AFCDB: Cucurbitacin A (FDB005284)

Record Information

Version

1.0

Creation date

2010-04-08 22:06:37 UTC

Update date

2019-11-26 03:00:28 UTC

Primary ID

FDB005284

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Cucurbitacin A

Description

Cucurbitacin a is a member of the class of compounds known as cucurbitacins. Cucurbitacins are polycyclic compounds containing the tetracyclic cucurbitane nucleus skeleton, 19-(10->9b)-abeo-10alanost-5-ene (also known as 9b-methyl-19-nor lanosta-5-ene), with a variety of oxygenation functionalities at different positions. Cucurbitacin a is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Cucurbitacin a can be found in cucumber, which makes cucurbitacin a a potential biomarker for the consumption of this food product.

CAS Number

Not Available

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.018 g/L	ALOGPS
logP	2.81	ALOGPS
logP	1.85	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	12.8	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	158.43 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	152.82 m³·mol⁻¹	ChemAxon
Polarizability	62.05 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C32H46O9

IUPAC name

(3E)-6-[4,13-dihydroxy-1-(hydroxymethyl)-6,6,11,15-tetramethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate

InChI Identifier

InChI=1S/C32H46O9/c1-17(34)41-27(2,3)12-11-23(37)31(8,40)25-21(36)14-29(6)22-10-9-18-19(13-20(35)26(39)28(18,4)5)32(22,16-33)24(38)15-30(25,29)7/h9,11-12,19-22,25,33,35-36,40H,10,13-16H2,1-8H3/b12-11+

InChI Key

IHTCCHVMPGDDSL-VAWYXSNFSA-N

Isomeric SMILES

CC(=O)OC(C)(C)\C=C\C(=O)C(C)(O)C1C(O)CC2(C)C3CC=C4C(CC(O)C(=O)C4(C)C)C3(CO)C(=O)CC12C

Average Molecular Weight

574.7022

Monoisotopic Molecular Weight

574.31418307

Classification

Description

Belongs to the class of organic compounds known as cucurbitacins. These are polycyclic compounds containing the tetracyclic cucurbitane nucleus skeleton, 19-(10->9b)-abeo-10alanost-5-ene (also known as 9b-methyl-19-nor lanosta-5-ene), with a variety of oxygenation functionalities at different positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cucurbitacins

Direct Parent

Cucurbitacins

Alternative Parents

Substituents

Cucurbitacin skeleton
Triterpenoid
22-oxosteroid
21-oxosteroid
20-hydroxysteroid
Steroid ester
3-oxo-delta-5-steroid
2-hydroxysteroid
Hydroxysteroid
11-oxosteroid
3-oxosteroid
Oxosteroid
16-hydroxysteroid
Delta-5-steroid
Acyloin
Acryloyl-group
Cyclic alcohol
Alpha,beta-unsaturated ketone
Alpha-hydroxy ketone
Tertiary alcohol
Enone
Cyclic ketone
Secondary alcohol
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Carbonyl group
Organic oxide
Alcohol
Primary alcohol
Organooxygen compound
Organic oxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
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

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0001190000-7b7be3b68804a4727497	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ap1-1304980000-3b9afd0e27bb922bfcf1	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ktr-3119760000-1bc95e418f4085b380d4	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0aba-3600190000-8a7eefab3b631d68113c	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-5903040000-39fa24ac541a1f96343a	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9105220000-48181e0121538c0d89aa	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-1300980000-1d99e9338fedf3784a07	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01p5-9600530000-13479b8c6bdd9b92f892	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014r-9401100000-d8dfb0f8970e6ab674a0	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000390000-d3ccb30a60f7df91a751	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000110000-7f9b5f8b92a15f73a7c4	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-5001940000-e5fa13bf4a5205397142	2021-10-21	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

HPY08-V:HRH47-N

EAFUS ID

Not Available

Dr. Duke ID

CUCURBITACIN-A

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
cytotoxic	52209	A role played by the molecular entity or part thereof which causes the development of a pathological process.	DUKE

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

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

Cucurbitacin A (FDB005284)

Structure for FDB005284 (Cucurbitacin A)