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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2022-09-09 21:11:21 UTC

Update Date

2022-09-22 18:35:15 UTC

HMDB ID

HMDB0341437

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3-Heptenoylglycine

Description

2-[(1-hydroxyhept-3-en-1-ylidene)amino]acetic acid belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. 2-[(1-hydroxyhept-3-en-1-ylidene)amino]acetic acid is a moderately basic compound (based on its pKa).

Structure

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


  Mrv1652308021722082D          

 13 12  0  0  0  0            999 V2000
    4.5375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  2  0  0  0  0
  5  6  1  4  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  7  1  4  0  0  0
 10  8  2  0  0  0  0
 11  8  1  0  0  0  0
 12  9  2  0  0  0  0
 13  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341437

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCC=CCC(O)=NCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H15NO3/c1-2-3-4-5-6-8(11)10-7-9(12)13/h4-5H,2-3,6-7H2,1H3,(H,10,11)(H,12,13)

> <INCHI_KEY>
VCELCMWDUMJSBS-UHFFFAOYSA-N

> <FORMULA>
C9H15NO3

> <MOLECULAR_WEIGHT>
185.223

> <EXACT_MASS>
185.105193347

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
20.20972598447586

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1-hydroxyhept-3-en-1-ylidene)amino]acetic acid

> <ALOGPS_LOGP>
1.49

> <JCHEM_LOGP>
1.607864023333333

> <ALOGPS_LOGS>
-2.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
5.8532716726960565

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.02522087855976

> <JCHEM_PKA_STRONGEST_BASIC>
1.9588620281011946

> <JCHEM_POLAR_SURFACE_AREA>
69.89

> <JCHEM_REFRACTIVITY>
50.116400000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.18e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1-hydroxyhept-3-en-1-ylidene)amino]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-AUG-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-AUG-17         0                                  
HETATM    1  C   UNK     0       8.470  -1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.930  -1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.160   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.620   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.310  -1.334   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -3.080  -2.667   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -3.080   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    8                                                       
CONECT    7    9   10                                                       
CONECT    8    6   10   11                                                  
CONECT    9    7   12   13                                                  
CONECT   10    7    8                                                       
CONECT   11    8                                                            
CONECT   12    9                                                            
CONECT   13    9                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

COMPND    HMDB0094729
HETATM    1  C1  UNL     1      -3.427  -1.072  -1.134  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.204  -1.450  -0.299  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.110  -0.441   0.860  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.963   0.911   0.314  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.959   1.688   0.540  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.193   1.328   1.383  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.455   1.372   0.575  1.00  0.00           C  
HETATM    8  O1  UNL     1       1.809   2.568  -0.005  1.00  0.00           O  
HETATM    9  N1  UNL     1       2.130   0.291   0.474  1.00  0.00           N  
HETATM   10  C8  UNL     1       3.361   0.203  -0.274  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.676  -1.228  -0.469  1.00  0.00           C  
HETATM   12  O2  UNL     1       4.709  -1.559  -1.097  1.00  0.00           O  
HETATM   13  O3  UNL     1       2.864  -2.235   0.022  1.00  0.00           O  
HETATM   14  H1  UNL     1      -3.691  -1.868  -1.835  1.00  0.00           H  
HETATM   15  H2  UNL     1      -4.239  -0.871  -0.390  1.00  0.00           H  
HETATM   16  H3  UNL     1      -3.249  -0.137  -1.697  1.00  0.00           H  
HETATM   17  H4  UNL     1      -1.334  -1.333  -0.977  1.00  0.00           H  
HETATM   18  H5  UNL     1      -2.335  -2.459   0.100  1.00  0.00           H  
HETATM   19  H6  UNL     1      -3.107  -0.502   1.406  1.00  0.00           H  
HETATM   20  H7  UNL     1      -1.376  -0.791   1.567  1.00  0.00           H  
HETATM   21  H8  UNL     1      -2.767   1.312  -0.344  1.00  0.00           H  
HETATM   22  H9  UNL     1      -0.915   2.704   0.091  1.00  0.00           H  
HETATM   23  H10 UNL     1       0.362   2.136   2.166  1.00  0.00           H  
HETATM   24  H11 UNL     1       0.085   0.379   1.904  1.00  0.00           H  
HETATM   25  H12 UNL     1       2.356   2.640  -0.853  1.00  0.00           H  
HETATM   26  H13 UNL     1       3.169   0.717  -1.257  1.00  0.00           H  
HETATM   27  H14 UNL     1       4.198   0.757   0.215  1.00  0.00           H  
HETATM   28  H15 UNL     1       3.312  -3.061   0.392  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3   17   18
CONECT    3    4   19   20
CONECT    4    5    5   21
CONECT    5    6   22
CONECT    6    7   23   24
CONECT    7    8    9    9
CONECT    8   25
CONECT    9   10
CONECT   10   11   26   27
CONECT   11   12   12   13
CONECT   13   28
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-[(1-Hydroxyhept-3-en-1-ylidene)amino]acetate	Generator

Chemical Formula

C₉H₁₅NO₃

Average Molecular Weight

185.223

Monoisotopic Molecular Weight

185.105193347

IUPAC Name

2-[(1-hydroxyhept-3-en-1-ylidene)amino]acetic acid

Traditional Name

[(1-hydroxyhept-3-en-1-ylidene)amino]acetic acid

CAS Registry Number

Not Available

SMILES

CCCC=CCC(O)=NCC(O)=O

InChI Identifier

InChI=1S/C9H15NO3/c1-2-3-4-5-6-8(11)10-7-9(12)13/h4-5H,2-3,6-7H2,1H3,(H,10,11)(H,12,13)

InChI Key

VCELCMWDUMJSBS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents

Substituents

N-acyl-alpha-amino acid
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carbonyl group
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (PMID: 20971021)

Process

Not Available

Role

Not Available

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
logP	1.49	ALOGPS
logP	1.61	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	4.03	ChemAxon
pKa (Strongest Basic)	1.96	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	69.89 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	50.12 m³·mol⁻¹	ChemAxon
Polarizability	20.21 Å³	ChemAxon
Number of Rings	0	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]+	144.897	31661259
DarkChem	[M-H]-	141.185	31661259
DeepCCS	[M+H]+	139.696	30932474
DeepCCS	[M-H]-	135.865	30932474
DeepCCS	[M-2H]-	173.142	30932474
DeepCCS	[M+Na]+	148.723	30932474
AllCCS	[M+H]+	144.0	32859911
AllCCS	[M+H-H2O]+	140.2	32859911
AllCCS	[M+NH4]+	147.5	32859911
AllCCS	[M+Na]+	148.5	32859911
AllCCS	[M-H]-	143.9	32859911
AllCCS	[M+Na-2H]-	145.3	32859911
AllCCS	[M+HCOO]-	147.0	32859911

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hepteneoylglycine GC-MS (Non-derivatized) - 70eV, Positive	splash10-06rx-9300000000-5ad7c2cd2c263bc291ab	2017-09-14	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hepteneoylglycine GC-MS (2 TMS) - 70eV, Positive	splash10-00gi-9221000000-b7b0e0cd48efdb17001b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hepteneoylglycine 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 - 3-Heptenoylglycine 10V, Negative-QTOF	splash10-001i-0900000000-21cd4f979072c13a1d8c	2017-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Heptenoylglycine 20V, Negative-QTOF	splash10-0089-2900000000-eaee444d25174f22f322	2017-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Heptenoylglycine 40V, Negative-QTOF	splash10-00dl-9100000000-ca830ef1c8f448953d8e	2017-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Heptenoylglycine 10V, Positive-QTOF	splash10-00dr-9600000000-184104b4032257fec237	2017-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Heptenoylglycine 20V, Positive-QTOF	splash10-00fr-9100000000-8b8cb90842d2dbf0f2b9	2017-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Heptenoylglycine 40V, Positive-QTOF	splash10-0adi-9000000000-243d908adc7224f1a56c	2017-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Heptenoylglycine 10V, Negative-QTOF	splash10-00e9-7900000000-bd5bc187a809617c513a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Heptenoylglycine 20V, Negative-QTOF	splash10-00di-9300000000-51c821d1a0f05b858df2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Heptenoylglycine 40V, Negative-QTOF	splash10-05fr-9000000000-682e530f4fdb9f8b5a85	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Heptenoylglycine 10V, Positive-QTOF	splash10-0019-8900000000-c7479e48b3c3080fcfa5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Heptenoylglycine 20V, Positive-QTOF	splash10-0544-9000000000-c613023941a8410bf564	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Heptenoylglycine 40V, Positive-QTOF	splash10-0a4i-9000000000-3ff16464fbfd5e291be0	2021-09-24	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

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Asthma	33739820	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Asthma	33739820	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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

Meister I, Zhang P, Sinha A, Skold CM, Wheelock AM, Izumi T, Chaleckis R, Wheelock CE: High-Precision Automated Workflow for Urinary Untargeted Metabolomic Epidemiology. Anal Chem. 2021 Mar 30;93(12):5248-5258. doi: 10.1021/acs.analchem.1c00203. Epub 2021 Mar 19. [PubMed:33739820 ]

Showing metabocard for 3-Heptenoylglycine (HMDB0341437)

MOL for HMDB0341437 (3-Heptenoylglycine)

3D MOL for HMDB0341437 (3-Heptenoylglycine)

3D SDF for HMDB0341437 (3-Heptenoylglycine)

3D-SDF for HMDB0341437 (3-Heptenoylglycine)

PDB for HMDB0341437 (3-Heptenoylglycine)

3D PDB for HMDB0341437 (3-Heptenoylglycine)

SMILES for HMDB0341437 (3-Heptenoylglycine)

INCHI for HMDB0341437 (3-Heptenoylglycine)

Structure for HMDB0341437 (3-Heptenoylglycine)

3D Structure for HMDB0341437 (3-Heptenoylglycine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra