NP-MRD: Showing NP-Card for 3,5,7,4'-Tetrahydroxy-6-methoxyflavanone 3-acetate (NP0050592)

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Record Information

Version

2.0

Created at

2022-04-27 21:58:20 UTC

Updated at

2022-04-27 21:58:20 UTC

NP-MRD ID

NP0050592

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,5,7,4'-Tetrahydroxy-6-methoxyflavanone 3-acetate

Description

6-Methoxyaromadendrin 3-O-acetate belongs to the class of organic compounds known as 6-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone. 3,5,7,4'-Tetrahydroxy-6-methoxyflavanone 3-acetate is found in Eremophila glutinosa and Hymenoxys turneri. 3,5,7,4'-Tetrahydroxy-6-methoxyflavanone 3-acetate was first documented in 2020 (PMID: 33403280). Based on a literature review very few articles have been published on 6-methoxyaromadendrin 3-O-acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304272223582D          

 26 28  0  0  1  0            999 V2000
   -0.7145   -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
    0.0000   -1.6500    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  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
    1.4289   -2.4750    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
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    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
    2.8579    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
    4.2868    0.8250    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
    3.5724   -0.4125    0.0000 C   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
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   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
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  9 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  8 16  1  6  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 19 22  1  0  0  0  0
  3 23  1  0  0  0  0
  2 24  1  0  0  0  0
 24 25  1  0  0  0  0
  1 26  1  0  0  0  0
M  END


  Mrv1652304272223582D          

 26 28  0  0  1  0            999 V2000
   -0.7145   -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
    0.0000   -1.6500    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  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
    1.4289   -2.4750    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
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    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
    2.8579    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
    4.2868    0.8250    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
    3.5724   -0.4125    0.0000 C   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
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   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
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  9 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  8 16  1  6  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 19 22  1  0  0  0  0
  3 23  1  0  0  0  0
  2 24  1  0  0  0  0
 24 25  1  0  0  0  0
  1 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050592

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C2O[C@@H]([C@@H](OC(C)=O)C(=O)C2=C1O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O8/c1-8(19)25-18-15(23)13-12(7-11(21)17(24-2)14(13)22)26-16(18)9-3-5-10(20)6-4-9/h3-7,16,18,20-22H,1-2H3/t16-,18+/m1/s1

> <INCHI_KEY>
SZKFMAOEZUMSRT-AEFFLSMTSA-N

> <FORMULA>
C18H16O8

> <MOLECULAR_WEIGHT>
360.318

> <EXACT_MASS>
360.084517475

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
34.4477254862099

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-6-methoxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl acetate

> <ALOGPS_LOGP>
2.62

> <JCHEM_LOGP>
2.4034037343333323

> <ALOGPS_LOGS>
-3.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.35461189826977

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.253654660966426

> <JCHEM_PKA_STRONGEST_BASIC>
-4.221317217883301

> <JCHEM_POLAR_SURFACE_AREA>
122.52000000000001

> <JCHEM_REFRACTIVITY>
88.2427

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.91e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-6-methoxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    6   26                                                  
CONECT    2    1    3   24                                                  
CONECT    3    2    4   23                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    9   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    8   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22   19                                                            
CONECT   23    3                                                            
CONECT   24    2   25                                                       
CONECT   25   24                                                            
CONECT   26    1                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Value	Source
3,5,7,4'-Tetrahydroxy-6-methoxyflavanone 3-acetate	ChEBI
3,5,7,4'-Tetrahydroxy-6-methoxyflavanone 3-acetic acid	Generator
6-Methoxyaromadendrin 3-O-acetic acid	Generator

Chemical Formula

C₁₈H₁₆O₈

Average Mass

360.3180 Da

Monoisotopic Mass

360.08452 Da

IUPAC Name

(2R,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-6-methoxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl acetate

Traditional Name

(2R,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-6-methoxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl acetate

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C2O[C@@H]([C@@H](OC(C)=O)C(=O)C2=C1O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C18H16O8/c1-8(19)25-18-15(23)13-12(7-11(21)17(24-2)14(13)22)26-16(18)9-3-5-10(20)6-4-9/h3-7,16,18,20-22H,1-2H3/t16-,18+/m1/s1

InChI Key

SZKFMAOEZUMSRT-AEFFLSMTSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Eremophila glutinosa	Plant	KNApSAcK
Hymenoxys turneri	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

6-O-methylated flavonoids

Alternative Parents

Substituents

6-methoxyflavonoid-skeleton
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavanone
Flavanonol
Hydroxyflavonoid
Flavan
Chromone
Chromane
Benzopyran
1-benzopyran
Aryl alkyl ketone
Aryl ketone
Anisole
Phenol
Alkyl aryl ether
Alpha-acyloxy ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Carboxylic acid ester
Ether
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

acetate ester (CHEBI:2210 )
trihydroxyflavanone (CHEBI:2210 )
monomethoxyflavanone (CHEBI:2210 )
Dihyroflavonols (C09764 )

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	2.62	ALOGPS
logP	2.4	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	8.25	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	122.52 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	88.24 m³·mol⁻¹	ChemAxon
Polarizability	34.45 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

C00000979

Chemspider ID

390856

KEGG Compound ID

C09764

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442415

PDB ID

Not Available

ChEBI ID

2210

Good Scents ID

Not Available

References

General References

Kim S, Kim J, Kim N, Lee D, Lee H, Lee DY, Kim KH: Metabolomic Elucidation of the Effect of Sucrose on the Secondary Metabolite Profiles in Melissa officinalis by Ultraperformance Liquid Chromatography-Mass Spectrometry. ACS Omega. 2020 Dec 15;5(51):33186-33195. doi: 10.1021/acsomega.0c04745. eCollection 2020 Dec 29. [PubMed:33403280 ]

Showing NP-Card for 3,5,7,4'-Tetrahydroxy-6-methoxyflavanone 3-acetate (NP0050592)

MOL for NP0050592 (3,5,7,4'-Tetrahydroxy-6-methoxyflavanone 3-acetate)

3D MOL for NP0050592 (3,5,7,4'-Tetrahydroxy-6-methoxyflavanone 3-acetate)

3D SDF for NP0050592 (3,5,7,4'-Tetrahydroxy-6-methoxyflavanone 3-acetate)

3D-SDF for NP0050592 (3,5,7,4'-Tetrahydroxy-6-methoxyflavanone 3-acetate)

PDB for NP0050592 (3,5,7,4'-Tetrahydroxy-6-methoxyflavanone 3-acetate)

3D PDB for NP0050592 (3,5,7,4'-Tetrahydroxy-6-methoxyflavanone 3-acetate)

SMILES for NP0050592 (3,5,7,4'-Tetrahydroxy-6-methoxyflavanone 3-acetate)

INCHI for NP0050592 (3,5,7,4'-Tetrahydroxy-6-methoxyflavanone 3-acetate)

Structure for NP0050592 (3,5,7,4'-Tetrahydroxy-6-methoxyflavanone 3-acetate)

3D Structure for NP0050592 (3,5,7,4'-Tetrahydroxy-6-methoxyflavanone 3-acetate)