ChemFOnt: Showing chemical card for Demissidine (CFc000282898)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:35:40 UTC

Chemfont ID

CFc000282898

Molecule Identification

Common Name

Demissidine

Definition

3-epidemissidine belongs to solanidines and derivatives class of compounds. Those are steroids with a structure based on the solanidane skeleton. Solanidane arises from the conversion of a cholestane side-chain into a bicyclic system. 3-epidemissidine is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). 3-epidemissidine can be found in alcoholic beverages, potato, and root vegetables, which makes 3-epidemissidine a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(22R,23R,24S)-3alpha,22,23-Trihydroxy-7-oxa-5alpha-ergostane-6-one	Kegg
(22R,23R,24S)-3a,22,23-Trihydroxy-7-oxa-5a-ergostane-6-one	Generator
(22R,23R,24S)-3Α,22,23-trihydroxy-7-oxa-5α-ergostane-6-one	Generator

Chemical Formula

C₂₈H₄₈O₅

Average Molecular Weight

464.687

Monoisotopic Molecular Weight

464.350174646

IUPAC Name

(2R,5R,16S)-15-[(2S,3R,4R,5S)-3,4-dihydroxy-5,6-dimethylheptan-2-yl]-5-hydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.0^{2,7}.0^{12,16}]octadecan-8-one

Traditional Name

(2R,5R,16S)-15-[(2S,3R,4R,5S)-3,4-dihydroxy-5,6-dimethylheptan-2-yl]-5-hydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.0^{2,7}.0^{12,16}]octadecan-8-one

CAS Registry Number

474-08-8

SMILES

CC(C)[C@H](C)[C@@H](O)[C@H](O)[C@@H](C)C1CCC2C3COC(=O)C4C[C@H](O)CC[C@]4(C)C3CC[C@]12C

InChI Identifier

InChI=1S/C28H48O5/c1-15(2)16(3)24(30)25(31)17(4)20-7-8-21-19-14-33-26(32)23-13-18(29)9-11-28(23,6)22(19)10-12-27(20,21)5/h15-25,29-31H,7-14H2,1-6H3/t16-,17-,18+,19?,20?,21?,22?,23?,24+,25+,27+,28+/m0/s1

InChI Key

LLFIMDUWAVPJEJ-IPLAFFEMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as brassinolides and derivatives. These are cholestane based steroid lactones containing benzo[c]indeno[5,4-e]oxepin-3-one.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Brassinolides and derivatives

Alternative Parents

Substituents

Brassinolide-skeleton
Caprolactone
Oxepane
Cyclic alcohol
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxygen compound
Organic oxide
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

brassinosteroid (CHEBI:81307 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0303382)

Food

Vegetable

Tuber

Potato (FooDB: FOOD00175)

Not Available

EC 3.1.1.8 (cholinesterase) inhibitor (HMDB: HMDB0303382)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.016 g/L	ALOGPS
logP	3.44	ALOGPS
logP	4.2	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	13.64	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	129.05 m³·mol⁻¹	ChemAxon
Polarizability	54.51 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	No	ChemAxon