Showing Compound Grandiflorolic acid (FDB015899)

Record Information

Version

1.0

Creation date

2010-04-08 22:12:07 UTC

Update date

2019-11-26 03:12:25 UTC

Primary ID

FDB015899

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Grandiflorolic acid

Description

delta-Carotene-1,2-epoxide belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone. delta-Carotene-1,2-epoxide is an extremely weak basic (essentially neutral) compound (based on its pKa).

CAS Number

22338-69-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Δ-carotene-1,2-epoxide	Generator
1',2'-Epoxy-1',2'-dihydro-e,y-carotene	HMDB
1',2'-Epoxy-1',2'-dihydro-epsilon,psi-carotene	HMDB
D-Carotene-1,2-epoxide	HMDB
Gradifloric acid	HMDB
Grandifloric acid	HMDB
15-Hydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate	Generator
Grandiflorolate	Generator
Grandiflorolic acid	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.022 g/L	ALOGPS
logP	3.29	ALOGPS
logP	3.73	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	4.7	ChemAxon
pKa (Strongest Basic)	-0.74	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	88.73 m³·mol⁻¹	ChemAxon
Polarizability	36.24 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

C20H30O3

IUPAC name

15-hydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

InChI Identifier

InChI=1S/C20H30O3/c1-12-13-5-6-15-18(2)8-4-9-19(3,17(22)23)14(18)7-10-20(15,11-13)16(12)21/h13-16,21H,1,4-11H2,2-3H3,(H,22,23)

InChI Key

GVGJRXSJJHLPGZ-UHFFFAOYSA-N

Isomeric SMILES

CC12CCCC(C)(C1CCC13CC(CCC21)C(=C)C3O)C(O)=O

Average Molecular Weight

318.4504

Monoisotopic Molecular Weight

318.219494826

Classification

Description

Belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Tetraterpenoids

Direct Parent

Xanthophylls

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic heteromonocyclic 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 75.43%; H 9.49%; O 15.07%	DFC
Melting Point	Mp 216-218°	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	Grandiflorolic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0udi-0293000000-6d81233578562a5d26aa	Spectrum
Predicted GC-MS	Grandiflorolic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0092-7057900000-207d915177a4f066ae38	Spectrum
Predicted GC-MS	Grandiflorolic acid, 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	splash10-0uxr-0049000000-4b652304c7d71bce7fda	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0zfr-0295000000-15eccd134beb9a35a29c	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pvi-6891000000-4421f81b0af8e634e443	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0069000000-718245f7e353ddb6470b	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0601-0093000000-1abaaf43e0d70f316624	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ab9-0091000000-e4fe010c6ed57c8ce4f1	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009000000-062ad2a35e11d303cf23	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0009000000-4f15395cbd12cf9308a0	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-3059000000-ecaac400571ca670ba51	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00xr-0095000000-f5b39e03f542c252d9d4	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ar3-0192000000-43f487add55056118e00	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0670-2930000000-eb189dd440146f16ff22	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

383411

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

433554

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB36930

CRC / DFC (Dictionary of Food Compounds) ID

JGR61-I:KKJ13-U

EAFUS ID

Not Available

Dr. Duke ID

GRANDIFLORIC-ACID

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

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
allelopathic			DUKE
anti feedant			DUKE
anti trypanosomic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
larvicide			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
utero tonic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE