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Showing NP-Card for (+)-trans-chrysanthemic acid (NP0171017)

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Record Information
Version2.0
Created at2022-09-03 07:21:41 UTC
Updated at2022-09-03 07:21:41 UTC
NP-MRD IDNP0171017
Secondary Accession NumbersNone
Natural Product Identification
Common Name(+)-trans-chrysanthemic acid
Description(+)-Trans-chrysanthemic acid, also known as (1R,3R)-chrysanthemate or chrysanthemic acid D-trans-form, belongs to the class of organic compounds known as monocyclic monoterpenoids. These are monoterpenoids containing 1 ring in the isoprene chain. (+)-trans-chrysanthemic acid is found in Tanacetum cinerariifolium. (+)-trans-chrysanthemic acid was first documented in 2021 (PMID: 33819787). Based on a literature review very few articles have been published on (+)-trans-chrysanthemic acid.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0171017 ((+)-trans-chrysanthemic acid)


  Mrv1652309032209212D          

 12 12  0  0  1  0            999 V2000
    2.7941   -0.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0796    0.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0796    0.9993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3651   -0.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6507    0.1743    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1743    0.1743    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8888   -0.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8888   -1.0632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6033    0.1743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2382    0.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2350    1.5646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7114    1.5646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  6 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
M  END
Download

3D MOL for NP0171017 ((+)-trans-chrysanthemic acid)

     RDKit          3D

 28 28  0  0  0  0  0  0  0  0999 V2000
    3.4642   -0.2978   -0.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0876    0.2518   -0.0945 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8030    1.5289    0.6057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1653   -0.4066   -0.7673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2476    0.0235   -0.9139 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9299    0.3561    0.3907 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8016    1.5382    0.3651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4105    1.9343   -0.6548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9796    2.2776    1.5214 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3176   -0.8738   -0.4142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7024   -0.8287   -0.9530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8323   -2.2290    0.0599 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8835   -0.3232   -1.0663 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3876   -1.3281    0.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1219    0.2960    0.6340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5934    1.3241    1.6608 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0210    2.1321    0.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7201    2.1645    0.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4348   -1.3318   -1.2577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4971    0.6366   -1.7897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4395    0.0942    1.3460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2257    3.2502    1.5161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7681   -0.5038   -2.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3865   -0.1698   -0.3631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1511   -1.8387   -0.9094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1981   -2.1026    0.9389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6366   -2.9624    0.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1583   -2.6116   -0.7580 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  9  1  0
  7  8  2  0
  6 10  1  0
 10 11  1  0
 10 12  1  0
 10  5  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  5 20  1  6
  6 21  1  1
  9 22  1  0
 11 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
 12 27  1  0
 12 28  1  0
M  END
Download

3D SDF for NP0171017 ((+)-trans-chrysanthemic acid)


  Mrv1652309032209212D          

 12 12  0  0  1  0            999 V2000
    2.7941   -0.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0796    0.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0796    0.9993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3651   -0.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6507    0.1743    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1743    0.1743    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8888   -0.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8888   -1.0632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6033    0.1743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2382    0.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2350    1.5646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7114    1.5646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  6 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0171017

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=C[C@@H]1[C@@H](C(O)=O)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C10H16O2/c1-6(2)5-7-8(9(11)12)10(7,3)4/h5,7-8H,1-4H3,(H,11,12)/t7-,8+/m1/s1

> <INCHI_KEY>
XLOPRKKSAJMMEW-SFYZADRCSA-N

> <FORMULA>
C10H16O2

> <MOLECULAR_WEIGHT>
168.236

> <EXACT_MASS>
168.115029755

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
19.175967370249307

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylic acid

> <ALOGPS_LOGP>
2.44

> <JCHEM_LOGP>
2.2011127660000005

> <ALOGPS_LOGS>
-1.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.923334057229156

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
48.215799999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.88e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+)-trans-chrysanthemic acid

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0171017 ((+)-trans-chrysanthemic acid)

Download
PDB for NP0171017 ((+)-trans-chrysanthemic acid)
HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       5.216  -0.445   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.882   0.325   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.882   1.865   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.548  -0.445   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.215   0.325   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.325   0.325   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.659  -0.445   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.659  -1.985   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -2.993   0.325   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.445   1.659   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.439   2.921   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.328   2.921   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    6    5   11   12                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for NP0171017 ((+)-trans-chrysanthemic acid)
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SMILES for NP0171017 ((+)-trans-chrysanthemic acid)
CC(C)=C[C@@H]1[C@@H](C(O)=O)C1(C)C
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INCHI for NP0171017 ((+)-trans-chrysanthemic acid)
InChI=1S/C10H16O2/c1-6(2)5-7-8(9(11)12)10(7,3)4/h5,7-8H,1-4H3,(H,11,12)/t7-,8+/m1/s1
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View in JSmol
Synonyms
ValueSource
(+)-(1R,3R)-2,2-Dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylic acidChEBI
(+)-trans-ChrysanthemumsaeureChEBI
(1R,3R)-Chrysanthemic acidChEBI
(1R-trans)-2,2-Dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acidChEBI
(1R-trans)-Chrysanthemic acidChEBI
(R,R)-Chrysanthemic acidChEBI
Chrysanthemic acid D-trans-formChEBI
(+)-(1R,3R)-2,2-Dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylateGenerator
(1R,3R)-ChrysanthemateGenerator
(1R-trans)-2,2-Dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylateGenerator
(1R-trans)-ChrysanthemateGenerator
(R,R)-ChrysanthemateGenerator
Chrysanthemate D-trans-formGenerator
(+)-trans-ChrysanthemateGenerator
Chemical FormulaC10H16O2
Average Mass168.2360 Da
Monoisotopic Mass168.11503 Da
IUPAC Name(1R,3R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylic acid
Traditional Name(+)-trans-chrysanthemic acid
CAS Registry NumberNot Available
SMILES
CC(C)=C[C@@H]1[C@@H](C(O)=O)C1(C)C
InChI Identifier
InChI=1S/C10H16O2/c1-6(2)5-7-8(9(11)12)10(7,3)4/h5,7-8H,1-4H3,(H,11,12)/t7-,8+/m1/s1
InChI KeyXLOPRKKSAJMMEW-SFYZADRCSA-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
Chrysanthemum cinerariaefoliumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as monocyclic monoterpenoids. These are monoterpenoids containing 1 ring in the isoprene chain.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassMonoterpenoids  
Direct ParentMonocyclic monoterpenoids  
Alternative Parents
Substituents
  • Monocyclic monoterpenoid
    • 

  • Cyclopropanecarboxylic acid or derivatives
    • 

  • Cyclopropanecarboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic 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
logP2.44ALOGPS
logP2.2ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)4.92ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity48.22 m³·mol⁻¹ChemAxon
Polarizability19.18 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID15876  
KEGG Compound IDC09842  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16747  
PDB IDNot Available
ChEBI ID39100  
Good Scents IDNot Available
References
General References
  1. Danek M, Plonka J, Barchanska H: Metabolic profiles and non-targeted LC-MS/MS approach as a complementary tool to targeted analysis in assessment of plant exposure to pesticides. Food Chem. 2021 Sep 15;356:129680. doi: 10.1016/j.foodchem.2021.129680. Epub 2021 Mar 25. [PubMed:33819787  ] 
  2. LOTUS database [Link]