cadaverine (CHEBI:18127)

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CHEBI:18127 - cadaverine

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ChEBI Name	cadaverine

ChEBI ID	CHEBI:18127

Definition	An alkane-α,ω-diamine comprising a straight-chain pentane core with amino substitutents at positions 1 and 5. A colourless syrupy liquid diamine with a distinctive unpleasant odour, it is a homologue of putresceine and is formed by the bacterial decarboxylation of lysine that occurs during protein hydrolysis during putrefaction of animal tissue. It is also found in plants such as soyabean.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:44370, CHEBI:3288, CHEBI:13928, CHEBI:22974

Supplier Information	ChemicalBook:CB2177472, eMolecules:712832, eMolecules:27520527, eMolecules:518165

Download	Molfile XML SDF

more structures >>

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21 20 0 0 0 0 999 V2000

-0.3493 -0.2596 -0.0530 C 0 0 0 0 0 0 0 0 0 0 0 0

0.8611 -0.6546 0.8259 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.3493 1.2379 -0.4416 C 0 0 0 0 0 0 0 0 0 0 0 0

0.8477 -2.1476 1.2129 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.5633 1.6224 -1.3119 C 0 0 0 0 0 0 0 0 0 0 0 0

2.0026 -2.4711 2.0535 N 0 0 0 0 0 0 0 0 0 0 0 0

-1.5274 3.0486 -1.6431 N 0 0 0 0 0 0 0 0 0 0 0 0

-1.2721 -0.4857 0.4905 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.3420 -0.8645 -0.9632 H 0 0 0 0 0 0 0 0 0 0 0 0

0.8568 -0.0506 1.7383 H 0 0 0 0 0 0 0 0 0 0 0 0

1.7857 -0.4340 0.2847 H 0 0 0 0 0 0 0 0 0 0 0 0

0.5696 1.4675 -0.9887 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.3566 1.8466 0.4677 H 0 0 0 0 0 0 0 0 0 0 0 0

0.8853 -2.7726 0.3164 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.0603 -2.3899 1.7676 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.5592 1.0497 -2.2435 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.4941 1.4157 -0.7811 H 0 0 0 0 0 0 0 0 0 0 0 0

1.9709 -3.4767 2.2268 H 0 0 0 0 0 0 0 0 0 0 0 0

2.8360 -2.2875 1.4913 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.3175 3.2288 -2.2640 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.6753 3.2030 -2.1857 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 1 0 0 0 0

1 3 1 0 0 0 0

2 4 1 0 0 0 0

3 5 1 0 0 0 0

4 6 1 0 0 0 0

5 7 1 0 0 0 0

1 8 1 0 0 0 0

1 9 1 0 0 0 0

2 10 1 0 0 0 0

2 11 1 0 0 0 0

3 12 1 0 0 0 0

3 13 1 0 0 0 0

4 14 1 0 0 0 0

4 15 1 0 0 0 0

5 16 1 0 0 0 0

5 17 1 0 0 0 0

6 18 1 0 0 0 0

6 19 1 0 0 0 0

7 20 1 0 0 0 0

7 21 1 0 0 0 0

M END): 18 ms

reading 21 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

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Wikipedia	License
Histidine (symbol His or H) is an essential amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated –NH3+ form under biological conditions), a carboxylic acid group (which is in the deprotonated –COO− form under biological conditions), and an imidazole side chain (which is partially protonated), classifying it as a positively charged amino acid at physiological pH. Initially thought essential only for infants, it has now been shown in longer-term studies to be essential for adults also. It is encoded by the codons CAU and CAC. Histidine was first isolated by Albrecht Kossel and Sven Gustaf Hedin in 1896. The name stems from its discovery in tissue, from ἱστός histós "tissue". It is also a precursor to histamine, a vital inflammatory agent in immune responses. The acyl radical is histidyl.
Read full article at Wikipedia

Formula

C5H14N2

Net Charge

Average Mass

102.17810

Monoisotopic Mass

102.11570

InChI

InChI=1S/C5H14N2/c6-4-2-1-3-5-7/h1-7H2

InChIKey

VHRGRCVQAFMJIZ-UHFFFAOYSA-N

SMILES

NCCCCCN

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Daphnia magna (NCBI:txid35525)	See: PubMed
Glycine max (NCBI:txid3847)	See: PubMed
Escherichia coli (NCBI:txid562)	See: PubMed

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). Daphnia magna metabolite A Daphnia metabolite produced by the species Daphnia magna.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	cadaverine (CHEBI:18127) has role Daphnia magna metabolite (CHEBI:83056) cadaverine (CHEBI:18127) has role Escherichia coli metabolite (CHEBI:76971) cadaverine (CHEBI:18127) has role mouse metabolite (CHEBI:75771) cadaverine (CHEBI:18127) has role plant metabolite (CHEBI:76924) cadaverine (CHEBI:18127) is a alkane-α,ω-diamine (CHEBI:35411) cadaverine (CHEBI:18127) is conjugate base of cadaverine(2+) (CHEBI:58384)

Incoming	N-acetylcadaverine (CHEBI:88824) has functional parent cadaverine (CHEBI:18127) N-substituted cadaverine (CHEBI:50442) has functional parent cadaverine (CHEBI:18127) monodansylcadaverine (CHEBI:52007) has functional parent cadaverine (CHEBI:18127) pentamethonium (CHEBI:166825) has functional parent cadaverine (CHEBI:18127) cadaverine(2+) (CHEBI:58384) is conjugate acid of cadaverine (CHEBI:18127)

IUPAC Name

pentane-1,5-diamine

Synonyms	Sources
1,5-Diaminopentane	KEGG COMPOUND
1,5-pentamethylenediamine	NIST Chemistry WebBook
1,5-Pentanediamine	KEGG COMPOUND
Cadaverine	KEGG COMPOUND
DAPE	ChEBI
Pentamethylenediamine	KEGG COMPOUND
PENTANE-1,5-DIAMINE	PDBeChem

Manual Xrefs	Databases
C00001403	KNApSAcK
C01672	KEGG COMPOUND
Cadaverine	Wikipedia
CADAVERINE	MetaCyc
DB03854	DrugBank
HMDB0002322	HMDB
N2P	PDBeChem
View more database links

Registry Numbers	Types	Sources
1697256	Reaxys Registry Number	Reaxys
2310	Gmelin Registry Number	Gmelin
462-94-2	CAS Registry Number	KEGG COMPOUND
462-94-2	CAS Registry Number	ChemIDplus
462-94-2	CAS Registry Number	NIST Chemistry WebBook

Citations	Types	Sources
10930630	PubMed citation	Europe PMC
11397445	PubMed citation	Europe PMC
11517436	PubMed citation	Europe PMC
16346523	PubMed citation	Europe PMC
16668466	PubMed citation	Europe PMC
17439666	PubMed citation	Europe PMC
23561112	PubMed citation	Europe PMC
23794626	PubMed citation	Europe PMC
23811038	PubMed citation	Europe PMC
23887488	PubMed citation	Europe PMC

Last Modified

06 July 2021

CHEBI:18127 - cadaverine

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