MiMeDB: Showing metabocard for (S)-2,3-diaminopropanoic acid (MMDBc0054101)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 22:52:59 UTC

Update Date

2024-10-15 19:20:25 UTC

Metabolite ID

MMDBc0054101

Metabolite Identification

Common Name

(S)-2,3-diaminopropanoic acid

Description

2,3-Diaminopropionic acid, also known as L-2,3-diaminopropanoate or Dpr, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. 2,3-Diaminopropionic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 2,3-Diaminopropionic acid (2,3-diaminopropionate) is a non-proteinogenic amino acid found in certain secondary metabolites, including zwittermicin A and tuberactinomycin.2,3-Diaminopropionate is formed by the pyridoxal phosphate (PLP) mediated amination of serine. 2,3-Diaminopropionic acid exists in all living organisms, ranging from bacteria to humans.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

Synonyms

Value	Source
Dpr	ChEBI
L-2,3-Diaminopropanoate	ChEBI
L-2,3-Diaminopropanoic acid	ChEBI
L-2,3-Diaminopropionate	ChEBI
L-2,3-Diaminopropionic acid	ChEBI
3-Amino-L-alanine	Kegg
(S)-2,3-Diaminopropanoate	Kegg
(S)-2,3-Diaminopropanoic acid	Generator
2,3-Diaminopropionate	Generator
2,3-Diaminopropanoic acid	MeSH
2,3-Diaminopropionic acid, (D)-isomer	MeSH
2,3-Diaminopropionic acid, (DL)-isomer	MeSH
2,3-Diaminopropionic acid, (DL)-isomer, monohydrochloride	MeSH
2,3-Diaminopropionic acid, (L)-isomer	MeSH
2,3-Diaminopropionic acid, (L)-isomer, monohydrochloride	MeSH
2-Amino-beta-alanine	MeSH
3-Aminoalanine	MeSH
alpha,beta-Diaminopropionic acid	MeSH
beta-Aminoalanine	MeSH
(2S)-2,3-Diaminopropanoate	HMDB
(2S)-2,3-Diaminopropanoic acid	HMDB
2,3-Diamino-propionate	Generator, HMDB
2,3-Diaminopropionic acid	MeSH

Molecular Formula

C₃H₈N₂O₂

Average Mass

104.1078

Monoisotopic Mass

104.05857751

IUPAC Name

(2S)-2,3-diaminopropanoic acid

Traditional Name

L-2,3-diaminopropionic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C3H8N2O2/c4-1-2(5)3(6)7/h2H,1,4-5H2,(H,6,7)/t2-/m0/s1

InChI Key

PECYZEOJVXMISF-REOHCLBHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Amine
Organic oxide
Hydrocarbon derivative
Organopnictogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Primary aliphatic amine
Organic nitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:16303 )
L-alanine derivative (CHEBI:16303 )
3-aminoalanine (CHEBI:16303 )
Amino fatty acids (LMFA01100051 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	352 g/L	ALOGPS
logP	-3.9	ALOGPS
logP	-4	ChemAxon
logS	0.53	ALOGPS
pKa (Strongest Acidic)	2.1	ChemAxon
pKa (Strongest Basic)	9.57	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	89.34 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	23.7 m³·mol⁻¹	ChemAxon
Polarizability	9.88 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

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-053r-9000000000-c5fc8b7f3049c78db259	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0089-9400000000-ac9c548fe4984f658b4d	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-9100000000-0d9790594001471b30ed	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-9100000000-afc3c837d4193aee8288	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0pi9-9700000000-9694425dfef5b5a9b6a8	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0ab9-9000000000-47e5a6d43d4dd903ad2a	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0umi-9200000000-cdbef0d4f417da3f4d68	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0pb9-9500000000-453d4ec5b3b3fffa75c0	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0uk9-9700000000-556093b8c1142db10ca3	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-28b689d61557d0156a33	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-729b5b8797f416bce213	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-052r-9000000000-b1c23d0d8fa20eb4b050	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-2079e63ab371d840a83b	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-052f-9000000000-3f1fb8b7029a044c119e	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-052r-9000000000-168277f796b98136571f	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-deccf086827986dca60b	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9000000000-bf1eba665b4e9f152c2f	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-89f7476682642125bf80	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-9300000000-ab5e7bbdd93c33708014	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4l-9000000000-9a0039635b417ed57505	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-092731a1c0c67993ca40	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-3900000000-06bcb0fa2d300aaf959b	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udr-9800000000-aa154fa977a53ab8cfad	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0abl-9000000000-a1904446aa10d46b7228	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9100000000-bf29a0689dc1d006323e	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4l-9000000000-8630c46c35decca03a43	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-7df0d544cdfbca8fa883	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2012-12-05	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	5	Human ; Human feces
Bacteria	Firmicutes	1	Human

Exposure Sources

Source Type	Activity	Data Source	Reference
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified	<1				nmol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	19309105
Human Blood	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0002006

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022790

KNApSAcK ID

Not Available

Chemspider ID

87849

KEGG Compound ID

C03401

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

2,3-Diaminopropionic_acid

METLIN ID

6429

PubChem Compound

97328

PDB ID

Not Available

ChEBI ID

16303

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Cheema PS, Malathi K, Padmanaban G, Sarma PS: The neurotoxicity of beta-N-oxalyl-L-alphabeta-diaminopropionic acid, the neurotoxin from the pulse Lathyrus sativus. Biochem J. 1969 Mar;112(1):29-33. doi: 10.1042/bj1120029. [PubMed:5774501 ]

Showing metabocard for (S)-2,3-diaminopropanoic acid (MMDBc0054101)

MOL for #<Metabolite:0x00007fdb702c5440>

3D MOL for #<Metabolite:0x00007fdb702c5440>

3D SDF for #<Metabolite:0x00007fdb702c5440>

3D-SDF for #<Metabolite:0x00007fdb702c5440>

PDB for #<Metabolite:0x00007fdb702c5440>

3D PDB for #<Metabolite:0x00007fdb702c5440>

SMILES for #<Metabolite:0x00007fdb702c5440>

INCHI for #<Metabolite:0x00007fdb702c5440>

Structure for #<Metabolite:0x00007fdb702c5440>

3D Structure for #<Metabolite:0x00007fdb702c5440>