Showing Compound Carrotatoxin (FDB000702)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:40 UTC

Update date

2025-11-18 22:21:26 UTC

Primary ID

FDB000702

Secondary Accession Numbers

FDB019213

Chemical Information

FooDB Name

Carrotatoxin

Description

Carrotatoxin, also known as falcarinol, (Z)-isomer or panaxynol, is a member of the class of compounds known as long-chain fatty alcohols. Long-chain fatty alcohols are fatty alcohols that have an aliphatic tail of 13 to 21 carbon atoms. Carrotatoxin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Carrotatoxin can be found in carrot and wild carrot, which makes carrotatoxin a potential biomarker for the consumption of these food products.

CAS Number

21852-80-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(3S,9Z)-1,9-Heptadecadiene-4,6-diyn-3-ol	HMDB
(Z)-(-)-1,9-Heptadecadiene-4,6-diyne-3-ol	HMDB
Falcarinol	HMDB
Falcarinol, (Z)-isomer	MeSH, HMDB
Panaxynol	MeSH
(Z)-(R)-Heptadeca-1,9-diene-4,6-diyn-3-ol	biospider
Carotatoxin	db_source
Carrotatoxin	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.0032 g/L	ALOGPS
logP	5.78	ALOGPS
logP	5.45	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	13.29	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	81.26 m³·mol⁻¹	ChemAxon
Polarizability	31.86 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C17H24O

IUPAC name

(9E)-heptadeca-1,9-dien-4,6-diyn-3-ol

InChI Identifier

InChI=1S/C17H24O/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17(18)4-2/h4,10-11,17-18H,2-3,5-9,12H2,1H3/b11-10+

InChI Key

UGJAEDFOKNAMQD-ZHACJKMWSA-N

Isomeric SMILES

CCCCCCC\C=C\CC#CC#CC(O)C=C

Average Molecular Weight

244.3719

Monoisotopic Molecular Weight

244.18271539

Classification

Description

Belongs to the class of organic compounds known as long-chain fatty alcohols. These are fatty alcohols that have an aliphatic tail of 13 to 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Long-chain fatty alcohols

Alternative Parents

Substituents

Long chain fatty alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 83.55%; H 9.90%; O 6.55%	DFC
Melting Point	Not Available
Boiling Point	Bp0.02 115°	DFC
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]D -36.9 (c, 0.77 in CHCl3)	DFC
Spectroscopic UV Data	256 (e 445) (hexane) (Berdy)	DFC
Density	Not Available
Refractive Index	n18D 1.5018	DFC

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Carrotatoxin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0ar3-9650000000-ea6b62b12e6079422f8a	Spectrum
Predicted GC-MS	Carrotatoxin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-009i-9051000000-e547f9b86bd5f5d7df55	Spectrum
Predicted GC-MS	Carrotatoxin, 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	splash10-0002-0190000000-c61a5b104b45a3cded6f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-054t-4930000000-85e348ffb3542ae77939	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9600000000-c78591f03692fad905e6	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0190000000-b15c99312f2cac24edf8	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-2390000000-183e53007c445086666b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-7920000000-c494c396c15df91f1c15	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0090000000-62731d7c38803784835a	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-2290000000-eabafe1af748cb6e70d9	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-9800000000-a86595ae1399237a5922	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-4960000000-75fd76b2a12422e721c6	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0gdu-9500000000-e81e85533e07c78cad5b	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fbc-9500000000-1f7429ad2f134035d758	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

4510155

ChEMBL ID

Not Available

KEGG Compound ID

C17447

Pubchem Compound ID

5281149

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB0039588

CRC / DFC (Dictionary of Food Compounds) ID

BFQ75-T:BFQ76-U

EAFUS ID

Not Available

Dr. Duke ID

CAROTATOXIN

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
Crustacicide		An agent that kills organisms of the subphylum Crustacea, used to control crustacean populations in aquatic environments. Therapeutically, it may be applied to manage crustacean-borne diseases or infestations, with potential medical uses in treating conditions like swimmer's itch or crustacean-related allergic reactions.	DUKE
Neurotoxic	50910	A substance that damages or destroys nerve cells, disrupting normal brain function. It has no therapeutic applications, but is used in research to study neurodegenerative diseases. Key medical uses include understanding and developing treatments for conditions like Alzheimer's and Parkinson's diseases, where neurotoxicity plays a role.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	DUKE