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Showing NP-Card for (4as,6s,7r,7as)-6-hydroxy-7-methyl-hexahydro-1h-cyclopenta[c]pyran-3-one (NP0224233)

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Record Information
Version2.0
Created at2022-09-06 02:32:52 UTC
Updated at2022-09-06 02:32:52 UTC
NP-MRD IDNP0224233
Secondary Accession NumbersNone
Natural Product Identification
Common Name(4as,6s,7r,7as)-6-hydroxy-7-methyl-hexahydro-1h-cyclopenta[c]pyran-3-one
Description(4Abeta,6S,7aalpha)-6alpha-Hydroxy-7alpha-methylhexahydrocyclopenta[c]pyran-3(1H)-one belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. (4as,6s,7r,7as)-6-hydroxy-7-methyl-hexahydro-1h-cyclopenta[c]pyran-3-one is found in Caiophora coronata. Based on a literature review very few articles have been published on (4abeta,6S,7aalpha)-6alpha-Hydroxy-7alpha-methylhexahydrocyclopenta[c]pyran-3(1H)-one.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0224233 ((4as,6s,7r,7as)-6-hydroxy-7-methyl-hexahydro-1h-cyclopenta[c]pyran-3-one)


  Mrv1652309062204322D          

 12 13  0  0  1  0            999 V2000
    0.8838   -2.1500    0.0000 C   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  1  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 O   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
    1.9233   -0.2854    0.0000 C   0  0  1  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
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  6  0  0  0
  6 12  1  0  0  0  0
  2 12  1  0  0  0  0
M  END
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3D MOL for NP0224233 ((4as,6s,7r,7as)-6-hydroxy-7-methyl-hexahydro-1h-cyclopenta[c]pyran-3-one)

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3D SDF for NP0224233 ((4as,6s,7r,7as)-6-hydroxy-7-methyl-hexahydro-1h-cyclopenta[c]pyran-3-one)

  Mrv1652309062204322D          

 12 13  0  0  1  0            999 V2000
    0.8838   -2.1500    0.0000 C   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  1  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 O   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
    1.9233   -0.2854    0.0000 C   0  0  1  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
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  6  0  0  0
  6 12  1  0  0  0  0
  2 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0224233

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H14O3/c1-5-7-4-12-9(11)3-6(7)2-8(5)10/h5-8,10H,2-4H2,1H3/t5-,6+,7-,8+/m1/s1

> <INCHI_KEY>
DPDXVBIWZBJGSX-CWKFCGSDSA-N

> <FORMULA>
C9H14O3

> <MOLECULAR_WEIGHT>
170.208

> <EXACT_MASS>
170.094294311

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
17.886904547660112

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4aS,6S,7R,7aS)-6-hydroxy-7-methyl-octahydrocyclopenta[c]pyran-3-one

> <JCHEM_LOGP>
0.20520895500000014

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.936108465076789

> <JCHEM_PKA_STRONGEST_BASIC>
-2.826746157375413

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
42.869200000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4aS,6S,7R,7aS)-6-hydroxy-7-methyl-hexahydro-1H-cyclopenta[c]pyran-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0224233 ((4as,6s,7r,7as)-6-hydroxy-7-methyl-hexahydro-1h-cyclopenta[c]pyran-3-one)
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PDB for NP0224233 ((4as,6s,7r,7as)-6-hydroxy-7-methyl-hexahydro-1h-cyclopenta[c]pyran-3-one)
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       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.320  -1.303   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       7.591   0.237   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       6.258  -2.073   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    6    2                                                  
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

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3D PDB for NP0224233 ((4as,6s,7r,7as)-6-hydroxy-7-methyl-hexahydro-1h-cyclopenta[c]pyran-3-one)
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SMILES for NP0224233 ((4as,6s,7r,7as)-6-hydroxy-7-methyl-hexahydro-1h-cyclopenta[c]pyran-3-one)
C[C@H]1[C@@H](O)C[C@H]2CC(=O)OC[C@H]12
Download
INCHI for NP0224233 ((4as,6s,7r,7as)-6-hydroxy-7-methyl-hexahydro-1h-cyclopenta[c]pyran-3-one)
InChI=1S/C9H14O3/c1-5-7-4-12-9(11)3-6(7)2-8(5)10/h5-8,10H,2-4H2,1H3/t5-,6+,7-,8+/m1/s1
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View in JSmol
Synonyms
ValueSource
(4Abeta,6S,7aalpha)-6a-hydroxy-7a-methylhexahydrocyclopenta[c]pyran-3(1H)-oneGenerator
(4Abeta,6S,7aalpha)-6α-hydroxy-7α-methylhexahydrocyclopenta[c]pyran-3(1H)-oneGenerator
Chemical FormulaC9H14O3
Average Mass170.2080 Da
Monoisotopic Mass170.09429 Da
IUPAC Name(4aS,6S,7R,7aS)-6-hydroxy-7-methyl-octahydrocyclopenta[c]pyran-3-one
Traditional Name(4aS,6S,7R,7aS)-6-hydroxy-7-methyl-hexahydro-1H-cyclopenta[c]pyran-3-one
CAS Registry NumberNot Available
SMILES
C[C@H]1[C@@H](O)C[C@H]2CC(=O)OC[C@H]12
InChI Identifier
InChI=1S/C9H14O3/c1-5-7-4-12-9(11)3-6(7)2-8(5)10/h5-8,10H,2-4H2,1H3/t5-,6+,7-,8+/m1/s1
InChI KeyDPDXVBIWZBJGSX-CWKFCGSDSA-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
Caiophora coronataLOTUS 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
    • 

  • Oxane
    • 

  • Cyclic alcohol
    • 

  • Carboxylic acid ester
    • 

  • Lactone
    • 

  • Secondary alcohol
    • 

  • Organoheterocyclic compound
    • 

  • Oxacycle
    • 

  • Carboxylic acid derivative
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Alcohol
    • 

  • 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
logP0.21ChemAxon
pKa (Strongest Acidic)14.94ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity42.87 m³·mol⁻¹ChemAxon
Polarizability17.89 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 ID8901162  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10725829  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]