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

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2007-04-12 22:08:12 UTC

Update Date

2020-02-26 21:26:13 UTC

HMDB ID

HMDB0006078

Secondary Accession Numbers

HMDB06078

Metabolite Identification

Common Name

Putreanine

Description

Putreanine is a new amino acid isolated from mammalian and bird brain.Its structure represents a condensation of putrescine and b-alanine and is therefore named putreanine.This amino acid can be synthesized by condensation of 4-phthalimino-1-bromobutane and ethyl b-alaninate followed by add hydrolysis.It was only detected in the central nervous system of mammalian and avian organisms. Its concentration was highest in caudal regions of the brain, and the white matter of the cerebral and cerebellar cortices and the spinal cord contained more than grey matter of the corresponding areas. Putreanine appears in the brain of rats 2 weeks after birth and subsequently its concentration increases for several months.The concentration of this amino acid in mammalian brain is roughly 50 mmoles per g, which is comparable to the concentrations of branched amino acids, aromatic amino acids, histidine, and ornithine in the same tissue.[PMID:5350953 ].

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

COMPND    HMDB0006078
HETATM    1  N1  UNL     1       4.741   0.640   0.311  1.00  0.00           N1+
HETATM    2  C1  UNL     1       3.662  -0.037  -0.375  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.338   0.458   0.171  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.175  -0.236  -0.525  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.099   0.319   0.070  1.00  0.00           C  
HETATM    6  N2  UNL     1      -1.275  -0.292  -0.517  1.00  0.00           N  
HETATM    7  C5  UNL     1      -2.439   0.365   0.094  1.00  0.00           C  
HETATM    8  C6  UNL     1      -3.676  -0.328  -0.446  1.00  0.00           C  
HETATM    9  C7  UNL     1      -4.847   0.336   0.152  1.00  0.00           C  
HETATM   10  O1  UNL     1      -5.444   1.236  -0.481  1.00  0.00           O  
HETATM   11  O2  UNL     1      -5.281  -0.023   1.401  1.00  0.00           O  
HETATM   12  H1  UNL     1       5.664   0.353  -0.114  1.00  0.00           H  
HETATM   13  H2  UNL     1       4.691   1.676   0.202  1.00  0.00           H  
HETATM   14  H3  UNL     1       4.711   0.364   1.337  1.00  0.00           H  
HETATM   15  H4  UNL     1       3.796  -1.126  -0.222  1.00  0.00           H  
HETATM   16  H5  UNL     1       3.666   0.256  -1.449  1.00  0.00           H  
HETATM   17  H6  UNL     1       2.279   0.298   1.278  1.00  0.00           H  
HETATM   18  H7  UNL     1       2.216   1.542   0.008  1.00  0.00           H  
HETATM   19  H8  UNL     1       1.196  -0.050  -1.609  1.00  0.00           H  
HETATM   20  H9  UNL     1       1.277  -1.324  -0.339  1.00  0.00           H  
HETATM   21  H10 UNL     1      -0.172   1.404  -0.036  1.00  0.00           H  
HETATM   22  H11 UNL     1      -0.097   0.048   1.135  1.00  0.00           H  
HETATM   23  H12 UNL     1      -1.305  -0.181  -1.554  1.00  0.00           H  
HETATM   24  H13 UNL     1      -2.403   1.431  -0.189  1.00  0.00           H  
HETATM   25  H14 UNL     1      -2.402   0.309   1.195  1.00  0.00           H  
HETATM   26  H15 UNL     1      -3.736  -0.277  -1.545  1.00  0.00           H  
HETATM   27  H16 UNL     1      -3.579  -1.395  -0.112  1.00  0.00           H  
HETATM   28  H17 UNL     1      -4.659  -0.328   2.159  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3   15   16
CONECT    3    4   17   18
CONECT    4    5   19   20
CONECT    5    6   21   22
CONECT    6    7   23
CONECT    7    8   24   25
CONECT    8    9   26   27
CONECT    9   10   10   11
CONECT   11   28
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
N-(2-Carboxyethyl)putrescine	HMDB
N-(4-Aminobutyl)-3-aminopropionic acid	HMDB
N-(4-Aminobutyl)-beta-alanine	HMDB
3-[(4-Azaniumylbutyl)amino]propanoate	Generator, HMDB

Chemical Formula

C₇H₁₇N₂O₂

Average Molecular Weight

161.2221

Monoisotopic Molecular Weight

161.129002798

IUPAC Name

3-[(4-azaniumylbutyl)amino]propanoic acid

Traditional Name

3-[(4-ammoniobutyl)amino]propanoic acid

CAS Registry Number

25887-39-2

SMILES

[NH3+]CCCCNCCC(O)=O

InChI Identifier

InChI=1S/C7H16N2O2/c8-4-1-2-5-9-6-3-7(10)11/h9H,1-6,8H2,(H,10,11)/p+1

InChI Key

BTSHXVLJDRJCMM-UHFFFAOYSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Beta amino acids and derivatives

Alternative Parents

Substituents

Beta amino acid or derivatives
Amino acid
Carboxylic acid
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Secondary amine
Amine
Organic nitrogen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Organic oxide
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic cation
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0006078)

Excreta

Biofluid or Excreta

Urine (PMID: 3757213)

Source

Endogenous

Endogenous (HMDB: HMDB0006078)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	9.23 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-3.4	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	4.05	ChemAxon
pKa (Strongest Basic)	10.69	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	76.97 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	54.23 m³·mol⁻¹	ChemAxon
Polarizability	18.47 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	132.22	30932474
DeepCCS	[M-H]-	128.63	30932474
DeepCCS	[M-2H]-	165.392	30932474
DeepCCS	[M+Na]+	140.787	30932474
AllCCS	[M+H]+	134.0	32859911
AllCCS	[M+H-H2O]+	130.3	32859911
AllCCS	[M+NH4]+	137.5	32859911
AllCCS	[M+Na]+	138.5	32859911
AllCCS	[M-H]-	138.5	32859911
AllCCS	[M+Na-2H]-	140.5	32859911
AllCCS	[M+HCOO]-	142.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	0.95 minutes	32390414
Predicted by Siyang on May 30, 2022	8.4177 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	7.56 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	370.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	353.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	247.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	65.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	162.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	48.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	265.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	240.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	845.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	558.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	40.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	683.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	172.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	195.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	927.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	556.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	341.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Putreanine	[NH3+]CCCCNCCC(O)=O	2633.8	Standard polar	33892256
Putreanine	[NH3+]CCCCNCCC(O)=O	1491.4	Standard non polar	33892256
Putreanine	[NH3+]CCCCNCCC(O)=O	1481.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Putreanine,1TMS,isomer #1	C[Si](C)(C)OC(=O)CCNCCCC[NH3+]	1592.9	Semi standard non polar	33892256
Putreanine,1TMS,isomer #2	C[Si](C)(C)N(CCCC[NH3+])CCC(=O)O	1683.2	Semi standard non polar	33892256
Putreanine,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCN(CCCC[NH3+])[Si](C)(C)C	1713.3	Semi standard non polar	33892256
Putreanine,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCN(CCCC[NH3+])[Si](C)(C)C	1648.8	Standard non polar	33892256
Putreanine,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCN(CCCC[NH3+])[Si](C)(C)C	1854.9	Standard polar	33892256
Putreanine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCNCCCC[NH3+]	1836.9	Semi standard non polar	33892256
Putreanine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CCCC[NH3+])CCC(=O)O	1912.0	Semi standard non polar	33892256
Putreanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCN(CCCC[NH3+])[Si](C)(C)C(C)(C)C	2197.2	Semi standard non polar	33892256
Putreanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCN(CCCC[NH3+])[Si](C)(C)C(C)(C)C	2078.4	Standard non polar	33892256
Putreanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCN(CCCC[NH3+])[Si](C)(C)C(C)(C)C	2036.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Putreanine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001l-9200000000-acb9ac23a27032c7f413	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Putreanine GC-MS (1 TMS) - 70eV, Positive	splash10-00e9-9300000000-1bca2c5630f48f53263b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Putreanine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Putreanine 10V, Positive-QTOF	splash10-0002-1900000000-32ee50ddebbb9a1e89fd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Putreanine 20V, Positive-QTOF	splash10-05fs-9500000000-1bb8b92d76b541995e15	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Putreanine 40V, Positive-QTOF	splash10-00di-9000000000-0c788505a55f0ca986ce	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Putreanine 10V, Negative-QTOF	splash10-03di-1900000000-7185cc85b4bad1e0ae6e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Putreanine 20V, Negative-QTOF	splash10-03xu-4900000000-9e5901b25a515db47b67	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Putreanine 40V, Negative-QTOF	splash10-00du-9000000000-ad5d544137e11b1db39c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Putreanine 10V, Positive-QTOF	splash10-03dl-3900000000-5f30eda8472c97957178	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Putreanine 20V, Positive-QTOF	splash10-0ab9-9100000000-74ae3aeb78b35a5bd54c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Putreanine 40V, Positive-QTOF	splash10-0a4i-9000000000-e308fe2ecc21d7b7fada	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Detected and Quantified	0.24 (0.12-0.36) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	3757213	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023827

KNApSAcK ID

Not Available

Chemspider ID

21232259

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53477800

PDB ID

Not Available

ChEBI ID

89478

Food Biomarker Ontology

Not Available

VMH ID

CE2072

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Kakimoto Y, Nakajima T, Kumon A, Matsuoka Y, Imaoka N, Sano I: Putreanine, N-(4-aminobutyl)-3-aminopropionic acid. An amino acid occurring uniquely in the mammalian central nervous system. J Biol Chem. 1969 Nov 10;244(21):6003-7. [PubMed:5350953 ]

Showing metabocard for Putreanine (HMDB0006078)

MOL for HMDB0006078 (Putreanine)

3D MOL for HMDB0006078 (Putreanine)

3D SDF for HMDB0006078 (Putreanine)

3D-SDF for HMDB0006078 (Putreanine)

PDB for HMDB0006078 (Putreanine)

3D PDB for HMDB0006078 (Putreanine)

SMILES for HMDB0006078 (Putreanine)

INCHI for HMDB0006078 (Putreanine)

Structure for HMDB0006078 (Putreanine)

3D Structure for HMDB0006078 (Putreanine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra