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Showing NP-Card for 2-methyl-5-(prop-1-en-2-yl)cyclopentane-1-carbaldehyde (NP0165862)

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Record Information
Version2.0
Created at2022-09-03 01:06:26 UTC
Updated at2022-09-03 01:06:26 UTC
NP-MRD IDNP0165862
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-methyl-5-(prop-1-en-2-yl)cyclopentane-1-carbaldehyde
DescriptionPhotocitral A belongs to the class of organic compounds known as monocyclic monoterpenoids. These are monoterpenoids containing 1 ring in the isoprene chain. Photocitral A is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Photocitral A has been detected, but not quantified in, citrus and herbs and spices. 2-methyl-5-(prop-1-en-2-yl)cyclopentane-1-carbaldehyde is found in Pelargonium citronellum and Zingiber officinale. This could make photocitral a a potential biomarker for the consumption of these foods.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0165862 (2-methyl-5-(prop-1-en-2-yl)cyclopentane-1-carbaldehyde)


  Mrv0541 05061310212D          

 11 11  0  0  0  0            999 V2000
    1.2822    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    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
   -0.8843    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   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
    0.5678    1.1143    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
   -1.0558    1.6913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  7  1  2  0  0  0  0
  7  2  1  0  0  0  0
  8  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
  9  7  1  0  0  0  0
 10  6  1  0  0  0  0
 10  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11  6  2  0  0  0  0
M  END
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3D MOL for NP0165862 (2-methyl-5-(prop-1-en-2-yl)cyclopentane-1-carbaldehyde)

     RDKit          3D

 27 27  0  0  0  0  0  0  0  0999 V2000
    2.6142    0.8129   -0.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8291   -0.2158   -0.2576 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3460   -1.5550    0.2410 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5234   -0.1682   -0.9703 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1442    1.2105   -1.4673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4079    1.1648   -1.3760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4877    0.5782    0.0277 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8902    0.2628    0.4415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6212   -0.6486   -0.1237 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2286   -1.2061    1.1769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1259   -0.4768    2.1364 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5441    0.6681    0.5103 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3627    1.7876   -0.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4307   -1.6201   -0.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2545   -1.5496    1.3256 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8260   -2.4005   -0.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5844   -0.8472   -1.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4647    1.9625   -0.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4727    1.4361   -2.4786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8410    2.1556   -1.4629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7610    0.4028   -2.0716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9821    1.2853    0.7478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1843   -0.7761    0.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9448    0.3896    1.5574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6353    0.9699   -0.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2515   -1.3663   -0.7186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0352   -2.2561    1.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  9  1  0
  9 10  1  0
 10 11  2  0
  4  2  1  0
  2  3  1  0
  2  1  2  3
  9  7  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
  7 22  1  1
  6 20  1  0
  6 21  1  0
  5 18  1  0
  5 19  1  0
  4 17  1  6
  9 26  1  6
 10 27  1  0
  3 14  1  0
  3 15  1  0
  3 16  1  0
  1 12  1  0
  1 13  1  0
M  END
Download

3D SDF for NP0165862 (2-methyl-5-(prop-1-en-2-yl)cyclopentane-1-carbaldehyde)


  Mrv0541 05061310212D          

 11 11  0  0  0  0            999 V2000
    1.2822    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    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
   -0.8843    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   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
    0.5678    1.1143    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
   -1.0558    1.6913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  7  1  2  0  0  0  0
  7  2  1  0  0  0  0
  8  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
  9  7  1  0  0  0  0
 10  6  1  0  0  0  0
 10  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11  6  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0165862

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC(C1C=O)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)10(9)6-11/h6,8-10H,1,4-5H2,2-3H3

> <INCHI_KEY>
JCDLXWAYWSJVTP-UHFFFAOYSA-N

> <FORMULA>
C10H16O

> <MOLECULAR_WEIGHT>
152.2334

> <EXACT_MASS>
152.120115134

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
18.08986573390046

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methyl-5-(prop-1-en-2-yl)cyclopentane-1-carbaldehyde

> <ALOGPS_LOGP>
2.18

> <JCHEM_LOGP>
2.2449517290000003

> <ALOGPS_LOGS>
-2.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.567244502991688

> <JCHEM_PKA_STRONGEST_BASIC>
-7.040026466066432

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
46.3438

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.76e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methyl-5-(prop-1-en-2-yl)cyclopentane-1-carbaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0165862 (2-methyl-5-(prop-1-en-2-yl)cyclopentane-1-carbaldehyde)

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PDB for NP0165862 (2-methyl-5-(prop-1-en-2-yl)cyclopentane-1-carbaldehyde)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.393   4.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.615  -1.536   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.651   1.651   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.971   3.157   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    7                                                            
CONECT    3    8                                                            
CONECT    4    5    8                                                       
CONECT    5    4    9                                                       
CONECT    6   10   11                                                       
CONECT    7    1    2    9                                                  
CONECT    8    3    4   10                                                  
CONECT    9    5    7   10                                                  
CONECT   10    6    8    9                                                  
CONECT   11    6                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0165862 (2-methyl-5-(prop-1-en-2-yl)cyclopentane-1-carbaldehyde)
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SMILES for NP0165862 (2-methyl-5-(prop-1-en-2-yl)cyclopentane-1-carbaldehyde)
CC1CCC(C1C=O)C(C)=C
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INCHI for NP0165862 (2-methyl-5-(prop-1-en-2-yl)cyclopentane-1-carbaldehyde)
InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)10(9)6-11/h6,8-10H,1,4-5H2,2-3H3
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Synonyms
ValueSource
2-Isopropenyl-5-methylcyclopentanecarbaldehydeHMDB
Chemical FormulaC10H16O
Average Mass152.2334 Da
Monoisotopic Mass152.12012 Da
IUPAC Name2-methyl-5-(prop-1-en-2-yl)cyclopentane-1-carbaldehyde
Traditional Name2-methyl-5-(prop-1-en-2-yl)cyclopentane-1-carbaldehyde
CAS Registry NumberNot Available
SMILES
CC1CCC(C1C=O)C(C)=C
InChI Identifier
InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)10(9)6-11/h6,8-10H,1,4-5H2,2-3H3
InChI KeyJCDLXWAYWSJVTP-UHFFFAOYSA-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
Pelargonium citronellumLOTUS Database
Zingiber officinaleLOTUS 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
logP2.18ALOGPS
logP2.24ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)17.57ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity46.34 m³·mol⁻¹ChemAxon
Polarizability18.09 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0038290  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB017619  
KNApSAcK IDNot Available
Chemspider ID92751  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound102684  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]