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Showing NP-Card for methyl (4ar,7s,7as)-3,5-dioxo-hexahydrocyclopenta[c]pyran-7-carboxylate (NP0237918)

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Record Information
Version2.0
Created at2022-09-06 21:11:57 UTC
Updated at2022-09-06 21:11:57 UTC
NP-MRD IDNP0237918
Secondary Accession NumbersNone
Natural Product Identification
Common Namemethyl (4ar,7s,7as)-3,5-dioxo-hexahydrocyclopenta[c]pyran-7-carboxylate
DescriptionMethyl (4aR,7S,7aS)-3,5-dioxo-octahydrocyclopenta[c]pyran-7-carboxylate belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. methyl (4ar,7s,7as)-3,5-dioxo-hexahydrocyclopenta[c]pyran-7-carboxylate is found in Torricellia tiliifolia. Based on a literature review very few articles have been published on methyl (4aR,7S,7aS)-3,5-dioxo-octahydrocyclopenta[c]pyran-7-carboxylate.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0237918 (methyl (4ar,7s,7as)-3,5-dioxo-hexahydrocyclopenta[c]pyran-7-carboxylate)


  Mrv1652309062223112D          

 15 16  0  0  1  0            999 V2000
   -0.1781   -3.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -2.7631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  2  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
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  9  7  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  6  0  0  0
  5 15  1  0  0  0  0
  9 15  1  0  0  0  0
M  END
Download

3D MOL for NP0237918 (methyl (4ar,7s,7as)-3,5-dioxo-hexahydrocyclopenta[c]pyran-7-carboxylate)

     RDKit          3D

 27 28  0  0  0  0  0  0  0  0999 V2000
    4.0262    0.5970    0.4133 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6844    0.5937   -0.0170 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9596   -0.5427   -0.2988 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5030   -1.6586   -0.1731 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5680   -0.4521   -0.7410 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0859   -1.7656   -1.0075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5363   -1.3978   -0.8383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4609   -1.6483   -1.5617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5110   -0.6398    0.4689 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7926    0.0011    0.7949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9050    1.4160    0.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0175    1.9911    0.5576 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8108    2.1302    0.0963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5180    1.6160   -0.0754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3258    0.2097    0.3204 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5282   -0.3298    0.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1417    0.8258    1.4815 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5275    1.4390   -0.1469 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4979    0.1415   -1.6999 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1254   -2.2006   -1.9851 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1443   -2.4472   -0.1551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3148   -1.4464    1.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6150   -0.5383    0.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0249   -0.1310    1.8772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2390    1.8157   -1.1506 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1747    2.2730    0.5111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2767    0.1484    1.2741 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
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15  5  1  0
 15  9  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  5 19  1  6
  6 20  1  0
  6 21  1  0
  9 22  1  1
 10 23  1  0
 10 24  1  0
 14 25  1  0
 14 26  1  0
 15 27  1  1
M  END
Download

3D SDF for NP0237918 (methyl (4ar,7s,7as)-3,5-dioxo-hexahydrocyclopenta[c]pyran-7-carboxylate)


  Mrv1652309062223112D          

 15 16  0  0  1  0            999 V2000
   -0.1781   -3.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -2.7631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  2  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
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  9  7  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  6  0  0  0
  5 15  1  0  0  0  0
  9 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0237918

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@H]1CC(=O)[C@@H]2CC(=O)OC[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C10H12O5/c1-14-10(13)6-2-8(11)5-3-9(12)15-4-7(5)6/h5-7H,2-4H2,1H3/t5-,6+,7+/m1/s1

> <INCHI_KEY>
DYRZXVSFXIQNPW-VQVTYTSYSA-N

> <FORMULA>
C10H12O5

> <MOLECULAR_WEIGHT>
212.201

> <EXACT_MASS>
212.068473486

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
20.19918858396594

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (4aR,7S,7aS)-3,5-dioxo-octahydrocyclopenta[c]pyran-7-carboxylate

> <JCHEM_LOGP>
-0.3276573183333331

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.561054984187749

> <JCHEM_PKA_STRONGEST_BASIC>
-6.674267695918312

> <JCHEM_POLAR_SURFACE_AREA>
69.67

> <JCHEM_REFRACTIVITY>
48.40440000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (4aR,7S,7aS)-3,5-dioxo-hexahydrocyclopenta[c]pyran-7-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0237918 (methyl (4ar,7s,7as)-3,5-dioxo-hexahydrocyclopenta[c]pyran-7-carboxylate)

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PDB for NP0237918 (methyl (4ar,7s,7as)-3,5-dioxo-hexahydrocyclopenta[c]pyran-7-carboxylate)
HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.333  -5.798   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.143  -4.334   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.680  -5.158   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.650   1.408   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.591   0.237   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       6.258  -2.073   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    5    9                                                  
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

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3D PDB for NP0237918 (methyl (4ar,7s,7as)-3,5-dioxo-hexahydrocyclopenta[c]pyran-7-carboxylate)
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SMILES for NP0237918 (methyl (4ar,7s,7as)-3,5-dioxo-hexahydrocyclopenta[c]pyran-7-carboxylate)
COC(=O)[C@H]1CC(=O)[C@@H]2CC(=O)OC[C@H]12
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INCHI for NP0237918 (methyl (4ar,7s,7as)-3,5-dioxo-hexahydrocyclopenta[c]pyran-7-carboxylate)
InChI=1S/C10H12O5/c1-14-10(13)6-2-8(11)5-3-9(12)15-4-7(5)6/h5-7H,2-4H2,1H3/t5-,6+,7+/m1/s1
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View in JSmol
Synonyms
ValueSource
Methyl (4ar,7S,7as)-3,5-dioxo-octahydrocyclopenta[c]pyran-7-carboxylic acidGenerator
Chemical FormulaC10H12O5
Average Mass212.2010 Da
Monoisotopic Mass212.06847 Da
IUPAC Namemethyl (4aR,7S,7aS)-3,5-dioxo-octahydrocyclopenta[c]pyran-7-carboxylate
Traditional Namemethyl (4aR,7S,7aS)-3,5-dioxo-hexahydrocyclopenta[c]pyran-7-carboxylate
CAS Registry NumberNot Available
SMILES
COC(=O)[C@H]1CC(=O)[C@@H]2CC(=O)OC[C@H]12
InChI Identifier
InChI=1S/C10H12O5/c1-14-10(13)6-2-8(11)5-3-9(12)15-4-7(5)6/h5-7H,2-4H2,1H3/t5-,6+,7+/m1/s1
InChI KeyDYRZXVSFXIQNPW-VQVTYTSYSA-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
Torricellia tiliifoliaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassTerpene lactones  
Direct ParentTerpene lactones  
Alternative Parents
Substituents
  • Terpene lactone
    • 

  • Iridoid-skeleton
    • 

  • Bicyclic monoterpenoid
    • 

  • Monoterpenoid
    • 

  • Delta valerolactone
    • 

  • Delta_valerolactone
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Oxane
    • 

  • Methyl ester
    • 

  • Lactone
    • 

  • Ketone
    • 

  • Carboxylic acid ester
    • 

  • Organoheterocyclic compound
    • 

  • Oxacycle
    • 

  • Carboxylic acid derivative
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Carbonyl group
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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
logP-0.33ChemAxon
pKa (Strongest Acidic)15.56ChemAxon
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area69.67 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity48.4 m³·mol⁻¹ChemAxon
Polarizability20.2 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID28288437  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53495981  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]