ChemFOnt: Showing chemical card for 6-Keto-28-homobrassinolide (CFc000281922)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:33:47 UTC

Chemfont ID

CFc000281922

Molecule Identification

Common Name

6-Keto-28-homobrassinolide

Definition

6-keto-28-homobrassinolide belongs to stigmastanes and derivatives class of compounds. Those are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. 6-keto-28-homobrassinolide is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 6-keto-28-homobrassinolide can be found in tea, which makes 6-keto-28-homobrassinolide a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₉H₅₀O₅

Average Molecular Weight

478.7043

Monoisotopic Molecular Weight

478.36582471

IUPAC Name

(1S,2R,4R,5S,7S,10S,11S,14R,15S)-14-[(2S,3R,4R,5R)-5-ethyl-3,4-dihydroxy-6-methylheptan-2-yl]-4,5-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-8-one

Traditional Name

(1S,2R,4R,5S,7S,10S,11S,14R,15S)-14-[(2S,3R,4R,5R)-5-ethyl-3,4-dihydroxy-6-methylheptan-2-yl]-4,5-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-8-one

CAS Registry Number

None

SMILES

[H][C@@]12CC[C@H]([C@H](C)[C@@H](O)[C@H](O)[C@H](CC)C(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC(=O)[C@@]2([H])C[C@H](O)[C@H](O)C[C@]12C

InChI Identifier

InChI=1S/C29H50O5/c1-7-17(15(2)3)27(34)26(33)16(4)19-8-9-20-18-12-23(30)22-13-24(31)25(32)14-29(22,6)21(18)10-11-28(19,20)5/h15-22,24-27,31-34H,7-14H2,1-6H3/t16-,17+,18-,19+,20-,21-,22+,24-,25+,26+,27+,28+,29+/m0/s1

InChI Key

WADMTJKRYLAHQV-JZSPVGNFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Stigmastanes and derivatives

Direct Parent

Stigmastanes and derivatives

Alternative Parents

Substituents

C24-propyl-sterol-skeleton
Triterpenoid
Stigmastane-skeleton
Tetrahydroxy bile acid, alcohol, or derivatives
Ecdysteroid
Hydroxy bile acid, alcohol, or derivatives
23-hydroxysteroid
Bile acid, alcohol, or derivatives
22-hydroxysteroid
3-hydroxysteroid
6-oxosteroid
3-alpha-hydroxysteroid
Oxosteroid
2-hydroxysteroid
Hydroxysteroid
Cyclic alcohol
Secondary alcohol
Ketone
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302406)

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.026 g/L	ALOGPS
logP	3.27	ALOGPS
logP	3.95	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	13.45	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	133.82 m³·mol⁻¹	ChemAxon
Polarizability	56.71 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0302406

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB004435

KNApSAcK ID

Not Available

Chemspider ID

118384

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

134291

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 6-Keto-28-homobrassinolide (CFc000281922)

MOL for CFc000281922 (6-Keto-28-homobrassinolide)

3D MOL for CFc000281922 (6-Keto-28-homobrassinolide)

3D SDF for CFc000281922 (6-Keto-28-homobrassinolide)

3D-SDF for CFc000281922 (6-Keto-28-homobrassinolide)

PDB for CFc000281922 (6-Keto-28-homobrassinolide)

3D PDB for CFc000281922 (6-Keto-28-homobrassinolide)

SMILES for CFc000281922 (6-Keto-28-homobrassinolide)

INCHI for CFc000281922 (6-Keto-28-homobrassinolide)

Structure for CFc000281922 (6-Keto-28-homobrassinolide)

3D Structure for CFc000281922 (6-Keto-28-homobrassinolide)