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Showing NP-Card for Boschnialactone (NP0051763)

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Record Information
Version2.0
Created at2022-04-27 23:00:20 UTC
Updated at2022-04-27 23:00:20 UTC
NP-MRD IDNP0051763
Secondary Accession NumbersNone
Natural Product Identification
Common NameBoschnialactone
DescriptionBoschnialactone belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Boschnialactone is found in Boschniakia rossica. Boschnialactone was first documented in 2018 (PMID: 29766719). Based on a literature review very few articles have been published on Boschnialactone (PMID: 31250873).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0051763 (Boschnialactone)


  Mrv1652304282201002D          

 11 12  0  0  1  0            999 V2000
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 C   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
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  1  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  1  0  0  0
  8 11  1  1  0  0  0
M  END
Download

3D MOL for NP0051763 (Boschnialactone)

     RDKit          3D

 25 26  0  0  0  0  0  0  0  0999 V2000
    2.3888    1.1758   -0.0387 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4212    0.1160    0.3324 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2810   -0.9905   -0.6668 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0655   -1.7393   -0.1299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7244   -0.7363    0.6748 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1656   -0.6652    0.2978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6092    0.7525    0.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6076    1.0559    1.0354 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8738    1.6526   -0.4234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5451    1.2209   -0.7706 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0006    0.5953    0.4848 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2631    0.7346   -0.5902 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8430    1.5697    0.9168 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9708    2.0404   -0.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7116   -0.3428    1.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0541   -0.6137   -1.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1691   -1.6268   -0.7284 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4717   -2.5402    0.5408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5707   -2.1231   -0.9262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6447   -0.9557    1.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7860   -1.3133    0.9591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2666   -1.0707   -0.7508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7136    0.4471   -1.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0149    2.0813   -1.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1482    1.2755    1.3214 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  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  2  1  0
 11  5  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  1
  3 16  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  1
  6 21  1  0
  6 22  1  0
 10 23  1  0
 10 24  1  0
 11 25  1  1
M  END
Download

3D SDF for NP0051763 (Boschnialactone)


  Mrv1652304282201002D          

 11 12  0  0  1  0            999 V2000
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 C   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
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  1  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  1  0  0  0
  8 11  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0051763

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H14O2/c1-6-2-3-7-4-9(10)11-5-8(6)7/h6-8H,2-5H2,1H3/t6-,7-,8-/m1/s1

> <INCHI_KEY>
VGWJUWSHYRJZKH-BWZBUEFSSA-N

> <FORMULA>
C9H14O2

> <MOLECULAR_WEIGHT>
154.209

> <EXACT_MASS>
154.099379691

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
16.678568070942553

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4aR,7R,7aR)-7-methyl-octahydrocyclopenta[c]pyran-3-one

> <ALOGPS_LOGP>
1.67

> <JCHEM_LOGP>
1.513973752

> <ALOGPS_LOGS>
-2.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.03656884512401

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
41.2767

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.45e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
boschnialactone

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0051763 (Boschnialactone)

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PDB for NP0051763 (Boschnialactone)
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       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.454   1.540   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.788  -0.770   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.846   3.481   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    1    8                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    6                                                       
CONECT   11    8                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END

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3D PDB for NP0051763 (Boschnialactone)
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SMILES for NP0051763 (Boschnialactone)
C[C@@H]1CC[C@@H]2CC(=O)OC[C@H]12
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INCHI for NP0051763 (Boschnialactone)
InChI=1S/C9H14O2/c1-6-2-3-7-4-9(10)11-5-8(6)7/h6-8H,2-5H2,1H3/t6-,7-,8-/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC9H14O2
Average Mass154.2090 Da
Monoisotopic Mass154.09938 Da
IUPAC Name(4aR,7R,7aR)-7-methyl-octahydrocyclopenta[c]pyran-3-one
Traditional Nameboschnialactone
CAS Registry NumberNot Available
SMILES
C[C@@H]1CC[C@@H]2CC(=O)OC[C@H]12
InChI Identifier
InChI=1S/C9H14O2/c1-6-2-3-7-4-9(10)11-5-8(6)7/h6-8H,2-5H2,1H3/t6-,7-,8-/m1/s1
InChI KeyVGWJUWSHYRJZKH-BWZBUEFSSA-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
Boschniakia rossicaPlant
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
    • 

  • Carboxylic acid ester
    • 

  • Lactone
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Oxacycle
    • 

  • Carboxylic acid derivative
    • 

  • Organoheterocyclic compound
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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
logP1.67ALOGPS
logP1.51ChemAxon
logS-2ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity41.28 m³·mol⁻¹ChemAxon
Polarizability16.68 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00003074  
Chemspider ID390860  
KEGG Compound IDC09772  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound442420  
PDB IDNot Available
ChEBI ID3158  
Good Scents IDNot Available
References
General References
  1. Khan HPA, Das D, Chakraborty TK: Application of Cp2TiCl-Promoted Radical Cyclization: A Unified Strategy for the Syntheses of Iridoid Monoterpenes. J Org Chem. 2018 Jun 1;83(11):6086-6092. doi: 10.1021/acs.joc.8b00752. Epub 2018  May 22. [PubMed:29766719  ] 
  2. Salam A, Ray S, Zaid MA, Kumar D, Khan T: Total syntheses of several iridolactones and the putative structure of noriridoid scholarein A: an intramolecular Pauson-Khand reaction based one-stop synthetic solution. Org Biomol Chem. 2019 Jul 17;17(28):6831-6842. doi: 10.1039/c9ob00855a. [PubMed:31250873  ]