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Showing NP-Card for Chalcogran (NP0050660)

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Record Information
Version2.0
Created at2022-04-27 22:01:04 UTC
Updated at2022-04-27 22:01:04 UTC
NP-MRD IDNP0050660
Secondary Accession NumbersNone
Natural Product Identification
Common NameChalcogran
DescriptionChalcogran belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals. Chalcogran is found in Dracaena fragrans , Eria hyacinthoides, Liparis viridiflora and Oncidium rhynchum. Chalcogran was first documented in 2013 (PMID: 24073204). Based on a literature review a small amount of articles have been published on Chalcogran (PMID: 33106973) (PMID: 28575468) (PMID: 26510921).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0050660 (Chalcogran)


  Mrv1652304282200012D          

 11 12  0  0  1  0            999 V2000
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7545    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5391    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5391   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7545   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2065   -0.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9602   -0.1494    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
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  8 10  1  6  0  0  0
 10 11  1  0  0  0  0
M  END
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3D MOL for NP0050660 (Chalcogran)

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3D SDF for NP0050660 (Chalcogran)

  Mrv1652304282200012D          

 11 12  0  0  1  0            999 V2000
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7545    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5391    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5391   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7545   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2065   -0.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9602   -0.1494    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
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  8 10  1  6  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050660

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H]1CC[C@@]2(CCCO2)O1

> <INCHI_IDENTIFIER>
InChI=1S/C9H16O2/c1-2-8-4-6-9(11-8)5-3-7-10-9/h8H,2-7H2,1H3/t8-,9+/m0/s1

> <INCHI_KEY>
DCWKALWZHORJAO-DTWKUNHWSA-N

> <FORMULA>
C9H16O2

> <MOLECULAR_WEIGHT>
156.225

> <EXACT_MASS>
156.115029755

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
17.9013545038789

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,5R)-2-ethyl-1,6-dioxaspiro[4.4]nonane

> <ALOGPS_LOGP>
1.38

> <JCHEM_LOGP>
1.9310483879999998

> <ALOGPS_LOGS>
-1.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.045226111736946

> <JCHEM_POLAR_SURFACE_AREA>
18.46

> <JCHEM_REFRACTIVITY>
43.146800000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.27e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
chalcogran

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0050660 (Chalcogran)
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PDB for NP0050660 (Chalcogran)
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      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.465   2.016   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.275   2.016   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.740   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.740  -0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.275  -0.476   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.986  -0.905   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.392  -0.279   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6    9                                             
CONECT    5    4    1                                                       
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8    4                                                       
CONECT   10    8   11                                                       
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END

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3D PDB for NP0050660 (Chalcogran)
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SMILES for NP0050660 (Chalcogran)
CC[C@H]1CC[C@@]2(CCCO2)O1
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INCHI for NP0050660 (Chalcogran)
InChI=1S/C9H16O2/c1-2-8-4-6-9(11-8)5-3-7-10-9/h8H,2-7H2,1H3/t8-,9+/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC9H16O2
Average Mass156.2250 Da
Monoisotopic Mass156.11503 Da
IUPAC Name(2S,5R)-2-ethyl-1,6-dioxaspiro[4.4]nonane
Traditional Namechalcogran
CAS Registry NumberNot Available
SMILES
CC[C@H]1CC[C@@]2(CCCO2)O1
InChI Identifier
InChI=1S/C9H16O2/c1-2-8-4-6-9(11-8)5-3-7-10-9/h8H,2-7H2,1H3/t8-,9+/m0/s1
InChI KeyDCWKALWZHORJAO-DTWKUNHWSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Dracaena fragransPlant
Eria hyacinthoidesPlant
Liparis viridifloraPlant
Oncidium rhynchumPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassEthers  
Direct ParentKetals  
Alternative Parents
Substituents
  • Ketal
    • 

  • Tetrahydrofuran
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Hydrocarbon derivative
    • 

  • 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
logP1.38ALOGPS
logP1.93ChemAxon
logS-1.8ALOGPS
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area18.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity43.15 m³·mol⁻¹ChemAxon
Polarizability17.9 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 IDC00001303  
Chemspider ID390233  
KEGG Compound IDC08471  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound441558  
PDB IDNot Available
ChEBI ID3570  
Good Scents IDNot Available
References
General References
  1. Audley JP, Bostock RM, Seybold SJ: Trap Assays of the Walnut Twig Beetle, Pityophthorus juglandis Blackman (Coleoptera: Curculionidae: Scolytinae), Reveal an Effective Semiochemical Repellent Combination. J Chem Ecol. 2020 Dec;46(11-12):1047-1058. doi: 10.1007/s10886-020-01228-9. Epub  2020 Oct 27. [PubMed:33106973  ] 
  2. Owens D, Montgomery WS, Narvaez TI, Deyrup MA, Kendra PE: Evaluation of Lure Combinations Containing Essential Oils and Volatile Spiroketals for Detection of Host-Seeking Xyleborus glabratus (Coleoptera: Curculionidae: Scolytinae). J Econ Entomol. 2017 Aug 1;110(4):1596-1602. doi: 10.1093/jee/tox158. [PubMed:28575468  ] 
  3. Yoneda N, Fukata Y, Asano K, Matsubara S: Asymmetric Synthesis of Spiroketals with Aminothiourea Catalysts. Angew Chem Int Ed Engl. 2015 Dec 14;54(51):15497-500. doi:  10.1002/anie.201508405. Epub 2015 Oct 29. [PubMed:26510921  ] 
  4. Jaramillo J, Torto B, Mwenda D, Troeger A, Borgemeister C, Poehling HM, Francke W: Coffee berry borer joins bark beetles in coffee klatch. PLoS One. 2013 Sep 20;8(9):e74277. doi: 10.1371/journal.pone.0074277. eCollection  2013. [PubMed:24073204  ]