Showing chemical card for 24-Acetyl- 25-cinnamoylvulgaroside (CFc000022234)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:14:22 UTC

Chemfont ID

CFc000022234

Molecule Identification

Common Name

24-Acetyl- 25-cinnamoylvulgaroside

Definition

24-Acetyl- 25-cinnamoylvulgaroside is found in fruits. 24-Acetyl- 25-cinnamoylvulgaroside is a constituent of Cydonia vulgaris (quince).

Structure

MOL SDF PDB SMILES InChI

SMILES for CFc000022234 (24-Acetyl- 25-cinnamoylvulgaroside)

CC(=O)OCC1(O)CCC2C(C)(CCC3C(C)(C)CCCC23C)C1CC(O)C1=CC(=O)OC1OC(=O)\C=C\C1=CC=CC=C1

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INCHI for CFc000022234 (24-Acetyl- 25-cinnamoylvulgaroside)

InChI=1S/C36H48O8/c1-23(37)42-22-36(41)19-15-28-34(4)17-9-16-33(2,3)27(34)14-18-35(28,5)29(36)21-26(38)25-20-31(40)44-32(25)43-30(39)13-12-24-10-7-6-8-11-24/h6-8,10-13,20,26-29,32,38,41H,9,14-19,21-22H2,1-5H3/b13-12+

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Structure for CFc000022234 (24-Acetyl- 25-cinnamoylvulgaroside)

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3D Structure for CFc000022234 (24-Acetyl- 25-cinnamoylvulgaroside)

Synonyms

Value	Source
3-(2-{2-[(acetyloxy)methyl]-2-hydroxy-4b,8,8,10a-tetramethyl-tetradecahydrophenanthren-1-yl}-1-hydroxyethyl)-5-oxo-2,5-dihydrofuran-2-yl (2E)-3-phenylprop-2-enoic acid	HMDB

Chemical Formula

C₃₆H₄₈O₈

Average Molecular Weight

608.7615

Monoisotopic Molecular Weight

608.334918512

IUPAC Name

3-(2-{2-[(acetyloxy)methyl]-2-hydroxy-4b,8,8,10a-tetramethyl-tetradecahydrophenanthren-1-yl}-1-hydroxyethyl)-5-oxo-2,5-dihydrofuran-2-yl (2E)-3-phenylprop-2-enoate

Traditional Name

3-(2-{2-[(acetyloxy)methyl]-2-hydroxy-4b,8,8,10a-tetramethyl-decahydrophenanthren-1-yl}-1-hydroxyethyl)-5-oxo-2H-furan-2-yl (2E)-3-phenylprop-2-enoate

CAS Registry Number

172616-89-6

SMILES

CC(=O)OCC1(O)CCC2C(C)(CCC3C(C)(C)CCCC23C)C1CC(O)C1=CC(=O)OC1OC(=O)\C=C\C1=CC=CC=C1

InChI Identifier

InChI=1S/C36H48O8/c1-23(37)42-22-36(41)19-15-28-34(4)17-9-16-33(2,3)27(34)14-18-35(28,5)29(36)21-26(38)25-20-31(40)44-32(25)43-30(39)13-12-24-10-7-6-8-11-24/h6-8,10-13,20,26-29,32,38,41H,9,14-19,21-22H2,1-5H3/b13-12+

InChI Key

IMXZIJOCFAKDPZ-OUKQBFOZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cheilanthane sesterterpenoids. These are sesterterpnoids with a structure based on the cheilanthane backbone. Cheilanthane is a tricyclic compound consisting of a tetradecahydrophenanthrene ring system that carries two methyl groups at the 1-position, one methyl group at the 4a-,7-, and 8a-positions, as well as a 3-methylpentyl group at the 8-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Cheilanthane sesterterpenoids

Alternative Parents

16-hydroxysteroids
Hydrophenanthrenes
Cinnamic acid esters
Tricarboxylic acids and derivatives
Styrenes
Fatty acid esters
Acylals
Butenolides
Tertiary alcohols
Enoate esters
Secondary alcohols
Lactones
Cyclic alcohols and derivatives
Oxacyclic compounds
Acetals
Carbonyl compounds
Hydrocarbon derivatives
Organic oxides

Substituents

Cheilanthane sesterterpenoid
13-hydroxysteroid
Hydroxysteroid
16-hydroxysteroid
Steroid
Hydrophenanthrene
Phenanthrene
Cinnamic acid or derivatives
Cinnamic acid ester
Tricarboxylic acid or derivatives
Styrene
Acylal
Fatty acid ester
Benzenoid
Fatty acyl
Monocyclic benzene moiety
2-furanone
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Tertiary alcohol
Cyclic alcohol
Dihydrofuran
Secondary alcohol
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Acetal
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0041368)
Extracellular (HMDB: HMDB0041368)
Cytoplasm (HMDB: HMDB0041368)
Cell membrane (HMDB: HMDB0041368)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041368)

Source

Endogenous

Endogenous (HMDB: HMDB0041368)

Plant

Plant (HMDB: HMDB0041368)

Animal

Animal (HMDB: HMDB0041368)

Exogenous

Food

Food (HMDB: HMDB0041368)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0041368)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0041368)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0041368)

Lipid metabolism pathway (HMDB: HMDB0041368)

Cellular process

Cell signaling (HMDB: HMDB0041368)

Biochemical process

Lipid transport (HMDB: HMDB0041368)

Role

Biological role

Energy source (HMDB: HMDB0041368)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0041368)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.00048 g/L	ALOGPS
logP	4.93	ALOGPS
logP	6.26	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	1.89	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	165.89 m³·mol⁻¹	ChemAxon
Polarizability	67.16 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0041368

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021293

KNApSAcK ID

Not Available

Chemspider ID

35015162

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131753124

PDB ID

Not Available

ChEBI ID

172772

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 24-Acetyl- 25-cinnamoylvulgaroside (CFc000022234)

MOL for CFc000022234 (24-Acetyl- 25-cinnamoylvulgaroside)

3D MOL for CFc000022234 (24-Acetyl- 25-cinnamoylvulgaroside)

3D SDF for CFc000022234 (24-Acetyl- 25-cinnamoylvulgaroside)

3D-SDF for CFc000022234 (24-Acetyl- 25-cinnamoylvulgaroside)

PDB for CFc000022234 (24-Acetyl- 25-cinnamoylvulgaroside)

3D PDB for CFc000022234 (24-Acetyl- 25-cinnamoylvulgaroside)

SMILES for CFc000022234 (24-Acetyl- 25-cinnamoylvulgaroside)

INCHI for CFc000022234 (24-Acetyl- 25-cinnamoylvulgaroside)

Structure for CFc000022234 (24-Acetyl- 25-cinnamoylvulgaroside)

3D Structure for CFc000022234 (24-Acetyl- 25-cinnamoylvulgaroside)