Showing Compound Heliangin (FDB015624)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:57 UTC

Update date

2019-11-26 03:11:57 UTC

Primary ID

FDB015624

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Heliangin

Description

Heliangin belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Based on a literature review a significant number of articles have been published on Heliangin.

CAS Number

13323-48-3

Structure

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

Synonyms

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Synonym	Source
(9Z)-8-Hydroxy-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl (2E)-2-methylbut-2-enoic acid	Generator
Heliangin	MeSH
Heliangine	HMDB
Leptocarpin	HMDB
Leptocarpin, (1ar-(1ar,3S,4Z,5ar,8ar,9R(e),10ar))-isomer	MeSH
Leptocarpin, (1ar-(1ar,3S,4Z,5as,8ar,9S,10ar))-isomer	MeSH

Showing 1 to 6 of 6 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.3 g/L	ALOGPS
logP	1.45	ALOGPS
logP	2.41	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	6.22	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	85.36 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	95.54 m³·mol⁻¹	ChemAxon
Polarizability	38.36 Å³	ChemAxon
Number of Rings	3	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

C20H26O6

IUPAC name

(9Z)-8-hydroxy-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl (2E)-2-methylbut-2-enoate

InChI Identifier

InChI=1S/C20H26O6/c1-6-10(2)18(22)25-15-9-20(5)16(26-20)8-13(21)11(3)7-14-17(15)12(4)19(23)24-14/h6-7,13-17,21H,4,8-9H2,1-3,5H3/b10-6+,11-7-

InChI Key

DZTWAOVNNLDWNH-QZTBCQRESA-N

Isomeric SMILES

C\C=C(/C)C(=O)OC1CC2(C)OC2CC(O)\C(C)=C/C2OC(=O)C(=C)C12

Average Molecular Weight

362.4168

Monoisotopic Molecular Weight

362.172938564

Classification

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Sesquiterpenoid
Fatty acid ester
Dicarboxylic acid or derivatives
Gamma butyrolactone
Fatty acyl
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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

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 66.28%; H 7.23%; O 26.49%	DFC
Melting Point	Mp 227-229°	DFC
Optical Rotation	[a]23D -110 (c, 0.5 in CHCl3)	DFC

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Heliangin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-053s-9014000000-d4115525398926b17407	Spectrum
Predicted GC-MS	Heliangin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-053r-9001100000-6a89a281481d94379912	Spectrum
Predicted GC-MS	Heliangin, 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	splash10-03dj-2039000000-785f137b68ea1b583520	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06us-9184000000-645c0c1af1c3e2495ce8	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f89-9120000000-35228986d558858a4334	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0019000000-399bd5ed523ca36c8d99	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0901-5049000000-604186f0c012089dab02	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f81-9550000000-3dfd2150bf626a73e577	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-2092000000-a2107e87fa08cd77bbc5	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ot-9060000000-90926566628c185acbff	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-2090000000-7d965b00d72ca32904cf	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0090000000-be4f1c6baa4bb8ca15a9	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0094000000-6fae0e8f2a70227265cd	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052b-7098000000-677ea1d7babf76468eb6	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

C09474

Pubchem Compound ID

9998730

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB36692

CRC / DFC (Dictionary of Food Compounds) ID

KFB64-N:KFB77-T

EAFUS ID

Not Available

Dr. Duke ID

HELIANGIN

BIGG ID

Not Available

KNApSAcK ID

C00000235

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

Jerusalem artichoke	Expected but not quantified	Not Available	KNAPSACK, PHYTOHUB
Spinach	Expected but not quantified	Not Available	PHYTOHUB
Sunflower	Expected but not quantified	Not Available	DUKE, PHYTOHUB

Showing 1 to 3 of 3 entries

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
phytohormonal	26158	A plant growth regulator that modulates the formation of stems, leaves and flowers, as well as the development and ripening of fruit. The term includes endogenous and non-endogenous compounds (e.g. active compounds produced by bacteria on the leaf surface) as well as semi-synthetic and fully synthetic compounds.	DUKE

Showing 1 to 1 of 1 entries

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available