Spermine (YMDB00231)

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Identification

YMDB ID

YMDB00231

Name

Spermine

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Spermine, also known as gerontine or musculamine, belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen. Spermine is a very strong basic compound (based on its pKa). Spermine exists in all living species, ranging from bacteria to humans. Within yeast, spermine participates in a number of enzymatic reactions. In particular, 5'-methylthioadenosine and spermine can be biosynthesized from spermidine and S-adenosylmethioninamine; which is catalyzed by the enzyme spermine synthase. In addition, spermine can be converted into 3-aminopropanal and spermidine through the action of the enzyme polyamine oxidase. In yeast, spermine is involved in the metabolic pathway called the beta-alanine metabolism pathway. Spermine is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

1,5,10,14-Tetraazatetradecane
4,9-Diaza-1,12-dodecanediamine
4,9-Diazadodecamethylenediamine
4,9-Diazadodecane-1,12-diamine
diaminopropyl-tetramethylenediamine
Diaminopropyltetramethylenediamine
Gerontine
Musculamine
N,N'-bis(3-aminopropyl)-1,4-Butanediamine
N,N'-Bis(3-aminopropyl)-1,4-tetramethylenediamine
N,N'-Bis(3-aminopropyl)butane-1,4-diamine
N1,N4-bis(3-aminopropyl)-1,4-butanediamine
Neuridine
Spermin
Spermine
Spermine dihydrate
Spermine puriss
SPM

CAS number

71-44-3

Weight

Average: 202.3402
Monoisotopic: 202.215746852

InChI Key

PFNFFQXMRSDOHW-UHFFFAOYSA-N

InChI

InChI=1S/C10H26N4/c11-5-3-9-13-7-1-2-8-14-10-4-6-12/h13-14H,1-12H2

IUPAC Name

(3-aminopropyl)({4-[(3-aminopropyl)amino]butyl})amine

Traditional IUPAC Name

spermine

Chemical Formula

C₁₀H₂₆N₄

SMILES

[H]N([H])C([H])([H])C([H])([H])C([H])([H])N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])N([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H]

Chemical Taxonomy

Description

belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

Dialkylamines

Alternative Parents

Substituents

Secondary aliphatic amine
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Primary aliphatic amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

tetraamine (CHEBI:15746 )
polyazaalkane (CHEBI:15746 )

Physical Properties

State

Solid

Charge

Melting point

29 °C

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	2.19 g/L	ALOGPS
logP	-0.66	ALOGPS
logP	-1.5	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Basic)	10.8	ChemAxon
Physiological Charge	4	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	76.1 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	62.56 m³·mol⁻¹	ChemAxon
Polarizability	26.69 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

extracellular
cytoplasm

Organoleptic Properties

Not Available

SMPDB Pathways

Glutathione metabolism	PW002395
beta-Alanine metabolism	PW002381

KEGG Pathways

Arginine and proline metabolism	ec00330
Glutathione metabolism	ec00480
beta-Alanine metabolism	ec00410

SMPDB Reactions

Spermine + water + oxygen → Hydrogen peroxide + 3-Aminopropionaldehyde + Spermidine

Spermidine + S-Adenosylmethioninamine → hydron + 5'-Methylthioadenosine + Spermine

KEGG Reactions

Spermine + Acetyl-CoA → N1-Acetylspermine + hydron + Coenzyme A

Spermine + water + oxygen → Spermidine + 3-Aminopropionaldehyde + Hydrogen peroxide

Spermidine + S-Adenosylmethioninamine → Spermine + hydron + 5'-Methylthioadenosine

Concentrations

Intracellular Concentrations

Intracellular Concentration	Substrate	Growth Conditions	Strain	Citation
223 ± 11 µM	YEB media with 0.5 mM glucose	aerobic	Baker's yeast	Experimentally Determined Not Available
Conversion Details Here

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (x TMS)	splash10-014u-1900000000-e9620319823eaecceccc	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (x TMS)	splash10-00s6-3900000000-d7da5cd1c0be289412ee	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00r6-1900000000-861e0541e2eb67219b93	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)	splash10-00di-7900000000-9706a16d903df3f9e094	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)	splash10-00di-5900000000-eb1574dc4aea2972932b	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (5 TMS)	splash10-00ei-8900000000-710d44c573ed398f7db9	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (5 TMS)	splash10-00s6-3900000000-cb82c1371fa767015cff	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (6 TMS)	splash10-00rf-1900000000-ca3a2df44acb740134cd	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (6 TMS)	splash10-00y0-1900000000-7ba8e67861945901b381	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014u-1900000000-e9620319823eaecceccc	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00s6-3900000000-d7da5cd1c0be289412ee	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00r6-1900000000-861e0541e2eb67219b93	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-7900000000-9706a16d903df3f9e094	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-5900000000-eb1574dc4aea2972932b	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00ei-8900000000-710d44c573ed398f7db9	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00s6-3900000000-cb82c1371fa767015cff	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00rf-1900000000-ca3a2df44acb740134cd	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00y0-1900000000-7ba8e67861945901b381	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-01bl-1900000000-5a4875c4cf337f0cff9c	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000i-7900000000-4e66988ec8e890a03e13	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00rf-2900000000-9d5a63fbbd1662e5dc43	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-01w1-4900000000-f7c07f1cee7101fc31d7	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-053r-9300000000-2ce22d19e72f10b80f34	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0w29-2940000000-a8b05c7cfaea58c5d82d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-03di-1900000000-75ac3953e5378c465a62	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-001i-9000000000-e3b84db5723912be8a4f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0udi-0930000000-4bb02118dea11e2101f8	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0006-9000000000-468357ae06dea8985d85	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00b9-6900000000-cf244bbfdbb5b7889d7a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-004i-0900000000-c5af077deeab934c36b7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0udi-0940000000-098121f449eb29dd74be	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0006-9000000000-167ef7503b0827eb212f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-03di-0900000000-feb04e188e675948f795	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-004i-0900000000-93e15f4592fe9bbeb367	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0udi-0090000000-c22e98adb3dc62b1eb77	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-01t9-0900000000-76aa5e4bf523c2027cba	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-03di-4900000000-b762c20d8a09a78cf931	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-001i-9300000000-0428cb6df2b593ded567	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-001i-9000000000-c319f927047d78e2b69b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-004i-0900000000-b4f106f6fe26766fbf73	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-03di-0900000000-29d4a223bb44ded927b5	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-01q9-9500000000-d1b7e914e9ccee2d0f66	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udr-2970000000-268b93360fb5eaa19e49	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a73-9810000000-ee919f22493191f56708	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9200000000-f7cb18a7a6036554cb6b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000000-ea2e2f233958fa61cd8b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-3390000000-0ade7d389047531a84ee	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fu-9200000000-e760ec8b3259e54992ce	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-053u-9100000000-5a106273203d28e4a701	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Pirkov, I., Norbeck, J., Gustafsson, L., Albers, E. (2008). "A complete inventory of all enzymes in the eukaryotic methionine salvage pathway." FEBS J 275:4111-4120.18625006
Tomitori, H., Kashiwagi, K., Sakata, K., Kakinuma, Y., Igarashi, K. (1999). "Identification of a gene for a polyamine transport protein in yeast." J Biol Chem 274:3265-3267.9920864

Synthesis Reference:

Wrede, Fritz; Strack, Erich; Hettche, Otto. Spermine. VII. Z. physiol. Chem. (1928), 173 61-8.

External Links:

Resource	Link
CHEBI ID	15746
HMDB ID	HMDB01256
Pubchem Compound ID	1103
Kegg ID	C00750
ChemSpider ID	1072
FOODB ID	FDB003225
Wikipedia	Spermine
BioCyc ID	SPERMINE

Enzymes

Protein Details

1. Polyamine oxidase FMS1

General function:: Amino acid transport and metabolism
Specific function:: Involved in the production of beta-alanine, a precursor of pantothenic acid. Multicopy suppressor of fenpropimorph resistance
Gene Name:: FMS1
Uniprot ID:: P50264
Molecular weight:: 57805.10156

Reactions

Spermine + O(2) + H(2)O → spermidine + 3-aminopropanal + H(2)O(2).
Spermidine + O(2) + H(2)O → putrescine + 3-aminopropanal + H(2)O(2).
N(1)-acetylspermine + O(2) + H(2)O → spermidine + 3-acetamidopropanal + H(2)O(2).
N(1)-acetylspermidine + O(2) + H(2)O → putrescine + 3-acetamidopropanal + H(2)O(2).
N(8)-acetylspermidine + O(2) + H(2)O → 4-acetamidobutanal + trimethylenediamine + H(2)O(2).

Protein Details

2. Spermine synthase

General function:: Involved in catalytic activity
Specific function:: S-adenosylmethioninamine + spermidine = 5'- methylthioadenosine + spermine
Gene Name:: SPE4
Uniprot ID:: Q12455
Molecular weight:: 34090.5

Reactions

S-adenosylmethioninamine + spermidine → 5'-methylthioadenosine + spermine.

Transporters

Protein Details

1. Polyamine transporter 1

General function:: Involved in transmembrane transport
Specific function:: Cell membrane polyamine/proton antiporter, involved in the detoxification of excess polyamines in the cytoplasm. Catalyzes polyamine uptake at alkaline pH and excretion at acidic pH. Recognizes spermidine, spermine and putrescine, the polyamine analogs methylglyoxal bis(guanylhydrazone) (MGBG) and paraquat, the antimalarial drug quinidine, and cycloheximide. Confers resistance to the non-steroidal anti-inflammatory drug indomethacin
Gene Name:: TPO1
Uniprot ID:: Q07824
Molecular weight:: 64271.60156

Structure for #<Compound:0xacab0d2c>

Enzymes

Reactions

Reactions

Transporters