Cannabis Compound Database: Showing Compound Card for (S)-Methylmalonic acid semialdehyde (CDB005158)

Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (12) Show 13 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 19:15:10 UTC

Updated at

2020-11-18 16:39:27 UTC

CannabisDB ID

CDB005158

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

(S)-Methylmalonic acid semialdehyde

Description

(S)-Methylmalonic acid semialdehyde, also known as (2S)-2-methyl-3-oxopropanoate, belongs to the class of organic compounds known as 1,3-dicarbonyl compounds. These are carbonyl compounds with the generic formula O=C(R)C(H)C(R')=O, where R and R' can be any group (S)-Methylmalonic acid semialdehyde is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (S)-Methylmalonic acid semialdehyde exists in all living organisms, ranging from bacteria to humans. Within humans, (S)-methylmalonic acid semialdehyde participates in a number of enzymatic reactions. In particular, (S)-methylmalonic acid semialdehyde can be biosynthesized from (S)-3-hydroxyisobutyric acid; which is catalyzed by the enzymes 3-hydroxyisobutyrate dehydrogenase, mitochondrial and enoyl-CoA hydratase, mitochondrial. In addition, (S)-methylmalonic acid semialdehyde and L-glutamic acid can be biosynthesized from (S)-beta-aminoisobutyric acid and oxoglutaric acid; which is catalyzed by the enzyme 4-aminobutyrate aminotransferase, mitochondrial. In humans, (S)-methylmalonic acid semialdehyde is involved in the metabolic disorder called the 2-methyl-3-hydroxybutyryl-coa dehydrogenase deficiency pathway. 2-Methyl-3-oxopropanoic acid with configuration S at the chiral centre. (S)-Methylmalonic acid semialdehyde 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
(S)-Methylmalonate semialdehyde	ChEBI
(2S)-2-Methyl-3-oxopropanoate	HMDB
(2S)-2-Methyl-3-oxopropanoic acid	HMDB

Chemical Formula

C₄H₆O₃

Average Molecular Weight

102.09

Monoisotopic Molecular Weight

102.0317

IUPAC Name

(2S)-2-methyl-3-oxopropanoic acid

Traditional Name

(S)-methylmalonaldehydic acid

CAS Registry Number

99043-16-0

SMILES

C[C@@H](C=O)C(O)=O

InChI Identifier

InChI=1S/C4H6O3/c1-3(2-5)4(6)7/h2-3H,1H3,(H,6,7)/t3-/m0/s1

InChI Key

VOKUMXABRRXHAR-VKHMYHEASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,3-dicarbonyl compounds. These are carbonyl compounds with the generic formula O=C(R)C(H)C(R')=O, where R and R' can be any group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

1,3-dicarbonyl compounds

Alternative Parents

Substituents

1,3-dicarbonyl compound
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Short-chain aldehyde
Aldehyde
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

aldehydic acid (CHEBI:27821 )
2-methyl-3-oxopropanoic acid (CHEBI:27821 )
Oxo fatty acids (LMFA01060190 )

Ontology

Disposition

Source:

Endogenous

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	0	ALOGPS
logP	0.053	ChemAxon
logS	0.42	ALOGPS
pKa (Strongest Acidic)	3.98	ChemAxon
pKa (Strongest Basic)	-7.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	22.64 m³·mol⁻¹	ChemAxon
Polarizability	9.16 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	(S)-Methylmalonic acid semialdehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4i-9000000000-8b181508e3ce65539b46	Spectrum
Predicted GC-MS	(S)-Methylmalonic acid semialdehyde, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-9600000000-15e42a2e09123d5f22ad	Spectrum
Predicted GC-MS	(S)-Methylmalonic acid semialdehyde, 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	splash10-0zg0-9400000000-e46caa43ec4709ce7686	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-6c1632ad1d7983990262	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-6762a2cf4db52c84495c	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-2900000000-9066dc83487b73946c99	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9200000000-8fde49823ba2083f055f	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-a320f14ddfc09e798938	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0uk9-8900000000-0a76d84228c38b1cfe1d	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pb9-9300000000-dd49ef94a8379e8517cd	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-4f42a2a7dc0b37e742da	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-b5c480248a004c069416	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-6de8f6b91e5efd633c28	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4r-9000000000-a0e9ace5e33e8c50915e	2021-09-22	View Spectrum

NMR

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
Valine, Leucine and Isoleucine Degradation
Propanoate Metabolism
Beta-Ketothiolase Deficiency		Not Available
2-Methyl-3-Hydroxybutryl CoA Dehydrogenase Deficiency		Not Available
Propionic Acidemia		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Methylmalonate-semialdehyde dehydrogenase [acylating], mitochondrial	ALDH6A1	14q24.3	Q02252	details
Aldehyde oxidase	AOX1	2q33	Q06278	details
4-aminobutyrate aminotransferase, mitochondrial	ABAT	16p13.2	P80404	details
4-trimethylaminobutyraldehyde dehydrogenase	ALDH9A1	1q23.1	P49189	details
Alpha-aminoadipic semialdehyde dehydrogenase	ALDH7A1	5q31	P49419	details
Aldehyde dehydrogenase family 1 member A3	ALDH1A3	15q26.3	P47895	details
Aldehyde dehydrogenase, mitochondrial	ALDH2	12q24.2	P05091	details
Fatty aldehyde dehydrogenase	ALDH3A2	17p11.2	P51648	details
Aldehyde dehydrogenase X, mitochondrial	ALDH1B1	9p11.1	P30837	details
3-hydroxyacyl-CoA dehydrogenase type-2	HSD17B10	Xp11.2	Q99714	details
Hydroxyacyl-coenzyme A dehydrogenase, mitochondrial	HADH	4q22-q26	Q16836	details
3-hydroxyisobutyrate dehydrogenase, mitochondrial	HIBADH	7p15.2	P31937	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Aldehyde oxidase	AOX1	2q33	Q06278	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0002217

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022912

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Not Available

METLIN ID

6553

PubChem Compound

5462303

PDB ID

Not Available

ChEBI ID

27821

References

General References

Not Available

Only showing the first 10 proteins. There are 13 proteins in total.

Show All

Enzymes

Enzyme Details

1. Methylmalonate-semialdehyde dehydrogenase [acylating], mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: Plays a role in valine and pyrimidine metabolism. Binds fatty acyl-CoA.
Gene Name:: ALDH6A1
Uniprot ID:: Q02252
Molecular weight:: 57839.31

Enzyme Details

2. Aldehyde oxidase

General function:: Involved in oxidoreductase activity
Specific function:: Not Available
Gene Name:: AOX1
Uniprot ID:: Q06278
Molecular weight:: 147916.735

Enzyme Details

3. 4-aminobutyrate aminotransferase, mitochondrial

General function:: Involved in 4-aminobutyrate transaminase activity
Specific function:: Catalyzes the conversion of gamma-aminobutyrate and L-beta-aminoisobutyrate to succinate semialdehyde and methylmalonate semialdehyde, respectively. Can also convert delta-aminovalerate and beta-alanine.
Gene Name:: ABAT
Uniprot ID:: P80404
Molecular weight:: 56438.405

Enzyme Details

4. 4-trimethylaminobutyraldehyde dehydrogenase

General function:: Involved in oxidoreductase activity
Specific function:: Converts gamma-trimethylaminobutyraldehyde into gamma-butyrobetaine. Catalyzes the irreversible oxidation of a broad range of aldehydes to the corresponding acids in an NAD-dependent reaction.
Gene Name:: ALDH9A1
Uniprot ID:: P49189
Molecular weight:: 56291.485

Enzyme Details

5. Alpha-aminoadipic semialdehyde dehydrogenase

General function:: Involved in oxidoreductase activity
Specific function:: Multifunctional enzyme mediating important protective effects. Metabolizes betaine aldehyde to betaine, an important cellular osmolyte and methyl donor. Protects cells from oxidative stress by metabolizing a number of lipid peroxidation-derived aldehydes. Involved in lysine catabolism.
Gene Name:: ALDH7A1
Uniprot ID:: P49419
Molecular weight:: 58486.74

Enzyme Details

6. Aldehyde dehydrogenase family 1 member A3

General function:: Involved in oxidoreductase activity
Specific function:: Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:: ALDH1A3
Uniprot ID:: P47895
Molecular weight:: 56107.995

Enzyme Details

7. Aldehyde dehydrogenase, mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: Not Available
Gene Name:: ALDH2
Uniprot ID:: P05091
Molecular weight:: 56380.93

Enzyme Details

8. Fatty aldehyde dehydrogenase

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidation of long-chain aliphatic aldehydes to fatty acids. Active on a variety of saturated and unsaturated aliphatic aldehydes between 6 and 24 carbons in length. Responsible for conversion of the sphingosine 1-phosphate (S1P) degradation product hexadecenal to hexadecenoic acid.
Gene Name:: ALDH3A2
Uniprot ID:: P51648
Molecular weight:: 54847.36

Enzyme Details

9. Aldehyde dehydrogenase X, mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation.
Gene Name:: ALDH1B1
Uniprot ID:: P30837
Molecular weight:: 57248.96

Enzyme Details

10. 3-hydroxyacyl-CoA dehydrogenase type-2

General function:: Involved in oxidoreductase activity
Specific function:: Functions in mitochondrial tRNA maturation. Part of mitochondrial ribonuclease P, an enzyme composed of MRPP1/TRMT10C, MRPP2/HSD17B10 and MRPP3/KIAA0391, which cleaves tRNA molecules in their 5'-ends. By interacting with intracellular amyloid-beta, it may contribute to the neuronal dysfunction associated with Alzheimer disease (AD).
Gene Name:: HSD17B10
Uniprot ID:: Q99714
Molecular weight:: 25983.695

Only showing the first 10 proteins. There are 13 proteins in total.

Show All

Showing Compound Card for (S)-Methylmalonic acid semialdehyde (CDB005158)

Structure for CDB005158 ((S)-Methylmalonic acid semialdehyde)

Enzymes