Showing Compound Costunolide (FDB015618)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:57 UTC

Update date

2019-11-26 03:11:56 UTC

Primary ID

FDB015618

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Costunolide

Description

Costunolide 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 small amount of articles have been published on Costunolide.

CAS Number

553-21-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Costunlide	HMDB
Costunolid	HMDB
Costus lactone	HMDB
Isocostunolide	MeSH
Costunolide	MeSH

Predicted Properties

Property	Value	Source
Water Solubility	0.097 g/L	ALOGPS
logP	4.22	ALOGPS
logP	3.82	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.95 m³·mol⁻¹	ChemAxon
Polarizability	26.38 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C15H20O2

IUPAC name

6,10-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one

InChI Identifier

InChI=1S/C15H20O2/c1-10-5-4-6-11(2)9-14-13(8-7-10)12(3)15(16)17-14/h5,9,13-14H,3-4,6-8H2,1-2H3/b10-5-,11-9-

InChI Key

HRYLQFBHBWLLLL-GYIATTAWSA-N

Isomeric SMILES

C\C1=C\CC\C(C)=C/C2OC(=O)C(=C)C2CC1

Average Molecular Weight

232.3181

Monoisotopic Molecular Weight

232.146329884

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
Germacrane sesquiterpenoid
Sesquiterpenoid
Gamma butyrolactone
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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:

Pharmaceutical industry:

Antineoplastic agent:

Anticancer agent

Biological role:

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 77.55%; H 8.68%; O 13.77%	DFC
Melting Point	Mp 106-107°	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	[a]D +128 (c, 0.45 in CHCl3)	DFC
Spectroscopic UV Data	[neutral] lmax 204 (e 18800) (EtOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Costunolide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004i-4920000000-4e64fd5fdc43499db09c	Spectrum
Predicted GC-MS	Costunolide, 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	splash10-001i-0390000000-90b5c48b328b46f82204	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01qi-1930000000-6cfdc6b5c84eab2f9f7d	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0mi6-9710000000-ddda69ef8cc562458ad9	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0290000000-07ab038b28845f8d64a1	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001r-0790000000-f2b3e216b0db2d7a4dca	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-5900000000-157775eb321e2f75fa2d	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090000000-403b175a8d75af9b9dc4	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0390000000-16fbf014b5978f284c85	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01b9-9500000000-2ce7ff1d0912ac2d90ee	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0190000000-c5e9a61d3011edbf30f3	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001r-0980000000-0a8be66862e84091d6a4	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0900000000-9eaa625d0c4efee67791	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

4519051

ChEMBL ID

Not Available

KEGG Compound ID

C09382

Pubchem Compound ID

5367559

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB36688

CRC / DFC (Dictionary of Food Compounds) ID

KDX18-U:KDX19-V

EAFUS ID

Not Available

Dr. Duke ID

COSTUNOLIDE

BIGG ID

Not Available

KNApSAcK ID

C00003240

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

Descriptor	ID	Definition	Reference
allergenic	50904	A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.	DUKE
anti angiogenic	48422	An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.	DUKE
anti mutagenic			DUKE
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
dermatitigenic			DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
schistosomicide			DUKE
trematodicide			DUKE
VEGF inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE