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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:42:01 UTC

Update Date

2022-03-07 02:53:54 UTC

HMDB ID

HMDB0033926

Secondary Accession Numbers

HMDB33926

Metabolite Identification

Common Name

(3xi,6xi)-Cyclo(alanylvalyl)

Description

(3xi,6xi)-Cyclo(alanylvalyl) belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof (3xi,6xi)-Cyclo(alanylvalyl) has been detected, but not quantified in, cocoa and cocoa products and cocoa beans (Theobroma cacao). This could make (3XI,6XI)-cyclo(alanylvalyl) a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (3xi,6xi)-Cyclo(alanylvalyl).

Structure

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

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.663   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.663   0.000   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       0.668  -0.770   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       1.997   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.997   1.540   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       0.668   2.307   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0      -1.995   2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.998  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.332   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.998  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.332  -0.770   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.332   2.310   0.000  0.00  0.00           C+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6   12                                                  
CONECT    6    1    5                                                       
CONECT    7    1                                                            
CONECT    8    2    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    4                                                            
CONECT   12    5                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₈H₁₄N₂O₂

Average Molecular Weight

170.209

Monoisotopic Molecular Weight

170.105527702

IUPAC Name

3-methyl-6-(propan-2-yl)piperazine-2,5-dione

Traditional Name

3-isopropyl-6-methylpiperazine-2,5-dione

CAS Registry Number

Not Available

SMILES

CC(C)C1NC(=O)C(C)NC1=O

InChI Identifier

InChI=1S/C8H14N2O2/c1-4(2)6-8(12)9-5(3)7(11)10-6/h4-6H,1-3H3,(H,9,12)(H,10,11)

InChI Key

ORLDMMKUTCCBSM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Dioxopiperazine
2,5-dioxopiperazine
1,4-diazinane
Piperazine
Secondary carboxylic acid amide
Lactam
Carboxamide group
Azacycle
Organoheterocyclic compound
Organopnictogen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033926)
Cytoplasm (HMDB: HMDB0033926)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033926)

Source

Exogenous

Food

Food (HMDB: HMDB0033926)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Cocoa and cocoa products (FooDB: FOOD00860)

Endogenous

Plant

Theobroma cacao (HMDB: HMDB0033926)

Not Available

Nutrient (HMDB: HMDB0033926)

Physical Properties

State

Not Available

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	26 g/L	ALOGPS
logP	-0.27	ALOGPS
logP	-0.19	ChemAxon
logS	-0.82	ALOGPS
pKa (Strongest Acidic)	11.14	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.2 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	43.59 m³·mol⁻¹	ChemAxon
Polarizability	17.69 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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
DarkChem	[M+H]+	139.661	31661259
DarkChem	[M-H]-	135.48	31661259
DeepCCS	[M+H]+	135.873	30932474
DeepCCS	[M-H]-	132.041	30932474
DeepCCS	[M-2H]-	169.368	30932474
DeepCCS	[M+Na]+	144.908	30932474
AllCCS	[M+H]+	138.2	32859911
AllCCS	[M+H-H2O]+	134.1	32859911
AllCCS	[M+NH4]+	142.0	32859911
AllCCS	[M+Na]+	143.2	32859911
AllCCS	[M-H]-	137.8	32859911
AllCCS	[M+Na-2H]-	139.2	32859911
AllCCS	[M+HCOO]-	140.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(3xi,6xi)-Cyclo(alanylvalyl)	CC(C)C1NC(=O)C(C)NC1=O	2277.0	Standard polar	33892256
(3xi,6xi)-Cyclo(alanylvalyl)	CC(C)C1NC(=O)C(C)NC1=O	1206.4	Standard non polar	33892256
(3xi,6xi)-Cyclo(alanylvalyl)	CC(C)C1NC(=O)C(C)NC1=O	1714.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(3xi,6xi)-Cyclo(alanylvalyl),1TMS,isomer #1	CC1NC(=O)C(C(C)C)N([Si](C)(C)C)C1=O	1490.3	Semi standard non polar	33892256
(3xi,6xi)-Cyclo(alanylvalyl),1TMS,isomer #1	CC1NC(=O)C(C(C)C)N([Si](C)(C)C)C1=O	1576.3	Standard non polar	33892256
(3xi,6xi)-Cyclo(alanylvalyl),1TMS,isomer #2	CC(C)C1NC(=O)C(C)N([Si](C)(C)C)C1=O	1486.4	Semi standard non polar	33892256
(3xi,6xi)-Cyclo(alanylvalyl),1TMS,isomer #2	CC(C)C1NC(=O)C(C)N([Si](C)(C)C)C1=O	1592.5	Standard non polar	33892256
(3xi,6xi)-Cyclo(alanylvalyl),2TMS,isomer #1	CC(C)C1C(=O)N([Si](C)(C)C)C(C)C(=O)N1[Si](C)(C)C	1554.9	Semi standard non polar	33892256
(3xi,6xi)-Cyclo(alanylvalyl),2TMS,isomer #1	CC(C)C1C(=O)N([Si](C)(C)C)C(C)C(=O)N1[Si](C)(C)C	1667.7	Standard non polar	33892256
(3xi,6xi)-Cyclo(alanylvalyl),1TBDMS,isomer #1	CC1NC(=O)C(C(C)C)N([Si](C)(C)C(C)(C)C)C1=O	1725.7	Semi standard non polar	33892256
(3xi,6xi)-Cyclo(alanylvalyl),1TBDMS,isomer #1	CC1NC(=O)C(C(C)C)N([Si](C)(C)C(C)(C)C)C1=O	1846.6	Standard non polar	33892256
(3xi,6xi)-Cyclo(alanylvalyl),1TBDMS,isomer #2	CC(C)C1NC(=O)C(C)N([Si](C)(C)C(C)(C)C)C1=O	1744.2	Semi standard non polar	33892256
(3xi,6xi)-Cyclo(alanylvalyl),1TBDMS,isomer #2	CC(C)C1NC(=O)C(C)N([Si](C)(C)C(C)(C)C)C1=O	1847.4	Standard non polar	33892256
(3xi,6xi)-Cyclo(alanylvalyl),2TBDMS,isomer #1	CC(C)C1C(=O)N([Si](C)(C)C(C)(C)C)C(C)C(=O)N1[Si](C)(C)C(C)(C)C	1979.4	Semi standard non polar	33892256
(3xi,6xi)-Cyclo(alanylvalyl),2TBDMS,isomer #1	CC(C)C1C(=O)N([Si](C)(C)C(C)(C)C)C(C)C(=O)N1[Si](C)(C)C(C)(C)C	2125.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - (3xi,6xi)-Cyclo(alanylvalyl) EI-B (Non-derivatized)	splash10-004l-9300000000-da049db4a8457186b053	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - (3xi,6xi)-Cyclo(alanylvalyl) EI-B (Non-derivatized)	splash10-004i-5900000000-6cf02bcf0dcb851e4d2d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - (3xi,6xi)-Cyclo(alanylvalyl) EI-B (Non-derivatized)	splash10-03di-4900000000-10a20345a1a709d3b590	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - (3xi,6xi)-Cyclo(alanylvalyl) EI-B (Non-derivatized)	splash10-004l-9300000000-da049db4a8457186b053	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - (3xi,6xi)-Cyclo(alanylvalyl) EI-B (Non-derivatized)	splash10-004i-5900000000-6cf02bcf0dcb851e4d2d	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - (3xi,6xi)-Cyclo(alanylvalyl) EI-B (Non-derivatized)	splash10-03di-4900000000-10a20345a1a709d3b590	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (3xi,6xi)-Cyclo(alanylvalyl) GC-MS (Non-derivatized) - 70eV, Positive	splash10-056v-9400000000-7d042a4c4eadb33fc867	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (3xi,6xi)-Cyclo(alanylvalyl) 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 - (3xi,6xi)-Cyclo(alanylvalyl) 10V, Positive-QTOF	splash10-00di-0900000000-4f772d392fe57f4abe0d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3xi,6xi)-Cyclo(alanylvalyl) 20V, Positive-QTOF	splash10-00di-3900000000-48cee96ef586ddf07bb9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3xi,6xi)-Cyclo(alanylvalyl) 40V, Positive-QTOF	splash10-05fr-9000000000-8c8918114f8c428679bf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3xi,6xi)-Cyclo(alanylvalyl) 10V, Negative-QTOF	splash10-016r-1900000000-393879c902280889ab7b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3xi,6xi)-Cyclo(alanylvalyl) 20V, Negative-QTOF	splash10-0006-9100000000-bbcd44ff904cee04bf45	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3xi,6xi)-Cyclo(alanylvalyl) 40V, Negative-QTOF	splash10-006x-9000000000-d265522fd6aafb87ebf1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3xi,6xi)-Cyclo(alanylvalyl) 10V, Negative-QTOF	splash10-014i-0900000000-396a65119652ec6767fa	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3xi,6xi)-Cyclo(alanylvalyl) 20V, Negative-QTOF	splash10-014l-7900000000-2dd934e7cd9018bae499	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3xi,6xi)-Cyclo(alanylvalyl) 40V, Negative-QTOF	splash10-0006-9000000000-94abfda032d2b2827f25	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3xi,6xi)-Cyclo(alanylvalyl) 10V, Positive-QTOF	splash10-00di-0900000000-6037389b466772473f69	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3xi,6xi)-Cyclo(alanylvalyl) 20V, Positive-QTOF	splash10-00di-8900000000-8206f2a3730e151b5e7b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3xi,6xi)-Cyclo(alanylvalyl) 40V, Positive-QTOF	splash10-0abc-9000000000-61ea2bf89dabcc134722	2021-09-23	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

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB012126

KNApSAcK ID

Not Available

Chemspider ID

123373

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139895

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for (3xi,6xi)-Cyclo(alanylvalyl) (HMDB0033926)

MOL for HMDB0033926 ((3xi,6xi)-Cyclo(alanylvalyl))

3D MOL for HMDB0033926 ((3xi,6xi)-Cyclo(alanylvalyl))

3D SDF for HMDB0033926 ((3xi,6xi)-Cyclo(alanylvalyl))

3D-SDF for HMDB0033926 ((3xi,6xi)-Cyclo(alanylvalyl))

PDB for HMDB0033926 ((3xi,6xi)-Cyclo(alanylvalyl))

3D PDB for HMDB0033926 ((3xi,6xi)-Cyclo(alanylvalyl))

SMILES for HMDB0033926 ((3xi,6xi)-Cyclo(alanylvalyl))

INCHI for HMDB0033926 ((3xi,6xi)-Cyclo(alanylvalyl))

Structure for HMDB0033926 ((3xi,6xi)-Cyclo(alanylvalyl))

3D Structure for HMDB0033926 ((3xi,6xi)-Cyclo(alanylvalyl))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra