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Showing NP-Card for iridodial (NP0325177)

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Record Information
Version1.0
Created at2022-09-12 05:43:47 UTC
Updated at2022-09-12 05:43:47 UTC
NP-MRD IDNP0325177
Secondary Accession NumbersNone
Natural Product Identification
Common Nameiridodial
DescriptionIridodial belongs to the class of organic compounds known as monocyclic monoterpenoids. These are monoterpenoids containing 1 ring in the isoprene chain. iridodial is found in Eremophila deserti and Ontholestes murinus. It was first documented in 2012 (PMID: 23202979). Iridodial is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 25578278).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0325177 (iridodial)


  Mrv1533004201503502D          

 12 12  0  0  0  0            999 V2000
   -0.1467    2.3518    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
    1.2822    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    3.1768    0.0000 O   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
    0.9803   -0.1553    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
   -0.3297   -0.8227    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
   -0.8843    0.8843    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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
M  END
Download

3D MOL for NP0325177 (iridodial)

     RDKit          3D

 28 28  0  0  0  0  0  0  0  0999 V2000
   -2.4903   -0.5545   -0.3608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6958    0.3005    0.5934 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8368   -0.1573    1.9955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0489   -1.3398    2.1744 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2757    0.4848    0.1799 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2373    1.1546   -1.1796 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2259    0.9961   -1.5473 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7390   -0.1887   -0.7530 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5860    0.3585    0.3662 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4445   -0.7795   -0.1739 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6752   -1.7117    0.9015 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2952   -2.8582    0.8200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6592    0.0270   -1.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5138   -0.6597    0.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0302   -1.5365   -0.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1714    1.3255    0.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7693    0.4599    2.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2381    1.1342    0.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7954    0.5523   -1.9326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5588    2.2036   -1.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3736    0.8582   -2.6375 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7234    1.9516   -1.2388 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2569   -0.9227   -1.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0680    0.3604    1.3468 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4866   -0.2576    0.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8661    1.4377    0.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0814   -1.2164   -1.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1860   -1.4221    1.7997 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 10  5  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  1
  3 17  1  0
  5 18  1  1
  6 19  1  0
  6 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  6
  9 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  6
 11 28  1  0
M  END
Download

3D SDF for NP0325177 (iridodial)


  Mrv1533004201503502D          

 12 12  0  0  0  0            999 V2000
   -0.1467    2.3518    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
    1.2822    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    3.1768    0.0000 O   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
    0.9803   -0.1553    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
   -0.3297   -0.8227    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
   -0.8843    0.8843    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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0325177

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C=O)C1CCC(C)C1C=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H16O2/c1-7-3-4-9(8(2)5-11)10(7)6-12/h5-10H,3-4H2,1-2H3

> <INCHI_KEY>
HMCYXRFNNOPPPR-UHFFFAOYSA-N

> <FORMULA>
C10H16O2

> <MOLECULAR_WEIGHT>
168.236

> <EXACT_MASS>
168.115029755

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
18.851702721059993

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.56

> <JCHEM_LOGP>
1.3697067046666667

> <ALOGPS_LOGS>
-2.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.659185183840066

> <JCHEM_PKA_STRONGEST_BASIC>
-6.726099801926035

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
47.3322

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.44e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
iridodial

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0325177 (iridodial)

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PDB for NP0325177 (iridodial)
HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.393   4.390   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.393   5.930   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.830  -0.290   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      -0.615  -1.536   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  C   UNK     0      -1.651   1.651   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.971   3.157   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    5   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for NP0325177 (iridodial)
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SMILES for NP0325177 (iridodial)
CC(C=O)C1CCC(C)C1C=O
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INCHI for NP0325177 (iridodial)
InChI=1S/C10H16O2/c1-7-3-4-9(8(2)5-11)10(7)6-12/h5-10H,3-4H2,1-2H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC10H16O2
Average Mass168.2360 Da
Monoisotopic Mass168.11503 Da
IUPAC Name2-methyl-5-(1-oxopropan-2-yl)cyclopentane-1-carbaldehyde
Traditional Nameiridodial
CAS Registry NumberNot Available
SMILES
CC(C=O)C1CCC(C)C1C=O
InChI Identifier
InChI=1S/C10H16O2/c1-7-3-4-9(8(2)5-11)10(7)6-12/h5-10H,3-4H2,1-2H3
InChI KeyHMCYXRFNNOPPPR-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
Eremophila desertiLOTUS Database
Ontholestes murinusLOTUS 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 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
logP1.56ALOGPS
logP1.37ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)17.66ChemAxon
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.33 m³·mol⁻¹ChemAxon
Polarizability18.85 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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIridodial  
METLIN IDNot Available
PubChem Compound222140  
PDB IDNot Available
ChEBI ID5964  
Good Scents IDNot Available
References
General References
  1. Sun P, Song S, Zhou L, Zhang B, Qi J, Li X: Transcriptome analysis reveals putative genes involved in iridoid biosynthesis in Rehmannia glutinosa. Int J Mol Sci. 2012 Oct 23;13(10):13748-63. doi: 10.3390/ijms131013748. [PubMed:23202979  ] 
  2. Munkert J, Pollier J, Miettinen K, Van Moerkercke A, Payne R, Muller-Uri F, Burlat V, O'Connor SE, Memelink J, Kreis W, Goossens A: Iridoid synthase activity is common among the plant progesterone 5beta-reductase family. Mol Plant. 2015 Jan;8(1):136-52. doi: 10.1016/j.molp.2014.11.005. Epub 2014 Dec 11. [PubMed:25578278  ] 
  3. LOTUS database [Link]