ChemFOnt: Showing chemical card for Euscaphic acid (CFc000017588)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:07:40 UTC

Chemfont ID

CFc000017588

Molecule Identification

Common Name

Euscaphic acid

Definition

Euscaphic acid is found in herbs and spices. Euscaphic acid is a constituent of Coleus amboinicus (Cuban oregano).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Jacarandic acid	ChEBI
Tormentic acid	ChEBI
Jacarandate	Generator
Tormentate	Generator
Euscaphate	Generator
(2alpha,3beta)-Isomer OF euscaphic acid	MeSH
2alpha-Acetyl tormentic acid	MeSH
Acuminatic acid	HMDB

Chemical Formula

C₃₀H₄₈O₅

Average Molecular Weight

488.6991

Monoisotopic Molecular Weight

488.350174646

IUPAC Name

(1R,2R,4aS,6aS,6bR,8aR,10S,11R,12aR,12bR,14bS)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-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

(1R,2R,4aS,6aS,6bR,8aR,10S,11R,12aR,12bR,14bS)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

CAS Registry Number

53155-25-2

SMILES

[H][C@@]12CC[C@]3(C)[C@]([H])(CC=C4[C@]5([H])[C@](C)(O)[C@H](C)CC[C@@]5(CC[C@@]34C)C(O)=O)[C@@]1(C)C[C@@H](O)[C@@H](O)C2(C)C

InChI Identifier

InChI=1S/C30H48O5/c1-17-10-13-30(24(33)34)15-14-27(5)18(22(30)29(17,7)35)8-9-21-26(4)16-19(31)23(32)25(2,3)20(26)11-12-28(21,27)6/h8,17,19-23,31-32,35H,9-16H2,1-7H3,(H,33,34)/t17-,19-,20+,21-,22-,23-,26+,27-,28-,29-,30+/m1/s1

InChI Key

OXVUXGFZHDKYLS-QUFHAEKXSA-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
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

triol (CHEBI:67914 )
hydroxy monocarboxylic acid (CHEBI:67914 )
pentacyclic triterpenoid (CHEBI:67914 )
Ursanes (C17890 )
Dammarenes (C17890 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036651)

Source

Endogenous

Endogenous (HMDB: HMDB0036651)

Plant

Plant (HMDB: HMDB0036651)

Animal

Animal (HMDB: HMDB0036651)

Exogenous

Food

Food (HMDB: HMDB0036651)

Fruit

Tropical fruit

Loquat (FooDB: FOOD00076)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0036651)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036651)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036651)

Lipid metabolism pathway (HMDB: HMDB0036651)

Cellular process

Cell signaling (HMDB: HMDB0036651)

Biochemical process

Lipid transport (HMDB: HMDB0036651)

Role

Biological role

Energy source (HMDB: HMDB0036651)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036651)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0081 g/L	ALOGPS
logP	4.87	ALOGPS
logP	4.27	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	4.64	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	136.66 m³·mol⁻¹	ChemAxon
Polarizability	56.47 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon