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Showing NP-Card for (5s)-2-methyl-5-(1-oxopropan-2-yl)cyclopent-1-ene-1-carbaldehyde (NP0145087)

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Record Information
Version2.0
Created at2022-09-02 00:12:50 UTC
Updated at2022-09-02 00:12:50 UTC
NP-MRD IDNP0145087
Secondary Accession NumbersNone
Natural Product Identification
Common Name(5s)-2-methyl-5-(1-oxopropan-2-yl)cyclopent-1-ene-1-carbaldehyde
DescriptionChrysomelidial belongs to the class of organic compounds known as monocyclic monoterpenoids. These are monoterpenoids containing 1 ring in the isoprene chain. (5s)-2-methyl-5-(1-oxopropan-2-yl)cyclopent-1-ene-1-carbaldehyde is found in Phaedon cochleariae. (5s)-2-methyl-5-(1-oxopropan-2-yl)cyclopent-1-ene-1-carbaldehyde was first documented in 2011 (PMID: 21350972). Based on a literature review a small amount of articles have been published on Chrysomelidial (PMID: 31425853) (PMID: 30654252) (PMID: 23341265) (PMID: 22246522).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0145087 ((5s)-2-methyl-5-(1-oxopropan-2-yl)cyclopent-1-ene-1-carbaldehyde)


  Mrv1652309022202122D          

 12 12  0  0  1  0            999 V2000
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6329    0.3323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2857   -0.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1296   -1.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6145   -2.2438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   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
  4  5  2  0  0  0  0
  3  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
M  END
Download

3D MOL for NP0145087 ((5s)-2-methyl-5-(1-oxopropan-2-yl)cyclopent-1-ene-1-carbaldehyde)

     RDKit          3D

 26 26  0  0  0  0  0  0  0  0999 V2000
   -2.9998   -0.2114   -0.7338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6179   -0.4377   -0.2317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8144    0.4718    0.2717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2019    1.8924    0.4067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3251    2.2884    0.0418 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4862   -0.0770    0.6758 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5869    0.2113   -0.3162 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9235    1.6740   -0.4012 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7810   -0.5585    0.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9514   -1.0808    1.1576 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2541   -1.5728    0.6570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9517   -1.7567   -0.2354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9563    0.4756   -1.6265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6022    0.3247    0.0458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5100   -1.1400   -0.9816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5096    2.6059    0.8262 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7821    0.2236    1.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2427   -0.1618   -1.3054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1813    2.1391   -1.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9509    2.1769    0.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9140    1.7845   -0.8949 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5764   -0.6680   -0.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1052   -2.1176    0.1604 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0893   -1.9499    1.6871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6409   -2.5206    0.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6949   -2.0155   -1.2710 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  9  1  0
  9 10  2  0
  7  6  1  0
  6 11  1  0
 11 12  1  0
 12  2  1  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  3  6  1  0
  8 19  1  0
  8 20  1  0
  8 21  1  0
  7 18  1  6
  9 22  1  0
  6 17  1  1
 11 23  1  0
 11 24  1  0
 12 25  1  0
 12 26  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  4 16  1  0
M  END
Download

3D SDF for NP0145087 ((5s)-2-methyl-5-(1-oxopropan-2-yl)cyclopent-1-ene-1-carbaldehyde)


  Mrv1652309022202122D          

 12 12  0  0  1  0            999 V2000
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6329    0.3323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2857   -0.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1296   -1.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6145   -2.2438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   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
  4  5  2  0  0  0  0
  3  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0145087

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C=O)[C@@H]1CCC(C)=C1C=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H14O2/c1-7-3-4-9(8(2)5-11)10(7)6-12/h5-6,8-9H,3-4H2,1-2H3/t8?,9-/m0/s1

> <INCHI_KEY>
OPYIDDKLXUUEPE-GKAPJAKFSA-N

> <FORMULA>
C10H14O2

> <MOLECULAR_WEIGHT>
166.22

> <EXACT_MASS>
166.099379691

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
18.279590858238954

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S)-2-methyl-5-(1-oxopropan-2-yl)cyclopent-1-ene-1-carbaldehyde

> <ALOGPS_LOGP>
1.97

> <JCHEM_LOGP>
1.1764365806666663

> <ALOGPS_LOGS>
-1.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.288923912646162

> <JCHEM_PKA_STRONGEST_BASIC>
-4.303998782477072

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
47.941500000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.82e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S)-2-methyl-5-(1-oxopropan-2-yl)cyclopent-1-ene-1-carbaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0145087 ((5s)-2-methyl-5-(1-oxopropan-2-yl)cyclopent-1-ene-1-carbaldehyde)

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PDB for NP0145087 ((5s)-2-methyl-5-(1-oxopropan-2-yl)cyclopent-1-ene-1-carbaldehyde)
HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.770   1.651   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.915   0.620   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.735  -1.536   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.267  -1.375   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.109  -2.943   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.014  -4.188   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7   11                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9                                                            
CONECT   11    6   12                                                       
CONECT   12   11    2                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for NP0145087 ((5s)-2-methyl-5-(1-oxopropan-2-yl)cyclopent-1-ene-1-carbaldehyde)
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SMILES for NP0145087 ((5s)-2-methyl-5-(1-oxopropan-2-yl)cyclopent-1-ene-1-carbaldehyde)
CC(C=O)[C@@H]1CCC(C)=C1C=O
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INCHI for NP0145087 ((5s)-2-methyl-5-(1-oxopropan-2-yl)cyclopent-1-ene-1-carbaldehyde)
InChI=1S/C10H14O2/c1-7-3-4-9(8(2)5-11)10(7)6-12/h5-6,8-9H,3-4H2,1-2H3/t8?,9-/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC10H14O2
Average Mass166.2200 Da
Monoisotopic Mass166.09938 Da
IUPAC Name(5S)-2-methyl-5-(1-oxopropan-2-yl)cyclopent-1-ene-1-carbaldehyde
Traditional Name(5S)-2-methyl-5-(1-oxopropan-2-yl)cyclopent-1-ene-1-carbaldehyde
CAS Registry NumberNot Available
SMILES
CC(C=O)[C@@H]1CCC(C)=C1C=O
InChI Identifier
InChI=1S/C10H14O2/c1-7-3-4-9(8(2)5-11)10(7)6-12/h5-6,8-9H,3-4H2,1-2H3/t8?,9-/m0/s1
InChI KeyOPYIDDKLXUUEPE-GKAPJAKFSA-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
Phaedon cochleariaeLOTUS 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
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aldehyde
    • 

  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
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
logP1.97ALOGPS
logP1.18ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)17.29ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.94 m³·mol⁻¹ChemAxon
Polarizability18.28 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 IDC00010535  
Chemspider ID61477566  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101316923  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Fu N, Yang ZL, Pauchet Y, Paetz C, Brandt W, Boland W, Burse A: A cytochrome P450 from the mustard leaf beetles hydroxylates geraniol, a key step in iridoid biosynthesis. Insect Biochem Mol Biol. 2019 Oct;113:103212. doi: 10.1016/j.ibmb.2019.103212.  Epub 2019 Aug 16. [PubMed:31425853  ] 
  2. Muller T, Gesing MA, Segeler M, Muller C: Sublethal insecticide exposure of an herbivore alters the response of its predator. Environ Pollut. 2019 Apr;247:39-45. doi: 10.1016/j.envpol.2018.12.040. Epub 2019  Jan 7. [PubMed:30654252  ] 
  3. Kunert M, Rahfeld P, Shaker KH, Schneider B, David A, Dettner K, Pasteels JM, Boland W: Beetles do it differently: two stereodivergent cyclisation modes in iridoid-producing leaf-beetle larvae. Chembiochem. 2013 Feb 11;14(3):353-60. doi: 10.1002/cbic.201200689. Epub 2013 Jan  22. [PubMed:23341265  ] 
  4. Shimizu N, Yakumaru R, Sakata T, Shimano S, Kuwahara Y: The absolute configuration of chrysomelidial: a widely distributed defensive component among oribotririid mites (Acari: Oribatida). J Chem Ecol. 2012 Jan;38(1):29-35. doi: 10.1007/s10886-012-0064-3. Epub 2012 Jan  14. [PubMed:22246522  ] 
  5. Raspotnig G, Leutgeb V, Krisper G, Leis HJ: Discrimination of Oribotritia species by oil gland chemistry (Acari, Oribatida). Exp Appl Acarol. 2011 Jul;54(3):211-24. doi: 10.1007/s10493-011-9434-8. Epub 2011  Feb 25. [PubMed:21350972  ] 
  6. LOTUS database [Link]