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Showing NP-Card for (3ar,7as)-7a-methoxy-3-methylidene-tetrahydrofuro[3,2-c]pyran-6-one (NP0291663)

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Record Information
Version1.0
Created at2022-09-09 22:50:35 UTC
Updated at2022-09-09 22:50:36 UTC
NP-MRD IDNP0291663
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3ar,7as)-7a-methoxy-3-methylidene-tetrahydrofuro[3,2-c]pyran-6-one
Description(3AR)-3-Methylene-7abeta-methoxy-2,3,3abeta,7a-tetrahydro-4H-furo[3,2-c]pyran-6(7H)-one belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety. (3ar,7as)-7a-methoxy-3-methylidene-tetrahydrofuro[3,2-c]pyran-6-one is found in Sparassis crispa. Based on a literature review very few articles have been published on (3aR)-3-Methylene-7abeta-methoxy-2,3,3abeta,7a-tetrahydro-4H-furo[3,2-c]pyran-6(7H)-one.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0291663 ((3ar,7as)-7a-methoxy-3-methylidene-tetrahydrofuro[3,2-c]pyran-6-one)


  Mrv1652309102200502D          

 13 14  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  0  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 O   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
    1.8371    0.5350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5045    1.0200    0.0000 C   0  0  0  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  1  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13  2  1  1  0  0  0
  5 13  1  0  0  0  0
M  END
Download

3D MOL for NP0291663 ((3ar,7as)-7a-methoxy-3-methylidene-tetrahydrofuro[3,2-c]pyran-6-one)

     RDKit          3D

 25 26  0  0  0  0  0  0  0  0999 V2000
    2.9026   -0.4742    0.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6646   -0.3528   -0.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1887    0.1270   -1.5442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1983    0.0784   -1.5039 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5302    0.3218   -0.1830 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0938    1.6033    0.1242 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6599    2.5800   -0.6507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9753    0.0957    0.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2123   -1.2763    0.5784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2853   -1.5349    1.1844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3200   -2.3250    0.3888 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0562   -2.0849    0.2391 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3929   -0.6409    0.5392 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7145   -0.2204   -0.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1532   -0.8295    1.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4971    1.1476   -1.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5840   -0.6095   -2.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4826    2.4965   -1.7220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7721    2.5997   -0.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2296    3.5556   -0.3206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5845    0.2991   -0.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2759    0.8285    0.9015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6935   -2.7076    0.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2942   -2.2467   -0.8448 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4782   -0.4304    1.6079 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  5  6  1  1
  5  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
 13  5  1  0
  4  5  1  0
  7 18  1  0
  7 19  1  0
  7 20  1  0
  8 21  1  0
  8 22  1  0
 12 23  1  0
 12 24  1  0
 13 25  1  1
  1 14  1  0
  1 15  1  0
  3 16  1  0
  3 17  1  0
M  END
Download

3D SDF for NP0291663 ((3ar,7as)-7a-methoxy-3-methylidene-tetrahydrofuro[3,2-c]pyran-6-one)


  Mrv1652309102200502D          

 13 14  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  0  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 O   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
    1.8371    0.5350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5045    1.0200    0.0000 C   0  0  0  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  1  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13  2  1  1  0  0  0
  5 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0291663

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@]12CC(=O)OC[C@H]1C(=C)CO2

> <INCHI_IDENTIFIER>
InChI=1S/C9H12O4/c1-6-4-13-9(11-2)3-8(10)12-5-7(6)9/h7H,1,3-5H2,2H3/t7-,9-/m0/s1

> <INCHI_KEY>
DEJHQJQRBACQQV-CBAPKCEASA-N

> <FORMULA>
C9H12O4

> <MOLECULAR_WEIGHT>
184.191

> <EXACT_MASS>
184.073558866

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
17.843251499093817

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,7aS)-7a-methoxy-3-methylidene-hexahydro-2H-furo[3,2-c]pyran-6-one

> <JCHEM_LOGP>
0.593326976

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.045557798697053

> <JCHEM_POLAR_SURFACE_AREA>
44.760000000000005

> <JCHEM_REFRACTIVITY>
44.0008

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,7aS)-7a-methoxy-3-methylidene-tetrahydrofuro[3,2-c]pyran-6-one

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0291663 ((3ar,7as)-7a-methoxy-3-methylidene-tetrahydrofuro[3,2-c]pyran-6-one)

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PDB for NP0291663 ((3ar,7as)-7a-methoxy-3-methylidene-tetrahydrofuro[3,2-c]pyran-6-one)
HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-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       2.126  -0.057   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.429   0.999   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.675   1.904   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.591   0.237   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       6.258  -2.073   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    8   13                                             
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    2    5                                                  
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

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3D PDB for NP0291663 ((3ar,7as)-7a-methoxy-3-methylidene-tetrahydrofuro[3,2-c]pyran-6-one)
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SMILES for NP0291663 ((3ar,7as)-7a-methoxy-3-methylidene-tetrahydrofuro[3,2-c]pyran-6-one)
CO[C@]12CC(=O)OC[C@H]1C(=C)CO2
Download
INCHI for NP0291663 ((3ar,7as)-7a-methoxy-3-methylidene-tetrahydrofuro[3,2-c]pyran-6-one)
InChI=1S/C9H12O4/c1-6-4-13-9(11-2)3-8(10)12-5-7(6)9/h7H,1,3-5H2,2H3/t7-,9-/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC9H12O4
Average Mass184.1910 Da
Monoisotopic Mass184.07356 Da
IUPAC Name(3aR,7aS)-7a-methoxy-3-methylidene-hexahydro-2H-furo[3,2-c]pyran-6-one
Traditional Name(3aR,7aS)-7a-methoxy-3-methylidene-tetrahydrofuro[3,2-c]pyran-6-one
CAS Registry NumberNot Available
SMILES
CO[C@]12CC(=O)OC[C@H]1C(=C)CO2
InChI Identifier
InChI=1S/C9H12O4/c1-6-4-13-9(11-2)3-8(10)12-5-7(6)9/h7H,1,3-5H2,2H3/t7-,9-/m0/s1
InChI KeyDEJHQJQRBACQQV-CBAPKCEASA-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
Sparassis crispaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassLactones  
Sub ClassDelta valerolactones  
Direct ParentDelta valerolactones  
Alternative Parents
Substituents
  • Ketal
    • 

  • Delta valerolactone
    • 

  • Delta_valerolactone
    • 

  • Oxane
    • 

  • Tetrahydrofuran
    • 

  • Carboxylic acid ester
    • 

  • Acetal
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Carbonyl group
    • 

  • 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
logP0.59ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area44.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity44 m³·mol⁻¹ChemAxon
Polarizability17.84 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 ID28286854  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound102481729  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]