Showing Compound Squamone (FDB014742)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:26 UTC

Update date

2019-11-26 03:10:41 UTC

Primary ID

FDB014742

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Squamone

Description

Squamone belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. Thus, squamone is considered to be a fatty alcohol. Based on a literature review a small amount of articles have been published on Squamone.

CAS Number

126655-24-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Predicted Properties

Property	Value	Source
Water Solubility	0.00051 g/L	ALOGPS
logP	6.61	ALOGPS
logP	7.7	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	13.9	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.13 Å²	ChemAxon
Rotatable Bond Count	26	ChemAxon
Refractivity	166.46 m³·mol⁻¹	ChemAxon
Polarizability	73.6 Å³	ChemAxon
Number of Rings	2	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

C35H62O7

IUPAC name

5-{11-hydroxy-11-[5-(1-hydroxytridecyl)oxolan-2-yl]-5-oxoundecyl}-3-(2-oxopropyl)oxolan-2-one

InChI Identifier

InChI=1S/C35H62O7/c1-3-4-5-6-7-8-9-10-11-14-21-31(38)33-23-24-34(42-33)32(39)22-15-12-13-18-29(37)19-16-17-20-30-26-28(25-27(2)36)35(40)41-30/h28,30-34,38-39H,3-26H2,1-2H3

InChI Key

PAFMHAFYJMTISR-UHFFFAOYSA-N

Isomeric SMILES

CCCCCCCCCCCCC(O)C1CCC(O1)C(O)CCCCCC(=O)CCCCC1CC(CC(C)=O)C(=O)O1

Average Molecular Weight

594.8626

Monoisotopic Molecular Weight

594.449554338

Classification

Description

Belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Annonaceous acetogenins

Alternative Parents

Substituents

Annonaceae acetogenin skeleton
Long chain fatty alcohol
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Ketone
Lactone
Secondary alcohol
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Alcohol
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Biological location:

Biofluid and excreta:

Urine

Cell and elements:

Extracellular

Subcellular:

Process

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

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	C 70.67%; H 10.50%; O 18.83%	DFC
Melting Point	Mp 89°	DFC
Optical Rotation	[a]D +7 (c, 0.1 in CHCL3)	DFC

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Squamone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00mo-6596220000-5b6c66699b28401c8983	Spectrum
Predicted GC-MS	Squamone, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-7229212000-b5dd6ef19fb7fa1f78cf	Spectrum
Predicted GC-MS	Squamone, "Squamone,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Squamone, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Squamone, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Squamone, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Squamone, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Squamone, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Squamone, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Squamone, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Squamone, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Squamone, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Squamone, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Squamone, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Squamone, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Squamone, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Squamone, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Squamone, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Squamone, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Squamone, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Squamone, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Squamone, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Squamone, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Squamone, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Squamone, TBDMS_1_4, 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	splash10-004j-0000190000-7e1da57277920d2eeb70	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05r0-7930770000-8a23c27448b82364372f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-066r-9320200000-2de0531f68af2452da66	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0000090000-5fbb802336c96d7c487b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00ov-2232190000-0f58438c319153114446	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4m-9242010000-77317f747e2c89894672	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0001090000-d4ea1831769379e6b556	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-4345190000-e09eb40fdbb371d908e6	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9002010000-b5f5a335f27dbe4c846e	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-0000090000-c84d0496907a4f70c3e8	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-0212190000-54fb55b2ad40cc6afe84	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-054p-9802100000-79b8bb26411b239eb030	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

115760

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

130901

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB35939

CRC / DFC (Dictionary of Food Compounds) ID

JVN48-Q:JVN48-Q

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

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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

Showing Compound Squamone (FDB014742)

Structure for FDB014742 (Squamone)