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Showing NP-Card for Isoachifolidiene (NP0335518)

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Record Information
Version2.0
Created at2024-09-11 01:58:37 UTC
Updated at2024-09-11 01:58:37 UTC
NP-MRD IDNP0335518
Secondary Accession NumbersNone
Natural Product Identification
Common NameIsoachifolidiene
DescriptionIsoachifolidiene belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Isoachifolidiene was first documented in 1992 (PMID: 17226475). Based on a literature review very few articles have been published on Isoachifolidiene.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0335518 (Isoachifolidiene)


  Mrv2104 05262304302D          

 25 27  0  0  0  0            999 V2000
    2.2871    4.1627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8581    3.3377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8642   -2.4055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1007   -0.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2140    1.3090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2871    3.3377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9493   -1.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9864   -0.5895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5438    0.5047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5726    2.9252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1541   -1.6331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5878   -0.5895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3602   -0.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2140   -0.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2871    0.8627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6996   -0.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8746   -0.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5726    2.1002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248   -1.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304    0.5047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8581    1.6877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0202   -1.9280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8554    0.5047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2871    1.6877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201   -1.6331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  8  7  1  0  0  0  0
 10  2  1  0  0  0  0
 10  6  2  0  0  0  0
 11  3  1  0  0  0  0
 11  7  2  0  0  0  0
 12  4  2  0  0  0  0
 13  9  1  0  0  0  0
 13 12  1  0  0  0  0
 14  8  2  0  0  0  0
 15  9  1  0  0  0  0
 16 11  1  0  0  0  0
 16 14  1  0  0  0  0
 17 13  1  0  0  0  0
 17 16  1  0  0  0  0
 18 10  1  0  0  0  0
 19 12  1  0  0  0  0
 20  5  1  0  0  0  0
 20 14  1  0  0  0  0
 20 15  1  0  0  0  0
 21 18  2  0  0  0  0
 22 19  2  0  0  0  0
 23 20  1  0  0  0  0
 24 15  1  0  0  0  0
 24 18  1  0  0  0  0
 25 17  1  0  0  0  0
 25 19  1  0  0  0  0
M  END
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3D MOL for NP0335518 (Isoachifolidiene)

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3D SDF for NP0335518 (Isoachifolidiene)

  Mrv2104 05262304302D          

 25 27  0  0  0  0            999 V2000
    2.2871    4.1627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8581    3.3377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8642   -2.4055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1007   -0.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2140    1.3090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2871    3.3377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9493   -1.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9864   -0.5895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5438    0.5047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5726    2.9252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1541   -1.6331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5878   -0.5895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3602   -0.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2140   -0.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2871    0.8627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6996   -0.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8746   -0.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5726    2.1002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248   -1.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304    0.5047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8581    1.6877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0202   -1.9280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8554    0.5047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2871    1.6877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201   -1.6331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  8  7  1  0  0  0  0
 10  2  1  0  0  0  0
 10  6  2  0  0  0  0
 11  3  1  0  0  0  0
 11  7  2  0  0  0  0
 12  4  2  0  0  0  0
 13  9  1  0  0  0  0
 13 12  1  0  0  0  0
 14  8  2  0  0  0  0
 15  9  1  0  0  0  0
 16 11  1  0  0  0  0
 16 14  1  0  0  0  0
 17 13  1  0  0  0  0
 17 16  1  0  0  0  0
 18 10  1  0  0  0  0
 19 12  1  0  0  0  0
 20  5  1  0  0  0  0
 20 14  1  0  0  0  0
 20 15  1  0  0  0  0
 21 18  2  0  0  0  0
 22 19  2  0  0  0  0
 23 20  1  0  0  0  0
 24 15  1  0  0  0  0
 24 18  1  0  0  0  0
 25 17  1  0  0  0  0
 25 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0335518

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(/C)C(=O)OC1CC2C(OC(=O)C2=C)C2C(C)=CC=C2C1(C)O

> <INCHI_IDENTIFIER>
InChI=1/C20H24O5/c1-6-10(2)18(21)24-15-9-13-12(4)19(22)25-17(13)16-11(3)7-8-14(16)20(15,5)23/h6-8,13,15-17,23H,4,9H2,1-3,5H3/b10-6+

> <INCHI_KEY>
ITEVGBFEXWVGSM-UXBLZVDNNA-N

> <FORMULA>
C20H24O5

> <MOLECULAR_WEIGHT>
344.407

> <EXACT_MASS>
344.162373873

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
37.08532368071724

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-hydroxy-6,9-dimethyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,6H,9aH,9bH-azuleno[4,5-b]furan-5-yl (2E)-2-methylbut-2-enoate

> <JCHEM_LOGP>
2.860168009333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.19113930281645

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.26309289795531

> <JCHEM_PKA_STRONGEST_BASIC>
-3.484849941207924

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
94.91279999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxy-6,9-dimethyl-3-methylidene-2-oxo-3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-5-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0335518 (Isoachifolidiene)
Download
PDB for NP0335518 (Isoachifolidiene)
HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0       4.269   7.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.602   6.230   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.347  -4.490   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.188  -0.252   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.999   2.443   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.269   6.230   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.372  -2.639   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.441  -1.100   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.882   0.942   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.936   5.460   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.888  -3.048   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.097  -1.100   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.539  -0.559   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.999  -0.559   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.269   1.610   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.039  -1.763   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.499  -1.763   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.936   3.920   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.166  -2.639   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.657   0.942   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.602   3.150   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -0.038  -3.599   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       7.197   0.942   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.269   3.150   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       2.651  -3.048   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4   12                                                            
CONECT    5   20                                                            
CONECT    6    1   10                                                       
CONECT    7    8   11                                                       
CONECT    8    7   14                                                       
CONECT    9   13   15                                                       
CONECT   10    2    6   18                                                  
CONECT   11    3    7   16                                                  
CONECT   12    4   13   19                                                  
CONECT   13    9   12   17                                                  
CONECT   14    8   16   20                                                  
CONECT   15    9   20   24                                                  
CONECT   16   11   14   17                                                  
CONECT   17   13   16   25                                                  
CONECT   18   10   21   24                                                  
CONECT   19   12   22   25                                                  
CONECT   20    5   14   15   23                                             
CONECT   21   18                                                            
CONECT   22   19                                                            
CONECT   23   20                                                            
CONECT   24   15   18                                                       
CONECT   25   17   19                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

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3D PDB for NP0335518 (Isoachifolidiene)
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SMILES for NP0335518 (Isoachifolidiene)
C\C=C(/C)C(=O)OC1CC2C(OC(=O)C2=C)C2C(C)=CC=C2C1(C)O
Download
INCHI for NP0335518 (Isoachifolidiene)
InChI=1/C20H24O5/c1-6-10(2)18(21)24-15-9-13-12(4)19(22)25-17(13)16-11(3)7-8-14(16)20(15,5)23/h6-8,13,15-17,23H,4,9H2,1-3,5H3/b10-6+
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View in JSmol
SynonymsNot Available
Chemical FormulaC20H24O5
Average Mass344.4070 Da
Monoisotopic Mass344.16237 Da
IUPAC Name6-hydroxy-6,9-dimethyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,6H,9aH,9bH-azuleno[4,5-b]furan-5-yl (2E)-2-methylbut-2-enoate
Traditional Name6-hydroxy-6,9-dimethyl-3-methylidene-2-oxo-3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-5-yl (2E)-2-methylbut-2-enoate
CAS Registry NumberNot Available
SMILES
C\C=C(/C)C(=O)OC1CC2C(OC(=O)C2=C)C2C(C)=CC=C2C1(C)O
InChI Identifier
InChI=1/C20H24O5/c1-6-10(2)18(21)24-15-9-13-12(4)19(22)25-17(13)16-11(3)7-8-14(16)20(15,5)23/h6-8,13,15-17,23H,4,9H2,1-3,5H3/b10-6+
InChI KeyITEVGBFEXWVGSM-UXBLZVDNNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty acid esters  
Direct ParentFatty acid esters  
Alternative Parents
Substituents
  • Fatty acid ester
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Gamma butyrolactone
    • 

  • Cyclic alcohol
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Tetrahydrofuran
    • 

  • Tertiary alcohol
    • 

  • Carboxylic acid ester
    • 

  • Lactone
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Alcohol
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic 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
logP2.86ChemAxon
pKa (Strongest Acidic)13.26ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity94.91 m³·mol⁻¹ChemAxon
Polarizability37.09 ųChemAxon
Number of Rings3ChemAxon
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 CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Rucker G, Kiefer A, Breuer J: Isoachifolidiene, a Precursor of Guaianolide Peroxides from Achillea millefolium1. Planta Med. 1992 Jun;58(3):293-5. doi: 10.1055/s-2006-961464. [PubMed:17226475  ]