Showing Compound Demethylmedicarpin (FDB012305)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:06 UTC

Update date

2025-11-18 23:35:37 UTC

Primary ID

FDB012305

Secondary Accession Numbers

FDB017326

Chemical Information

FooDB Name

Demethylmedicarpin

Description

(6ar,11ar)-3,9-dihydroxypterocarpan is a member of the class of compounds known as pterocarpans. Pterocarpans are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids. Thus, (6ar,11ar)-3,9-dihydroxypterocarpan is considered to be a flavonoid lipid molecule (6ar,11ar)-3,9-dihydroxypterocarpan is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (6ar,11ar)-3,9-dihydroxypterocarpan can be found in a number of food items such as bayberry, sweet bay, agave, and red bell pepper, which makes (6ar,11ar)-3,9-dihydroxypterocarpan a potential biomarker for the consumption of these food products.

CAS Number

61135-91-9

Structure

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

Synonyms

Synonym	Source
6a,11a-Dihydro-6H-benzofuro[3,2-c][1]benzopyran-3,9-diol, 9CI	db_source
Demethylmedicarpin	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.25 g/L	ALOGPS
logP	2.59	ALOGPS
logP	2.36	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9.18	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.58 m³·mol⁻¹	ChemAxon
Polarizability	26.15 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C15H12O4

IUPAC name

8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2,4,6,11,13,15-hexaene-5,14-diol

InChI Identifier

InChI=1S/C15H12O4/c16-8-2-4-11-13(5-8)18-7-12-10-3-1-9(17)6-14(10)19-15(11)12/h1-6,12,15-17H,7H2

InChI Key

ODMIEGVTNZNSLD-UHFFFAOYSA-N

Isomeric SMILES

OC1=CC2=C(C=C1)C1COC3=C(C=CC(O)=C3)C1O2

Average Molecular Weight

256.2534

Monoisotopic Molecular Weight

256.073558872

Classification

Description

Belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Furanoisoflavonoids

Direct Parent

Pterocarpans

Alternative Parents

Substituents

Isoflavanol
Pterocarpan
Isoflavan
Chromane
Benzopyran
1-benzopyran
Benzofuran
Coumaran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Ether
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Pterocarpans (LMPK12070029 )
a small molecule (CPD-4402 )

Ontology

Disposition

Source:

Endogenous

Biological:

Plant

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 70.31%; H 4.72%; O 24.97%	DFC
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	297 () (EtOH/NaOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Demethylmedicarpin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00g0-6329000000-fc29454cfabfe5b90489	Spectrum
Predicted GC-MS	Demethylmedicarpin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a7l-0490000000-d0d6aad3768f4394b54e	Spectrum
Predicted GC-MS	Demethylmedicarpin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Demethylmedicarpin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0090000000-b4d3d962d4edda524b4a	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0090000000-e8ba73a8069699b1ccf3	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fr2-9340000000-d4db6ecce14b6731a8e9	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0090000000-b65dbf8f578624acf482	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0090000000-2606bdd52dafe16779e5	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0079-2690000000-aa5bd5132609138ef347	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0090000000-82e226df9342cd67d796	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0090000000-2b9b6b8baddb6aa1ed17	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udr-1290000000-52130369d2ad4e66a503	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0090000000-b46e3a63d530434294a2	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0090000000-972b3b65f4d4b2006980	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-7690000000-d513b6f5f51de88969fe	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

2594447

ChEMBL ID

CHEMBL238823

KEGG Compound ID

Not Available

Pubchem Compound ID

3347979

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

HFV12-L:HFV12-L

EAFUS ID

Not Available

Dr. Duke ID

DEMETHYLMEDICARPIN|DEMTHYLMEDICARPIN

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Medicarpin

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Fungicide	24127	An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	DUKE
Phytoalexin	26115	A plant-derived compound that plays a biological role in defense against pathogens. It has therapeutic applications as an antimicrobial, antioxidant, and anti-inflammatory agent, with key medical uses in managing infections, cancer, and neurodegenerative diseases.	DUKE