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Showing NP-Card for Calaminthone (NP0057717)

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Record Information
Version2.0
Created at2022-04-28 03:07:32 UTC
Updated at2022-04-28 03:07:32 UTC
NP-MRD IDNP0057717
Secondary Accession NumbersNone
Natural Product Identification
Common NameCalaminthone
Description(5S,6S)-3-hydroxy-6-methyl-4-oxo-4,5,6,7-tetrahydro-1-benzofuran-5-yl acetate belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Calaminthone is found in Calamintha ashei. Based on a literature review very few articles have been published on (5S,6S)-3-hydroxy-6-methyl-4-oxo-4,5,6,7-tetrahydro-1-benzofuran-5-yl acetate.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0057717 (Calaminthone)


  Mrv1652304282205072D          

 16 17  0  0  1  0            999 V2000
    2.0701    1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.0709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -0.5396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.5396    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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  6  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
  1 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
M  END
Download

3D MOL for NP0057717 (Calaminthone)

     RDKit          3D

 28 29  0  0  0  0  0  0  0  0999 V2000
    4.1926   -0.4301   -0.1507 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8393   -0.3523    0.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7350   -0.4823    1.7422 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6879   -0.1395   -0.2365 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4478   -0.0740    0.4096 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4568   -1.1849    0.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0325   -2.3504   -0.2078 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8714   -0.9556   -0.1061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0145   -1.7375    0.0794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9904   -3.0538    0.4742 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0909   -0.9236   -0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6396    0.2618   -0.5454 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3283    0.2844   -0.4967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2843    1.3138   -0.7608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2150    1.2717    0.2779 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8618    2.2799   -0.0707 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1640   -1.2929   -0.8773 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9347   -0.6990    0.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4177    0.5164   -0.6776 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6279   -0.2189    1.5032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1140   -3.5210    0.6510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1261   -1.2302   -0.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8105    1.0795   -1.7489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7026    2.3218   -0.8115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6770    1.6044    1.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2032    2.8501    0.8320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4799    3.0571   -0.7759 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7619    1.8049   -0.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
  8  6  1  0
  6  7  2  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  5 15  1  0
 12 13  1  0
 16 26  1  0
 16 27  1  0
 16 28  1  0
 15 25  1  1
 14 23  1  0
 14 24  1  0
 10 21  1  0
 11 22  1  0
  5 20  1  1
  1 17  1  0
  1 18  1  0
  1 19  1  0
M  END
Download

3D SDF for NP0057717 (Calaminthone)


  Mrv1652304282205072D          

 16 17  0  0  1  0            999 V2000
    2.0701    1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.0709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -0.5396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.5396    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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  6  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
  1 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0057717

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CC2=C(C(O)=CO2)C(=O)[C@H]1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H12O5/c1-5-3-8-9(7(13)4-15-8)10(14)11(5)16-6(2)12/h4-5,11,13H,3H2,1-2H3/t5-,11-/m0/s1

> <INCHI_KEY>
ASYWVBBBOMJYAC-DYEAUMGKSA-N

> <FORMULA>
C11H12O5

> <MOLECULAR_WEIGHT>
224.212

> <EXACT_MASS>
224.068473486

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
21.696124704505714

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S,6S)-3-hydroxy-6-methyl-4-oxo-4,5,6,7-tetrahydro-1-benzofuran-5-yl acetate

> <ALOGPS_LOGP>
1.56

> <JCHEM_LOGP>
1.466930846666667

> <ALOGPS_LOGS>
-1.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.995674803456676

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.843349525679495

> <JCHEM_PKA_STRONGEST_BASIC>
-2.933517207688897

> <JCHEM_POLAR_SURFACE_AREA>
76.74000000000001

> <JCHEM_REFRACTIVITY>
53.967800000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.51e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S,6S)-3-hydroxy-6-methyl-4-oxo-6,7-dihydro-5H-1-benzofuran-5-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0057717 (Calaminthone)

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PDB for NP0057717 (Calaminthone)
HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.530  -0.237   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.198   4.383   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.268   4.089   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.268   1.597   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.744   0.132   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       5.198   1.303   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.198  -0.237   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.531  -1.007   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.864  -1.007   0.000  0.00  0.00           C+0
CONECT    1    2    7   13                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   11                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    1    8                                                  
CONECT    8    7                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    4   12                                                  
CONECT   12   11                                                            
CONECT   13    1   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

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3D PDB for NP0057717 (Calaminthone)
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SMILES for NP0057717 (Calaminthone)
C[C@H]1CC2=C(C(O)=CO2)C(=O)[C@H]1OC(C)=O
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INCHI for NP0057717 (Calaminthone)
InChI=1S/C11H12O5/c1-5-3-8-9(7(13)4-15-8)10(14)11(5)16-6(2)12/h4-5,11,13H,3H2,1-2H3/t5-,11-/m0/s1
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View in JSmol
Synonyms
ValueSource
(5S,6S)-3-Hydroxy-6-methyl-4-oxo-4,5,6,7-tetrahydro-1-benzofuran-5-yl acetic acidGenerator
Chemical FormulaC11H12O5
Average Mass224.2120 Da
Monoisotopic Mass224.06847 Da
IUPAC Name(5S,6S)-3-hydroxy-6-methyl-4-oxo-4,5,6,7-tetrahydro-1-benzofuran-5-yl acetate
Traditional Name(5S,6S)-3-hydroxy-6-methyl-4-oxo-6,7-dihydro-5H-1-benzofuran-5-yl acetate
CAS Registry NumberNot Available
SMILES
C[C@H]1CC2=C(C(O)=CO2)C(=O)[C@H]1OC(C)=O
InChI Identifier
InChI=1S/C11H12O5/c1-5-3-8-9(7(13)4-15-8)10(14)11(5)16-6(2)12/h4-5,11,13H,3H2,1-2H3/t5-,11-/m0/s1
InChI KeyASYWVBBBOMJYAC-DYEAUMGKSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Calamintha asheiPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassBenzofurans  
Sub ClassNot Available
Direct ParentBenzofurans  
Alternative Parents
Substituents
  • Benzofuran
    • 

  • Aryl alkyl ketone
    • 

  • Aryl ketone
    • 

  • Alpha-acyloxy ketone
    • 

  • Heteroaromatic compound
    • 

  • Vinylogous acid
    • 

  • Furan
    • 

  • Ketone
    • 

  • Carboxylic acid ester
    • 

  • Oxacycle
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic 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
logP1.56ALOGPS
logP1.47ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)6.84ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area76.74 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity53.97 m³·mol⁻¹ChemAxon
Polarizability21.7 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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound163103409  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available