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Showing metabocard for Angelic acid (HMDB0029608)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:31:26 UTC
Update Date2022-03-07 02:52:13 UTC
HMDB IDHMDB0029608
Secondary Accession Numbers
  • HMDB29608
Metabolite Identification
Common NameAngelic acid
DescriptionAngelic acid is found in fats and oils. Angelic acid is a constituent of Angelica archangelica (angelica) Angelic acid has a double bond between the second and third carbons of the chain. Together with tiglic acid form a pair of cis-trans isomers. Angelic acid is a volatile body, of biting acid taste and pungent sour odour. It crystallizes in colorless monoclinic prisms. Angelic acid was formerly used therapeutically as a sedative. Angelic acid is a monocarboxylic unsaturated organic acid. It is found in garden angelica (Angelica archangelica), Umbelliferae, and many other plants. It was also isolated from the defensive secretion of certain carabid beetles
Structure
Data?1582753441
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0029608 (Angelic acid)


  Mrv1652307301920082D          

  7  6  0  0  0  0            999 V2000
    1.2375   -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
    0.0000    0.0000    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
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   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  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
M  END
Download

3D MOL for HMDB0029608 (Angelic acid)

HMDB0029608
     RDKit          3D
Angelic acid
 15 14  0  0  0  0  0  0  0  0999 V2000
    2.0705   -0.2598   -0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7367   -0.9014   -0.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3660   -0.2162    0.0080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7058   -0.9120   -0.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2974    1.2024    0.3258 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7665    1.8546    0.4167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4770    1.8980    0.5465 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2059    0.5571   -0.8617 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8660   -1.0045   -0.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2898    0.1652    0.8825 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6405   -1.9748   -0.4444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6743   -1.8951    0.4335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4675   -0.3022    0.4370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9893   -1.0421   -1.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5986    2.8309    0.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  4 12  1  0
  4 13  1  0
  4 14  1  0
  7 15  1  0
M  END
Download

3D SDF for HMDB0029608 (Angelic acid)


  Mrv1652307301920082D          

  7  6  0  0  0  0            999 V2000
    1.2375   -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
    0.0000    0.0000    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
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   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  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029608

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C=C(\C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H8O2/c1-3-4(2)5(6)7/h3H,1-2H3,(H,6,7)/b4-3-

> <INCHI_KEY>
UIERETOOQGIECD-ARJAWSKDSA-N

> <FORMULA>
C5H8O2

> <MOLECULAR_WEIGHT>
100.1158

> <EXACT_MASS>
100.0524295

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
10.349067072097935

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z)-2-methylbut-2-enoic acid

> <JCHEM_LOGP>
1.3151327766666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.971335232759619

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
27.322000000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
angelic acid

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0029608 (Angelic acid)

HMDB0029608
     RDKit          3D
Angelic acid
 15 14  0  0  0  0  0  0  0  0999 V2000
    2.0705   -0.2598   -0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7367   -0.9014   -0.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3660   -0.2162    0.0080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7058   -0.9120   -0.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2974    1.2024    0.3258 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7665    1.8546    0.4167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4770    1.8980    0.5465 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2059    0.5571   -0.8617 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8660   -1.0045   -0.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2898    0.1652    0.8825 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6405   -1.9748   -0.4444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6743   -1.8951    0.4335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4675   -0.3022    0.4370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9893   -1.0421   -1.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5986    2.8309    0.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  4 12  1  0
  4 13  1  0
  4 14  1  0
  7 15  1  0
M  END
Download

PDB for HMDB0029608 (Angelic acid)

HEADER    PROTEIN                                 30-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUL-19         0                                  
HETATM    1  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.000  -2.667   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -2.310  -1.334   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for HMDB0029608 (Angelic acid)

COMPND    HMDB0029608
HETATM    1  C1  UNL     1       2.071  -0.260  -0.132  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.737  -0.901  -0.206  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.366  -0.216   0.008  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.706  -0.912  -0.078  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.297   1.202   0.326  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.767   1.855   0.417  1.00  0.00           O  
HETATM    7  O2  UNL     1      -1.477   1.898   0.547  1.00  0.00           O  
HETATM    8  H1  UNL     1       2.206   0.557  -0.862  1.00  0.00           H  
HETATM    9  H2  UNL     1       2.866  -1.004  -0.355  1.00  0.00           H  
HETATM   10  H3  UNL     1       2.290   0.165   0.883  1.00  0.00           H  
HETATM   11  H4  UNL     1       0.641  -1.975  -0.444  1.00  0.00           H  
HETATM   12  H5  UNL     1      -1.674  -1.895   0.433  1.00  0.00           H  
HETATM   13  H6  UNL     1      -2.467  -0.302   0.437  1.00  0.00           H  
HETATM   14  H7  UNL     1      -1.989  -1.042  -1.151  1.00  0.00           H  
HETATM   15  H8  UNL     1      -1.599   2.831   0.179  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3    3   11
CONECT    3    4    5
CONECT    4   12   13   14
CONECT    5    6    6    7
CONECT    7   15
END
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SMILES for HMDB0029608 (Angelic acid)

C\C=C(\C)C(O)=O
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INCHI for HMDB0029608 (Angelic acid)

InChI=1S/C5H8O2/c1-3-4(2)5(6)7/h3H,1-2H3,(H,6,7)/b4-3-
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View in JSmolView Stereo Labels
Synonyms
ValueSource
(Z)-2-Methylcrotonic acidChEBI
2-Methyl-2Z-butenoic acidChEBI
2-Methylisocrotonic acidChEBI
Acide angeliqueChEBI
Acido angelicoChEBI
alpha-Methylisocrotonic acidChEBI
AngelicasaeureChEBI
AngelikasaeureChEBI
cis-2,3-Dimethylacrylic acidChEBI
cis-2-Dimethylcrotonic acidChEBI
cis-2-Methyl-2-butenoic acidChEBI
Z-2-Methyl-2-butenoic acidChEBI
Z-2-Methylcrotonic acidChEBI
(Z)-2-MethylcrotonateGenerator
2-Methyl-2Z-butenoateGenerator
2-MethylisocrotonateGenerator
a-MethylisocrotonateGenerator
a-Methylisocrotonic acidGenerator
alpha-MethylisocrotonateGenerator
Α-methylisocrotonateGenerator
Α-methylisocrotonic acidGenerator
cis-2,3-DimethylacrylateGenerator
cis-2-DimethylcrotonateGenerator
cis-2-Methyl-2-butenoateGenerator
Z-2-Methyl-2-butenoateGenerator
Z-2-MethylcrotonateGenerator
AngelateGenerator
(2Z)-2-Methylbut-2-enoic acidHMDB
(Z)-2-Methyl-2-butenoic acidHMDB
2-Methyl-(2Z)-2-butenoic acidHMDB
2-Methyl-(Z)-2-butenoic acidHMDB
2-Methyl-(Z)-crotonic acidHMDB
2-Methyl-2-butenoic acid, cisHMDB
alpha-Methyl isocrotonic acidHMDB
Crotonic acid, 2-methyl-, (Z)- (8ci)HMDB
(2Z)-2-Methyl-2-butenoic acidHMDB
(Z)-2-Methylbut-2-enoic acidHMDB
(Z)-2-Methylbutenoic acidHMDB
Angelic acidHMDB
cis-alpha,beta-Dimethylacrylic acidHMDB
cis-α,β-Dimethylacrylic acidHMDB
TiglateGenerator
Chemical FormulaC5H8O2
Average Molecular Weight100.1158
Monoisotopic Molecular Weight100.0524295
IUPAC Name(2Z)-2-methylbut-2-enoic acid
Traditional Nameangelic acid
CAS Registry Number565-63-9
SMILES
C\C=C(\C)C(O)=O
InChI Identifier
InChI=1S/C5H8O2/c1-3-4(2)5(6)7/h3H,1-2H3,(H,6,7)/b4-3-
InChI KeyUIERETOOQGIECD-ARJAWSKDSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMethyl-branched fatty acids
Alternative Parents
Substituents
  • Methyl-branched fatty acid
  • Unsaturated fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationSource
ProcessNot Available
Role
Industrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point45 °CNot Available
Boiling Point85.50 to 87.50 °C. @ 13.00 mm HgThe Good Scents Company Information System
Water Solubility0 soluble in hot waterThe Good Scents Company Information System
LogP1.076 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility83 g/LALOGPS
logP1.32ChemAxon
pKa (Strongest Acidic)4.97ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity27.32 m³·mol⁻¹ChemAxon
Polarizability10.35 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+121.1231661259
DarkChem[M-H]-115.64531661259
DeepCCS[M+H]+124.32930932474
DeepCCS[M-H]-121.52930932474
DeepCCS[M-2H]-157.90830932474
DeepCCS[M+Na]+132.54830932474
AllCCS[M+H]+125.132859911
AllCCS[M+H-H2O]+120.732859911
AllCCS[M+NH4]+129.232859911
AllCCS[M+Na]+130.432859911
AllCCS[M-H]-123.232859911
AllCCS[M+Na-2H]-127.132859911
AllCCS[M+HCOO]-131.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Angelic acidC\C=C(\C)C(O)=O1807.6Standard polar33892256
Angelic acidC\C=C(\C)C(O)=O961.5Standard non polar33892256
Angelic acidC\C=C(\C)C(O)=O934.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Angelic acid,1TMS,isomer #1C/C=C(/C)C(=O)O[Si](C)(C)C1006.6Semi standard non polar33892256
Angelic acid,1TBDMS,isomer #1C/C=C(/C)C(=O)O[Si](C)(C)C(C)(C)C1225.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Angelic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zi0-9000000000-4314e75ba9656b7fb97f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Angelic acid GC-MS (1 TMS) - 70eV, Positivesplash10-0ab9-9200000000-1e8cf22de89b50fd327d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Angelic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Angelic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Angelic acid 10V, Positive-QTOFsplash10-0udi-8900000000-68b09835981f85d65f902016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Angelic acid 20V, Positive-QTOFsplash10-0a4i-9100000000-7999b5228e0df947f9492016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Angelic acid 40V, Positive-QTOFsplash10-0a4i-9000000000-179be6ce006eb4e9f0842016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Angelic acid 10V, Negative-QTOFsplash10-0002-9000000000-357a7c774a32d7c0444f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Angelic acid 20V, Negative-QTOFsplash10-0a4j-9000000000-78eae8b34531c3c1bc272016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Angelic acid 40V, Negative-QTOFsplash10-0a4i-9000000000-eb61c33f642ca5d4e6762016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Angelic acid 10V, Positive-QTOFsplash10-001i-9000000000-0cc8aed45af20d83ec922021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Angelic acid 20V, Positive-QTOFsplash10-0a4i-9000000000-821598b1a2e8057a35672021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Angelic acid 40V, Positive-QTOFsplash10-0a4r-9000000000-5e5e9fc82472025ff5032021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Angelic acid 10V, Negative-QTOFsplash10-0002-9000000000-5289cc75fe7aae11de792021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Angelic acid 20V, Negative-QTOFsplash10-000t-9000000000-16cd54f70787a892bf2b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Angelic acid 40V, Negative-QTOFsplash10-052f-9000000000-59b712b76240ebaa68882021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000774
KNApSAcK IDC00054028
Chemspider ID559009
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAngelic_acid
METLIN IDNot Available
PubChem Compound643915
PDB IDMB8
ChEBI ID36431
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1010801
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
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