Showing Compound (3S)-2,3-epoxy-2,3-dihydrosqualene (FDB030118)

Record Information

Version

1.0

Creation date

2015-05-07 18:39:01 UTC

Update date

2019-11-26 03:21:36 UTC

Primary ID

FDB030118

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(3S)-2,3-epoxy-2,3-dihydrosqualene

Description

(3s)-2,3-epoxy-2,3-dihydrosqualene, also known as 2,3-oxidosqualene or (S)-squalene-2,3-epoxide, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Thus, (3s)-2,3-epoxy-2,3-dihydrosqualene is considered to be an isoprenoid lipid molecule (3s)-2,3-epoxy-2,3-dihydrosqualene is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). (3s)-2,3-epoxy-2,3-dihydrosqualene can be found in a number of food items such as garden rhubarb, sourdough, mexican oregano, and red raspberry, which makes (3s)-2,3-epoxy-2,3-dihydrosqualene a potential biomarker for the consumption of these food products (3s)-2,3-epoxy-2,3-dihydrosqualene exists in all eukaryotes, ranging from yeast to humans.

CAS Number

Not Available

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(3R,S)-Oxidosqualene	HMDB
(3S)-2,2-Dimethyl-3-[(3E,7E,11E,15E)-3,7,12,16,20-pentamethyl-3,7,11,15,19-heneicosapentaen-1-yl]oxirane	HMDB
(3S)-2,3-Dihydro-2,3-epoxysqualene	ChEBI
(3S)-2,3-Epoxy-2,3-dihydrosqualene	ChEBI
(3S)-2,3-Epoxysqualene	HMDB
(3S)-2,3-Oxidosqualene	HMDB
(3S)-Oxidosqualene	HMDB
(3S)-Squalene-2,3-epoxide	HMDB
(R,S)-Squalene 2,3-epoxide	HMDB
(RS)-2,3-Epoxy-2,3-dihydrosqualene	HMDB

Showing 1 to 10 of 41 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.00042 g/L	ALOGPS
logP	8.58	ALOGPS
logP	9.44	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.53 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	143.46 m³·mol⁻¹	ChemAxon
Polarizability	57.02 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C30H50O

IUPAC name

(3S)-2,2-dimethyl-3-[(3E,7E,11E,15E)-3,7,12,16,20-pentamethylhenicosa-3,7,11,15,19-pentaen-1-yl]oxirane

InChI Identifier

InChI=1S/C30H50O/c1-24(2)14-11-17-27(5)20-12-18-25(3)15-9-10-16-26(4)19-13-21-28(6)22-23-29-30(7,8)31-29/h14-16,20-21,29H,9-13,17-19,22-23H2,1-8H3/b25-15+,26-16+,27-20+,28-21+/t29-/m0/s1

InChI Key

QYIMSPSDBYKPPY-RSKUXYSASA-N

Isomeric SMILES

CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CC[C@@H]1OC1(C)C

Average Molecular Weight

426.7174

Monoisotopic Molecular Weight

426.386166222

Classification

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

2,3-epoxysqualene (CHEBI:15441 )
Acyclic triterpenoids (C01054 )
Liner triterpenes (C01054 )
Acyclic triterpenoids (LMPR0106010010 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	(S)-2,3-Epoxysqualene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01rf-3696400000-dd04dae2363e5ff874a8	Spectrum
Predicted GC-MS	(S)-2,3-Epoxysqualene, 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	splash10-004i-0424900000-7fc557d70c5c9e3da792	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-4859200000-154cc236135feb13b7fe	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gb9-7493000000-f50f29f61b0b15da33f7	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000900000-51b63741b5f02135d106	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-2000900000-5a6929cb0f28227226e9	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9105300000-2fc6b31bfdb56acb80f9	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000900000-590c9e4adfdd12b64d93	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-1101900000-db9a88388cd111945a57	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052u-2339100000-6f4e24f11b72c0cb1c24	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05rr-4545900000-9f67cba78f15989d34a8	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-066r-5609300000-19d2e2da63dd111fdd58	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-053u-9603000000-d795105f1da47d79c7dd	2021-09-25	View 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

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

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

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Abalone	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Abiyuch	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Acerola	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Acorn	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Adzuki bean	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Agar	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Agave	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Alaska blueberry	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Alaska wild rhubarb	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Alfalfa	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis