NP-MRD: Showing NP-Card for 2-Dehydro-O-desmethylangolensin (NP0339413)

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Record Information

Version

2.0

Created at

2024-09-11 21:42:52 UTC

Updated at

2024-09-11 21:42:52 UTC

NP-MRD ID

NP0339413

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-Dehydro-O-desmethylangolensin

Description

2-Dehydro-O-desmethylangolensin belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. 2-Dehydro-O-desmethylangolensin is a polyphenol metabolite detected in biological fluids (PMID: 20428313 ). 2-Dehydro-O-desmethylangolensin is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02271201282D          

 19 20  0  0  0  0            999 V2000
    1.4289   -0.3039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.1289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.5414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.1289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5723   -1.5414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5723   -2.3664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.7789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.7789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.3664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.5414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.3664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.1289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.5414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.3664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.1289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.3039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.1086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.3039    0.0000 C   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
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 12 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339413

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=C1)C(=C)C(=O)C1=C(O)C=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O4/c1-9(10-2-4-11(16)5-3-10)15(19)13-7-6-12(17)8-14(13)18/h2-8,16-18H,1H2

> <INCHI_KEY>
MPNKZWIUITZJCR-UHFFFAOYSA-N

> <FORMULA>
C15H12O4

> <MOLECULAR_WEIGHT>
256.2534

> <EXACT_MASS>
256.073558872

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
25.812361794423367

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(2,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)prop-2-en-1-one

> <ALOGPS_LOGP>
2.98

> <JCHEM_LOGP>
3.694578172

> <ALOGPS_LOGS>
-2.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.810108014477263

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.716540156433847

> <JCHEM_PKA_STRONGEST_BASIC>
-5.922553552955372

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
71.50330000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.18e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(2,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)prop-2-en-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  C   UNK     0       2.667  -0.567   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -2.107   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -2.877   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -2.107   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -2.877   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -4.417   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.002  -5.187   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.335  -5.187   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -4.417   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.877   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334  -4.417   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.000  -2.107   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334  -2.877   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.334  -4.417   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.667  -2.107   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667  -0.567   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.001   0.203   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.334   0.203   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000  -0.567   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8    3                                                       
CONECT   10    2   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   19                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   12                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₂O₄

Average Mass

256.2534 Da

Monoisotopic Mass

256.07356 Da

IUPAC Name

1-(2,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)prop-2-en-1-one

Traditional Name

1-(2,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)prop-2-en-1-one

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1)C(=C)C(=O)C1=C(O)C=C(O)C=C1

InChI Identifier

InChI=1S/C15H12O4/c1-9(10-2-4-11(16)5-3-10)15(19)13-7-6-12(17)8-14(13)18/h2-8,16-18H,1H2

InChI Key

MPNKZWIUITZJCR-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Benzoyl
Resorcinol
Aryl ketone
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Alpha-branched alpha,beta-unsaturated-ketone
Benzenoid
Acryloyl-group
Enone
Vinylogous acid
Alpha,beta-unsaturated ketone
Ketone
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	2.98	ALOGPS
logP	3.69	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	7.72	ChemAxon
pKa (Strongest Basic)	-5.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	71.5 m³·mol⁻¹	ChemAxon
Polarizability	25.81 Å³	ChemAxon
Number of Rings	2	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

HMDB0041647

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029802

KNApSAcK ID

Not Available

Chemspider ID

8396211

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10220719

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 2-Dehydro-O-desmethylangolensin (NP0339413)

MOL for NP0339413 (2-Dehydro-O-desmethylangolensin)

3D MOL for NP0339413 (2-Dehydro-O-desmethylangolensin)

3D SDF for NP0339413 (2-Dehydro-O-desmethylangolensin)

3D-SDF for NP0339413 (2-Dehydro-O-desmethylangolensin)

PDB for NP0339413 (2-Dehydro-O-desmethylangolensin)

3D PDB for NP0339413 (2-Dehydro-O-desmethylangolensin)

SMILES for NP0339413 (2-Dehydro-O-desmethylangolensin)

INCHI for NP0339413 (2-Dehydro-O-desmethylangolensin)

Structure for NP0339413 (2-Dehydro-O-desmethylangolensin)

3D Structure for NP0339413 (2-Dehydro-O-desmethylangolensin)