AFCDB: Crustecdysone (FDB001996)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:12 UTC

Update date

2019-11-26 02:56:51 UTC

Primary ID

FDB001996

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Crustecdysone

Description

Ecdysterone, also known as .beta-ecdysterone or crustecdyson, belongs to the class of organic compounds known as hydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or derivatives bearing at least hydroxyl group. Based on a literature review a significant number of articles have been published on Ecdysterone.

CAS Number

5289-74-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.42 g/L	ALOGPS
logP	1.3	ALOGPS
logP	0.61	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	13.26	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	138.45 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	128.88 m³·mol⁻¹	ChemAxon
Polarizability	53.47 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	No	ChemAxon

Chemical Formula

C27H44O7

IUPAC name

4,5,11-trihydroxy-2,15-dimethyl-14-(2,3,6-trihydroxy-6-methylheptan-2-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

InChI Identifier

InChI=1S/C27H44O7/c1-23(2,32)9-8-22(31)26(5,33)21-7-11-27(34)16-12-18(28)17-13-19(29)20(30)14-24(17,3)15(16)6-10-25(21,27)4/h12,15,17,19-22,29-34H,6-11,13-14H2,1-5H3

InChI Key

NKDFYOWSKOHCCO-UHFFFAOYSA-N

Isomeric SMILES

CC(C)(O)CCC(O)C(C)(O)C1CCC2(O)C3=CC(=O)C4CC(O)C(O)CC4(C)C3CCC12C

Average Molecular Weight

480.6341

Monoisotopic Molecular Weight

480.308703762

Classification

Description

Belongs to the class of organic compounds known as hydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or derivatives bearing at least hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Hydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Hexahydroxy bile acid, alcohol, or derivatives
Cholesterol
Cholesterol-skeleton
Cholestane-skeleton
Ecdysteroid
25-hydroxysteroid
Hydroxy bile acid, alcohol, or derivatives
22-hydroxysteroid
20-hydroxysteroid
3-hydroxy-delta-7-steroid
2-hydroxysteroid
Oxosteroid
6-oxosteroid
Hydroxysteroid
3-hydroxysteroid
14-hydroxysteroid
Delta-7-steroid
Cyclohexenone
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Ketone
Polyol
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Alcohol
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

a steroid (CPD-276 )

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 67.47%; H 9.23%; O 23.30%	DFC
Melting Point	Mp 237.5-239.5° (243°)	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 +61.8 (CHCl3)	DFC
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	Crustecdysone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01t9-2182900000-afa971d64803cfeeb793	Spectrum
Predicted GC-MS	Crustecdysone, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001i-2204019000-e365dafd10479253fd57	Spectrum
Predicted GC-MS	Crustecdysone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Crustecdysone, 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	splash10-01ot-0000900000-aa6fb1d316be758b5d85	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-2105900000-256723a6eec9de26e1e8	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kk-9137700000-dc5fe9a7d820280c6948	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01ot-0000900000-aa6fb1d316be758b5d85	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-2105900000-256723a6eec9de26e1e8	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kk-9137700000-dc5fe9a7d820280c6948	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01ot-0000900000-aa6fb1d316be758b5d85	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-2105900000-256723a6eec9de26e1e8	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kk-9137700000-dc5fe9a7d820280c6948	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01t9-0001900000-2c9b71140a7f68ebc2fd	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-1209800000-14a48adcc0079f021b19	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0304-3229100000-7c17d137d0776972f66b	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01t9-0001900000-2c9b71140a7f68ebc2fd	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-1209800000-14a48adcc0079f021b19	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0304-3229100000-7c17d137d0776972f66b	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01t9-0001900000-2c9b71140a7f68ebc2fd	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-1209800000-14a48adcc0079f021b19	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0304-3229100000-7c17d137d0776972f66b	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01qa-0100900000-c3823ec9d64dc47c45d9	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0005-6902300000-00332d9e60679cef66c7	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aor-7928000000-a6b13141cb26359cf913	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000900000-75b6ff99e4177dc88738	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-1001900000-6bdb177d329eff14952f	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ufs-5204900000-1c107cdd2fc28cbd894c	2021-10-12	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

238902

ChEMBL ID

Not Available

KEGG Compound ID

C02633

Pubchem Compound ID

271605

Pubchem Substance ID

Not Available

ChEBI ID

16587

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB30180

CRC / DFC (Dictionary of Food Compounds) ID

HFW37-B:CCP81-D

EAFUS ID

Not Available

Dr. Duke ID

BETA-ECDYSONE

BIGG ID

Not Available

KNApSAcK ID

C00003654

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
hypocholesterolemic			DUKE
lipolytic			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).

Crustecdysone (FDB001996)

Structure for FDB001996 (Crustecdysone)