NP-MRD: Showing NP-Card for Dihydroglycitein (NP0339417)

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Record Information

Version

2.0

Created at

2024-09-11 21:44:01 UTC

Updated at

2024-09-11 21:44:01 UTC

NP-MRD ID

NP0339417

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dihydroglycitein

Description

Dihydroglycitein belongs to the class of organic compounds known as 6-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C6 atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one. Dihydroglycitein was first documented in 2005 (PMID: 16248547). Based on a literature review a small amount of articles have been published on Dihydroglycitein (PMID: 38687561) (PMID: 26706281).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05272300162D          

 21 23  0  0  0  0            999 V2000
    2.1096   -1.5223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3952   -1.1098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3952   -0.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1096    0.1277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8241   -0.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8241   -1.1098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0338   -1.1098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0338   -0.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6807    0.1277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6807    0.9527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0338    1.3652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8917    1.3652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1772    0.9527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4627    1.3652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7482    0.9527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7482    0.1277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4627   -0.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1772    0.1277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8917   -0.2848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8917   -1.1098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5386   -1.5223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  9  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 16  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 15  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 18  2  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
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  6 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339417

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C2OCC(C(=O)C2=C1)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1/C16H14O5/c1-20-15-6-11-14(7-13(15)18)21-8-12(16(11)19)9-2-4-10(17)5-3-9/h2-7,12,17-18H,8H2,1H3

> <INCHI_KEY>
HEZSALBPROZVOO-UHFFFAOYNA-N

> <FORMULA>
C16H14O5

> <MOLECULAR_WEIGHT>
286.283

> <EXACT_MASS>
286.084123551

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
28.87860546310053

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-3,4-dihydro-2H-1-benzopyran-4-one

> <JCHEM_LOGP>
2.2235521700000005

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.515659510163184

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.204948900447087

> <JCHEM_PKA_STRONGEST_BASIC>
-4.587152087919364

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
76.1588

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
7-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-23         0                                  
HETATM    1  C   UNK     0       3.938  -2.842   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.604  -2.072   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.604  -0.532   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.938   0.238   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.272  -0.532   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.272  -2.072   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.063  -2.072   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.063  -0.532   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.271   0.238   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.271   1.778   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.063   2.548   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -5.398   2.548   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -4.064   1.778   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.730   2.548   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.397   1.778   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.397   0.238   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.730  -0.532   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.064   0.238   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -5.398  -0.532   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -5.398  -2.072   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.605  -2.842   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5   21                                                  
CONECT    7    8                                                            
CONECT    8    7    9   16                                                  
CONECT    9    3    8   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   15                                                       
CONECT   12   13                                                            
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   11   14   16                                                  
CONECT   16    8   15   17                                                  
CONECT   17   16   18                                                       
CONECT   18   13   17   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21    6                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₄O₅

Average Mass

286.2830 Da

Monoisotopic Mass

286.08412 Da

IUPAC Name

7-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

7-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C2OCC(C(=O)C2=C1)C1=CC=C(O)C=C1

InChI Identifier

InChI=1/C16H14O5/c1-20-15-6-11-14(7-13(15)18)21-8-12(16(11)19)9-2-4-10(17)5-3-9/h2-7,12,17-18H,8H2,1H3

InChI Key

HEZSALBPROZVOO-UHFFFAOYNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as 6-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C6 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

6-O-methylated isoflavonoids

Alternative Parents

Substituents

6-methoxyisoflavonoid-skeleton
Isoflavanol
Hydroxyisoflavonoid
Isoflavanone
Isoflavan
Chromone
Chromane
Benzopyran
1-benzopyran
Anisole
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
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	2.22	ChemAxon
pKa (Strongest Acidic)	8.2	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	76.16 m³·mol⁻¹	ChemAxon
Polarizability	28.88 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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Simons AL, Renouf M, Hendrich S, Murphy PA: Metabolism of glycitein (7,4'-dihydroxy-6-methoxy-isoflavone) by human gut microflora. J Agric Food Chem. 2005 Nov 2;53(22):8519-25. doi: 10.1021/jf051546d. [PubMed:16248547 ]
Lee SB, Gupta H, Min BH, Ganesan R, Sharma SP, Won SM, Jeong JJ, Cha MG, Kwon GH, Jeong MK, Hyun JY, Eom JA, Park HJ, Yoon SJ, Lee SY, Choi MR, Kim DJ, Oh KK, Suk KT: A consortium of Hordeum vulgare and gut microbiota against non-alcoholic fatty liver disease via data-driven analysis. Artif Cells Nanomed Biotechnol. 2024 Dec;52(1):250-260. doi: 10.1080/21691401.2024.2347380. Epub 2024 Apr 30. [PubMed:38687561 ]
Tchoumtchoua J, Makropoulou M, Ateba SB, Boulaka A, Halabalaki M, Lambrinidis G, Meligova AK, Mbanya JC, Mikros E, Skaltsounis AL, Mitsiou DJ, Njamen D, Alexis MN: Estrogenic activity of isoflavonoids from the stem bark of the tropical tree Amphimas pterocarpoides, a source of traditional medicines. J Steroid Biochem Mol Biol. 2016 Apr;158:138-148. doi: 10.1016/j.jsbmb.2015.12.015. Epub 2015 Dec 17. [PubMed:26706281 ]

Showing NP-Card for Dihydroglycitein (NP0339417)

MOL for NP0339417 (Dihydroglycitein)

3D MOL for NP0339417 (Dihydroglycitein)

3D SDF for NP0339417 (Dihydroglycitein)

3D-SDF for NP0339417 (Dihydroglycitein)

PDB for NP0339417 (Dihydroglycitein)

3D PDB for NP0339417 (Dihydroglycitein)

SMILES for NP0339417 (Dihydroglycitein)

INCHI for NP0339417 (Dihydroglycitein)

Structure for NP0339417 (Dihydroglycitein)

3D Structure for NP0339417 (Dihydroglycitein)