁₈O₅

Average Mass

302.3218 Da

Monoisotopic Mass

302.11542 Da

IUPAC Name

3-(3-hydroxy-2,4-dimethoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol

Traditional Name

3-(3-hydroxy-2,4-dimethoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol

CAS Registry Number

57128-11-7

SMILES

COC1=C(O)C(OC)=C(C=C1)C1COC2=CC(O)=CC=C2C1

InChI Identifier

InChI=1S/C17H18O5/c1-20-14-6-5-13(17(21-2)16(14)19)11-7-10-3-4-12(18)8-15(10)22-9-11/h3-6,8,11,18-19H,7,9H2,1-2H3

InChI Key

NUNFZNIXYWTZMW-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
Astragalus adsurgens	LOTUS Database	35616633
Astragalus cicer	Plant	KNApSAcK
Dalbergia candenatensis	LOTUS Database	35616633
Dalbergia ecastaphyllum	LOTUS Database	35616633
Dalbergia odorifera	LOTUS Database	35616633
Dalbergia parviflora	LOTUS Database	35616633
Dalbergia variabilis	Plant	KNApSAcK
Indigofera aspalathoides	LOTUS Database	35616633
Machaerium mucronulatum	Plant	KNApSAcK
Oxytropis falcata	LOTUS Database	35616633
Phaseolus vulgaris	FooDB	KNAPSACK
Pterocarpus soyauxii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3'-hydroxy,4'-methoxyisoflavonoids. These are isoflavonoids carrying a methoxy group attached to the C4' atom, as well as a hydroxyl group at the C3'-position of the isoflavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

3'-hydroxy,4'-methoxyisoflavonoids

Alternative Parents

Substituents

3'-hydroxy,4'-methoxyisoflavonoid
2p-methoxyisoflavonoid-skeleton
Isoflavanol
Hydroxyisoflavonoid
Isoflavan
Benzopyran
M-dimethoxybenzene
Dimethoxybenzene
Methoxyphenol
Chromane
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Oxacycle
Organoheterocyclic compound
Ether
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	2.76	ALOGPS
logP	2.88	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	9.25	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	68.15 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	81.89 m³·mol⁻¹	ChemAxon
Polarizability	31.74 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

HMDB0030717

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002640

KNApSAcK ID

C00009715

Chemspider ID

3682776

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4484949

PDB ID

Not Available

ChEBI ID

605421

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (±)-3',7-Dihydroxy-2',4'-dimethoxyisoflavan (NP0045994)

MOL for NP0045994 ((±)-3',7-Dihydroxy-2',4'-dimethoxyisoflavan)

3D MOL for NP0045994 ((±)-3',7-Dihydroxy-2',4'-dimethoxyisoflavan)

3D SDF for NP0045994 ((±)-3',7-Dihydroxy-2',4'-dimethoxyisoflavan)

3D-SDF for NP0045994 ((±)-3',7-Dihydroxy-2',4'-dimethoxyisoflavan)

PDB for NP0045994 ((±)-3',7-Dihydroxy-2',4'-dimethoxyisoflavan)

3D PDB for NP0045994 ((±)-3',7-Dihydroxy-2',4'-dimethoxyisoflavan)

SMILES for NP0045994 ((±)-3',7-Dihydroxy-2',4'-dimethoxyisoflavan)

INCHI for NP0045994 ((±)-3',7-Dihydroxy-2',4'-dimethoxyisoflavan)

Structure for NP0045994 ((±)-3',7-Dihydroxy-2',4'-dimethoxyisoflavan)

3D Structure for NP0045994 ((±)-3',7-Dihydroxy-2',4'-dimethoxyisoflavan)