Cannabis Compound Database: Showing Compound Card for Isopropylmaleic acid (CDB005020)

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Record Information

Version

1.0

Created at

2020-04-17 19:01:08 UTC

Updated at

2020-12-07 19:11:27 UTC

CannabisDB ID

CDB005020

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Isopropylmaleic acid

Description

Isopropylmaleate belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present. Isopropylmaleate is a moderately acidic compound (based on its pKa). Isopropylmaleic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Isopropylmaleate	ChEBI
beta-Isopropylmaleate	ChEBI
2-Isopropylmaleic acid	Generator
b-Isopropylmaleate	Generator
b-Isopropylmaleic acid	Generator
beta-Isopropylmaleic acid	Generator
Β-isopropylmaleate	Generator
Β-isopropylmaleic acid	Generator
Isopropylmaleate	Generator
Isopropylmaleic acid	Generator
(2Z)-2-(1-Methylethyl)-2-butenedioic acid	HMDB

Chemical Formula

C₇H₁₀O₄

Average Molecular Weight

158.15

Monoisotopic Molecular Weight

158.0579

IUPAC Name

(2Z)-2-(propan-2-yl)but-2-enedioic acid

Traditional Name

2-isopropylmaleic acid

CAS Registry Number

44976-69-4

SMILES

CC(C)C(=C\C(O)=O)\C(O)=O

InChI Identifier

InChI=1S/C7H10O4/c1-4(2)5(7(10)11)3-6(8)9/h3-4H,1-2H3,(H,8,9)(H,10,11)/b5-3-

InChI Key

NJMGRJLQRLFQQX-HYXAFXHYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Methyl-branched fatty acids

Alternative Parents

Substituents

Methyl-branched fatty acid
Unsaturated fatty acid
Dicarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dicarboxylic acid (CHEBI:17275 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Biofluid and excreta:

Urine

Cell and elements:

Extracellular

Subcellular:

Role

Industrial application:

Biological role:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.05	ALOGPS
logP	1.09	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	2.79	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	38.11 m³·mol⁻¹	ChemAxon
Polarizability	15.11 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Isopropylmaleic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01ox-9800000000-c1dc75af0432077c0384	Spectrum
Predicted GC-MS	Isopropylmaleic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00dr-9470000000-5b930a576d9e4924347a	Spectrum
Predicted GC-MS	Isopropylmaleic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-1900000000-45d74194c5fbfea04a10	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ox-7900000000-7e85e22040474be6339c	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014j-9100000000-672bc73595a1f6b84201	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0bt9-1900000000-48b9e2f85f15343470ae	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-090a-5900000000-5c4991c8530e2f8a6eda	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kb-9400000000-0d37fa6e2313dc5f09a3	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01ow-6900000000-9e65c798b41317f5b6e9	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kb-9200000000-6dfbad4c912b766f9b7e	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-9000000000-74dbf533069b6e671b6c	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03xr-9800000000-698f88590edad48bf4c2	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-02t9-9400000000-d1228db2dbcd7906ae8a	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014j-9000000000-a5bd12b0d9ab424964cc	2021-09-25	View Spectrum