ChemFOnt: Showing chemical card for Oryzanol (CFc000282201)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:34:20 UTC

Chemfont ID

CFc000282201

Molecule Identification

Common Name

Oryzanol

Definition

Oryzanol belongs to cycloartanols and derivatives class of compounds. Those are steroids containing a cycloartanol moiety. Oryzanol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Oryzanol can be found in barley, which makes oryzanol a potential biomarker for the consumption of this food product. Rice bran oil is the oil extracted from the hard outer brown layer of rice after chaff (rice husk). It is known for its high smoke point of 232 ¬∞C (450 ¬∞F) and mild flavor, making it suitable for high-temperature cooking methods such as stir frying and deep frying. It is popular as a cooking oil in several Asian countries, including Bangladesh, Japan, India and China .

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₄₀H₅₈O₄

Average Molecular Weight

602.8861

Monoisotopic Molecular Weight

602.433510344

IUPAC Name

(1S,3R,6S,12S,15R,16R)-7,7,12,16-tetramethyl-15-(6-methylhept-5-en-2-yl)pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Traditional Name

(1S,3R,6S,12S,15R,16R)-7,7,12,16-tetramethyl-15-(6-methylhept-5-en-2-yl)pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

CAS Registry Number

11042-64-1

SMILES

COC1=C(O)C=CC(\C=C\C(=O)O[C@H]2CC[C@]34C[C@]33CC[C@]5(C)[C@H](CC[C@@]5(C)C3CCC4C2(C)C)C(C)CCC=C(C)C)=C1

InChI Identifier

InChI=1S/C40H58O4/c1-26(2)10-9-11-27(3)29-18-20-38(7)33-16-15-32-36(4,5)34(19-21-39(32)25-40(33,39)23-22-37(29,38)6)44-35(42)17-13-28-12-14-30(41)31(24-28)43-8/h10,12-14,17,24,27,29,32-34,41H,9,11,15-16,18-23,25H2,1-8H3/b17-13+/t27?,29-,32?,33?,34+,37-,38+,39-,40+/m1/s1

InChI Key

FODTZLFLDFKIQH-AEUNZGHWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cycloartanols and derivatives. These are steroids containing a cycloartanol moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cycloartanols and derivatives

Direct Parent

Cycloartanols and derivatives

Alternative Parents

Substituents

Cycloartanol-skeleton
Cycloartane-skeleton
9b,19-cyclo-lanostane-skeleton
Triterpenoid
Steroid ester
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Coumaric acid or derivatives
Cinnamic acid or derivatives
Methoxyphenol
Phenoxy compound
Styrene
Anisole
Phenol ether
Methoxybenzene
Fatty acid ester
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Ether
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302685)

Food

Cereal and cereal product

Cereal

Barley (FooDB: FOOD00088)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.4e-05 g/L	ALOGPS
logP	8.54	ALOGPS
logP	10.12	ChemAxon
logS	-7.6	ALOGPS
pKa (Strongest Acidic)	9.87	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	180.04 m³·mol⁻¹	ChemAxon
Polarizability	74.83 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

HMDB0302685

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB005790

KNApSAcK ID

Not Available

Chemspider ID

4952834

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Γ-Oryzanol

METLIN ID

Not Available

PubChem Compound

6450219

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Oryzanol (CFc000282201)

MOL for CFc000282201 (Oryzanol)

3D MOL for CFc000282201 (Oryzanol)

3D SDF for CFc000282201 (Oryzanol)

3D-SDF for CFc000282201 (Oryzanol)

PDB for CFc000282201 (Oryzanol)

3D PDB for CFc000282201 (Oryzanol)

SMILES for CFc000282201 (Oryzanol)

INCHI for CFc000282201 (Oryzanol)

Structure for CFc000282201 (Oryzanol)

3D Structure for CFc000282201 (Oryzanol)