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Record Information
Version1.0
Created at2020-04-17 18:48:29 UTC
Updated at2022-12-13 23:36:25 UTC
CannabisDB IDCDB004900
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameSpermine
DescriptionSpermine, 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. Spermine is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
Synonyms
Chemical FormulaC10H26N4
Average Molecular Weight202.34
Monoisotopic Molecular Weight202.2157
IUPAC Name(3-aminopropyl)({4-[(3-aminopropyl)amino]butyl})amine
Traditional Namespermine
CAS Registry Number71-44-3
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 KeyPFNFFQXMRSDOHW-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.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentDialkylamines
Alternative Parents
Substituents
  • Secondary aliphatic amine
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Primary aliphatic amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point29 °CNot Available
Boiling Point150.1 °CWikipedia
Water SolubilityNot AvailableNot Available
logP0.0Wikipedia
Predicted Properties
PropertyValueSource
logP-0.66ALOGPS
logP-1.5ChemAxon
logS-2ALOGPS
pKa (Strongest Basic)10.8ChemAxon
Physiological Charge4ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area76.1 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity62.56 m³·mol⁻¹ChemAxon
Polarizability26.69 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
MS/MS
NMR
Pathways
Pathways
Protein Targets
Enzymes
Transporters
Protein NameGene NameLocusUniprot IDDetails
Solute carrier family 22 member 4SLC22A45q31.1Q9H015 details
Solute carrier family 22 member 1SLC22A16q26O15245 details
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Xanthine dehydrogenase/oxidaseXDH2p23.1P47989 details
Gamma-butyrobetaine dioxygenaseBBOX111p14.2O75936 details
Amiloride-sensitive amine oxidase [copper-containing]ABP17q36.1P19801 details
Betaine--homocysteine S-methyltransferase 1BHMT5q14.1Q93088 details
Agmatinase, mitochondrialAGMAT1p36.21Q9BSE5 details
Trimethyllysine dioxygenase, mitochondrialTMLHEXq28Q9NVH6 details
S-methylmethionine--homocysteine S-methyltransferase BHMT2BHMT25q13Q9H2M3 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Amiloride-sensitive amine oxidase [copper-containing]ABP17q36.1P19801 details
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.000947 mg/g dry wt
    • David S. Wishart,...
details
GabriolaDetected and Quantified0.000308 mg/g dry wt
    • David S. Wishart,...
details
Island HoneyDetected and Quantified0.00153 mg/g dry wt
    • David S. Wishart,...
details
QuadraDetected and Quantified0.000222 mg/g dry wt
    • David S. Wishart,...
details
Sensi StarDetected and Quantified0.000953 mg/g dry wt
    • David S. Wishart,...
details
Tangerine DreamDetected and Quantified0.000773 mg/g dry wt
    • David S. Wishart,...
details
HMDB IDHMDB0001256
DrugBank IDDB00127
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003225
KNApSAcK IDC00001432
Chemspider ID1072
KEGG Compound IDC00750
BioCyc IDSPERMINE
BiGG ID35875
Wikipedia LinkSpermine
METLIN ID255
PubChem Compound1103
PDB IDNot Available
ChEBI ID15746
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 33 proteins in total.

Enzymes

General function:
Involved in N-acetyltransferase activity
Specific function:
Enzyme which catalyzes the acetylation of polyamines. Substrate specificity: norspermidine > spermidine = spermine >> N(1)acetylspermine = putrescine.
Gene Name:
SAT2
Uniprot ID:
Q96F10
Molecular weight:
19154.905
General function:
Involved in N-acetyltransferase activity
Specific function:
Enzyme which catalyzes the acetylation of polyamines. Substrate specificity: norspermidine = spermidine >> spermine > N(1)-acetylspermine > putrescine. This highly regulated enzyme allows a fine attenuation of the intracellular concentration of polyamines. Also involved in the regulation of polyamine transport out of cells. Acts on 1,3-diaminopropane, 1,5-diaminopentane, putrescine, spermidine (forming N(1)- and N(8)-acetylspermidine), spermine, N(1)-acetylspermidine and N(8)-acetylspermidine.
Gene Name:
SAT1
Uniprot ID:
P21673
Molecular weight:
20023.8
General function:
Involved in oxidoreductase activity
Specific function:
Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro).
Gene Name:
XDH
Uniprot ID:
P47989
Molecular weight:
146422.99
General function:
Involved in oxidoreductase activity, acting on CH-OH group of donors
Specific function:
Not Available
Gene Name:
CHDH
Uniprot ID:
Q8NE62
Molecular weight:
65358.005
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
DMGDH
Uniprot ID:
Q9UI17
Molecular weight:
96810.135
General function:
Involved in spermine synthase activity
Specific function:
Catalyzes the production of spermine from spermidine and decarboxylated S-adenosylmethionine (dcSAM).
Gene Name:
SMS
Uniprot ID:
P52788
Molecular weight:
35278.2
General function:
Involved in catalytic activity
Specific function:
Catalyzes the production of spermidine from putrescine and decarboxylated S-adenosylmethionine (dcSAM). Has a strong preference for putrescine as substrate, and has very low activity towards 1,3-diaminopropane. Has extremely low activity towards spermidine.
Gene Name:
SRM
Uniprot ID:
P19623
Molecular weight:
33824.455
General function:
Involved in oxidoreductase activity
Specific function:
Converts gamma-trimethylaminobutyraldehyde into gamma-butyrobetaine. Catalyzes the irreversible oxidation of a broad range of aldehydes to the corresponding acids in an NAD-dependent reaction.
Gene Name:
ALDH9A1
Uniprot ID:
P49189
Molecular weight:
56291.485
General function:
Involved in iron ion binding
Specific function:
Catalyzes the formation of L-carnitine from gamma-butyrobetaine.
Gene Name:
BBOX1
Uniprot ID:
O75936
Molecular weight:
44714.6
General function:
Involved in copper ion binding
Specific function:
Catalyzes the degradation of compounds such as putrescine, histamine, spermine, and spermidine, substances involved in allergic and immune responses, cell proliferation, tissue differentiation, tumor formation, and possibly apoptosis. Placental DAO is thought to play a role in the regulation of the female reproductive function.
Gene Name:
ABP1
Uniprot ID:
P19801
Molecular weight:
85377.1

Transporters

General function:
Involved in ion transmembrane transporter activity
Specific function:
Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Relative uptake activity ratio of carnitine to TEA is 1.78. A key substrate of this transporter seems to be ergothioneine (ET)
Gene Name:
SLC22A4
Uniprot ID:
Q9H015
Molecular weight:
62154.5
General function:
Involved in ion transmembrane transporter activity
Specific function:
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)- N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin- dependent kinase II and LCK tyrosine kinase
Gene Name:
SLC22A1
Uniprot ID:
O15245
Molecular weight:
61187.4

Only showing the first 10 proteins. There are 33 proteins in total.