ChemFOnt: Showing chemical card for 23-trans-p-Coumaroyloxytormentic acid (CFc000021553)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:13:24 UTC

Chemfont ID

CFc000021553

Molecule Identification

Common Name

23-trans-p-Coumaroyloxytormentic acid

Definition

23-cis-p-Coumaroyloxytormentic acid is found in fruits. 23-cis-p-Coumaroyloxytormentic acid is a constituent of Eriobotrya japonica (loquat).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
23-trans-p-Coumaroyloxytormentate	Generator
1,10,11-Trihydroxy-9-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate	HMDB

Chemical Formula

C₃₉H₅₄O₈

Average Molecular Weight

650.8413

Monoisotopic Molecular Weight

650.381868704

IUPAC Name

1,10,11-trihydroxy-9-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

Traditional Name

1,10,11-trihydroxy-9-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

CAS Registry Number

144604-14-8

SMILES

CC1CCC2(CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(COC(=O)\C=C\C6=CC=C(O)C=C6)C5CCC34C)C2C1(C)O)C(O)=O

InChI Identifier

InChI=1S/C39H54O8/c1-23-15-18-39(33(44)45)20-19-36(4)26(31(39)38(23,6)46)12-13-29-34(2)21-27(41)32(43)35(3,28(34)16-17-37(29,36)5)22-47-30(42)14-9-24-7-10-25(40)11-8-24/h7-12,14,23,27-29,31-32,40-41,43,46H,13,15-22H2,1-6H3,(H,44,45)/b14-9+

InChI Key

SWEBUECVVVXRRV-NTEUORMPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
12-hydroxysteroid
Hydroxysteroid
Steroid
Coumaric acid ester
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Styrene
Phenol
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Polyol
Carboxylic acid derivative
Carboxylic acid
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040682)

Source

Exogenous

Food

Food (HMDB: HMDB0040682)

Fruit

Tropical fruit

Loquat (FooDB: FOOD00076)

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0040682)

Endogenous

Plant

Plant (HMDB: HMDB0040682)

Animal

Animal (HMDB: HMDB0040682)

Endogenous (HMDB: HMDB0040682)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0040682)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0040682)

Lipid metabolism pathway (HMDB: HMDB0040682)

Cellular process

Cell signaling (HMDB: HMDB0040682)

Biochemical process

Lipid transport (HMDB: HMDB0040682)

Role

Biological role

Energy source (HMDB: HMDB0040682)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0040682)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0014 g/L	ALOGPS
logP	5.18	ALOGPS
logP	5.72	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	4.64	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	144.52 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	179.99 m³·mol⁻¹	ChemAxon
Polarizability	72.45 Å³	ChemAxon
Number of Rings	6	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

HMDB0040682

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB020480

KNApSAcK ID

C00054366

Chemspider ID

35015001

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752904

PDB ID

Not Available

ChEBI ID

168707

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 23-trans-p-Coumaroyloxytormentic acid (CFc000021553)

MOL for CFc000021553 (23-trans-p-Coumaroyloxytormentic acid)

3D MOL for CFc000021553 (23-trans-p-Coumaroyloxytormentic acid)

3D SDF for CFc000021553 (23-trans-p-Coumaroyloxytormentic acid)

3D-SDF for CFc000021553 (23-trans-p-Coumaroyloxytormentic acid)

PDB for CFc000021553 (23-trans-p-Coumaroyloxytormentic acid)

3D PDB for CFc000021553 (23-trans-p-Coumaroyloxytormentic acid)

SMILES for CFc000021553 (23-trans-p-Coumaroyloxytormentic acid)

INCHI for CFc000021553 (23-trans-p-Coumaroyloxytormentic acid)

Structure for CFc000021553 (23-trans-p-Coumaroyloxytormentic acid)

3D Structure for CFc000021553 (23-trans-p-Coumaroyloxytormentic acid)