Showing Compound Diaminopimelic acid (FDB022583)

Record Information

Version

1.0

Creation date

2011-09-21 00:16:18 UTC

Update date

2020-09-17 15:40:36 UTC

Primary ID

FDB022583

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Diaminopimelic acid

Description

Diaminopimelic acid, also known as LL-2,6-diaminopimelate or DAPA, 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. A Diaminopimelic acid in which both chiral centres have S configuration. Diaminopimelic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Diaminopimelic acid exists in all living species, ranging from bacteria to humans. Outside of the human body, Diaminopimelic acid has been detected, but not quantified in, several different foods, such as breadfruits, horned melons, daikon radish, malabar spinachs, and hard wheats. This could make diaminopimelic acid a potential biomarker for the consumption of these foods.

CAS Number

583-93-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(S,S)-2,6-Diaminopimelic acid	ChEBI
(S-(R,r))-2,6-diaminoheptanedioic acid	ChEBI
L,L-2,6-Diaminopimelic acid	ChEBI
LL-2,6-Diaminoheptanedioate	ChEBI
LL-2,6-Diaminopimelate	ChEBI
LL-2,6-Diaminopimelic acid	Kegg
(S,S)-2,6-Diaminopimelate	Generator
(S-(R,r))-2,6-diaminoheptanedioate	Generator
L,L-2,6-Diaminopimelate	Generator
LL-2,6-Diaminoheptanedioic acid	Generator
Diaminopimelate	Generator
( (R,s)-2,6-diamino-heptanedioate	HMDB
( (R,s)-2,6-diamino-heptanedioic acid	HMDB
(2R,6S)-2,6-diamino-Heptanedioate	HMDB
(2R,6S)-2,6-diamino-Heptanedioic acid	HMDB
(R,s)-2,6-diamino-heptanedioate	HMDB
(R,s)-2,6-diamino-heptanedioic acid	HMDB
2,6-diamino-Heptanedioate	HMDB
2,6-diamino-Heptanedioic acid	HMDB
2,6-Diaminoheptanedioate	HMDB
2,6-Diaminoheptanedioic acid	HMDB
2,6-Diaminopimelate	HMDB
2,6-Diaminopimelic acid	HMDB, MeSH
a,A'-diaminopimelate	HMDB
a,A'-diaminopimelic acid	HMDB
a,e-Diaminopimelate	HMDB
a,e-Diaminopimelic acid	HMDB
D,L-Diaminopimelate	HMDB
D,L-meso-Diaminoheptanedioate	HMDB
D,L-meso-Diaminoheptanedioic acid	HMDB
DAPA	HMDB
DL-2,6-Diaminoheptanedioate	HMDB
DL-2,6-Diaminoheptanedioic acid	HMDB
DL-2,6-Diaminopimelate	HMDB
DL-2,6-Diaminopimelic acid	HMDB
L,L-2,6-Diaminoheptanedioate	HMDB
L,L-2,6-Diaminoheptanedioic acid	HMDB
L,L-Diaminopimelate	HMDB
meso-1-alpha,epsilon-Diaminopimelate	HMDB
meso-2,6-diamino-Heptanedioate	HMDB
meso-2,6-diamino-Heptanedioic acid	HMDB
meso-2,6-Diaminoheptanedioate	HMDB
meso-2,6-Diaminoheptanedioic acid	HMDB
meso-alpha,Alpha'-diaminopimelate	HMDB
meso-alpha,Alpha'-diaminopimelic acid	HMDB
meso-alpha,epsilon-Diaminopimelate	HMDB
meso-alpha,epsilon-Diaminopimelic acid	HMDB
meso-Diaminoheptanedioate	HMDB
meso-Diaminoheptanedioic acid	HMDB
meso-Diaminopimelate	HMDB
Acid, diaminopimelic	MeSH, HMDB
2,6 Diaminopimelic acid	MeSH, HMDB
Acid, 2,6-diaminopimelic	MeSH, HMDB
Diamino-pimelate	Generator, HMDB
Diaminopimelic acid	MeSH
( (R,S)-2,6-diamino-Heptanedioate	hmdb
( (R,S)-2,6-diamino-Heptanedioic acid	hmdb
(2R,6S)-2,6-diamino-heptanedioate	hmdb
(2R,6S)-2,6-diamino-heptanedioic acid	hmdb
(R,S)-2,6-diamino-Heptanedioate	hmdb
(R,S)-2,6-diamino-Heptanedioic acid	hmdb
a,a'-Diaminopimelate	hmdb
a,a'-Diaminopimelic acid	hmdb
D,L-diaminopimelate	hmdb
D,L-meso-diaminoheptanedioate	hmdb
D,L-meso-diaminoheptanedioic acid	hmdb
dl-2,6-Diaminoheptanedioate	hmdb
dl-2,6-Diaminoheptanedioic acid	hmdb
L,L-2,6-diaminoheptanedioate	hmdb
L,L-2,6-diaminoheptanedioic acid	hmdb
L,L-2,6-diaminopimelate	hmdb
L,L-diaminopimelate	hmdb
LL-2,6-diaminoheptanedioate	hmdb
LL-2,6-diaminoheptanedioic acid	hmdb
LL-2,6-diaminopimelate	ChEBI
meso-1-alpha,epsilon-diaminopimelate	hmdb
meso-2,6-diaminoheptanedioate	hmdb
meso-2,6-diaminoheptanedioic acid	hmdb
meso-alpha,alpha'-Diaminopimelate	hmdb
meso-alpha,alpha'-Diaminopimelic acid	hmdb
meso-diaminoheptanedioate	hmdb
meso-diaminoheptanedioic acid	hmdb
meso-diaminopimelate	hmdb

Predicted Properties

Property	Value	Source
Water Solubility	14.1 g/L	ALOGPS
logP	-4.1	ALOGPS
logP	-5.5	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	1.85	ChemAxon
pKa (Strongest Basic)	9.83	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	126.64 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	43.64 m³·mol⁻¹	ChemAxon
Polarizability	18.93 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

Chemical Formula

C7H14N2O4

IUPAC name

(2S,6S)-2,6-diaminoheptanedioic acid

InChI Identifier

InChI=1S/C7H14N2O4/c8-4(6(10)11)2-1-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)/t4-,5-/m0/s1

InChI Key

GMKMEZVLHJARHF-WHFBIAKZSA-N

Isomeric SMILES

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

Average Molecular Weight

190.1971

Monoisotopic Molecular Weight

190.095356946

Classification

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
Medium-chain fatty acid
Amino fatty acid
Dicarboxylic acid or derivatives
Fatty acid
Fatty acyl
Amino acid
Carboxylic acid
Organopnictogen compound
Organic nitrogen compound
Amine
Organic oxygen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2,6-diaminopimelic acid (CHEBI:16026 )
Dicarboxylic acids (LMFA01170102 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Diaminopimelic acid, 4 TMS, GC-MS Spectrum	splash10-0umi-1950000000-749403a0eb6d05c7903e	Spectrum
GC-MS	Diaminopimelic acid, 4 TMS, GC-MS Spectrum	splash10-0uk9-1980000000-1b092f9141e7549bee24	Spectrum
GC-MS	Diaminopimelic acid, non-derivatized, GC-MS Spectrum	splash10-0umi-1950000000-749403a0eb6d05c7903e	Spectrum
GC-MS	Diaminopimelic acid, non-derivatized, GC-MS Spectrum	splash10-0uk9-1980000000-1b092f9141e7549bee24	Spectrum
Predicted GC-MS	Diaminopimelic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00dm-9500000000-5d0aafd0747a1090e055	Spectrum
Predicted GC-MS	Diaminopimelic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-014i-4590000000-b941e92697a8b7800912	Spectrum
Predicted GC-MS	Diaminopimelic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-004l-0900000000-d85213bd7ac426f10cd7	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-9100000000-add590f1b216bdb40334	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-001i-9000000000-de98ed3bb8c48b6f9852	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-2c8a0ca138ef6ea5ef43	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-003r-9600000000-19f54d2417fe44d0eba3	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-e8b0bbffeaa501a6fedd	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-91296097628a67dd97ef	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-e5c4e034dcab0695e0ce	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-002r-0900000000-2a19445fee9eade1d538	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000000000-f44538bc8ae3a51cbbc6	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-003r-9700000000-3baa36a29b4ed6172da0	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-004i-1900000000-cf39d89ce72ac9ddaf51	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0200-6900000000-6f21b7798408480c1bfc	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9300000000-6e778092666f89ff4211	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-28fbb202ae5558af7594	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-004i-1900000000-8a1ee3da7fbe94f840c2	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-8caae42eda716644fdc1	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0005-1900000000-be94a16bee7fad24d5d9	2016-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-5900000000-896859ce722942f9dd68	2016-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006t-9200000000-50c1b5a4f7b19e8ff0db	2016-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-5ecd829b51ba774883f6	2016-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-1900000000-53b7aee01233b5b73d3e	2016-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9400000000-2cc35eb21a44b2d472b5	2016-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0079-0900000000-a0ce1f9601e9b8d83ccf	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dj-6900000000-cc22f522673c5549366c	2021-09-22	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum