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Showing NP-Card for (5r)-2-methyl-5-(2-oxoethyl)cyclopent-1-ene-1-carbaldehyde (NP0192989)

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Record Information
Version2.0
Created at2022-09-04 10:19:25 UTC
Updated at2022-09-04 10:19:25 UTC
NP-MRD IDNP0192989
Secondary Accession NumbersNone
Natural Product Identification
Common Name(5r)-2-methyl-5-(2-oxoethyl)cyclopent-1-ene-1-carbaldehyde
Description(+)-Rotundial belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open. (5r)-2-methyl-5-(2-oxoethyl)cyclopent-1-ene-1-carbaldehyde is found in Alberta magna and Vitex trifolia. Based on a literature review very few articles have been published on (+)-Rotundial.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0192989 ((5r)-2-methyl-5-(2-oxoethyl)cyclopent-1-ene-1-carbaldehyde)


  Mrv1652309042212192D          

 11 11  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  1  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
    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  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
M  END
Download

3D MOL for NP0192989 ((5r)-2-methyl-5-(2-oxoethyl)cyclopent-1-ene-1-carbaldehyde)

     RDKit          3D

 23 23  0  0  0  0  0  0  0  0999 V2000
   -2.8783    0.2507   -0.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4235    0.4050   -0.1511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5813   -0.4082    0.4673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9906   -1.6334    1.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1817   -2.0045    1.2177 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7912    0.1247    0.3371 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8431   -0.9421    0.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1653   -0.2703    0.2043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3073    0.9375    0.1221 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6836    0.8318   -1.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6488    1.5526   -0.7471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3270    1.2076   -0.5438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3363   -0.0379    0.7238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1846   -0.5217   -1.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2471   -2.2488    1.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9894    0.9157    1.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8423   -1.4505    1.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7152   -1.6935   -0.4433 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0858   -0.8615    0.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4908    1.5269   -1.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4720    0.1051   -1.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0985    1.9338   -1.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4881    2.2810    0.0472 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
  4  5  2  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  6 10  1  0
 10 11  1  0
 11  2  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  4 15  1  0
  6 16  1  1
  7 17  1  0
  7 18  1  0
  8 19  1  0
 10 20  1  0
 10 21  1  0
 11 22  1  0
 11 23  1  0
M  END
Download

3D SDF for NP0192989 ((5r)-2-methyl-5-(2-oxoethyl)cyclopent-1-ene-1-carbaldehyde)


  Mrv1652309042212192D          

 11 11  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  1  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
    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  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0192989

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(C=O)[C@@H](CC=O)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C9H12O2/c1-7-2-3-8(4-5-10)9(7)6-11/h5-6,8H,2-4H2,1H3/t8-/m1/s1

> <INCHI_KEY>
KBJJMMFFLYXMPU-MRVPVSSYSA-N

> <FORMULA>
C9H12O2

> <MOLECULAR_WEIGHT>
152.193

> <EXACT_MASS>
152.083729626

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
16.466528947854208

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5R)-2-methyl-5-(2-oxoethyl)cyclopent-1-ene-1-carbaldehyde

> <JCHEM_LOGP>
0.6334503023333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.777425634454705

> <JCHEM_PKA_STRONGEST_BASIC>
-4.28207945347787

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
43.367000000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(5R)-2-methyl-5-(2-oxoethyl)cyclopent-1-ene-1-carbaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0192989 ((5r)-2-methyl-5-(2-oxoethyl)cyclopent-1-ene-1-carbaldehyde)

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PDB for NP0192989 ((5r)-2-methyl-5-(2-oxoethyl)cyclopent-1-ene-1-carbaldehyde)
HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-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       2.109  -2.943   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.014  -4.188   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    6   11                                                       
CONECT   11   10    2                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0192989 ((5r)-2-methyl-5-(2-oxoethyl)cyclopent-1-ene-1-carbaldehyde)
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SMILES for NP0192989 ((5r)-2-methyl-5-(2-oxoethyl)cyclopent-1-ene-1-carbaldehyde)
CC1=C(C=O)[C@@H](CC=O)CC1
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INCHI for NP0192989 ((5r)-2-methyl-5-(2-oxoethyl)cyclopent-1-ene-1-carbaldehyde)
InChI=1S/C9H12O2/c1-7-2-3-8(4-5-10)9(7)6-11/h5-6,8H,2-4H2,1H3/t8-/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC9H12O2
Average Mass152.1930 Da
Monoisotopic Mass152.08373 Da
IUPAC Name(5R)-2-methyl-5-(2-oxoethyl)cyclopent-1-ene-1-carbaldehyde
Traditional Name(5R)-2-methyl-5-(2-oxoethyl)cyclopent-1-ene-1-carbaldehyde
CAS Registry NumberNot Available
SMILES
CC1=C(C=O)[C@@H](CC=O)CC1
InChI Identifier
InChI=1S/C9H12O2/c1-7-2-3-8(4-5-10)9(7)6-11/h5-6,8H,2-4H2,1H3/t8-/m1/s1
InChI KeyKBJJMMFFLYXMPU-MRVPVSSYSA-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
Alberta magnaLOTUS Database
Vitex trifoliaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassMonoterpenoids  
Direct ParentIridoids and derivatives  
Alternative Parents
Substituents
  • Monocyclic monoterpenoid
    • 

  • 11-noriridane monoterpenoid
    • 

  • Alpha-hydrogen aldehyde
    • 

  • 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
logP0.63ChemAxon
pKa (Strongest Acidic)16.78ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity43.37 m³·mol⁻¹ChemAxon
Polarizability16.47 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9280685  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11105549  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]