NP-MRD: Showing NP-Card for O-Desmethylangolensin (NP0087187)

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Record Information

Version

2.0

Created at

2022-05-11 16:42:32 UTC

Updated at

2022-05-11 16:42:32 UTC

NP-MRD ID

NP0087187

Secondary Accession Numbers

None

Natural Product Identification

Common Name

O-Desmethylangolensin

Description

O-Desmethylangolensin belongs to the class of organic compounds known as alpha-methyldeoxybenzoin flavonoids. These are flavonoids with a structure based on a 1,2-diphenyl-2-propan-2-one. It is an intestinal bacterial metabolite of the soy phytoestrogen daidzein. O-Desmethylangolensin is an extremely weak basic (essentially neutral) compound (based on its pKa). O-Desmethylangolensin is a potentially toxic compound. O-DMA producers were associated with 69% greater mammographic density and 6% bone density. O-Desmethylangolensin (O-DMA) is a phytoestrogen. O-Desmethylangolensin was first documented in 2007 (PMID: 17506823). It produced in some people, deemed O-DMA producers, but not others (PMID: 18326607).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 34  0  0  0  0  0  0  0  0999 V2000
   -1.4315   -0.8167   -2.5569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5561   -0.8712   -1.2864 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5733    0.0444   -1.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5995    0.6912   -2.5600 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6377    0.2330   -0.5169 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5476   -0.5418    0.6406 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5094   -0.4581    1.6305 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5918    0.3892    1.5160 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5354    0.4395    2.5389 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6809    1.1470    0.3846 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7074    1.0755   -0.6384 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8720    1.8710   -1.7423 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4600   -0.5078   -0.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0769   -1.5125    0.5394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9371   -1.2491    1.6006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1989    0.0499    1.9783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0632    0.3385    3.0456 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5779    1.0544    1.2662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7150    0.7947    0.2020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9048   -1.3296   -3.3767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5578    0.2639   -2.7743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4242   -1.2647   -2.3278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2743   -1.9426   -1.1983 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7215   -1.2176    0.7609 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4415   -1.0595    2.5317 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3257    1.0641    2.4456 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5172    1.8155    0.2733 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3162    1.9557   -2.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9089   -2.5456    0.2880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4278   -2.0345    2.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0573    0.4714    2.8959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7803    2.0751    1.5591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2251    1.5774   -0.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5 11  2  0
 11 12  1  0
 11 10  1  0
 10  8  2  0
  8  9  1  0
  8  7  1  0
  7  6  2  0
  2 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
  6  5  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  1
 12 28  1  0
 10 27  1  0
  9 26  1  0
  7 25  1  0
  6 24  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
M  END


  Mrv1652310011709302D          

 19 20  0  0  0  0            999 V2000
   19.2481  -16.0110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5335  -17.2486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6770  -12.7110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9625  -19.7236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6770  -16.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6770  -15.1860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9625  -16.4236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3915  -16.4236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9625  -17.2486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9625  -14.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3915  -14.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2481  -17.6611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6770  -17.6611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9625  -13.9485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3915  -13.9485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6770  -13.5360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2481  -18.4861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6770  -18.4861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9625  -18.8985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  2  0  0  0  0
  2 12  1  0  0  0  0
  3 16  1  0  0  0  0
  4 19  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6 10  2  0  0  0  0
  6 11  1  0  0  0  0
  7  9  1  0  0  0  0
  9 12  2  0  0  0  0
  9 13  1  0  0  0  0
 10 14  1  0  0  0  0
 11 15  2  0  0  0  0
 12 17  1  0  0  0  0
 13 18  2  0  0  0  0
 14 16  2  0  0  0  0
 15 16  1  0  0  0  0
 17 19  2  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0087187

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O4/c1-9(10-2-4-11(16)5-3-10)15(19)13-7-6-12(17)8-14(13)18/h2-9,16-18H,1H3

> <INCHI_KEY>
JDJPNKPFDDUBFV-UHFFFAOYSA-N

> <FORMULA>
C15H14O4

> <MOLECULAR_WEIGHT>
258.2693

> <EXACT_MASS>
258.089208936

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
26.376559364739467

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.98

> <JCHEM_LOGP>
3.647523467666667

> <ALOGPS_LOGS>
-3.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.333559153112283

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.832218337443113

> <JCHEM_PKA_STRONGEST_BASIC>
-4.912202076859793

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
71.69990000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.39e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
O-desmethylangolensin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 01-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-OCT-17         0                                  
HETATM    1  O   UNK     0      35.930 -29.887   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      34.596 -32.197   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      38.597 -23.727   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      37.263 -36.817   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      38.597 -29.887   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      38.597 -28.347   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      37.263 -30.657   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      39.931 -30.657   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      37.263 -32.197   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      37.263 -27.577   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      39.931 -27.577   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      35.930 -32.967   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      38.597 -32.967   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      37.263 -26.037   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      39.931 -26.037   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      38.597 -25.267   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      35.930 -34.507   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      38.597 -34.507   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      37.263 -35.277   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2   12                                                            
CONECT    3   16                                                            
CONECT    4   19                                                            
CONECT    5    6    7    8                                                  
CONECT    6    5   10   11                                                  
CONECT    7    1    5    9                                                  
CONECT    8    5                                                            
CONECT    9    7   12   13                                                  
CONECT   10    6   14                                                       
CONECT   11    6   15                                                       
CONECT   12    2    9   17                                                  
CONECT   13    9   18                                                       
CONECT   14   10   16                                                       
CONECT   15   11   16                                                       
CONECT   16    3   14   15                                                  
CONECT   17   12   19                                                       
CONECT   18   13   19                                                       
CONECT   19    4   17   18                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Value	Source
2',4'-Dihydroxy-2-(p-hydroxyphenyl)-propiophenone	HMDB
2,4-Dihydroxyphenyl p-hydroxyphenethyl ketone	HMDB
O-Demethylangolensin	HMDB
O-Demethylangolesin	HMDB
O-Desmethylangolensin	MeSH

Chemical Formula

C₁₅H₁₄O₄

Average Mass

258.2693 Da

Monoisotopic Mass

258.08921 Da

IUPAC Name

1-(2,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)propan-1-one

Traditional Name

O-desmethylangolensin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H14O4/c1-9(10-2-4-11(16)5-3-10)15(19)13-7-6-12(17)8-14(13)18/h2-9,16-18H,1H3

InChI Key

JDJPNKPFDDUBFV-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha-methyldeoxybenzoin flavonoids. These are flavonoids with a structure based on a 1,2-diphenyl-2-propan-2-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Alpha-methyldeoxybenzoin flavonoids

Sub Class

Not Available

Direct Parent

Alpha-methyldeoxybenzoin flavonoids

Alternative Parents

Substituents

Alpha-methyldeoxybenzoin flavonoid
Stilbene
Alkyl-phenylketone
Phenylketone
Phenylpropane
Benzoyl
Aryl alkyl ketone
Aryl ketone
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
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	3.65	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	7.83	ChemAxon
pKa (Strongest Basic)	-4.9	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	71.7 m³·mol⁻¹	ChemAxon
Polarizability	26.38 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

HMDB0004629

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023387

KNApSAcK ID

Not Available

Chemspider ID

80750

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

O-Desmethylangolensin

METLIN ID

Not Available

PubChem Compound

89472

PDB ID

Not Available

ChEBI ID

88902

Good Scents ID

Not Available

References

General References

Atkinson C, Newton KM, Bowles EJ, Yong M, Lampe JW: Demographic, anthropometric, and lifestyle factors and dietary intakes in relation to daidzein-metabolizing phenotypes among premenopausal women in the United States. Am J Clin Nutr. 2008 Mar;87(3):679-87. doi: 10.1093/ajcn/87.3.679. [PubMed:18326607 ]
Possemiers S, Bolca S, Eeckhaut E, Depypere H, Verstraete W: Metabolism of isoflavones, lignans and prenylflavonoids by intestinal bacteria: producer phenotyping and relation with intestinal community. FEMS Microbiol Ecol. 2007 Aug;61(2):372-83. doi: 10.1111/j.1574-6941.2007.00330.x. Epub 2007 May 16. [PubMed:17506823 ]

Showing NP-Card for O-Desmethylangolensin (NP0087187)

MOL for NP0087187 (O-Desmethylangolensin)

3D MOL for NP0087187 (O-Desmethylangolensin)

3D SDF for NP0087187 (O-Desmethylangolensin)

3D-SDF for NP0087187 (O-Desmethylangolensin)

PDB for NP0087187 (O-Desmethylangolensin)

3D PDB for NP0087187 (O-Desmethylangolensin)

SMILES for NP0087187 (O-Desmethylangolensin)

INCHI for NP0087187 (O-Desmethylangolensin)

Structure for NP0087187 (O-Desmethylangolensin)

3D Structure for NP0087187 (O-Desmethylangolensin)