Molecule

homocysteine zwitterion

AlkaPlorer ID: AK004504

Synonym: '', 'homocysteine', 'L-2-Amino-4-mercaptobutyric acid', 'L-homocysteine', 'L-2-amino-4-mercaptobutyric acid', '2-Amino-4-mercaptobutyric acid', '2-ammonio-4-sulfanylbutanoate', 'L-Homocysteine', 'Homocysteine', 'Hcy', 'DL-Homocysteine'

IUPAC Name: (2S)-2-amino-4-sulfanylbutanoic acid

Structure

SMILES: N[C@@H](CCS)C(=O)O

InChI: InChI=1S/C4H9NO2S/c5-3(1-2-8)4(6)7/h3,8H,1-2,5H2,(H,6,7)/t3-/m0/s1

InChIKey: FFFHZYDWPBMWHY-VKHMYHEASA-N

Reference

A community-driven global reconstruction of human metabolism

PubChem CID: 6971015

CAS: 6027-13-0

LOTUS: LTS0225753

SuperNatural Ⅲ: SN0084099-02

NPASS: NPC49952

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Homo sapiens	Homo	Hominidae	Primates	Mammalia	Chordata	Metazoa	Eukaryota
Saccharomyces cerevisiae	Saccharomyces	Saccharomycetaceae	Saccharomycetales	Saccharomycetes	Ascomycota	Fungi	Eukaryota
Mus musculus	Mus	Muridae	Rodentia	Mammalia	Chordata	Metazoa	Eukaryota
Escherichia coli	Escherichia	Enterobacteriaceae	Enterobacterales	Gammaproteobacteria	Pseudomonadota	None	Bacteria

Properties Information

Molecule Weight: 135.188

TPSA？: 63.32000000000001

MolLogP？: -0.2818000000000003

Number of H-Donors: 3

Number of H-Acceptors: 3

RingCount: 0

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Homo sapiens	N(G),N(G)-dimethylarginine dimethylaminohydrolase 1	Activity	nan	None	10.1074/jbc.m707231200
Homo sapiens	N(G),N(G)-dimethylarginine dimethylaminohydrolase 1	IC50	640000.0	nM	10.1074/jbc.m707231200
Homo sapiens	N(G),N(G)-dimethylarginine dimethylaminohydrolase 1	K	0.65	10'-3/s	10.1074/jbc.m707231200
Rattus norvegicus	Amino acid transporter	Inhibition	25.0	%	None
None	NON-PROTEIN TARGET	Activity	30.0	%	10.1016/j.bmc.2008.09.068
None	NON-PROTEIN TARGET	Activity	31.0	%	10.1016/j.bmc.2008.09.068
None	NON-PROTEIN TARGET	Activity	40.0	%	10.1016/j.bmc.2008.09.068
None	NON-PROTEIN TARGET	Activity	nan	None	10.1016/j.bmc.2008.09.068
None	No relevant target	Activity	81.1	%	10.1016/j.bmc.2008.09.068
None	No relevant target	Activity	84.1	%	10.1016/j.bmc.2008.09.068
None	No relevant target	Activity	85.3	%	10.1016/j.bmc.2008.09.068
None	No relevant target	Activity	86.1	%	10.1016/j.bmc.2008.09.068
None	No relevant target	Activity	nan	None	10.1016/j.bmc.2008.09.068
None	Radical scavenging activity	Activity	72.0	%	10.1016/j.bmc.2008.09.068
None	Radical scavenging activity	Activity	nan	None	10.1016/j.bmc.2008.09.068

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT000097	*C(=O)CC[C@H](NC(=O)c1ccc(NC[C@H]2CNc3nc(N)[nH]c(=O)c3N2C)cc1)C(=O)O.N[C@@H](CCS)C(=O)O>>CSCC[C@H](N)C(=O)O	HOMOCYSMETB12-RXN
AKRT000705	N[C@@H](Cc1c[nH]c[n+]1[Co-3]123(C)N4C5=C(C)C6=[N+]1C(=CC1=[N+]2C(=C(C)C2=[N+]3[C@@](C)([C@H]4[C@H](CC(N)=O)[C@@]5(C)CCC(=O)NC[C@@H](C)OP(=O)(O)O[C@@H]3[C@@H](CO)O[C@H](n4cnc5cc(C)c(C)cc54)[C@@H]3O)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O)[C@@](C)(CC(N)=O)[C@@H]1CCC(N)=O)C(C)(C)[C@@H]6CCC(N)=O)C()=O.N[C@@H](CCS)C(=O)O>>CSCC[C@H](N)C(=O)O	RXN-21538
AKRT001993	CC(=O)C(=O)C(O)CO.N[C@@H](CCS)C(=O)O>>NC(CCSC1OC(CO)C(O)C1O)C(=O)O	MNXR146294
AKRT002119	CC(=O)C(=O)O.N[C@@H](CCS)C(=O)O>>NC(CCSCC(N)C(=O)O)C(=O)O	MNXR151504
AKRT002120	CC(=O)C(=O)O.N[C@@H](CCS)C(=O)O>>N[C@H](CSCC[C@@H](N)C(=O)O)C(=O)O	MNXR151505
AKRT004168	CC(=O)OCC[C@H](N)C(=O)O.N[C@@H](CCS)C(=O)O>>N[C@@H](CCSCC[C@H](N)C(=O)O)C(=O)O	enzymemap_40647
AKRT004180	CC(=O)OCC[C@H](N)C(=O)O>>CC(=O)O.N[C@@H](CCS)C(=O)O	None
AKRT004182	CC(=O)OCC[C@H](N)C(=O)O>>N[C@@H](CCS)C(=O)O	ACETYLHOMOSER-CYS-RXN
AKRT004262	CC(=O)OC[C@H](N)C(=O)O.N[C@@H](CCS)C(=O)O>>CC(=O)O.N[C@@H](CCSC[C@H](N)C(=O)O)C(=O)O	None
AKRT004263	CC(=O)OC[C@H](N)C(=O)O.N[C@@H](CCS)C(=O)O>>N[C@@H](CCSC[C@H](N)C(=O)O)C(=O)O	RXN-17600
AKRT004264	CC(=O)OC[C@H](N)C(=O)O.N[C@@H](CCS)C(=O)O>>N[C@H](CSCC[C@@H](N)C(=O)O)C(=O)O	MNXR136522
AKRT006983	CC1=C2[N+]3=C(C=C4[N+]5=C(C(C)=C6N7[C@@H]8[C@H](CC(N)=O)[C@@]6(C)CCC(=O)NC[C@@H](C)OP(=O)(O)O[C@@H]6[C@@H](CO)O[C@@H]([C@@H]6O)n6c[n+](c9cc(O)ccc96)[Co-3]753(C)[N+]3=C1[C@@H](CCC(N)=O)[C@](C)(CC(N)=O)[C@]83C)[C@@H](CCC(N)=O)C4(C)C)[C@@H](CCC(N)=O)[C@]2(C)CC(N)=O.N[C@@H](CCS)C(=O)O>>CSCC[C@H](N)C(=O)O	RXN-21955
AKRT010328	CC[SAH].N[C@@H](CCS)C(=O)O>>CCSCC[C@H](N)C(=O)O	enzymemap_25665
AKRT010616	CN1c2c([nH]c(=N)[nH]c2=O)NCC1CNc1ccc(C(=O)N[C@@H](CCC(=O)N[C@@H](CCC(=O)O)C(=O)O)C(=O)O)cc1.N[C@@H](CCS)C(=O)O>>CSCC[C@H](N)C(=O)O	enzymemap_25888
AKRT010618	CN1c2c([nH]c(=N)[nH]c2=O)NC[C@@H]1CNc1ccc(C(=O)N[C@@H](CCC(=O)N[C@@H](CCC(=O)N[C@@H](CCC(=O)O)C(=O)O)C(=O)O)C(=O)O)cc1.N[C@@H](CCS)C(=O)O>>CSCC[C@H](N)C(=O)O	enzymemap_25840
AKRT010619	CN1c2c([nH]c(=N)[nH]c2=O)NC[C@@H]1CNc1ccc(C(=O)N[C@@H](CCC(=O)N[C@@H](CCC(=O)N[C@@H](CCC(=O)O)C(=O)O)C(=O)O)C(=O)O)cc1.N[C@@H](CCS)C(=O)O>>CSCC[C@H](N)C(=O)O.N=c1[nH]c2c(c(=O)[nH]1)N[C@@H](CNc1ccc(C(=O)N[C@@H](CCC(=O)N[C@@H](CCC(=O)N[C@@H](CCC(=O)O)C(=O)O)C(=O)O)C(=O)O)cc1)CN2	None
AKRT010623	CN1c2c([nH]c(=N)[nH]c2=O)NC[C@@H]1CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1.N[C@@H](CCS)C(=O)O>>CSCC[C@H](N)C(=O)O	enzymemap_25837
AKRT010624	CN1c2c([nH]c(=N)[nH]c2=O)NC[C@@H]1CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1.N[C@@H](CCS)C(=O)O>>CSCC[C@H](N)C(=O)O.N=c1[nH]c2c(c(=O)[nH]1)N[C@@H](CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2	None
AKRT010629	CN1c2c(nc(N)[nH]c2=O)NC[C@@H]1CNc1ccc(C(=O)N[C@@H](CCC(=O)N[C@@H](CCC(=O)N[C@@H](CCC(=O)O)C(=O)O)C(=O)O)C(=O)O)cc1.N[C@@H](CCS)C(=O)O>>CSCC[C@H](N)C(=O)O	HOMOCYSMET-RXN
AKRT010630	CN1c2c(nc(N)[nH]c2=O)NC[C@@H]1CNc1ccc(C(=O)N[C@@H](CCC(=O)N[C@@H](CCC(=O)N[C@@H](CCC(=O)O)C(=O)O)C(=O)O)C(=O)O)cc1.N[C@@H](CCS)C(=O)O>>CSCC[C@H](N)C(=O)O.Nc1nc2c(c(=O)[nH]1)N[C@@H](CNc1ccc(C(=O)N[C@@H](CCC(=O)N[C@@H](CCC(=O)N[C@@H](CCC(=O)O)C(=O)O)C(=O)O)C(=O)O)cc1)CN2	None
AKRT010638	CN1c2c(nc(N)[nH]c2=O)NC[C@@H]1CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1.N[C@@H](CCS)C(=O)O>>CSCC[C@H](N)C(=O)O	R00946
AKRT010639	CN1c2c(nc(N)[nH]c2=O)NC[C@@H]1CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1.N[C@@H](CCS)C(=O)O>>CSCC[C@H](N)C(=O)O.Nc1nc2c(c(=O)[nH]1)N[C@@H](CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2	None
AKRT011880	COc1ccc2c(c1)ncn2[C@H]1O[C@H](CO)[C@@H](OP(=O)(O)O[C@H](C)CNC(=O)CC[C@@]2(C)C3=C(C)C4=[N+]5C(=CC6=[N+]7C(=C(C)C8=[N+]9[C@@](C)([C@@H]([C@@H]2CC(N)=O)N3[Co-2]579C)[C@@](C)(CC(N)=O)[C@@H]8CCC(N)=O)[C@@](C)(CC(N)=O)[C@@H]6CCC(N)=O)C(C)(C)[C@@H]4CCC(N)=O)[C@H]1O.N[C@@H](CCS)C(=O)O>>CSCC[C@H](N)C(=O)O	RXN-22105
AKRT012443	CSCC[C@H](N)C(=O)O>>N[C@@H](CCS)C(=O)O	RXN-17004
AKRT012652	C[33S].N[C@@H](CCS)C(=O)O>>CSCC[C@H](N)C(=O)O	None
AKRT014269	C[N+](C)(C)CC(=O)O.N[C@@H](CCS)C(=O)O>>CN(C)CC(=O)O.CSCC[C@H](N)C(=O)O	None
AKRT014270	C[N+](C)(C)CC(=O)O.N[C@@H](CCS)C(=O)O>>CSCC[C@H](N)C(=O)O	2.1.1.5-RXN
AKRT014457	C[S+](C)CC(=O)O.N[C@@H](CCS)C(=O)O>>CSCC[C@H](N)C(=O)O	2.1.1.3-RXN
AKRT014460	C[S+](C)CC[C@H](N)C(=O)O.N[C@@H](CCS)C(=O)O>>CSCC[C@H](N)C(=O)O	MMUM-RXN
AKRT014461	C[S+](C)CC[C@H](N)C(=O)O.N[C@@H](CCS)C(=O)O>>CSCC[C@H](N)C(=O)O.CSCC[C@H](N)C(=O)O	None
AKRT014670	C[SAH].N[C@@H](CCS)C(=O)O>>CSCC[C@H](N)C(=O)O	R00650
AKRT014770	C[S](C)CCC(N)C(=O)O.N[C@@H](CCS)C(=O)O>>CSCC[C@H](N)C(=O)O	MNXR145177
AKRT015610	N#CCCC(N)C(=O)O.N[C@@H](CCS)C(=O)O>>N[C@@H](CCSSCC[C@H](N)C(=O)O)C(=O)O	MNXR142005
AKRT016744	N=c1[nH]ccc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O.N[C@@H](CCS)C(=O)O>>N=c1[nH]ccc2c1ncn2C1O[C@H](CSCC[C@H](N)C(=O)O)[C@@H](O)[C@H]1O	MNXR133696
AKRT018769	N[C@@H](CC=O)C(=O)O>>N[C@@H](CCS)C(=O)O	RXN-19380
AKRT018901	N[C@@H](CCC(=O)N[C@@H](CS)C(=O)NCC(=O)O)C(=O)O>>N[C@@H](CCS)C(=O)O	R01292
AKRT018966	N[C@@H](CCC(=O)N[C@@H](CSSC[C@H](NC(=O)CC[C@H](N)C(=O)O)C(=O)NCC(=O)O)C(=O)NCC(=O)O)C(=O)O.N[C@@H](CCS)C(=O)O.N[C@@H](CCS)C(=O)O>>N[C@@H](CCSSCC[C@H](N)C(=O)O)C(=O)O	R01292
AKRT018967	N[C@@H](CCC(=O)N[C@@H](CSSC[C@H](NC(=O)CC[C@H](N)C(=O)O)C(=O)NCC(=O)O)C(=O)NCC(=O)O)C(=O)O.N[C@@H](CCS)C(=O)O>>N[C@@H](CCC(=O)N[C@@H](CS)C(=O)NCC(=O)O)C(=O)O	R01292
AKRT019355	N[C@@H](CCO)C(=O)O>>N[C@@H](CCS)C(=O)O	enzymemap_40672
AKRT019365	N[C@@H](CCOC(=O)CCC(=O)O)C(=O)O>>N[C@@H](CCS)C(=O)O	R01288
AKRT019381	N[C@@H](CCS)C(=O)O.N[C@@H](CCC(=O)O)C(=O)O>>N[C@@H](CCC(=O)N[C@@H](CCS)C(=O)O)C(=O)O	enzymemap_90556
AKRT019382	N[C@@H](CCS)C(=O)O.N[C@@H](CCS)C(=O)O>>NC(CCSSCC[C@H](N)C(=O)O)C(=O)O	MNXR159186
AKRT019383	N[C@@H](CCS)C(=O)O.N[C@@H](CCS)C(=O)O>>N[C@@H](CCSCC[C@H](N)C(=O)O)C(=O)O	RXN-14632
AKRT019384	N[C@@H](CCS)C(=O)O.N[C@@H](CCS)C(=O)O>>N[C@@H](CCSSCC[C@H](N)C(=O)O)C(=O)O	enzymemap_25128
AKRT019385	N[C@@H](CCS)C(=O)O.N[C@@H](CO)C(=O)O>>N[C@@H](CCSC[C@H](N)C(=O)O)C(=O)O	CYSTATHIONINE-BETA-SYNTHASE-RXN
AKRT019386	N[C@@H](CCS)C(=O)O.N[C@@H](CO)C(=O)O>>N[C@H](CSCC[C@@H](N)C(=O)O)C(=O)O	MNXR147209
AKRT019387	N[C@@H](CCS)C(=O)O.N[C@@H](COC(=O)CCC(=O)O)C(=O)O>>N[C@@H](CCSC[C@H](N)C(=O)O)C(=O)O	enzymemap_40609
AKRT019388	N[C@@H](CCS)C(=O)O.N[C@@H](CS)C(=O)O>>N[C@@H](CCSC[C@H](N)C(=O)O)C(=O)O	RXN66-562
AKRT019389	N[C@@H](CCS)C(=O)O.Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O>>Nc1ncnc2c1ncn2[C@@H]1O[C@H](CSCC[C@H](N)C(=O)O)[C@@H](O)[C@H]1O	enzymemap_64351
AKRT019390	N[C@@H](CCS)C(=O)O.O=C(O)CCC(=O)O>>N[C@@H](CCOC(=O)CCC(=O)O)C(=O)O	MNXR182712
AKRT019391	N[C@@H](CCS)C(=O)O.O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O>>N[C@@H](CCSC[C@H]1O[C@@H](n2cnc3c(=O)[nH]cnc32)[C@H](O)[C@@H]1O)C(=O)O	enzymemap_58396
AKRT019392	N[C@@H](CCS)C(=O)O.OC[C@H]1OC(O)[C@H](O)[C@@H]1O>>NC(CCSC1OC(CO)C(O)C1O)C(=O)O	MNXR146297
AKRT019393	N[C@@H](CCS)C(=O)O.OC[C@H]1OC(O)[C@H](O)[C@@H]1O>>N[C@@H](CCSC[C@H]1O[C@@H](O)[C@H](O)[C@@H]1O)C(=O)O	MNXR146298
AKRT019394	N[C@@H](CCS)C(=O)O>>C/C=C(\N)C(=O)O	RXN-15148
AKRT019395	N[C@@H](CCS)C(=O)O>>CCC(=O)C(=O)O	HOMOCYSTEINE-DESULFHYDRASE-RXN
AKRT019396	N[C@@H](CCS)C(=O)O>>N[C@@H](CCOP(=O)(O)O)C(=O)O	MNXR131673
AKRT019397	N[C@@H](CCS)C(=O)O>>N[C@H]1CCSC1=O	RXN-21218
AKRT019398	N[C@@H](CCS)C(=O)O>>O=C(O)C(=O)CCS	enzymemap_22178
AKRT019404	N[C@@H](CCSC[C@H](N)C(=O)O)C(=O)O>>N[C@@H](CCS)C(=O)O	CYSTATHIONINE-BETA-LYASE-RXN
AKRT019405	N[C@@H](CCSC[C@H](N)C(=O)O)C(=O)O>>N[C@@H](CCS)C(=O)O.N[C@@H](CO)C(=O)O	None
AKRT019406	N[C@@H](CCSC[C@H](N)C(=O)O)C(=O)O>>N[C@@H](CCS)C(=O)O.N[C@@H](CS)C(=O)O	None
AKRT019409	N[C@@H](CCSC[C@H]1OC(O)[C@H](O)[C@@H]1O)C(=O)O>>N[C@@H](CCS)C(=O)O	RIBOSYLHOMOCYSTEINASE-RXN
AKRT019411	N[C@@H](CCSC[C@H]1O[C@@H](O)[C@H](O)[C@@H]1O)C(=O)O>>N[C@@H](CCS)C(=O)O	enzymemap_86176
AKRT019412	N[C@@H](CCSC[C@H]1O[C@@H](n2cnc3c(=O)[nH]cnc32)[C@H](O)[C@@H]1O)C(=O)O>>N[C@@H](CCS)C(=O)O	enzymemap_58395
AKRT019413	N[C@@H](CCSC[C@H]1O[C@@H](n2cnc3c(=O)[nH]cnc32)[C@H](O)[C@@H]1O)C(=O)O>>N[C@@H](CCS)C(=O)O.O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O	None
AKRT019415	N[C@@H](CCSC[C@H]1O[C@@H](n2cnc3c(=O)nc[nH]c32)[C@H](O)[C@@H]1O)C(=O)O>>N[C@@H](CCS)C(=O)O	RXN-20698
AKRT019417	N[C@@H](CCSC[C@H]1O[C@H](O)[C@H](O)[C@@H]1O)C(=O)O>>N[C@@H](CCS)C(=O)O	enzymemap_86176
AKRT019418	N[C@@H](CCSSCC[C@H](N)C(=O)O)C(=O)O>>N[C@@H](CCS)C(=O)O	R01292
AKRT020415	N[C@H]1CCSC1=O>>N[C@@H](CCS)C(=O)O	RXN-21218
AKRT022209	Nc1ncnc2c1ncn2[C@@H]1O[C@H](CSCC[C@H](N)C(=O)O)[C@@H](O)[C@H]1O>>N[C@@H](CCS)C(=O)O	ADENOSYLHOMOCYSTEINASE-RXN
AKRT022575	O=C(O)C(=O)CCS>>N[C@@H](CCS)C(=O)O	enzymemap_42728