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			{{Short description\|Foul-smelling diamine compound}}
	{{chembox
			{{Chembox
	\| verifiedrevid = 443493210
			\| Watchedfields = changed
	\|ImageFile=Cadaverine-2D-skeletal.png
			\| verifiedrevid = 443671098
	\|ImageSize=
			\| ImageFile1 = Pentane-1,5-diamine 200.svg
	\|ImageFile2=Cadaverine-3D-balls.png
			\| ImageFile1_Ref = {{chemboximage\|correct\|??}}
	\|IUPACName=pentane-1,5-diamine
			\| ImageSize1 = 200
	\|OtherNames=
			\| ImageName1 = Skeletal formula of cadaverine
	\|Section1= {{Chembox Identifiers
			\| ImageCaption1 = ]
	\| KEGG_Ref = {{keggcite\|correct\|kegg}}
			\| ImageFile2 = Cadaverine-3D-balls.png
	\| KEGG = C01672
			\| ImageFile2_Ref = {{chemboximage\|correct\|??}}
	\| InChI = 1/C5H14N2/c6-4-2-1-3-5-7/h1-7H2
			\| ImageSize2 = 160
	\| InChIKey = VHRGRCVQAFMJIZ-UHFFFAOYAX
			\| ImageName2 = Ball and stick model of cadaverine
	\| ChEMBL_Ref = {{ebicite\|correct\|EBI}}
			\| ImageCaption2 = ]<ref>{{Cite journal\|url=https://dx.doi.org/10.5517/cc4g861\|title = CSD Entry: QATWEN : 1,5-Pentanediamine\|website=]: Access Structures\| year=2001 \|publisher=]\|doi=10.5517/cc4g861\|access-date = 2021-11-07\| last1=Thalladi \| first1=V.R. \| last2=Boese \| first2=R. \| last3=Weiss \| first3=H.-C. }}</ref>
	\| ChEMBL = 119296
			\| PIN = Pentane-1,5-diamine
	\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
			\| OtherNames = 1,5-Diaminopentane, pentamethylenediamine
	\| StdInChI = 1S/C5H14N2/c6-4-2-1-3-5-7/h1-7H2
			\| Section1 = {{Chembox Identifiers
	\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
			\|CASNo = 462-94-2
	\| StdInChIKey = VHRGRCVQAFMJIZ-UHFFFAOYSA-N
	\| CASNo_Ref = {{cascite\|correct\|CAS}}		\|CASNo_Ref = {{cascite\|correct\|CAS}}
			\|PubChem = 273
	\| CASNo=462-94-2
			\|ChemSpiderID = 13866593
	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
			\|ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| ChemSpiderID = 13866593
			\|UNII = L90BEN6OLL
	\| PubChem=273
	\| UNII_Ref = {{fdacite\|correct\|FDA}}		\|UNII_Ref = {{fdacite\|correct\|FDA}}
			\|EINECS = 207-329-0
	\| UNII = L90BEN6OLL
			\|UNNumber = 2735
	\| ChEBI_Ref = {{ebicite\|correct\|EBI}}
	\| ~~ChEBI~~ = ~~18127~~		\|DrugBank = DB03854
			\|DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}
	\| DrugBank = DB03854
			\|KEGG = C01672
	\| SMILES=NCCCCCN
			\|KEGG_Ref = {{keggcite\|correct\|kegg}}
	\| MeSHName=Cadaverine
			\|MeSHName = Cadaverine
	}}
			\|ChEBI = 18127
	\|Section2= {{Chembox Properties
			\|ChEBI_Ref = {{ebicite\|correct\|EBI}}
	\| Formula=C<sub>5</sub>H<sub>14</sub>N<sub>2</sub>
			\|ChEMBL = 119296
	\| MolarMass=102.178
			\|ChEMBL_Ref = {{ebicite\|correct\|EBI}}
	\| Appearance=
			\|RTECS = SA0200000
	\| Density=0.870 g/cm³
			\|Beilstein = 1697256
	\| MeltingPt=9 °C
			\|Gmelin = 2310
	\| BoilingPt=178-180 °C
			\|3DMet = B00334
	\| Solubility=
			\|SMILES = NCCCCCN
	}}
			\|StdInChI = 1S/C5H14N2/c6-4-2-1-3-5-7/h1-7H2
	\|Section3= {{Chembox Hazards
			\|StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
	\| MainHazards=
			\|StdInChIKey = VHRGRCVQAFMJIZ-UHFFFAOYSA-N
	\| FlashPt=
			\|StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
	\| Autoignition=
	}}
	}}		}}
			\| Section2 = {{Chembox Properties
	'''Cadaverine''' is a foul-smelling compound produced by ] ] during ] of animal tissue. Cadaverine is a toxic<ref>Lewis 1998, Page 212</ref> ] with the formula NH<sub>2</sub>(CH<sub>2</sub>)<sub>5</sub>NH<sub>2</sub>, which is similar to ]. Cadaverine is also known by the names '''1,5-pentanediamine''' and '''pentamethylenediamine'''.
			\|C = 5 \|H = 14 \|N = 2

			\|Appearance = Colourless liquid
	==History==
			\|Odor = very unpleasant; putrid
	]<ref>Ludwig Brieger, "Weitere Untersuchungen über Ptomaine" (Berlin, Germany: August Hirschwald, 1885), .</ref> and cadaverine<ref>Ludwig Brieger, "Weitere Untersuchungen über Ptomaine" (Berlin, Germany: August Hirschwald, 1885), . From page 39: Ich nenne das neue Diamin C<sub>5</sub>H<sub>16</sub>N<sub>2</sub>: "Cadaverin", da ausser der empirischen Zussamsetzung, welche die neue Base als ein Hydrür des Neuridins für den flüchtigen Blick erscheinen lässt, keine Anhaltspunkte für die Berechtigung dieser Auffassung zu erheben waren. (I call the new di-amine, C<sub>5</sub>H<sub>16</sub>N<sub>2</sub>, "cadaverine," since besides its empirical composition, which allows the new base to appear superficially as a hydride of neuridine, no clues for the justification of this view arose.)</ref> were first described in 1885 by the ] physician ] (1849–1919).<ref>Brief biography of (in German).</ref>
			\|Density = 873,0 g/l
			\|MeltingPtC = 11.83<ref>{{cite journal\|title=The Melting Point Alternation in ''α'',''ω''-Alkanediols and ''α'',''ω''-Alkanediamines: Interplay between Hydrogen Bonding and Hydrophobic Interactions\|first1=V. R.\|last1=Thalladi\|first2=R.\|last2=Boese\|first3=H. C.\|last3=Weiss\|journal=]\|year=2000\|volume=39\|issue=5\|pages=918–922\|doi=10.1002/(SICI)1521-3773(20000303)39:5<918::AID-ANIE918>3.0.CO;2-E\|pmid=10760893 }}</ref>
			\|BoilingPtK = 452.2
			\|Solubility = Soluble
			\|SolubleOther = conventional organic solvents
			\|Solvent = other solvents
			\|LogP = −0.123
			\|RefractIndex = 1.458
			\|pKa = 10.25, 9.13
			}}
			\| Section3 = {{Chembox Hazards
			\|GHSPictograms = {{GHS corrosion}}
			\|GHSSignalWord = '''DANGER'''
			\|HPhrases = {{H-phrases\|314}}
			\|PPhrases = {{P-phrases\|280\|305+351+338\|310}}
			\|NFPA-H = 3 \|NFPA-F = 2 \|NFPA-R = 0
			\|FlashPtC = 62
			\|LD50 = 2000 mg/kg (oral, rat)
			}}
			\| Section4 = {{Chembox Related
			\|OtherFunction_label = alkanamines
			\|OtherFunction = {{Unbulleted list\|]\|]\|]\|]}}
			}}
			}}
			'''Cadaverine''' is an ] with the formula (CH<sub>2</sub>)<sub>5</sub>(NH<sub>2</sub>)<sub>2</sub>. Classified as a ], it is a colorless liquid with an unpleasant odor.<ref name=Ull>{{Ullmann\|doi=10.1002/14356007.a02_001\|title=Amines, Aliphatic\|year=2000\|last1=Eller\|first1=Karsten\|last2=Henkes\|first2=Erhard\|last3=Rossbacher\|first3=Roland\|last4=Höke\|first4=Hartmut\|isbn=3527306730}}</ref> It is present in small quantities in living organisms but is often associated with the ] of ]. Together with ], it is largely responsible for the foul odor of putrefying flesh, but also contributes to other unpleasant odors.

	==Production==		==Production==
			Cadaverine is produced by ] of ].<ref name=Legrum>Wolfgang Legrum: ''Riechstoffe, zwischen Gestank und Duft'', Vieweg + Teubner Verlag (2011) S. 65, {{ISBN\|978-3-8348-1245-2}}</ref> It can be synthesized by many methods including the hydrogenation of ] and the reactions of 1,5-dichloropentane.<ref name=Ull/>
	Cadaverine is the ] product of the ] ].

			==History==
	However, this diamine is not purely associated with putrefaction. It is also produced in small quantities by living beings. It is partially responsible for the distinctive odors of ] and ].
			]<ref>Ludwig Brieger, "Weitere Untersuchungen über Ptomaine" (Berlin, Germany: August Hirschwald, 1885), .</ref> and cadaverine<ref>Ludwig Brieger, "Weitere Untersuchungen über Ptomaine" (Berlin, Germany: August Hirschwald, 1885), . From page 39: Ich nenne das neue Diamin C<sub>5</sub>H<sub>16</sub>N<sub>2</sub>: "Cadaverin", da ausser der empirischen Zussamsetzung, welche die neue Base als ein Hydrür des Neuridins für den flüchtigen Blick erscheinen lässt, keine Anhaltspunkte für die Berechtigung dieser Auffassung zu erheben waren. (I call the new di-amine, C<sub>5</sub>H<sub>16</sub>N<sub>2</sub>, "cadaverine," since besides its empirical composition, which allows the new base to appear superficially as a hydride of neuridine, no clues for the justification of this view arose.)</ref> were first described in 1885 by the ] physician ] (1849–1919).<ref>Brief biography of {{Webarchive\|url=https://web.archive.org/web/20111003041704/http://www.sammlungen.hu-berlin.de/dokumente/14948/ \|date=2011-10-03 }} (in German). Biography of in English.</ref> It was named from the English adjective ''cadaverous''.

			==Receptors==
			In ], the ] 13c (or TAAR13c) has been identified as a high-affinity receptor for cadaverine.<ref>{{cite journal\|author=Li, Q\|author2=Tachie-Baffour, Y\|author3=Liu, Z\|author4=Baldwin, MW\|author5=Kruse, AC\|author6=Liberles, SD\|title=Non-classical amine recognition evolved in a large clade of olfactory receptors.\|journal=eLife\|year=2015\|volume=4\|pages=e10441\|doi=10.7554/eLife.10441\|pmid=26519734\|pmc=4695389 \|doi-access=free }}</ref> In humans, molecular modelling and docking experiments have shown that cadaverine fits into the binding pocket of the human ] and ].<ref>{{cite journal\|author=Izquierdo, C\|author2=Gomez-Tamayo, JC\|author3=Nebel, J-C\|author4=Pardo, L\|author5=Gonzalez, A\|title=Identifying human diamine sensors for death related putrescine and cadaverine molecules.\|journal=PLOS Computational Biology\|year=2018\|volume=14\|issue=1\|pages=e1005945\|doi=10.1371/journal.pcbi.1005945\|pmid=29324768\|pmc=5783396\|bibcode=2018PLSCB..14E5945I \|doi-access=free }}</ref>

	==Clinical significance==		==Clinical significance==
			] contains cadaverine as basic amines.<ref>{{cite journal\|author= Jana Vitku\|author2= Lucie Kolatorova\|author3=Richard Hampl\|title=Occurrence and reproductive roles of hormones in seminal plasma.\|journal= Basic Clin Androl \|year=2017\|volume=27\|issue=19\|page= 19\|doi=10.1186/s12610-017-0062-y\|pmid=29046808\|pmc=5640966\|bibcode=\|doi-access=free}}</ref> Elevated levels of cadaverine have been found in the urine of some patients with defects in lysine metabolism. The odor commonly associated with ] has been linked to cadaverine and ].<ref>{{cite journal\|author=Yeoman, CJ\|author2=Thomas, SM\|author3=Miller, ME\|author4=Ulanov, AV\|author5=Torralba, M\|author6=Lucas, S\|author7=Gillis, M\|author8=Cregger, M\|author9=Gomez, A\|author10=Ho, M\|author11=Leigh, SR\|author12=Stumpf, R\|author13=Creedon, DJ\|author14=Smith, MA\|author15=Weisbaum, JS\|author16=Nelson, KE\|author17=Wilson, BA\|author18=White, BA\|title=A multi-omic systems-based approach reveals metabolic markers of bacterial vaginosis and insight into the disease.\|journal=PLOS ONE\|year=2013\|volume=8\|issue=2\|pages=e56111\|doi=10.1371/journal.pone.0056111\|pmid=23405259\|pmc=3566083\|bibcode=2013PLoSO...856111Y\|doi-access=free}}</ref>
	Elevated levels of cadaverine have been found in the urine of some patients with defects in lysine metabolism.

			==Derivatives==
			*] and ].

	==Toxicity==		==Toxicity==
	~~Cadaverine is toxic in large doses. In rats it had an~~ ] of ~~more~~ ~~than~~ ~~2000~~ mg/kg body weight.<ref></ref>		] of cadaverine is 2,000 mg/kg body weight; its no-observed-adverse-effect level is 2,000 ppm (180 mg/kg body weight/day).<ref>{{cite journal \|last1=Til\|first1=H.P.\|last2=Falke\|first2=H.E.\|last3=Prinsen\|first3=M.K.\|last4=Willems\|first4=M.I.\|title=Acute and subacute toxicity of tyramine, spermidine, spermine, putrescine and cadaverine in rats\|journal=Food and Chemical Toxicology \|volume=35\|issue=3–4\|year=1997\|pages=337–348\|issn=0278-6915\|doi=10.1016/S0278-6915(97)00121-X\|pmid=9207896}}</ref>

	== See also ==		==See also==
	* ]		* ]
			* ]

	==~~Notes~~==		== References ==
	{{reflist}}

			{{reflist \| 30em}}
	==References==
	*{{cite book
	\| last =Lewis
	\| first =Robert Alan
	\| title =Lewis' Dictionary of Toxicology
	\| publisher =CRC Press
	\| year =1998
	\| isbn =1566702232 }}

			==External links==
	]
			*{{Commonscatinline\|Pentamethylenediamine}}
	]
			*

			{{Amino acid metabolism intermediates}}
	]
			{{Authority control}}
	]

	]
	]		]
			]
	]
			]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]

Latest revision as of 00:19, 13 January 2025

Foul-smelling diamine compound

Cadaverine
Names
Skeletal formula of cadaverine Skeletal formula
Ball and stick model of cadaverine Ball-and-stick model
Preferred IUPAC name Pentane-1,5-diamine
Other names 1,5-Diaminopentane, pentamethylenediamine
Identifiers
CAS Number	462-94-2
3D model (JSmol)	Interactive image
Beilstein Reference	1697256
ChEBI	CHEBI:18127
ChEMBL	ChEMBL119296
ChemSpider	13866593
DrugBank	DB03854
ECHA InfoCard	100.006.664
EC Number	207-329-0
Gmelin Reference	2310
KEGG	C01672
MeSH	Cadaverine
PubChem CID	273
RTECS number	SA0200000
UNII	L90BEN6OLL
UN number	2735
CompTox Dashboard (EPA)	DTXSID5075448
InChI InChI=1S/C5H14N2/c6-4-2-1-3-5-7/h1-7H2Key: VHRGRCVQAFMJIZ-UHFFFAOYSA-N
SMILES NCCCCCN
Properties
Chemical formula	C₅H₁₄N₂
Molar mass	102.181 g·mol
Appearance	Colourless liquid
Odor	very unpleasant; putrid
Density	873,0 g/l
Melting point	11.83 °C (53.29 °F; 284.98 K)
Boiling point	179.1 °C; 354.3 °F; 452.2 K
Solubility in water	Soluble
Solubility in other solvents	conventional organic solvents
log P	−0.123
Acidity (pK_a)	10.25, 9.13
Refractive index (n_D)	1.458
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H314
Precautionary statements	P280, P305+P351+P338, P310
NFPA 704 (fire diamond)	3 2 0
Flash point	62 °C (144 °F; 335 K)
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	2000 mg/kg (oral, rat)
Related compounds
Related alkanamines	n-Butylamine Putrescine Pentylamine Hexamethylenediamine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is ?) Infobox references

Chemical compound

Cadaverine is an organic compound with the formula (CH₂)₅(NH₂)₂. Classified as a diamine, it is a colorless liquid with an unpleasant odor. It is present in small quantities in living organisms but is often associated with the putrefaction of animal tissue. Together with putrescine, it is largely responsible for the foul odor of putrefying flesh, but also contributes to other unpleasant odors.

Production

Cadaverine is produced by decarboxylation of lysine. It can be synthesized by many methods including the hydrogenation of glutaronitrile and the reactions of 1,5-dichloropentane.

History

Putrescine and cadaverine were first described in 1885 by the Berlin physician Ludwig Brieger (1849–1919). It was named from the English adjective cadaverous.

Receptors

In zebrafish, the trace amine-associated receptor 13c (or TAAR13c) has been identified as a high-affinity receptor for cadaverine. In humans, molecular modelling and docking experiments have shown that cadaverine fits into the binding pocket of the human TAAR6 and TAAR8.

Clinical significance

Seminal plasma contains cadaverine as basic amines. Elevated levels of cadaverine have been found in the urine of some patients with defects in lysine metabolism. The odor commonly associated with bacterial vaginosis has been linked to cadaverine and putrescine.

Derivatives

Pentolinium and pentamethonium.

Toxicity

Acute oral toxicity of cadaverine is 2,000 mg/kg body weight; its no-observed-adverse-effect level is 2,000 ppm (180 mg/kg body weight/day).

References

Thalladi, V.R.; Boese, R.; Weiss, H.-C. (2001). "CSD Entry: QATWEN : 1,5-Pentanediamine". Cambridge Structural Database: Access Structures. Cambridge Crystallographic Data Centre. doi:10.5517/cc4g861. Retrieved 2021-11-07.
Thalladi, V. R.; Boese, R.; Weiss, H. C. (2000). "The Melting Point Alternation in α,ω-Alkanediols and α,ω-Alkanediamines: Interplay between Hydrogen Bonding and Hydrophobic Interactions". Angew. Chem. Int. Ed. 39 (5): 918–922. doi:10.1002/(SICI)1521-3773(20000303)39:5<918::AID-ANIE918>3.0.CO;2-E. PMID 10760893.
^ Eller, Karsten; Henkes, Erhard; Rossbacher, Roland; Höke, Hartmut (2000). "Amines, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_001. ISBN 3527306730.
Wolfgang Legrum: Riechstoffe, zwischen Gestank und Duft, Vieweg + Teubner Verlag (2011) S. 65, ISBN 978-3-8348-1245-2
Ludwig Brieger, "Weitere Untersuchungen über Ptomaine" (Berlin, Germany: August Hirschwald, 1885), page 43.
Ludwig Brieger, "Weitere Untersuchungen über Ptomaine" (Berlin, Germany: August Hirschwald, 1885), page 39. From page 39: Ich nenne das neue Diamin C₅H₁₆N₂: "Cadaverin", da ausser der empirischen Zussamsetzung, welche die neue Base als ein Hydrür des Neuridins für den flüchtigen Blick erscheinen lässt, keine Anhaltspunkte für die Berechtigung dieser Auffassung zu erheben waren. (I call the new di-amine, C₅H₁₆N₂, "cadaverine," since besides its empirical composition, which allows the new base to appear superficially as a hydride of neuridine, no clues for the justification of this view arose.)
Brief biography of Ludwig Brieger Archived 2011-10-03 at the Wayback Machine (in German). Biography of Ludwig Brieger in English.
Li, Q; Tachie-Baffour, Y; Liu, Z; Baldwin, MW; Kruse, AC; Liberles, SD (2015). "Non-classical amine recognition evolved in a large clade of olfactory receptors". eLife. 4: e10441. doi:10.7554/eLife.10441. PMC 4695389. PMID 26519734.
Izquierdo, C; Gomez-Tamayo, JC; Nebel, J-C; Pardo, L; Gonzalez, A (2018). "Identifying human diamine sensors for death related putrescine and cadaverine molecules". PLOS Computational Biology. 14 (1): e1005945. Bibcode:2018PLSCB..14E5945I. doi:10.1371/journal.pcbi.1005945. PMC 5783396. PMID 29324768.
Jana Vitku; Lucie Kolatorova; Richard Hampl (2017). "Occurrence and reproductive roles of hormones in seminal plasma". Basic Clin Androl. 27 (19): 19. doi:10.1186/s12610-017-0062-y. PMC 5640966. PMID 29046808.
Yeoman, CJ; Thomas, SM; Miller, ME; Ulanov, AV; Torralba, M; Lucas, S; Gillis, M; Cregger, M; Gomez, A; Ho, M; Leigh, SR; Stumpf, R; Creedon, DJ; Smith, MA; Weisbaum, JS; Nelson, KE; Wilson, BA; White, BA (2013). "A multi-omic systems-based approach reveals metabolic markers of bacterial vaginosis and insight into the disease". PLOS ONE. 8 (2): e56111. Bibcode:2013PLoSO...856111Y. doi:10.1371/journal.pone.0056111. PMC 3566083. PMID 23405259.
Til, H.P.; Falke, H.E.; Prinsen, M.K.; Willems, M.I. (1997). "Acute and subacute toxicity of tyramine, spermidine, spermine, putrescine and cadaverine in rats". Food and Chemical Toxicology. 35 (3–4): 337–348. doi:10.1016/S0278-6915(97)00121-X. ISSN 0278-6915. PMID 9207896.

External links

[REDACTED] Media related to Pentamethylenediamine at Wikimedia Commons
GMD MS Spectrum

Amino acid metabolism metabolic intermediates

K→acetyl-CoA

lysine→	Saccharopine Allysine α-Aminoadipic acid 2-Oxoadipic acid Glutaryl-CoA Glutaconyl-CoA Crotonyl-CoA β-Hydroxybutyryl-CoA
leucine→	β-Hydroxy β-methylbutyric acid β-Hydroxy β-methylbutyryl-CoA Isovaleryl-CoA α-Ketoisocaproic acid β-Ketoisocaproic acid β-Ketoisocaproyl-CoA β-Leucine β-Methylcrotonyl-CoA β-Methylglutaconyl-CoA β-Hydroxy β-methylglutaryl-CoA
tryptophan→alanine→	N′-Formylkynurenine Kynurenine Anthranilic acid 3-Hydroxykynurenine 3-Hydroxyanthranilic acid 2-Amino-3-carboxymuconic semialdehyde 2-Aminomuconic semialdehyde 2-Aminomuconic acid Glutaryl-CoA

G→pyruvate→
citrate

glycine→
serine→

3-Phosphoglyceric acid

G→glutamate→
α-ketoglutarate

histidine→	Urocanic acid Imidazol-4-one-5-propionic acid Formiminoglutamic acid Glutamate-1-semialdehyde
proline→	1-Pyrroline-5-carboxylic acid
arginine→	Agmatine Ornithine Citrulline Cadaverine Putrescine
other	cysteine+glutamate→glutathione: γ-Glutamylcysteine

G→propionyl-CoA→
succinyl-CoA

valine→	α-Ketoisovaleric acid Isobutyryl-CoA Methacrylyl-CoA 3-Hydroxyisobutyryl-CoA 3-Hydroxyisobutyric acid 2-Methyl-3-oxopropanoic acid
isoleucine→	2,3-Dihydroxy-3-methylpentanoic acid 2-Methylbutyryl-CoA Tiglyl-CoA 2-Methylacetoacetyl-CoA
methionine→	generation of homocysteine: S-Adenosyl methionine S-Adenosyl-L-homocysteine Homocysteine conversion to cysteine: Cystathionine α-Ketobutyric acid + Cysteine
threonine→	α-Ketobutyric acid
propionyl-CoA→	Methylmalonyl-CoA

G→fumarate

phenylalanine→tyrosine→	4-Hydroxyphenylpyruvic acid Homogentisic acid 4-Maleylacetoacetic acid

G→oxaloacetate

see urea cycle

Other

Cysteine metabolism	Cysteine sulfinic acid

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