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Showing metabocard for Tiglic acid (HMDB0001470)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:44 UTC
HMDB IDHMDB0001470
Secondary Accession Numbers
  • HMDB01470
Metabolite Identification
Common NameTiglic acid
DescriptionTiglic acid is a monocarboxylic unsaturated organic acid. It is found in croton oil and in several other natural products. It has also been isolated from the defensive secretion of certain beetles. Tiglic acid, also known as tiglate or tiglinsaeure, 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. Tiglic acid has a double bond between the second and third carbons of the chain. Tiglic acid and angelic acid form a pair of cis-trans isomers. Tiglic acid is a volatile and crystallizable substance with a sweet, warm, spicy odour. It is used in making perfumes and flavoring agents. The salts and esters of tiglic acid are called tiglates.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001470 (Tiglic acid)

  Mrv1652305271900302D          

  7  6  0  0  0  0            999 V2000
    0.1029   -0.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6140    0.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8160    0.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1029   -1.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3272   -0.1750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6140    1.0596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5330   -0.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  2  0  0  0  0
  3  7  1  0  0  0  0
M  END
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3D MOL for HMDB0001470 (Tiglic acid)

HMDB0001470
     RDKit          3D
Tiglic acid
 15 14  0  0  0  0  0  0  0  0999 V2000
   -1.9830   -0.5252   -0.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5968   -1.0219   -0.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3460   -0.1004    0.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0064    1.3321    0.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7220   -0.5405    0.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0075   -1.7782    0.2852 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6934    0.4237    0.4488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6180   -1.4254   -0.4930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0943    0.1618   -1.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4109   -0.1207    0.7011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3523   -2.0914   -0.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9277    1.8996   -0.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4264    1.6808    1.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7033    1.6067   -0.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4948    0.4991   -0.1615 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
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3D SDF for HMDB0001470 (Tiglic acid)

  Mrv1652305271900302D          

  7  6  0  0  0  0            999 V2000
    0.1029   -0.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6140    0.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8160    0.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1029   -1.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3272   -0.1750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6140    1.0596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5330   -0.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  2  0  0  0  0
  3  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001470

> <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-ONEGZZNKSA-N

> <FORMULA>
C5H8O2

> <MOLECULAR_WEIGHT>
100.1158

> <EXACT_MASS>
100.0524295

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
10.386001376060808

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.13

> <JCHEM_LOGP>
1.3151327766666667

> <ALOGPS_LOGS>
-0.08

> <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

> <ALOGPS_SOLUBILITY>
8.30e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tiglic acid

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0001470 (Tiglic acid)

HMDB0001470
     RDKit          3D
Tiglic acid
 15 14  0  0  0  0  0  0  0  0999 V2000
   -1.9830   -0.5252   -0.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5968   -1.0219   -0.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3460   -0.1004    0.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0064    1.3321    0.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7220   -0.5405    0.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0075   -1.7782    0.2852 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6934    0.4237    0.4488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6180   -1.4254   -0.4930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0943    0.1618   -1.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4109   -0.1207    0.7011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3523   -2.0914   -0.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9277    1.8996   -0.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4264    1.6808    1.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7033    1.6067   -0.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4948    0.4991   -0.1615 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
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PDB for HMDB0001470 (Tiglic acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       0.192  -0.327   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.146   0.435   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.523   0.435   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.192  -1.869   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.477  -0.327   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -1.146   1.978   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.862  -0.327   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1                                                            
CONECT    5    2                                                            
CONECT    6    2                                                            
CONECT    7    3                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for HMDB0001470 (Tiglic acid)

COMPND    HMDB0001470
HETATM    1  C1  UNL     1      -1.983  -0.525  -0.250  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.597  -1.022  -0.066  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.346  -0.100   0.096  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.006   1.332   0.088  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.722  -0.541   0.281  1.00  0.00           C  
HETATM    6  O1  UNL     1       2.007  -1.778   0.285  1.00  0.00           O  
HETATM    7  O2  UNL     1       2.693   0.424   0.449  1.00  0.00           O  
HETATM    8  H1  UNL     1      -2.618  -1.425  -0.493  1.00  0.00           H  
HETATM    9  H2  UNL     1      -2.094   0.162  -1.100  1.00  0.00           H  
HETATM   10  H3  UNL     1      -2.411  -0.121   0.701  1.00  0.00           H  
HETATM   11  H4  UNL     1      -0.352  -2.091  -0.063  1.00  0.00           H  
HETATM   12  H5  UNL     1       0.928   1.900  -0.100  1.00  0.00           H  
HETATM   13  H6  UNL     1      -0.426   1.681   1.062  1.00  0.00           H  
HETATM   14  H7  UNL     1      -0.703   1.607  -0.729  1.00  0.00           H  
HETATM   15  H8  UNL     1       3.495   0.499  -0.161  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 HMDB0001470 (Tiglic acid)

C\C=C(/C)C(O)=O
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INCHI for HMDB0001470 (Tiglic 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 NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC5H8O2
Average Molecular Weight100.1158
Monoisotopic Molecular Weight100.0524295
IUPAC Name(2E)-2-methylbut-2-enoic acid
Traditional Nametiglic acid
CAS Registry Number80-59-1
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-ONEGZZNKSA-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
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point61 - 65 °CNot Available
Boiling Point95.00 to 96.00 °C. @ 12.00 mm HgThe Good Scents Company Information System
Water Solubility1 mg/mLNot Available
LogP1.076 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • 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 IDC00001207
Chemspider ID111629
KEGG Compound IDC08279
BioCyc IDCPD-7077
BiGG IDNot Available
Wikipedia LinkTiglic_acid
METLIN ID6261
PubChem Compound125468
PDB IDNot Available
ChEBI ID9592
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1010371
References
Synthesis ReferenceJacob, Carl; Hafner, Walter; Wick, Manfred. Tiglic acid. Ger. Offen. (1976), 6 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Leete E, Murrill JB: Biosynthesis of the tiglic acid moiety of meteloidine in Datura meteloides. Tetrahedron Lett. 1967 May;18:1727-30. [PubMed:6045963 ]

Enzymes

Enzyme Details
1. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Tiglic acid → 3,4,5-trihydroxy-6-{[(2E)-2-methylbut-2-enoyl]oxy}oxane-2-carboxylic aciddetails