spermidine (CHEBI:16610)

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CHEBI:16610 - spermidine

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ChEBI Name	spermidine

ChEBI ID	CHEBI:16610

Definition	A triamine that is the 1,5,10-triaza derivative of decane.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:26733, CHEBI:45647, CHEBI:15095, CHEBI:9218, CHEBI:15097, CHEBI:26732

Supplier Information	ChemicalBook:CB2165662, eMolecules:476108, ZINC000001532612

Download	Molfile XML SDF

more structures >>

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29 28 0 0 0 0 999 V2000

5.0715 -5.4276 -0.1878 N 0 0 0 0 0 0 0 0 0 0 0 0

6.1147 -5.3964 0.8473 C 0 0 0 0 0 0 0 0 0 0 0 0

6.4535 -3.9398 1.1804 C 0 0 0 0 0 0 0 0 0 0 0 0

5.2101 -3.2020 1.6909 C 0 0 0 0 0 0 0 0 0 0 0 0

4.1378 -3.1367 0.5943 C 0 0 0 0 0 0 0 0 0 0 0 0

2.9645 -2.3826 1.0643 N 0 0 0 0 0 0 0 0 0 0 0 0

3.2898 -0.9526 1.1858 C 0 0 0 0 0 0 0 0 0 0 0 0

2.0492 -0.1788 1.6350 C 0 0 0 0 0 0 0 0 0 0 0 0

1.5920 -0.6974 2.9995 C 0 0 0 0 0 0 0 0 0 0 0 0

2.6578 -0.4837 3.9889 N 0 0 0 0 0 0 0 0 0 0 0 0

4.4735 -4.5630 -0.1096 H 0 0 0 0 0 0 0 0 0 0 0 0

4.4707 -6.2835 -0.0550 H 0 0 0 0 0 0 0 0 0 0 0 0

7.0137 -5.9237 0.4622 H 0 0 0 0 0 0 0 0 0 0 0 0

5.7356 -5.9210 1.7502 H 0 0 0 0 0 0 0 0 0 0 0 0

6.8292 -3.4338 0.2655 H 0 0 0 0 0 0 0 0 0 0 0 0

7.2396 -3.9181 1.9653 H 0 0 0 0 0 0 0 0 0 0 0 0

5.4938 -2.1697 1.9875 H 0 0 0 0 0 0 0 0 0 0 0 0

4.8008 -3.7417 2.5716 H 0 0 0 0 0 0 0 0 0 0 0 0

3.8078 -4.1622 0.3224 H 0 0 0 0 0 0 0 0 0 0 0 0

4.5433 -2.6268 -0.3055 H 0 0 0 0 0 0 0 0 0 0 0 0

2.6681 -2.7524 2.0056 H 0 0 0 0 0 0 0 0 0 0 0 0

3.6357 -0.5822 0.1971 H 0 0 0 0 0 0 0 0 0 0 0 0

4.1051 -0.8363 1.9314 H 0 0 0 0 0 0 0 0 0 0 0 0

1.2349 -0.3216 0.8928 H 0 0 0 0 0 0 0 0 0 0 0 0

2.2947 0.9019 1.7128 H 0 0 0 0 0 0 0 0 0 0 0 0

1.3725 -1.7851 2.9436 H 0 0 0 0 0 0 0 0 0 0 0 0

0.6833 -0.1523 3.3332 H 0 0 0 0 0 0 0 0 0 0 0 0

2.5942 0.4983 4.3668 H 0 0 0 0 0 0 0 0 0 0 0 0

3.5963 -0.6232 3.5298 H 0 0 0 0 0 0 0 0 0 0 0 0

9 10 1 0 0 0 0

8 9 1 0 0 0 0

7 8 1 0 0 0 0

6 7 1 0 0 0 0

5 6 1 0 0 0 0

4 5 1 0 0 0 0

3 4 1 0 0 0 0

2 3 1 0 0 0 0

1 2 1 0 0 0 0

11 1 1 0 0 0 0

12 1 1 0 0 0 0

13 2 1 0 0 0 0

14 2 1 0 0 0 0

15 3 1 0 0 0 0

16 3 1 0 0 0 0

17 4 1 0 0 0 0

18 4 1 0 0 0 0

19 5 1 0 0 0 0

20 5 1 0 0 0 0

21 6 1 0 0 0 0

22 7 1 0 0 0 0

23 7 1 0 0 0 0

24 8 1 0 0 0 0

25 8 1 0 0 0 0

26 9 1 0 0 0 0

27 9 1 0 0 0 0

28 10 1 0 0 0 0

29 10 1 0 0 0 0

M END): 18 ms

reading 29 atoms

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29 atoms created

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Wikipedia	License
Spermidine is a polyamine compound (C7H19N3) found in ribosomes and living tissues and having various metabolic functions within organisms.
Read full article at Wikipedia

Formula

C7H19N3

Net Charge

Average Mass

145.24598

Monoisotopic Mass

145.15790

InChI

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

InChIKey

ATHGHQPFGPMSJY-UHFFFAOYSA-N

SMILES

NCCCCNCCCN

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Escherichia coli (NCBI:txid562)	See: PubMed

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	fundamental metabolite Any metabolite produced by all living cells. autophagy inducer Any compound that induces the process of autophagy (the self-digestion of one or more components of a cell through the action of enzymes originating within the same cell).

Application(s):	geroprotector Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	spermidine (CHEBI:16610) has role autophagy inducer (CHEBI:138880) spermidine (CHEBI:16610) has role fundamental metabolite (CHEBI:78675) spermidine (CHEBI:16610) has role geroprotector (CHEBI:176497) spermidine (CHEBI:16610) is a polyazaalkane (CHEBI:39474) spermidine (CHEBI:16610) is a triamine (CHEBI:38751) spermidine (CHEBI:16610) is conjugate base of spermidine(3+) (CHEBI:57834)

Incoming	N-(3-aminopropyl)but-2-ene-1,4-diamine (CHEBI:48008) has functional parent spermidine (CHEBI:16610) N-[(E)-4-aminobutylidene]propane-1,3-diamine (CHEBI:48007) has functional parent spermidine (CHEBI:16610) N-caffeoylspermidine (CHEBI:138030) has functional parent spermidine (CHEBI:16610) N¹,N⁸-bis(caffeoyl)spermidine (CHEBI:138028) has functional parent spermidine (CHEBI:16610) N¹,N⁸-bis(coumaroyl)spermidine (CHEBI:85530) has functional parent spermidine (CHEBI:16610) N¹,N⁸-bis(sinapoyl)-spermidine (CHEBI:85300) has functional parent spermidine (CHEBI:16610) N¹,N⁸-bis-(dihydrocaffeoyl)spermidine (CHEBI:142881) has functional parent spermidine (CHEBI:16610) N⁴-aminopropylspermidine (CHEBI:83547) has functional parent spermidine (CHEBI:16610) acetylspermidine (CHEBI:22204) has functional parent spermidine (CHEBI:16610) glutathionylspermidine (CHEBI:16613) has functional parent spermidine (CHEBI:16610) mygalin (CHEBI:64901) has functional parent spermidine (CHEBI:16610) spermidine alkaloid (CHEBI:38524) has functional parent spermidine (CHEBI:16610) spermidine hydroxycinnamic acid conjugate (CHEBI:61233) has functional parent spermidine (CHEBI:16610) spermidine trihydrochloride (CHEBI:233088) has functional parent spermidine (CHEBI:16610) trypanothione (CHEBI:17842) has functional parent spermidine (CHEBI:16610) carboxyspermidine (CHEBI:66868) has parent hydride spermidine (CHEBI:16610) spermidine-(butyl-¹³C₄) (CHEBI:195243) is a spermidine (CHEBI:16610) spermidine(3+) (CHEBI:57834) is conjugate acid of spermidine (CHEBI:16610)

IUPAC Name

N-(3-aminopropyl)butane-1,4-diamine

Synonyms	Sources
1,5,10-triazadecane	ChemIDplus
4-azaoctamethylenediamine	ChemIDplus
4-azaoctane-1,8-diamine	IUBMB
N-(3-Aminopropyl)-1,4-butane-diamine	KEGG COMPOUND
Spermidin	ChEBI
Spermidine	KEGG COMPOUND
SPERMIDINE	PDBeChem

Manual Xrefs	Databases
C00001431	KNApSAcK
C00315	KEGG COMPOUND
DB03566	DrugBank
HMDB0001257	HMDB
LSM-37075	LINCS
SPD	PDBeChem
Spermidine	Wikipedia
SPERMIDINE	MetaCyc
View more database links

Registry Numbers	Types	Sources
124-20-9	CAS Registry Number	KEGG COMPOUND
124-20-9	CAS Registry Number	ChemIDplus
1698591	Reaxys Registry Number	Reaxys
454510	Gmelin Registry Number	Gmelin

Citations

Madeo F, Bauer MA, Carmona-Gutierrez D, Kroemer G (2019)
Spermidine: a physiological autophagy inducer acting as an anti-aging vitamin in humans?
Autophagy 15, 165-168 [PubMed:30306826]
[show Abstract]

Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C (2012)
Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer.
Analytical chemistry 84, 6429-6437 [PubMed:22770225]
[show Abstract]

Eisenberg T, Knauer H, Schauer A, Büttner S, Ruckenstuhl C, Carmona-Gutierrez D, Ring J, Schroeder S, Magnes C, Antonacci L, Fussi H, Deszcz L, Hartl R, Schraml E, Criollo A, Megalou E, Weiskopf D, Laun P, Heeren G, Breitenbach M, Grubeck-Loebenstein B, Herker E, Fahrenkrog B, Fröhlich KU, Sinner F, Tavernarakis N, Minois N, Kroemer G, Madeo F (2009)
Induction of autophagy by spermidine promotes longevity.
Nature cell biology 11, 1305-1314 [PubMed:19801973]
[show Abstract]

Uehara N, Shirakawa S, Uchino H, Saeki Y (1980)
Elevated contents of spermidine and spermine in the erythrocytes of cancer patients.
Cancer 45, 108-111 [PubMed:7350997]
[show Abstract]

Chaisiri P, Harper ME, Blamey RW, Peeling WB, Griffiths K (1980)
Plasma spermidine concentrations in patients with tumours of the breast or prostate or testis.
Clinica chimica acta; international journal of clinical chemistry 104, 367-375 [PubMed:6156039]
[show Abstract]

Mirzoian PA, Promyslov MSh (1979)
[Contents of putrescine, spermidine and spermine in tissue of the human brain glial tumors].
Ukrainskii biokhimicheskii zhurnal (1978) 51, 474-476 [PubMed:516181]
[show Abstract]

Proctor MS, Fletcher HV, Shukla JB, Rennert OM (1975)
Elevated spermidine and spermine levels in the blood of psoriasis patients.
The Journal of investigative dermatology 65, 409-411 [PubMed:1176793]
[show Abstract]

Last Modified

21 October 2024

CHEBI:16610 - spermidine

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