Molecule

Spermidine

AlkaPlorer ID: AK004761

Synonym: N-(3-Aminopropyl)-1,4-butanediamine, 1,5,10-Triazadecane, 1,8-Diamino-4-azaoctane

IUPAC Name: 4-azaniumylbutyl(3-azaniumylpropyl)azanium

Structure

SMILES: [NH3+]CCCC[NH2+]CCC[NH3+]

InChI: InChI=1S/C7H19N3/c8-4-1-2-6-10-7-3-5-9/h10H,1-9H2/p+3

InChIKey: ATHGHQPFGPMSJY-UHFFFAOYSA-Q

Reference

Salmonella modulates metabolism during growth under conditions that induce expression of virulence genes

PubChem CID: 6992097

CAS: 124-20-9

LOTUS: LTS0061428

SuperNatural Ⅲ: SN0014844

NPASS: NPC322806

COCONUT: CNP0279184

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
None	Stichopus	Stichopodidae	Aspidochirotida	Holothuroidea	Echinodermata	Metazoa	Eukaryota
Homo sapiens	Homo	Hominidae	Primates	Mammalia	Chordata	Metazoa	Eukaryota
Thermoleophilum album	Thermoleophilum	Thermoleophilaceae	Thermoleophilales	Thermoleophilia	Actinomycetota	None	Bacteria
Crassostrea gigas	Crassostrea	Ostreidae	Ostreida	Bivalvia	Mollusca	Metazoa	Eukaryota
Hydrogenobacter thermophilus	Hydrogenobacter	Aquificaceae	Aquificales	Aquificae	Aquificota	None	Bacteria
Saccharomyces cerevisiae	Saccharomyces	Saccharomycetaceae	Saccharomycetales	Saccharomycetes	Ascomycota	Fungi	Eukaryota
Thermoleophilum minutum	Thermoleophilum	Thermoleophilaceae	Thermoleophilales	Thermoleophilia	Actinomycetota	None	Bacteria

Properties Information

Molecule Weight: 148.27400000000003

TPSA？: 71.89

MolLogP？: -2.7960999999999974

Number of H-Donors: 3

Number of H-Acceptors: 0

RingCount: 0

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Bacillus anthracis	Bacillus anthracis	MIC	nan	None	10.1039/c4md00572d
Bacillus cereus	Bacillus cereus	MIC	nan	None	10.1039/c4md00572d
Bacillus subtilis	Bacillus subtilis	MIC	nan	None	10.1039/c4md00572d
Bos taurus	Calf thymus DNA	Delta Tm	7.0	degrees C	10.1021/acs.jmedchem.1c00445
Bos taurus	Calf thymus DNA	Delta Tm	12.0	degrees C	10.1021/acs.jmedchem.1c00445
Bos taurus	Calf thymus DNA	IC50	130000.0	nM	10.1021/jm00112a016
Bos taurus	Calf thymus DNA	Tm	73.0	degrees C	10.1021/acs.jmedchem.1c00445
Bos taurus	Calf thymus DNA	Tm	78.0	degrees C	10.1021/acs.jmedchem.1c00445
Bos taurus	Ornithine decarboxylase	Ki	3000000.0	nM	10.1021/jm00199a009
Bos taurus	Phosphodiesterase 1	IC50	500000.0	nM	10.1021/jm050018q
Cricetulus griseus	CHO	IC50	100000.0	nM	10.1016/j.bmc.2008.05.069
Cricetulus griseus	CHO-MG	IC50	100000.0	nM	10.1021/jm050018q
Escherichia coli	Escherichia coli	Activity	nan	None	10.1128/aac.01472-06
Escherichia coli	Escherichia coli	MIC	nan	None	10.1039/c4md00572d
Escherichia coli	Escherichia coli	MIC99	512.0	ug ml-1	10.1021/acs.jmedchem.5b01912
Haemophilus influenzae	Haemophilus influenzae	MIC	nan	None	10.1039/c4md00572d
Homo sapiens	Arachidonate 15-lipoxygenase	Potency	12589.3	nM	None
Homo sapiens	Arachidonate 15-lipoxygenase, type II	Potency	5011.9	nM	None
Homo sapiens	Arachidonate 15-lipoxygenase, type II	Potency	12589.3	nM	None
Homo sapiens	ATPase family AAA domain-containing protein 5	Potency	2058.8	nM	None
Homo sapiens	Carbonic anhydrase I	Ki	1400.0	nM	10.1021/jm1003667
Homo sapiens	Carbonic anhydrase II	Ki	1110.0	nM	10.1021/jm1003667
Homo sapiens	Carbonic anhydrase III	Ki	11500.0	nM	10.1021/jm1003667
Homo sapiens	Carbonic anhydrase IV	Ki	112.0	nM	10.1021/jm1003667
Homo sapiens	Carbonic anhydrase IX	Ki	1370.0	nM	10.1021/jm1003667
Homo sapiens	Carbonic anhydrase VA	Ki	1220.0	nM	10.1021/jm1003667
Homo sapiens	Carbonic anhydrase VB	Ki	1440.0	nM	10.1021/jm1003667
Homo sapiens	Carbonic anhydrase VI	Ki	1410.0	nM	10.1021/jm1003667
Homo sapiens	Carbonic anhydrase VII	Ki	1230.0	nM	10.1021/jm1003667
Homo sapiens	Carbonic anhydrase XII	Ki	44100.0	nM	10.1021/jm1003667
Homo sapiens	Carbonic anhydrase XIV	Ki	1000.0	nM	10.1021/jm1003667
Homo sapiens	Coagulation factor XIII	IC50	100000.0	nM	10.1016/j.ejmech.2020.112442
Homo sapiens	Cytochrome P450 1A2	AC50	31622.78	nM	None
Homo sapiens	Cytochrome P450 1A2	AC50	nan	None	None
Homo sapiens	Cytochrome P450 2C19	AC50	nan	None	None
Homo sapiens	Cytochrome P450 2C9	AC50	12589.25	nM	None
Homo sapiens	Cytochrome P450 2C9	AC50	nan	None	None
Homo sapiens	Cytochrome P450 2C9	Potency	12589.3	nM	None
Homo sapiens	Cytochrome P450 2D6	AC50	nan	None	None
Homo sapiens	Cytochrome P450 3A4	AC50	nan	None	None
Homo sapiens	DNA-(apurinic or apyrimidinic site) lyase	Potency	12589.3	nM	None
Homo sapiens	DNA topoisomerase II alpha	IC50	1000000.0	nM	10.1016/j.bmcl.2017.09.011
Homo sapiens	DU-145	Activity	5.0	pmol	10.1021/jm200293r
Homo sapiens	DU-145	Activity	89.0	%	10.1021/jm200293r
Homo sapiens	DU-145	Activity	126.0	pmol	10.1021/jm200293r
Homo sapiens	DU-145	IC50	nan	None	10.1016/j.bmc.2008.05.069
Homo sapiens	DU-145	Stability	nan	%	10.1021/jm200293r
Homo sapiens	HEK293	Potency	6510.4	nM	None
Homo sapiens	HeLa	Activity	nan	None	10.1016/j.ejmech.2013.06.044
Homo sapiens	HeLa	IC50	100000.0	nM	10.1021/jm00112a016
Homo sapiens	HeLa	IC50	1500000.0	nM	10.1021/jm00112a016
Homo sapiens	Histone acetyltransferase GCN5	Potency	39810.7	nM	None
Homo sapiens	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Potency	10621.3	nM	None
Homo sapiens	Homo sapiens	Level	0.4	nM (mg of protein)-1	10.1021/jm00082a013
Homo sapiens	HT-29	Level	0.3	nM (mg of protein)-1	10.1021/jm00082a013
Homo sapiens	HT-29	Level	0.4	nM (mg of protein)-1	10.1021/jm00082a013
Homo sapiens	HT-29	Level	0.7	nM (mg of protein)-1	10.1021/jm00082a013
Homo sapiens	HT-29	Level	1.0	nM (mg of protein)-1	10.1021/jm00082a013
Homo sapiens	HT-29	Level	4.4	nM (mg of protein)-1	10.1021/jm00082a013
Homo sapiens	HT-29	Level	4.8	nM (mg of protein)-1	10.1021/jm00082a013
Homo sapiens	HT-29	Level	7.9	nM (mg of protein)-1	10.1021/jm00082a013
Homo sapiens	HT-29	Level	9.8	nM (mg of protein)-1	10.1021/jm00082a013
Homo sapiens	HT-29	Level	13.4	nM (mg of protein)-1	10.1021/jm00082a013
Homo sapiens	HT-29	Level	23.6	nM (mg of protein)-1	10.1021/jm00082a013
Homo sapiens	HT-29	Level	25.1	nM (mg of protein)-1	10.1021/jm00082a013
Homo sapiens	HT-29	Level	nan	None	10.1021/jm00082a013
Homo sapiens	K562	IC50	nan	None	10.1016/j.bmc.2008.05.069
Homo sapiens	MCF7	IC50	nan	None	10.1016/j.bmc.2008.05.069
Homo sapiens	MDA-MB-231	Ki	113.0	nM	10.1021/jm0101040
Homo sapiens	Polyamine oxidase	Stability	nan	%	10.1021/jm200293r
Homo sapiens	Pyruvate kinase isozymes M1/M2	IC50	1410.0	nM	10.1021/acs.jmedchem.1c00981
Homo sapiens	Serine/threonine-protein kinase mTOR	Potency	23280.9	nM	None
Homo sapiens	Serine/threonine-protein kinase mTOR	Potency	26121.6	nM	None
Homo sapiens	Solute carrier family 22 member 4	Activity	nan	None	None
Homo sapiens	T47D	Ki	4400.0	nM	10.1016/s0960-894x(99)00262-0
Homo sapiens	T47D	Ki	nan	nM	10.1016/s0960-894x(99)00262-0
Homo sapiens	T47D	Km	4400.0	nM	10.1016/s0960-894x(03)00668-1
Homo sapiens	Thrombopoietin	Potency	6309.6	nM	None
Homo sapiens	Thyroid stimulating hormone receptor	Potency	31622.8	nM	None
Homo sapiens	U-251	IC50	nan	None	10.1016/j.bmc.2008.05.069
Homo sapiens	U-937	Activity	nan	None	10.1021/jm901063e
Homo sapiens	U-937	IC50	nan	None	10.1021/jm901063e
Mus musculus	Carbonic anhydrase 15	Ki	10000.0	nM	10.1021/jm1003667
Mus musculus	Carbonic anhydrase XIII	Ki	11600.0	nM	10.1021/jm1003667
Mus musculus	FL5.12	Activity	5.52	%	10.1021/jm070794t
Mus musculus	FL5.12	Activity	6.07	%	10.1021/jm070794t
Mus musculus	FL5.12	Activity	58.16	%	10.1021/jm070794t
Mus musculus	L1210	IC50	100000.0	nM	10.1016/j.bmc.2008.05.069
Mus musculus	L1210	IC50	100000.0	nM	10.1021/jm960849j
Mus musculus	L1210	Level	0.2	nM (mg of protein)-1	10.1021/jm00082a013
Mus musculus	L1210	Level	1.0	nM (mg of protein)-1	10.1021/jm00082a013
Mus musculus	L1210	Level	6.4	nM (mg of protein)-1	10.1021/jm00082a013
Mus musculus	L1210	Level	38.0	nM (mg of protein)-1	10.1021/jm00082a013
Mus musculus	L1210	Level	41.0	nM (mg of protein)-1	10.1021/jm00082a013
Mus musculus	L1210	Level	nan	None	10.1021/jm00082a013
Mus musculus	L1210	Polyamine	0.0	%	10.1021/jm960849j
Mus musculus	L1210	Polyamine	108.0	%	10.1021/jm960849j
Mus musculus	L1210	Polyamine	117.0	%	10.1021/jm960849j
Mus musculus	L1210	Polyamine	118.0	%	10.1021/jm960849j
Mus musculus	L1210	Polyamine	145.0	%	10.1021/jm960849j
Mus musculus	Mus musculus	CC50	100000.0	nM	10.1016/j.bmc.2016.10.013
Mus musculus	P19	Activity	nan	None	10.1021/jm901063e
Mus musculus	P19	IC50	nan	None	10.1021/jm901063e
Mus musculus	S-adenosylmethionine decarboxylase 1	AdoMetDC	43.0	%	10.1021/jm960849j
Mus musculus	Spermidine/spermine N(1)-acetyltransferase (SAT)	SSAT	160.0	%	10.1021/jm960849j
Mus musculus	Sulfate anion transporter 1	Km	151000.0	nM	10.1021/jm200293r
Mus musculus	Sulfate anion transporter 1	Vmax	4.28	umol/min/mg	10.1021/jm200293r
Mus musculus	SV3T3	Level	0.3	nM (mg of protein)-1	10.1021/jm00082a013
Mus musculus	SV3T3	Level	2.6	nM (mg of protein)-1	10.1021/jm00082a013
Mus musculus	SV3T3	Level	3.1	nM (mg of protein)-1	10.1021/jm00082a013
Mus musculus	SV3T3	Level	8.7	nM (mg of protein)-1	10.1021/jm00082a013
Mus musculus	SV3T3	Level	11.5	nM (mg of protein)-1	10.1021/jm00082a013
Mus musculus	SV3T3	Level	26.4	nM (mg of protein)-1	10.1021/jm00082a013
Mus musculus	SV3T3	Level	nan	None	10.1021/jm00082a013
Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC99	512.0	ug ml-1	10.1021/acs.jmedchem.5b01912
Rattus norvegicus	Muscarinic acetylcholine receptor M1	Potency	8912.5	nM	None
Rattus norvegicus	Ornithine decarboxylase	Ki	2700000.0	nM	10.1021/jm00199a009
Rattus norvegicus	Rattus norvegicus	Inhibition	nan	%	10.1016/j.bmc.2015.10.022
Rattus norvegicus	Solute carrier family 22 member 1	Activity	nan	None	10.1074/jbc.271.51.32599
Rattus norvegicus	Thioredoxin reductase 1, cytoplasmic	Potency	398.1	nM	None
Salmonella enterica subsp. enterica serovar Typhimurium	Salmonella typhimurium	Activity	nan	None	10.1128/aac.01472-06
Severe acute respiratory syndrome coronavirus 2	Replicase polyprotein 1ab	Inhibition	17.15	%	10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2	SARS-CoV-2	Inhibition	0.14	%	10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2	SARS-CoV-2	Inhibition	85.0	%	10.1016/j.ejmech.2022.114600
Staphylococcus aureus	Staphylococcus aureus	Activity	nan	None	10.1128/aac.01472-06
Staphylococcus aureus	Staphylococcus aureus	MIC	nan	None	10.1039/c4md00572d
Staphylococcus aureus	Staphylococcus aureus	MIC99	512.0	ug ml-1	10.1021/acs.jmedchem.5b01912
None	ADMET	C50	50.0	uM	10.1021/jm00385a015
None	ADMET	NA	nan	None	10.1021/jm00385a015
None	ADMET	tR	33.9	min	10.1021/jm00082a013
None	Molecular identity unknown	Ki	2200.0	nM	10.1021/jm960849j
None	NON-PROTEIN TARGET	IC50	3300.0	nM	10.1016/j.bmc.2016.10.013
None	NON-PROTEIN TARGET	IC50	8300.0	nM	10.1016/j.bmc.2016.10.013
None	NON-PROTEIN TARGET	IC50	100000.0	nM	10.1016/j.bmc.2016.10.013
None	NON-PROTEIN TARGET	IC50	100000.0	nM	10.1021/jm960787x
None	NON-PROTEIN TARGET	IC50	nan	None	10.1016/j.bmc.2008.05.069
None	NON-PROTEIN TARGET	Potency	0.7	nM	None
None	NON-PROTEIN TARGET	Potency	1.1	nM	None
None	NON-PROTEIN TARGET	Potency	8407.1	nM	None
None	No relevant target	Activity	nan	None	10.1016/j.bmc.2015.10.022
None	No relevant target	Inhibition	nan	%	10.1016/j.bmc.2015.10.022
None	No relevant target	Kd	700000.0	nM	10.1021/jm00199a009
None	No relevant target	pK1	8.15	None	10.1021/jm950488s
None	No relevant target	pK1	8.93	None	10.1021/jm950488s
None	No relevant target	pK2	9.74	None	10.1021/jm950488s
None	No relevant target	pK2	10.3	None	10.1021/jm950488s
None	No relevant target	pK3	10.24	None	10.1021/jm950488s
None	No relevant target	pK3	10.86	None	10.1021/jm950488s
None	Nucleic Acid	IC50	98000.0	nM	10.1021/jm010897q
None	Nucleic Acid	IC50	105000.0	nM	10.1021/jm980703f
None	Nucleic Acid	IC50	110000.0	nM	10.1021/jm00112a016
None	Nucleic Acid	IC50	175000.0	nM	10.1021/jm960787x
None	Nucleic Acid	IC50	300000.0	nM	10.1021/jm00112a016
None	Unchecked	Activity	nan	None	10.1021/jm200293r
None	Unchecked	IC50	100000.0	nM	10.1021/jm980703f
None	Unchecked	IC50	nan	None	10.1016/j.bmc.2015.10.022
None	Unchecked	Inhibition	4.8	%	10.1021/jm701198s
None	Unchecked	Kapp	1.47	10'5L/mol	10.1039/C7MD00389G
None	Unchecked	Km	110.0	nM	10.1016/s0960-894x(01)00659-x
None	Unchecked	Km	2460.0	nM	10.1021/jm020598g
None	Unchecked	Log K	5.4	None	10.1016/s0960-894x(99)00189-4
None	Unchecked	ODC	16.0	%	10.1021/jm960849j
None	Unchecked	Potency	6309.6	nM	None
None	Unchecked	Ratio CC50/IC50	12.0	None	10.1016/j.bmc.2016.10.013
None	Unchecked	Ratio CC50/IC50	29.0	None	10.1016/j.bmc.2016.10.013

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT000560	NC(=O)[C@H](CCCCN)NC()=O.NCCCCNCCCN>>NC(=O)C(CCCCNCCCCN)NC()=O	MNXR149193
AKRT000634	N[C@@H](CCCCN)C()=O.NCCCCNCCCN>>N[C@@H](CCCCNCCCCN)C()=O	MNXR174170
AKRT002431	CC(=O)NCCCCNCCCN>>CC(=O)O.NCCCCNCCCN	None
AKRT002432	CC(=O)NCCCCNCCCN>>NCCCCNCCCN	ACETYLSPERMIDINE-DEACETYLASE-RXN
AKRT002451	CC(=O)NCCCNCCCCN>>CC(=O)O.NCCCCNCCCN	None
AKRT002454	CC(=O)NCCCNCCCCN>>NCCCCNCCCN	51900
AKRT002458	CC(=O)NCCCNCCCCNCCCN>>CC(=O)NCCC=O.NCCCCNCCCN	None
AKRT002464	CC(=O)NCCCNCCCCNCCCN>>NCCCCNCCCN	RXN-9940
AKRT004403	CC(=O)[32S].NCCCCNCCCN>>CC(=O)NCCCNCCCCN	None
AKRT004626	CC(=O)[CoA].NCCCCNCCCN>>CC(=O)NCCCCNCCCN	RXN0-7165
AKRT004627	CC(=O)[CoA].NCCCCNCCCN>>CC(=O)NCCCNCCCCN	SPERMACTRAN-RXN
AKRT006356	CC(C)[C@H](NC(=O)CC[C@H](N)C(=O)O)C(=O)NCC(=O)O.NCCCCNCCCN>>CC(C)[C@H](NC(=O)CC[C@H](N)C(=O)O)C(=O)NCC(=O)NCCCNCCCCN	enzymemap_90260
AKRT009467	CCCCSC[C@H](NC(=O)CC[C@H](N)C(=O)O)C(=O)NCC(=O)O.NCCCCNCCCN>>CCCCSC[C@H](NC(=O)CC[C@H](N)C(=O)O)C(=O)NCC(=O)NCCCNCCCCN	enzymemap_90256
AKRT009558	CCCSC[C@H](NC(=O)CC[C@H](N)C(=O)O)C(=O)NCC(=O)O.NCCCCNCCCN>>CCCSC[C@H](NC(=O)CC[C@H](N)C(=O)O)C(=O)NCC(=O)NCCCNCCCCN	enzymemap_90255
AKRT009662	CCNCCCNCCCCNCCCN>>NCCCCNCCCN	enzymemap_23365
AKRT009802	CCSC[C@H](NC(=O)CC[C@H](N)C(=O)O)C(=O)NCC(=O)O.NCCCCNCCCN>>CCSC[C@H](NC(=O)CC[C@H](N)C(=O)O)C(=O)NCC(=O)NCCCNCCCCN	enzymemap_90254
AKRT010039	CC[C@H](C)[C@H](NC(=O)CC[C@H](N)C(=O)O)C(=O)NCC(=O)O.NCCCCNCCCN>>CC[C@H](C)[C@H](NC(=O)CC[C@H](N)C(=O)O)C(=O)NCC(=O)NCCCNCCCCN	enzymemap_90261
AKRT011431	COc1cc(/C=C/C(=O)NCCCCNCCCNC(=O)/C=C/c2cc(OC)c(O)c(OC)c2)cc(OC)c1O>>NCCCCNCCCN	RXN-16472
AKRT011490	COc1cc(/C=C/C(=O)[CoA])cc(OC)c1O.COc1cc(/C=C/C(=O)[CoA])cc(OC)c1O.NCCCCNCCCN>>COc1cc(/C=C/C(=O)NCCCCNCCCNC(=O)/C=C/c2cc(OC)c(O)c(OC)c2)cc(OC)c1O	RXN-16472
AKRT011501	COc1cc(/C=C/C(=O)[CoA])ccc1O.COc1cc(/C=C/C(=O)[CoA])ccc1O.COc1cc(/C=C/C(=O)[CoA])ccc1O.NCCCCNCCCN>>COc1cc(/C=C/C(=O)NCCCCN(CCCNC(=O)/C=C/c2ccc(O)c(OC)c2)C(=O)/C=C/c2ccc(O)c(OC)c2)ccc1O	RXN-11259
AKRT012601	CSC[C@H](NC(=O)CC[C@H](N)C(=O)O)C(=O)NCC(=O)O.NCCCCNCCCN>>CSC[C@H](NC(=O)CC[C@H](N)C(=O)O)C(=O)NCC(=O)NCCCNCCCCN	enzymemap_90253
AKRT012616	CSC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O.NCCCCNCCCN.O=C=O>>C[S@@+](CC[C@H](N)C(=O)O)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O	MNXR137342
AKRT013699	C[C@H](NC(=O)CC[C@H](N)C(=O)O)C(=O)NCC(=O)O.NCCCCNCCCN>>C[C@H](NC(=O)CC[C@H](N)C(=O)O)C(=O)NCC(=O)NCCCNCCCCN	enzymemap_90259
AKRT014471	C[S+](CCCN)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O.C[S+](CCCN)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O.NCCCCNCCCN>>NCCCC[N+](CCCN)(CCCN)CCCN	RXN-15866
AKRT014478	C[S+](CCCN)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O.NCCCCN>>NCCCCNCCCN	SPERMIDINESYN-RXN
AKRT014479	C[S+](CCCN)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O.NCCCCNCCCN>>CSC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O.NCCCCN(CCCN)CCCN	None
AKRT014480	C[S+](CCCN)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O.NCCCCNCCCN>>CSC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O.NCCCCNCCCNCCCN	None
AKRT014481	C[S+](CCCN)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O.NCCCCNCCCN>>CSC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O.NCCCNCCCCNCCCN	None
AKRT014482	C[S+](CCCN)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O.NCCCCNCCCN>>NCCCCN(CCCN)CCCN	RXN-15864
AKRT014483	C[S+](CCCN)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O.NCCCCNCCCN>>NCCCCNCCCNCCCN	RXN-11190
AKRT014484	C[S+](CCCN)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O.NCCCCNCCCN>>NCCCNCCCCNCCCN	SPERMINE-SYNTHASE-RXN
AKRT015910	N=C(N)NCCCCNCCCN>>NCCCCNCCCN	RXN-12515
AKRT017150	NC(=O)OP(=O)(O)O.NCCCCNCCCN>>N=C(O)NCCCCNCCCN	MNXR130369
AKRT017151	NC(=O)OP(=O)(O)O.NCCCCNCCCN>>NCCCCNCCCNC(N)=O	enzymemap_28138
AKRT017152	NC(=O)OP(=O)(O)O.NCCCCNCCCN>>NCCCNCCCCNC(N)=O	enzymemap_28138
AKRT017896	NCCCC=O.NCCCN>>NCCCCNCCCN	MNXR137818
AKRT017964	NCCCCN.NCCCCNCCCN>>NCCCCN(CCCN)CCCCN	enzymemap_40537
AKRT017965	NCCCCN.NCCCCNCCCN>>NCCCCNCCCCN	2.5.1.45-RXN
AKRT017966	NCCCCN.NCCCCNCCCN>>NCCCCNCCCCNCCCN	enzymemap_40537
AKRT017967	NCCCCN.NCCCCNCCCN>>NCCCN	2.5.1.45-RXN
AKRT018001	NCCCCNCCC(N)C(=O)O>>NCCCCNCCCN	R09081
AKRT018002	NCCCCNCCC(N)C(=O)O>>NCCCCNCCCN.O=C=O	None
AKRT018009	NCCCCNCCCN.NCCCC[C@H](N)C(=O)O>>NCCCCNCCCC[C@H](N)C(=O)O	MNXR103564
AKRT018010	NCCCCNCCCN.NCCCNCCCCNC(=O)CC(O)(CC(=O)O)C(=O)O>>NCCCNCCCCNC(=O)CC(O)(CC(=O)NCCCCNCCCN)C(=O)O	RXN-10681
AKRT018011	NCCCCNCCCN.N[C@@H](CCC(=O)N[C@@H](CS)C(=O)NCC(=O)O)C(=O)O.Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O>>NCCCCNCCCNC(=O)CNC(=O)[C@H](CS)NC(=O)CC[C@H](N)C(=O)O.Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O	None
AKRT018012	NCCCCNCCCN.N[C@@H](CCC(=O)N[C@@H](CS)C(=O)NCC(=O)O)C(=O)O>>NCCCCNCCCNC(=O)CNC(=O)[C@H](CS)NC(=O)CC[C@H](N)C(=O)O	R01917
AKRT018013	NCCCCNCCCN.N[C@@H](CCC(=O)N[C@@H](CS)C(=O)NCC(=O)O)C(=O)O>>NCCCNCCCCNC(=O)CNC(=O)[C@H](CS)NC(=O)CC[C@H](N)C(=O)O	GSPSYN-RXN
AKRT018014	NCCCCNCCCN.O=C(O)CC(O)(CC(=O)NCCCCNCCCNC(=O)c1ccc(O)c(O)c1)C(=O)O>>NCCCNCCCCNC(=O)CC(O)(CC(=O)NCCCCNCCCNC(=O)c1ccc(O)c(O)c1)C(=O)O	RXN-10678
AKRT018015	NCCCCNCCCN.O=C(O)CC(O)(CC(=O)O)C(=O)O>>NCCCNCCCCNC(=O)CC(O)(CC(=O)O)C(=O)O	RXN-10680
AKRT018016	NCCCCNCCCN.O=C([CoA])/C=C/c1ccc(O)c(O)c1.O=C([CoA])/C=C/c1ccc(O)c(O)c1.O=C([CoA])/C=C/c1ccc(O)c(O)c1>>O=C(/C=C/c1ccc(O)c(O)c1)NCCCCN(CCCNC(=O)/C=C/c1ccc(O)c(O)c1)C(=O)/C=C/c1ccc(O)c(O)c1	RXN-11258
AKRT018017	NCCCCNCCCN.O=C([CoA])/C=C/c1ccc(O)cc1.O=C([CoA])/C=C/c1ccc(O)cc1.O=C([CoA])/C=C/c1ccc(O)cc1>>O=C(/C=C/c1ccc(O)cc1)NCCCCN(CCCNC(=O)/C=C/c1ccc(O)cc1)C(=O)/C=C/c1ccc(O)cc1	RXN-11257
AKRT018018	NCCCCNCCCN.O=C([CoA])/C=C/c1ccc(O)cc1.O=C([CoA])/C=C/c1ccc(O)cc1>>O=C(/C=C/c1ccc(O)cc1)NCCCCNCCCNC(=O)/C=C/c1ccc(O)cc1	RXN-16473
AKRT018019	NCCCCNCCCN>>C1=NCCC1	33287
AKRT018020	NCCCCNCCCN>>NCCC/C=N/CCCN	RXN-13414
AKRT018021	NCCCCNCCCN>>NCCC=O	RXN-12089
AKRT018022	NCCCCNCCCN>>NCCC=O.NCCCCN	None
AKRT018023	NCCCCNCCCN>>NCCCC=O	RXN-10747
AKRT018024	NCCCCNCCCN>>NCCCCN	RXN-12089
AKRT018025	NCCCCNCCCN>>NCCCCNCCC=O	59604
AKRT018026	NCCCCNCCCN>>NCCCN	RXN-10747
AKRT018027	NCCCCNCCCN>>NCCCNCCCC=O	MNXR103468
AKRT018029	NCCCCNCCCNC(=O)CNC(=O)[C@H](CS)NC(=O)CC[C@H](N)C(=O)O>>NCCCCNCCCN	R01918
AKRT018030	NCCCCNCCCNC(=O)CNC(=O)[C@H](CS)NC(=O)CC[C@H](N)C(=O)O>>NCCCCNCCCN.N[C@@H](CCC(=O)N[C@@H](CS)C(=O)NCC(=O)O)C(=O)O	None
AKRT018033	NCCCCNCCCNCCCN>>NCCCCNCCCN	57836
AKRT018194	NCCCNCCCC=O>>NCCCCNCCCN	RXN-22064
AKRT018195	NCCCNCCCCNC(=O)CC[C@H](N)C(=O)O>>NCCCCNCCCN	enzymemap_85832
AKRT018198	NCCCNCCCCNC(=O)CNC(=O)[C@H](CS)NC(=O)CC[C@H](N)C(=O)O>>NCCCCNCCCN	GSPAMID-RXN
AKRT018200	NCCCNCCCCNC(=O)O>>NCCCCNCCCN	enzymemap_82188
AKRT018201	NCCCNCCCCNC(=O)O>>NCCCCNCCCN.O=C=O	None
AKRT018202	NCCCNCCCCNCCC=O>>NCCCCNCCCN	69152
AKRT018205	NCCCNCCCCNCCCN>>NCCC=O.NCCCCNCCCN	None
AKRT018206	NCCCNCCCCNCCCN>>NCCCCNCCCN	RXN-9015
AKRT018216	NCCCNCCC[C@H](N)C(=O)O>>NCCCCNCCCN	RXN-11564
AKRT018217	NCCCNCCC[C@H](N)C(=O)O>>NCCCCNCCCN.O=C=O	None
AKRT018772	N[C@@H](CCC(=O)NCC(=O)NCC(=O)O)C(=O)O.NCCCCNCCCN>>NCCCCNCCCNC(=O)CNC(=O)CNC(=O)CC[C@H](N)C(=O)O	enzymemap_90258
AKRT018806	N[C@@H](CCC(=O)N[C@@H](CO)C(=O)NCC(=O)O)C(=O)O.NCCCCNCCCN>>NCCCCNCCCNC(=O)CNC(=O)[C@H](CO)NC(=O)CC[C@H](N)C(=O)O	enzymemap_90257
AKRT018813	N[C@@H](CCC(=O)N[C@@H](CS)C(=O)NCC(=O)O)C(=O)O.NCCCCNCCCN>>NCCCCNCCCNC(=O)CNC(=O)[C@H](CS)NC(=O)CC[C@H](N)C(=O)O	enzymemap_90251
AKRT022310	O=C(/C=C/c1ccc(O)cc1)NCCCCNCCCNC(=O)/C=C/c1ccc(O)cc1>>NCCCCNCCCN	RXN-16473