Showing Compound Epirosmanol (FDB014571)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:21 UTC

Update date

2019-11-26 03:10:21 UTC

Primary ID

FDB014571

Secondary Accession Numbers

FDB014574

Chemical Information

FooDB Name

Epirosmanol

Description

Epirosmanol belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Epirosmanol is an extremely weak basic (essentially neutral) compound (based on its pKa).

CAS Number

93380-12-2

Structure

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

Synonyms

Synonym	Source
Epirosmanol	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.71 g/L	ALOGPS
logP	3.23	ALOGPS
logP	3.58	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	9.18	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	92.71 m³·mol⁻¹	ChemAxon
Polarizability	36.71 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

C20H26O5

IUPAC name

3,4,8-trihydroxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one

InChI Identifier

InChI=1S/C20H26O5/c1-9(2)10-8-11-12(15(23)13(10)21)20-7-5-6-19(3,4)17(20)16(14(11)22)25-18(20)24/h8-9,14,16-17,21-23H,5-7H2,1-4H3

InChI Key

LCAZOMIGFDQMNC-UHFFFAOYSA-N

Isomeric SMILES

CC(C)C1=CC2=C(C(O)=C1O)C13CCCC(C)(C)C1C(OC3=O)C2O

Average Molecular Weight

346.4174

Monoisotopic Molecular Weight

346.178023942

Classification

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Cell and elements:

Extracellular

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 69.34%; H 7.56%; O 23.09%	DFC
Melting Point	Mp 221-225°	DFC
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	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Epirosmanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0ge9-2109000000-9d93dccd8ed743137d57	Spectrum
Predicted GC-MS	Epirosmanol, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fxt-2000390000-498f9fca21840b17028c	Spectrum
Predicted GC-MS	Epirosmanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Epirosmanol, 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	splash10-0002-0009000000-905a732cb2d82347cdb2	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ktb-1229000000-b8e22561e1a73e0239ff	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-060r-9665000000-54ec222ff6eb3f978056	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0009000000-677a82e821e0052e35d9	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0009000000-7c88f112edd15629a635	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0q2d-0694000000-3230629662f4e7a284ab	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0009000000-832de73587d391ac4226	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0009000000-7fd36dd751a1f109b0ef	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-2592000000-1717072eb6877429afcb	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0009000000-04a8446e8df9492a0080	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0109000000-313f339b0098e27e3fdd	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01bi-2961000000-86ecd9e9fb577e080fb5	Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

669

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

JSS66-Y:JSS55-U

EAFUS ID

Not Available

Dr. Duke ID

EPIROSMANOL

BIGG ID

Not Available

KNApSAcK ID

C00030193

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

Not Available

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

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Showing Compound Epirosmanol (FDB014571)

Structure for FDB014571 (Epirosmanol)