ChemFOnt: Showing chemical card for ent-16b-Kauran-16,19-diol (CFc000282178)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:34:17 UTC

Chemfont ID

CFc000282178

Molecule Identification

Common Name

ent-16b-Kauran-16,19-diol

Definition

Ent-16b-kauran-16,19-diol is a member of the class of compounds known as kaurane diterpenoids. Kaurane diterpenoids 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. Ent-16b-kauran-16,19-diol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Ent-16b-kauran-16,19-diol can be found in sunflower, which makes ent-16b-kauran-16,19-diol a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₀H₃₄O₂

Average Molecular Weight

306.4828

Monoisotopic Molecular Weight

306.255880332

IUPAC Name

(1S,4S,5R,9S,10R,13R,14R)-5-(hydroxymethyl)-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-ol

Traditional Name

(1S,4S,5R,9S,10R,13R,14R)-5-(hydroxymethyl)-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-ol

CAS Registry Number

68-22-4

SMILES

[H][C@@]12CC[C@@H]3C[C@]1(C[C@@]3(C)O)CC[C@]1([H])[C@](C)(CO)CCC[C@@]21C

InChI Identifier

InChI=1S/C20H34O2/c1-17(13-21)8-4-9-18(2)15(17)7-10-20-11-14(5-6-16(18)20)19(3,22)12-20/h14-16,21-22H,4-13H2,1-3H3/t14-,15-,16+,17+,18-,19-,20+/m1/s1

InChI Key

XZESVXVYTBMYCR-WVMNWVHYSA-N

Chemical Taxonomy

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
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302662)

Food

Herb and spice

Oilseed crop

Sunflower (FooDB: FOOD00086)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0064 g/L	ALOGPS
logP	3.72	ALOGPS
logP	3.37	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	18.59	ChemAxon
pKa (Strongest Basic)	-0.57	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	89.33 m³·mol⁻¹	ChemAxon
Polarizability	36.88 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

External Links

HMDB ID

HMDB0302662

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB005670

KNApSAcK ID

Not Available

Chemspider ID

59696373

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

52916190

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for ent-16b-Kauran-16,19-diol (CFc000282178)

MOL for CFc000282178 (ent-16b-Kauran-16,19-diol)

3D MOL for CFc000282178 (ent-16b-Kauran-16,19-diol)

3D SDF for CFc000282178 (ent-16b-Kauran-16,19-diol)

3D-SDF for CFc000282178 (ent-16b-Kauran-16,19-diol)

PDB for CFc000282178 (ent-16b-Kauran-16,19-diol)

3D PDB for CFc000282178 (ent-16b-Kauran-16,19-diol)

SMILES for CFc000282178 (ent-16b-Kauran-16,19-diol)

INCHI for CFc000282178 (ent-16b-Kauran-16,19-diol)

Structure for CFc000282178 (ent-16b-Kauran-16,19-diol)

3D Structure for CFc000282178 (ent-16b-Kauran-16,19-diol)