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Showing NP-Card for Cycloaraneosene (NP0050368)

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Record Information
Version2.0
Created at2022-04-27 20:55:58 UTC
Updated at2022-04-27 20:55:58 UTC
NP-MRD IDNP0050368
Secondary Accession NumbersNone
Natural Product Identification
Common NameCycloaraneosene
DescriptionCycloaraneosene belongs to the class of organic compounds known as branched unsaturated hydrocarbons. These are hydrocarbons that contains one or more unsaturated carbon atoms, and an aliphatic branch. Cycloaraneosene 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. Cycloaraneosene is found in Sordaria araneosa. Cycloaraneosene was first documented in 2016 (PMID: 27072286). Based on a literature review a small amount of articles have been published on cycloaraneosene (PMID: 35170947).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0050368 (Cycloaraneosene)


  Mrv1652304272222552D          

 20 22  0  0  1  0            999 V2000
    4.3083    2.8787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6240    2.1165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4465    2.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6391    1.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9356    0.8185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3083    1.3543    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5461    1.0386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7839    1.3543    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4682    2.1165    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7839    2.8787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2005    3.4621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5461    3.1944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6457    2.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4531    1.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1566    0.8185    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2213   -0.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1792    0.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9823    2.6791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7069    3.4568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7935    2.5288    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  1 12  1  0  0  0  0
  9 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  6  0  0  0
  6 17  1  6  0  0  0
  3 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
M  END
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3D MOL for NP0050368 (Cycloaraneosene)

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3D SDF for NP0050368 (Cycloaraneosene)

  Mrv1652304272222552D          

 20 22  0  0  1  0            999 V2000
    4.3083    2.8787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6240    2.1165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4465    2.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6391    1.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9356    0.8185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3083    1.3543    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5461    1.0386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7839    1.3543    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4682    2.1165    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7839    2.8787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2005    3.4621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5461    3.1944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6457    2.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4531    1.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1566    0.8185    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2213   -0.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1792    0.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9823    2.6791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7069    3.4568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7935    2.5288    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  1 12  1  0  0  0  0
  9 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  6  0  0  0
  6 17  1  6  0  0  0
  3 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050368

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=C2CCC(=C)[C@@H]3CC[C@@H](C)[C@H]3C[C@]2(C)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C20H32/c1-13(2)16-10-11-20(5)12-18-15(4)6-8-17(18)14(3)7-9-19(16)20/h13,15,17-18H,3,6-12H2,1-2,4-5H3/t15-,17+,18-,20+/m1/s1

> <INCHI_KEY>
RROMSRXZXPWQPJ-QEEHTWDDSA-N

> <FORMULA>
C20H32

> <MOLECULAR_WEIGHT>
272.476

> <EXACT_MASS>
272.25040103

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
34.27660932118229

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3S,11R,14R)-3,14-dimethyl-10-methylidene-6-(propan-2-yl)tricyclo[9.3.0.0^{3,7}]tetradec-6-ene

> <ALOGPS_LOGP>
6.10

> <JCHEM_LOGP>
5.762120283333334

> <ALOGPS_LOGS>
-5.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
88.2314

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.96e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3S,11R,14R)-6-isopropyl-3,14-dimethyl-10-methylidenetricyclo[9.3.0.0^{3,7}]tetradec-6-ene

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0050368 (Cycloaraneosene)
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PDB for NP0050368 (Cycloaraneosene)
HEADER    PROTEIN                                 27-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-22         0                                  
HETATM    1  C   UNK     0       8.042   5.374   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.632   3.951   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.167   3.830   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.526   2.333   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.213   1.528   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.042   2.528   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.619   1.939   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.197   2.528   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.607   3.951   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.197   5.374   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.108   6.463   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.619   5.963   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.072   3.830   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.713   2.333   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.026   1.528   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.146  -0.007   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.801   1.007   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.167   5.001   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.653   6.453   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.681   4.720   0.000  0.00  0.00           C+0
CONECT    1    2   12                                                       
CONECT    2    1    3    6                                                  
CONECT    3    2    4   18                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    2    7   17                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   15                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    1                                                       
CONECT   13    9   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    8   16                                                  
CONECT   16   15                                                            
CONECT   17    6                                                            
CONECT   18    3   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

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3D PDB for NP0050368 (Cycloaraneosene)
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SMILES for NP0050368 (Cycloaraneosene)
CC(C)C1=C2CCC(=C)[C@@H]3CC[C@@H](C)[C@H]3C[C@]2(C)CC1
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INCHI for NP0050368 (Cycloaraneosene)
InChI=1S/C20H32/c1-13(2)16-10-11-20(5)12-18-15(4)6-8-17(18)14(3)7-9-19(16)20/h13,15,17-18H,3,6-12H2,1-2,4-5H3/t15-,17+,18-,20+/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC20H32
Average Mass272.4760 Da
Monoisotopic Mass272.25040 Da
IUPAC Name(1R,3S,11R,14R)-3,14-dimethyl-10-methylidene-6-(propan-2-yl)tricyclo[9.3.0.0^{3,7}]tetradec-6-ene
Traditional Name(1R,3S,11R,14R)-6-isopropyl-3,14-dimethyl-10-methylidenetricyclo[9.3.0.0^{3,7}]tetradec-6-ene
CAS Registry NumberNot Available
SMILES
CC(C)C1=C2CCC(=C)[C@@H]3CC[C@@H](C)[C@H]3C[C@]2(C)CC1
InChI Identifier
InChI=1S/C20H32/c1-13(2)16-10-11-20(5)12-18-15(4)6-8-17(18)14(3)7-9-19(16)20/h13,15,17-18H,3,6-12H2,1-2,4-5H3/t15-,17+,18-,20+/m1/s1
InChI KeyRROMSRXZXPWQPJ-QEEHTWDDSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Sordaria araneosaFungi
Chemical Taxonomy
Description Belongs to the class of organic compounds known as branched unsaturated hydrocarbons. These are hydrocarbons that contains one or more unsaturated carbon atoms, and an aliphatic branch.
KingdomOrganic compounds  
Super ClassHydrocarbons  
ClassUnsaturated hydrocarbons  
Sub ClassBranched unsaturated hydrocarbons  
Direct ParentBranched unsaturated hydrocarbons  
Alternative Parents
Substituents
  • Branched unsaturated hydrocarbon
    • 

  • Polycyclic hydrocarbon
    • 

  • Cyclic olefin
    • 

  • Unsaturated aliphatic hydrocarbon
    • 

  • Olefin
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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
logP6.1ALOGPS
logP5.76ChemAxon
logS-5.5ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity88.23 m³·mol⁻¹ChemAxon
Polarizability34.28 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 IDC00000507  
Chemspider ID64808223  
KEGG Compound IDNot Available
BioCyc IDCPD-20446  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14165900  
PDB IDNot Available
ChEBI ID138247  
Good Scents IDNot Available
References
General References
  1. Kudo F, Matsuura Y, Hayashi T, Fukushima M, Eguchi T: Genome mining of the sordarin biosynthetic gene cluster from Sordaria araneosa Cain ATCC 36386: characterization of cycloaraneosene synthase and GDP-6-deoxyaltrose transferase. J Antibiot (Tokyo). 2016 Jul;69(7):541-8. doi: 10.1038/ja.2016.40. Epub 2016 Apr  13. [PubMed:27072286  ] 
  2. Chen Q, Yuan G, Yuan T, Zeng H, Zou ZR, Tu ZC, Gao J, Zou Y: Set of Cytochrome P450s Cooperatively Catalyzes the Synthesis of a Highly Oxidized and Rearranged Diterpene-Class Sordarinane Architecture. J Am Chem Soc. 2022 Mar 2;144(8):3580-3589. doi: 10.1021/jacs.1c12427. Epub 2022  Feb 16. [PubMed:35170947  ]