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Showing NP-Card for Angelic acid (NP0136956)

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Record Information
Version2.0
Created at2022-05-30 16:37:15 UTC
Updated at2022-05-30 16:37:15 UTC
NP-MRD IDNP0136956
Secondary Accession NumbersNone
Natural Product Identification
Common NameAngelic acid
DescriptionAngelic acid, also known as acide angelique or angelicasaeure, 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. Angelic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Angelic acid is a sweet, caramel, and dry tasting compound. Outside of the human body, Angelic acid has been detected, but not quantified in, several different foods, such as burdocks, evergreen blackberries, carrots, wild carrots, and wild celeries. This could make angelic acid a potential biomarker for the consumption of these foods. These plants include Angelica archangelica, Peucedanum ostruthium (masterwort), Levisticum officinale (lovage), Euryangium sumbul and Laserpitium latifolium. Angelic acid was first isolated by the German pharmacist Ludwig Andreas Buchner (1813–1897) in 1842 from the roots of the garden plant angelica (Angelica archangelica) that gave the acid its name. The former can be entirely converted to the latter by boiling for about 40 hours, by reaction with sulfuric and other acids, by heating with a base to a temperature above 100 °C, or simply by storing the acid for about 25 years. Angelic acid is found in Angelica archangelica, Angelica sinensis, Euryops arabicus, Lomatium nuttallii, Senecio linifolius and Tussilago farfara. Angelic acid was first documented in 1978 (PMID: 720485). The angelic acid esters of sesquiterpene alcohols, such as petasin, are the active chemical behind the strong pain-relieving and spasmolytic action of extracts from the plant butterbur.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0136956 (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 NP0136956 (Angelic acid)

     RDKit          3D

 15 14  0  0  0  0  0  0  0  0999 V2000
    2.1077   -0.0756   -0.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7841   -0.7568   -0.2797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3474   -0.1580    0.0408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6152   -0.9423   -0.0524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3356    1.2335    0.4717 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7331    1.8822    0.5462 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5404    1.8532    0.8074 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3704    0.2458    0.8168 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1830    0.7744   -0.9047 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8976   -0.8274   -0.4808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7268   -1.8100   -0.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6027   -1.5607   -0.9724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7302   -1.6414    0.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4672   -0.2497   -0.0080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1641    2.0326    0.0285 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  7  1  0
  5  6  2  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 NP0136956 (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>
NP0136956

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
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3D-SDF for NP0136956 (Angelic acid)

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PDB for NP0136956 (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 NP0136956 (Angelic acid)
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SMILES for NP0136956 (Angelic acid)
C\C=C(\C)C(O)=O
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INCHI for NP0136956 (Angelic acid)
InChI=1S/C5H8O2/c1-3-4(2)5(6)7/h3H,1-2H3,(H,6,7)/b4-3-
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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
cis-alpha,beta-Dimethylacrylic acidHMDB
cis-Α,β-dimethylacrylic acidHMDB
Angelic acidHMDB
TiglateGenerator
Chemical FormulaC5H8O2
Average Mass100.1158 Da
Monoisotopic Mass100.05243 Da
IUPAC Name(2Z)-2-methylbut-2-enoic acid
Traditional Nameangelic acid
CAS Registry NumberNot Available
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
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Angelica archangelicaLOTUS Database
Angelica sinensisLOTUS Database
Euryops arabicusLOTUS Database
Lomatium nuttalliiLOTUS Database
Senecio linifoliusLOTUS Database
Tussilago farfaraLOTUS Database
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
HMDB IDHMDB0029608  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000774  
KNApSAcK IDNot Available
Chemspider ID559009  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAngelic_acid  
METLIN IDNot Available
PubChem Compound643915  
PDB IDMB8  
ChEBI ID36431  
Good Scents IDNot Available
References
General References
  1. Papageorgiou VP: Wound healing properties of naphthaquinone pigments from Alkanna tinctoria. Experientia. 1978 Nov 15;34(11):1499-501. doi: 10.1007/BF01932375. [PubMed:720485  ]