Showing Compound ent-16a-Hydroxy-17-acetoxy-19-kauranal (FDB021465)

Record Information

Version

1.0

Creation date

2010-04-08 22:15:43 UTC

Update date

2019-11-26 03:20:25 UTC

Primary ID

FDB021465

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

ent-16a-Hydroxy-17-acetoxy-19-kauranal

Description

ent-16a-Hydroxy-17-acetoxy-19-kauranal belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. Based on a literature review a small amount of articles have been published on ent-16a-Hydroxy-17-acetoxy-19-kauranal.

CAS Number

177742-55-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
17-(Acetyloxy)-16-hydroxy-(4alpha,16alpha)-kauran-18-al	HMDB
Annosquamosin a (terpene)	HMDB
Annosquamosin A [terpene]	manual
Annosquamosin a?	HMDB
Annosquamosin A?	db_source
ent-16a-Hydroxy-17-acetoxy-19-kauranal	manual
{5-formyl-14-hydroxy-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetic acid	Generator

Showing 1 to 7 of 7 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.0039 g/L	ALOGPS
logP	3.11	ALOGPS
logP	3.08	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	13.75	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	99.04 m³·mol⁻¹	ChemAxon
Polarizability	41.04 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

C22H34O4

IUPAC name

{5-formyl-14-hydroxy-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate

InChI Identifier

InChI=1S/C22H34O4/c1-15(24)26-14-22(25)12-21-10-7-17-19(2,13-23)8-4-9-20(17,3)18(21)6-5-16(22)11-21/h13,16-18,25H,4-12,14H2,1-3H3

InChI Key

FCHGRGOUMXZTFS-UHFFFAOYSA-N

Isomeric SMILES

CC(=O)OCC1(O)CC23CC1CCC2C1(C)CCCC(C)(C=O)C1CC3

Average Molecular Weight

362.503

Monoisotopic Molecular Weight

362.245709576

Classification

Description

Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Kaurane diterpenoids

Alternative Parents

Substituents

Kaurane diterpenoid
Tertiary alcohol
Cyclic alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 72.89%; H 9.45%; O 17.65%	DFC
Melting Point	Mp 162-164°	DFC
Optical Rotation	[a]24D -64 (c, 0.2 in CHCl3)	DFC

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	ent-16a-Hydroxy-17-acetoxy-19-kauranal, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0002-2093000000-f88d4e65f5821a536dde	Spectrum
Predicted GC-MS	ent-16a-Hydroxy-17-acetoxy-19-kauranal, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05vy-9257600000-c5ce5b4024d192e590f8	Spectrum
Predicted GC-MS	ent-16a-Hydroxy-17-acetoxy-19-kauranal, 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	splash10-0ik9-0009000000-601730cc795d54dcec25	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udj-1249000000-6f7fdeab20f4a0727747	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ox-4592000000-0723b57af8338ac5e737	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-5009000000-1435685bf3d29f6d2435	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bt9-9007000000-339dabc3914bf7448828	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9051000000-4ed3107bae59a0e34a78	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0009000000-64c7eccecc0e967c403c	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0029000000-9a68be9e7af1b9aa936e	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0079-2090000000-8ac52bcc9d493686ae93	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01q9-0049000000-15a296bfd2bde7abc4c9	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02mi-0594000000-8cf01656333229e29aea	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01w1-0921000000-36ca0c7950a7b831bfac	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

73753379

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB41495

CRC / DFC (Dictionary of Food Compounds) ID

JFQ12-I:NXR33-I

EAFUS ID

Not Available

Dr. Duke ID

Not Available

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

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

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

Showing Compound ent-16a-Hydroxy-17-acetoxy-19-kauranal (FDB021465)

Structure for FDB021465 (ent-16a-Hydroxy-17-acetoxy-19-kauranal)