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Showing NP-Card for 4-Methylthiocanthin-6-on (NP0138434)

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Record Information
Version1.0
Created at2022-06-29 17:29:25 UTC
Updated at2022-06-29 17:29:25 UTC
NP-MRD IDNP0138434
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Methylthiocanthin-6-on
DescriptionTalarodiene is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 4-Methylthiocanthin-6-on is found in Pulveroboletus curtisii. It was first documented in 2022 (PMID: 36126322). Based on a literature review very few articles have been published on talarodiene.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0138434 (4-Methylthiocanthin-6-on)


  Mrv1652310172220322D          

 22 24  0  0  1  0            999 V2000
    2.1762   -0.5307    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3514   -0.5460    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6529    0.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0588    0.7943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4091    0.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1770    0.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5068   -0.5060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3226   -0.3832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8369   -1.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3829   -0.4098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5408   -1.4586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5354   -1.7962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7196   -1.9190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2053   -1.2740    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4491   -1.6038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0066   -2.0747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5303   -0.6260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3526   -1.4317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0639   -1.8496    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1439   -2.6707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6812   -1.3023    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8253   -2.1146    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  1  0  0  0
  2 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
  2 21  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  6  0  0  0
M  END
Download

3D MOL for NP0138434 (4-Methylthiocanthin-6-on)

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3D SDF for NP0138434 (4-Methylthiocanthin-6-on)

  Mrv1652310172220322D          

 22 24  0  0  1  0            999 V2000
    2.1762   -0.5307    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3514   -0.5460    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6529    0.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0588    0.7943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4091    0.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1770    0.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5068   -0.5060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3226   -0.3832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8369   -1.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3829   -0.4098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5408   -1.4586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5354   -1.7962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7196   -1.9190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2053   -1.2740    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4491   -1.6038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0066   -2.0747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5303   -0.6260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3526   -1.4317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0639   -1.8496    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1439   -2.6707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6812   -1.3023    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8253   -2.1146    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  1  0  0  0
  2 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
  2 21  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0138434

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12C[C@@]3(C)CCC(C)(C)C=C3C\C=C(C)/[C@]1([H])CC[C@@H]2C

> <INCHI_IDENTIFIER>
InChI=1S/C20H32/c1-14-6-8-16-12-19(3,4)10-11-20(16,5)13-18-15(2)7-9-17(14)18/h6,12,15,17-18H,7-11,13H2,1-5H3/b14-6-/t15-,17-,18-,20+/m0/s1

> <INCHI_KEY>
XTOGEKDHHWZDDZ-JAMRKFNNSA-N

> <FORMULA>
C20H32

> <MOLECULAR_WEIGHT>
272.476

> <EXACT_MASS>
272.25040103

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
34.72821418819143

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3S,4S,7R,8Z)-1,4,8,13,13-pentamethyltricyclo[9.4.0.0^{3,7}]pentadeca-8,11-diene

> <ALOGPS_LOGP>
6.33

> <JCHEM_LOGP>
5.760872461333333

> <ALOGPS_LOGS>
-5.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
89.49699999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.32e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3S,4S,7R,8Z)-1,4,8,13,13-pentamethyltricyclo[9.4.0.0^{3,7}]pentadeca-8,11-diene

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0138434 (4-Methylthiocanthin-6-on)
Download
PDB for NP0138434 (4-Methylthiocanthin-6-on)
HEADER    PROTEIN                                 17-OCT-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-OCT-22         0                                  
HETATM    1  H   UNK     0       4.062  -0.991   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       2.523  -1.019   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.085   0.414   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.976   1.483   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.497   1.030   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.930   0.467   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.546  -0.945   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.069  -0.715   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.029  -1.919   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.048  -0.765   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.343  -2.723   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.466  -3.353   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.943  -3.582   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.983  -2.378   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.572  -2.994   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.612  -3.873   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.990  -1.169   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.658  -2.672   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.986  -3.453   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.135  -4.985   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.138  -2.431   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0       3.407  -3.947   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   17   21                                             
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    7   15   16                                             
CONECT   15   14   21                                                       
CONECT   16   14                                                            
CONECT   17    2   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    2   15   22                                             
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

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3D PDB for NP0138434 (4-Methylthiocanthin-6-on)
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SMILES for NP0138434 (4-Methylthiocanthin-6-on)
[H][C@@]12C[C@@]3(C)CCC(C)(C)C=C3C\C=C(C)/[C@]1([H])CC[C@@H]2C
Download
INCHI for NP0138434 (4-Methylthiocanthin-6-on)
InChI=1S/C20H32/c1-14-6-8-16-12-19(3,4)10-11-20(16,5)13-18-15(2)7-9-17(14)18/h6,12,15,17-18H,7-11,13H2,1-5H3/b14-6-/t15-,17-,18-,20+/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC15H10N2OS
Average Mass266.3200 Da
Monoisotopic Mass266.05138 Da
IUPAC Name(1R,3S,4S,7R,8Z)-1,4,8,13,13-pentamethyltricyclo[9.4.0.0^{3,7}]pentadeca-8,11-diene
Traditional Name(1R,3S,4S,7R,8Z)-1,4,8,13,13-pentamethyltricyclo[9.4.0.0^{3,7}]pentadeca-8,11-diene
CAS Registry Number500299-14-9
SMILES
CSC1=CC(=O)N2C3=C(C=CC=C3)C3=C2C1=NC=C3
InChI Identifier
InChI=1S/C15H10N2OS/c1-19-12-8-13(18)17-11-5-3-2-4-9(11)10-6-7-16-14(12)15(10)17/h2-8H,1H3
InChI KeyHCKATCNEEDQXNJ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Pulveroboletus curtisiiLOTUS Database
Chemical Taxonomy
ClassificationNot classified
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
logP6.33ALOGPS
logP5.76ChemAxon
logS-5.7ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity89.5 m³·mol⁻¹ChemAxon
Polarizability34.73 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
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 CompoundNot Available
PDB IDNot Available
ChEBI ID193158  
Good Scents IDNot Available
References
General References
  1. Zhang P, Wu G, Heard SC, Niu C, Bell SA, Li F, Ye Y, Zhang Y, Winter JM: Identification and Characterization of a Cryptic Bifunctional Type I Diterpene Synthase Involved in Talaronoid Biosynthesis from a Marine-Derived Fungus. Org Lett. 2022 Sep 30;24(38):7037-7041. doi: 10.1021/acs.orglett.2c02904. Epub  2022 Sep 20. [PubMed:36126322  ]