NP-MRD: Showing NP-Card for Isomucronulatol (NP0047572)

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Record Information

Version

2.0

Created at

2022-03-17 20:42:22 UTC

Updated at

2022-03-17 20:42:22 UTC

NP-MRD ID

NP0047572

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isomucronulatol

Description

Isomucronulatol, also known as astraisoflavan, belongs to the class of organic compounds known as 4'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C4' atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one. Thus, isomucronulatol is considered to be a flavonoid lipid molecule. Isomucronulatol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Isomucronulatol has been detected, but not quantified in, several different foods, such as common beans, green beans, herbs and spices, tea, and yellow wax beans. Isomucronulatol is found in Astragalus mongholicus, Centrolobium sclerophyllum, Colutea arborescens, Gliricidia sepium , Glycyrrhiza glabra , Oxytropis falcata, Polygonatum kingianum , Robinia pseudoacacia, Sphaerophysa salsula and Wisteria brachybotrys. This could make isomucronulatol a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI

  Mrv0541 05061306582D          

 22 24  0  0  0  0            999 V2000
    6.4302    2.0625    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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    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
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  5  2  0  0  0  0
 10  3  1  0  0  0  0
 10  7  1  0  0  0  0
 11  7  1  0  0  0  0
 11  9  1  0  0  0  0
 12  4  1  0  0  0  0
 12  8  2  0  0  0  0
 13  5  1  0  0  0  0
 13 11  1  0  0  0  0
 14  6  1  0  0  0  0
 15  8  1  0  0  0  0
 15 10  2  0  0  0  0
 16 13  2  0  0  0  0
 17 14  2  0  0  0  0
 17 16  1  0  0  0  0
 18 12  1  0  0  0  0
 19 16  1  0  0  0  0
 20  1  1  0  0  0  0
 20 14  1  0  0  0  0
 21  2  1  0  0  0  0
 21 17  1  0  0  0  0
 22  9  1  0  0  0  0
 22 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047572

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C(O)=C(C=C1)C1COC2=C(C1)C=CC(O)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C17H18O5/c1-20-14-6-5-13(16(19)17(14)21-2)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>
NQRBAPDEZYMKFL-UHFFFAOYSA-N

> <FORMULA>
C17H18O5

> <MOLECULAR_WEIGHT>
302.3218

> <EXACT_MASS>
302.115423686

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
32.17713433089571

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.76

> <JCHEM_LOGP>
2.8763353459999994

> <ALOGPS_LOGS>
-3.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.444819214034608

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.673582950436826

> <JCHEM_PKA_STRONGEST_BASIC>
-4.424854346806153

> <JCHEM_POLAR_SURFACE_AREA>
68.15

> <JCHEM_REFRACTIVITY>
81.8866

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.22e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isomucronulatol

> <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      12.003   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   21                                                            
CONECT    3    4   10                                                       
CONECT    4    3   12                                                       
CONECT    5    6   13                                                       
CONECT    6    5   14                                                       
CONECT    7   10   11                                                       
CONECT    8   12   15                                                       
CONECT    9   11   22                                                       
CONECT   10    3    7   15                                                  
CONECT   11    7    9   13                                                  
CONECT   12    4    8   18                                                  
CONECT   13    5   11   16                                                  
CONECT   14    6   17   20                                                  
CONECT   15    8   10   22                                                  
CONECT   16   13   17   19                                                  
CONECT   17   14   16   21                                                  
CONECT   18   12                                                            
CONECT   19   16                                                            
CONECT   20    1   14                                                       
CONECT   21    2   17                                                       
CONECT   22    9   15                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
2',7-Dihydroxy-3',4'-dimethoxyisoflavan	HMDB
7,2'-Dihydroxy-3',4'-dimethoxyisoflavan	HMDB
Astraisoflavan	HMDB

Chemical Formula

C₁₇H₁₈O₅

Average Mass

302.3218 Da

Monoisotopic Mass

302.11542 Da

IUPAC Name

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

Traditional Name

isomucronulatol

CAS Registry Number

64474-51-7

SMILES

COC1=C(OC)C(O)=C(C=C1)C1COC2=C(C1)C=CC(O)=C2

InChI Identifier

InChI=1S/C17H18O5/c1-20-14-6-5-13(16(19)17(14)21-2)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

NQRBAPDEZYMKFL-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Astragalus mongholicus	Plant	KNApSAcK
Centrolobium sclerophyllum	LOTUS Database	35616633
Colutea arborescens	Plant	KNApSAcK
Gliricidia sepium	Plant	KNApSAcK
Glycyrrhiza glabra	Plant	KNApSAcK
Oxytropis falcata	LOTUS Database	35616633
Phaseolus vulgaris	FooDB	KNAPSACK
Polygonatum kingianum	Plant	KNApSAcK
Robinia pseudoacacia	LOTUS Database	35616633
Sphaerophysa salsula	Plant	KNApSAcK
Wisteria brachybotrys	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C4' atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

4'-O-methylated isoflavonoids

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Isoflavans (LMPK12080033 )

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)	9.67	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	32.18 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

HMDB0033189

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011201

KNApSAcK ID

C00009714

Chemspider ID

523468

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

602152

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Isomucronulatol (NP0047572)

MOL for NP0047572 (Isomucronulatol)

3D MOL for NP0047572 (Isomucronulatol)

3D SDF for NP0047572 (Isomucronulatol)

3D-SDF for NP0047572 (Isomucronulatol)

PDB for NP0047572 (Isomucronulatol)

3D PDB for NP0047572 (Isomucronulatol)

SMILES for NP0047572 (Isomucronulatol)

INCHI for NP0047572 (Isomucronulatol)

Structure for NP0047572 (Isomucronulatol)

3D Structure for NP0047572 (Isomucronulatol)