NP-MRD: Showing NP-Card for Aromadendrin 7-methyl ether (NP0047874)

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Record Information

Version

2.0

Created at

2022-03-17 20:47:22 UTC

Updated at

2022-03-17 20:47:23 UTC

NP-MRD ID

NP0047874

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Aromadendrin 7-methyl ether

Description

Aromadendrin 7-methyl ether is found in Afzelia bella, Ageratina ligustrina, Artemisia dracunculus, Artemisia scoparia , Artemisia spp. , Chromolaena odorata, Corymbia maculata, Dittrichia graveolens, Dittrichia viscosa , Eucalyptus spp. , Eupatorium capillifolium, Pulicaria undulata , Glycyrrhiza glabra , Inula graveolens, Iris pseudacorus, Iris tectorum, Podocarpus nivalis, Populus alba and Populus tremula.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241218532D          

 22 24  0  0  0  0            999 V2000
    2.8573   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8573   -1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1437   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4287   -1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4287   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1437   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5723   -1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4287    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4287    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1437    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1437   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8573   -0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4287   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7151   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7151    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0001    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0001    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0001   -0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7149   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7149    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4287    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5723   -0.2076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2  7  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
  5 19  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 15  2  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 22  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 18  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 20  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047874

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(=O)C(O)C(OC2=C1)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O6/c1-21-10-6-11(18)13-12(7-10)22-16(15(20)14(13)19)8-2-4-9(17)5-3-8/h2-7,15-18,20H,1H3

> <INCHI_KEY>
LZLGHWHSUZVUFZ-UHFFFAOYSA-N

> <FORMULA>
C16H14O6

> <MOLECULAR_WEIGHT>
302.2788

> <EXACT_MASS>
302.07903818

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
30.152362530841202

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.78

> <JCHEM_LOGP>
2.265843645666667

> <ALOGPS_LOGS>
-2.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.941597916787153

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.291140087000118

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9292704190853494

> <JCHEM_POLAR_SURFACE_AREA>
96.22

> <JCHEM_REFRACTIVITY>
77.11030000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.44e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,5-dihydroxy-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydro-1-benzopyran-4-one

> <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       5.334  -1.155   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.334  -2.695   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.002  -3.465   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -2.695   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -1.155   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.002  -0.385   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.668  -3.465   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -2.667   3.465   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.667   1.925   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.002   1.155   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.002  -0.385   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -5.334  -1.155   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.667  -1.155   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.335  -0.385   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.335   1.155   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.000   1.925   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.000   3.465   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -0.000  -1.155   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.334  -0.385   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334   1.155   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.667   1.925   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -6.668  -0.388   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   19                                                  
CONECT    6    1    5                                                       
CONECT    7    2                                                            
CONECT    8    9                                                            
CONECT    9    8   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11   22                                                       
CONECT   13   11   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15    9   14   16                                                  
CONECT   16   15   17   20                                                  
CONECT   17   16                                                            
CONECT   18   14   19                                                       
CONECT   19    5   18   20                                                  
CONECT   20   16   19   21                                                  
CONECT   21   20                                                            
CONECT   22   12                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
7-Methoxy-aromadendrin	ChEMBL

Chemical Formula

C₁₆H₁₄O₆

Average Mass

302.2788 Da

Monoisotopic Mass

302.07904 Da

IUPAC Name

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

Traditional Name

3,5-dihydroxy-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

37971-69-0

SMILES

COC1=CC(O)=C2C(=O)C(O)C(OC2=C1)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C16H14O6/c1-21-10-6-11(18)13-12(7-10)22-16(15(20)14(13)19)8-2-4-9(17)5-3-8/h2-7,15-18,20H,1H3

InChI Key

LZLGHWHSUZVUFZ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Afzelia bella	LOTUS Database	35616633
Ageratina ligustrina	LOTUS Database	35616633
Artemisia dracunculus	LOTUS Database	35616633
Artemisia scoparia	Plant	KNApSAcK
Artemisia spp.	Plant	KNApSAcK
Chromolaena odorata	LOTUS Database	35616633
Corymbia maculata	LOTUS Database	35616633
Dittrichia graveolens	LOTUS Database	35616633
Dittrichia viscosa	Plant	KNApSAcK
Eucalyptus spp.	Plant	KNApSAcK
Eupatorium capillifolium	LOTUS Database	35616633
Francoeuria undulata	Plant	KNApSAcK
Glycyrrhiza glabra	Plant	KNApSAcK
Inula graveolens	Plant	KNApSAcK
Iris pseudacorus	LOTUS Database	35616633
Iris tectorum	LOTUS Database	35616633
Podocarpus nivalis	Plant	KNApSAcK
Populus alba	Plant	KNApSAcK
Populus tremula	LOTUS Database	35616633
Prunus avium	FooDB	KNAPSACK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

7-O-methylated flavonoids

Alternative Parents

Substituents

7-methoxyflavonoid-skeleton
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavanone
Flavanonol
Hydroxyflavonoid
Flavan
Chromone
Chromane
Benzopyran
1-benzopyran
Anisole
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Secondary alcohol
Ether
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Alcohol
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	1.78	ALOGPS
logP	2.27	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	9.29	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	77.11 m³·mol⁻¹	ChemAxon
Polarizability	30.15 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

FDB012429

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

Not Available

Showing NP-Card for Aromadendrin 7-methyl ether (NP0047874)

MOL for NP0047874 (Aromadendrin 7-methyl ether)

3D MOL for NP0047874 (Aromadendrin 7-methyl ether)

3D SDF for NP0047874 (Aromadendrin 7-methyl ether)

3D-SDF for NP0047874 (Aromadendrin 7-methyl ether)

PDB for NP0047874 (Aromadendrin 7-methyl ether)

3D PDB for NP0047874 (Aromadendrin 7-methyl ether)

SMILES for NP0047874 (Aromadendrin 7-methyl ether)

INCHI for NP0047874 (Aromadendrin 7-methyl ether)

Structure for NP0047874 (Aromadendrin 7-methyl ether)

3D Structure for NP0047874 (Aromadendrin 7-methyl ether)