T3DB: O-Desmethylangolensin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (2)XML

Targets (2)

Record Information

Version

2.0

Creation Date

2014-08-29 04:47:47 UTC

Update Date

2014-12-24 20:26:35 UTC

Accession Number

T3D3965

Identification

Common Name

O-Desmethylangolensin

Class

Small Molecule

Description

O-Desmethylangolensin (ODMA) is a metabolite of the soy isoflavone daidzein by intestinal bacteria in approximately 80-90% of persons. Studies suggest beneficial health effects associated with daidzein-metabolizing phenotypes, and there is some small association between ODMA production and some phenotypes. Few dietary factors are associated with daidzein-metabolizing phenotypes. However, it remains unclear why some, but not all, persons harbor ODMA-producing bacteria. ODMA production is inversely associated with age, height, weight, and body mass index. In addition, Asians are less likely than whites to be ODMA producers, and former smokers were more likely than never smokers to be ODMA producers. Investigators have attempted to identify the bacteria involved in ODMA production, and several candidate bacteria were associated, but not definitely identified. ODMA production is correlated with the abundance of methanogens, indicating that the metabolic fate of daidzein may be related to intestinal H(2) metabolism. (1, 2).

Compound Type

Animal Toxin
Ester
Food Toxin
Industrial/Workplace Toxin
Metabolite
Natural Compound
Organic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym
2',4'-Dihydroxy-2-(p-hydroxyphenyl)-Propiophenone
2,4-Dihydroxyphenyl p-hydroxyphenethyl ketone
O-Demethylangolensin
O-Demethylangolesin

Chemical Formula

C₁₅H₁₄O₄

Average Molecular Mass

258.269 g/mol

Monoisotopic Mass

258.089 g/mol

CAS Registry Number

21255-69-6

IUPAC Name

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

Traditional Name

O-desmethylangolensin

SMILES

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

InChI Identifier

InChI=1/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

InChIKey=JDJPNKPFDDUBFV-UHFFFAOYNA-N

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

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available
LogP	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.084 g/L	ALOGPS
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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-1900000000-39495ea1c0376894fddf	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0a4i-4430900000-0e7b58ddbbc19e665858	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0390000000-95a81edd733d13d61677	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000b-1930000000-6a844b2d3f64f75db87b	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-4900000000-3c4808d490aaff85f058	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0190000000-1b486ce055fb4c745e83	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0490000000-f6b7ddbf92a2c481414b	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0aou-6910000000-ef3d7901fc4103baf88d	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0090000000-c2a50a42dfada53572a9	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-2590000000-ff1a68dd0b89bc03287c	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-6900000000-8f8d3654f73a1a919a16	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0390000000-1ca6275f205a504ebd5c	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-1910000000-a1d96f103a978278101f	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00fu-8900000000-a6ac1b1337f1eee505a2	2021-09-24	View Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

O-desmethylangolensin (ODMA) exerts androgen receptor antagonistic activity and agonistic activity towards estrogen receptor (ER)-α and ERβ. The structure of ODMA is somewhat similar to estrogen. (3)

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB04629

PubChem Compound ID

89472

ChEMBL ID

Not Available

ChemSpider ID

80750

KEGG ID

Not Available

UniProt ID

Not Available

OMIM ID

ChEBI ID

Not Available

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Not Available

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Not Available

References

Synthesis Reference

Salakka, A.; Wahala, K. Synthesis of a-methyldeoxybenzoins. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1999), (18), 2601-2604.

MSDS

Not Available

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. [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. Epub 2007 May 16. [17506823 ]
Frankenfeld CL, Atkinson C, Wahala K, Lampe JW: Obesity prevalence in relation to gut microbial environments capable of producing equol or O-desmethylangolensin from the isoflavone daidzein. Eur J Clin Nutr. 2014 Apr;68(4):526-30. doi: 10.1038/ejcn.2014.23. Epub 2014 Feb 26. [24569543 ]

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. Estrogen receptor

General Function:: Zinc ion binding
Specific Function:: Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
Gene Name:: ESR1
Uniprot ID:: P03372
Molecular Weight:: 66215.45 Da

Target Details

2. Estrogen receptor beta

General Function:: Zinc ion binding
Specific Function:: Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560). Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA-binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual.
Gene Name:: ESR2
Uniprot ID:: Q92731
Molecular Weight:: 59215.765 Da

O-Desmethylangolensin (T3D3965)

Structure for T3D3965: O-Desmethylangolensin

Targets