ContaminantDB: Oxyhumulinic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-26 03:18:34 UTC

Update Date

2016-11-09 01:19:26 UTC

Accession Number

CHEM032325

Identification

Common Name

Oxyhumulinic acid

Class

Small Molecule

Description

Oxyhumulinic acid is found in alcoholic beverages. Secondary produced present in beer derived from Humulone HGM37-K.

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Oxyhumulinate	Generator
3,4,5-Trihydroxy-5-(3-methyl-2-butenyl)-2-(3-methyl-1-oxobutyl)-2-cyclopenten-1-one, 9ci	HMDB

Chemical Formula

C₁₅H₂₂O₅

Average Molecular Mass

282.332 g/mol

Monoisotopic Mass

282.147 g/mol

CAS Registry Number

469-30-7

IUPAC Name

3,4,5-trihydroxy-5-(3-methylbut-2-en-1-yl)-2-(3-methylbutanoyl)cyclopent-2-en-1-one

Traditional Name

3,4,5-trihydroxy-5-(3-methylbut-2-en-1-yl)-2-(3-methylbutanoyl)cyclopent-2-en-1-one

SMILES

CC(C)CC(=O)C1=C(O)C(O)C(O)(CC=C(C)C)C1=O

InChI Identifier

InChI=1S/C15H22O5/c1-8(2)5-6-15(20)13(18)11(12(17)14(15)19)10(16)7-9(3)4/h5,9,14,17,19-20H,6-7H2,1-4H3

InChI Key

QSHUUGSBRMSXKV-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Acyloins

Alternative Parents

Substituents

Acyloin
Vinylogous acid
Tertiary alcohol
Cyclic ketone
Secondary alcohol
Ketone
1,2-diol
Polyol
Enol
Organic oxide
Hydrocarbon derivative
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	2.51 g/L	ALOGPS
logP	1.05	ALOGPS
logP	1.66	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	1.07	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	76.57 m³·mol⁻¹	ChemAxon
Polarizability	30.1 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9650000000-bfb717398ff796438f61	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-003r-7511900000-2b2451a57852555c8b2a	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-1190000000-015c943a4a404b5ebef7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-066r-9360000000-b42fe17d315a44315d16	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aor-9410000000-020c3b7b99c03068d201	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0190000000-264179c763742b377988	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000t-7980000000-043b081c5eeac7825dcf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00l7-9410000000-4b392c31b2f393aabc02	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090000000-54331f56903560001ecc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0059-0930000000-4013f06d1dc40a5e1fda	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-054k-9520000000-e952b6aa801bd390c63f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0190000000-72d7bfdfb32140a15a71	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00lu-9270000000-0acbb722d77cd7c3f4e3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-066u-9200000000-8f5102b9440be54faeb7	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0038989

FooDB ID

FDB018475

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

20039731

ChEBI ID

Not Available

PubChem Compound ID

45115175

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

Oxyhumulinic acid (CHEM032325)

Structure for CHEM032325: Oxyhumulinic acid