Livestock Metabolome Database: Showing metabocard for Spermine (LMDB00310)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:47:01 UTC

Update Date

2021-04-30 20:57:45 UTC

Lmdb

LMDB00310

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Spermine

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 drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. Spermine is a very strong basic compound (based on its pKa). Spermine exists in all living species, ranging from bacteria to humans. 5'-methylthioadenosine and spermine can be biosynthesized from S-adenosylmethioninamine and spermidine through the action of the enzyme spermine synthase. In humans, spermine is involved in spermidine and spermine biosynthesis. Outside of the human body, Spermine is found, on average, in the highest concentration within a few different foods, such as milk (cow), oats, and white wines and in a lower concentration in red wines. Spermine has also been detected, but not quantified in, several different foods, such as annual wild rices, fruits, breadfruits, saffrons, and kelps. This could make spermine a potential biomarker for the consumption of these foods. Spermine is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

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

Chemical Formula

C₁₀H₂₆N₄

Average Molecular Weight

202.3402

Monoisotopic Molecular Weight

202.215746852

IUPAC Name

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

Traditional Name

spermine

CAS Registry Number

71-44-3

SMILES

NCCCNCCCCNCCCN

InChI Identifier

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

InChI Key

PFNFFQXMRSDOHW-UHFFFAOYSA-N

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 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

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

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Plasma
Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	20231903	details
Serum	Detected and Quantified	0.4537 +/- 0.7318 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.1339 +/- 0.0988 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.02 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	0.03 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	0.04 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	0.04 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	0.2651 +/- 0.1747 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.6771 +/- 0.9509 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.1492 +/- 0.0622 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.2527 +/- 0.1626 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.13 +/- 0.06 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected and Quantified	0.4672 +/- 0.372 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.1666 +/- 0.1196 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.2107 +/- 0.0986 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.1376 +/- 0.0509 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.5791 +/- 0.5709 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.4362 +/- 0.6163 uM	Normal	Ovine	Goldansaz et al.,...	details