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Showing NP-Card for 5-[5-(furan-3-yl)-2-methylpent-1-en-1-yl]-3-[3-(furan-3-yl)propylidene]oxolan-2-one (NP0296818)

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Record Information
Version2.0
Created at2022-09-10 06:38:39 UTC
Updated at2022-09-10 06:38:39 UTC
NP-MRD IDNP0296818
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-[5-(furan-3-yl)-2-methylpent-1-en-1-yl]-3-[3-(furan-3-yl)propylidene]oxolan-2-one
DescriptionAC1L7VWN belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. 5-[5-(furan-3-yl)-2-methylpent-1-en-1-yl]-3-[3-(furan-3-yl)propylidene]oxolan-2-one is found in Spongia agaricina and Spongia officinalis. AC1L7VWN is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0296818 (5-[5-(furan-3-yl)-2-methylpent-1-en-1-yl]-3-[3-(furan-3-yl)propylidene]oxolan-2-one)


  Mrv1533004171504022D          

 25 27  0  0  0  0            999 V2000
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   -1.6382   -2.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1063    0.0653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  4  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
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  4 17  1  0  0  0  0
  2 18  1  0  0  0  0
 18 19  1  0  0  0  0
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M  END
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3D MOL for NP0296818 (5-[5-(furan-3-yl)-2-methylpent-1-en-1-yl]-3-[3-(furan-3-yl)propylidene]oxolan-2-one)

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3D SDF for NP0296818 (5-[5-(furan-3-yl)-2-methylpent-1-en-1-yl]-3-[3-(furan-3-yl)propylidene]oxolan-2-one)

  Mrv1533004171504022D          

 25 27  0  0  0  0            999 V2000
   -3.0671   -2.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3526   -2.0742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6382   -2.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6382   -3.3117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9707   -3.7966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2257   -4.5812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7407   -5.2487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797   -5.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5647   -5.8299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3851   -5.7436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7976   -5.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6046   -5.2007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6909   -6.0212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9372   -6.3567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0507   -4.5812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5356   -5.2487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3056   -3.7966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6382   -0.8367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6382   -0.0117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3526    0.4008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6583    0.6784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2458    1.3928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4389    1.2213    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  4  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  4  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
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 11 12  1  0  0  0  0
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 10 14  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  4 17  1  0  0  0  0
  2 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
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 21 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0296818

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCCC1=COC=C1)=CC1CC(=CCCC2=COC=C2)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C21H24O4/c1-16(4-2-5-17-8-10-23-14-17)12-20-13-19(21(22)25-20)7-3-6-18-9-11-24-15-18/h7-12,14-15,20H,2-6,13H2,1H3

> <INCHI_KEY>
YHLJEGITRQRPJZ-UHFFFAOYSA-N

> <FORMULA>
C21H24O4

> <MOLECULAR_WEIGHT>
340.419

> <EXACT_MASS>
340.167459253

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
37.50775398873051

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[5-(furan-3-yl)-2-methylpent-1-en-1-yl]-3-[3-(furan-3-yl)propylidene]oxolan-2-one

> <ALOGPS_LOGP>
4.95

> <JCHEM_LOGP>
5.412782753666667

> <ALOGPS_LOGS>
-4.67

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.484250036733517

> <JCHEM_POLAR_SURFACE_AREA>
52.58

> <JCHEM_REFRACTIVITY>
97.36970000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.22e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[5-(furan-3-yl)-2-methylpent-1-en-1-yl]-3-[3-(furan-3-yl)propylidene]oxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0296818 (5-[5-(furan-3-yl)-2-methylpent-1-en-1-yl]-3-[3-(furan-3-yl)propylidene]oxolan-2-one)
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PDB for NP0296818 (5-[5-(furan-3-yl)-2-methylpent-1-en-1-yl]-3-[3-(furan-3-yl)propylidene]oxolan-2-one)
HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      -5.725  -4.642   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.392  -3.872   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.058  -4.642   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.058  -6.182   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.812  -7.087   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.288  -8.552   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.383  -9.798   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.149  -9.637   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.054 -10.882   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.586 -10.721   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.356  -9.388   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.862  -9.708   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.023 -11.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.616 -11.866   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.828  -8.552   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -4.733  -9.798   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -4.304  -7.087   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -4.392  -2.332   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.058  -1.562   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.058  -0.022   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.392   0.748   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.798   0.122   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -6.829   1.266   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -6.059   2.600   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.553   2.280   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   17                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15    6   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    4                                                       
CONECT   18    2   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   21                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

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3D PDB for NP0296818 (5-[5-(furan-3-yl)-2-methylpent-1-en-1-yl]-3-[3-(furan-3-yl)propylidene]oxolan-2-one)
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SMILES for NP0296818 (5-[5-(furan-3-yl)-2-methylpent-1-en-1-yl]-3-[3-(furan-3-yl)propylidene]oxolan-2-one)
CC(CCCC1=COC=C1)=CC1CC(=CCCC2=COC=C2)C(=O)O1
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INCHI for NP0296818 (5-[5-(furan-3-yl)-2-methylpent-1-en-1-yl]-3-[3-(furan-3-yl)propylidene]oxolan-2-one)
InChI=1S/C21H24O4/c1-16(4-2-5-17-8-10-23-14-17)12-20-13-19(21(22)25-20)7-3-6-18-9-11-24-15-18/h7-12,14-15,20H,2-6,13H2,1H3
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SynonymsNot Available
Chemical FormulaC21H24O4
Average Mass340.4190 Da
Monoisotopic Mass340.16746 Da
IUPAC Name5-[5-(furan-3-yl)-2-methylpent-1-en-1-yl]-3-[3-(furan-3-yl)propylidene]oxolan-2-one
Traditional Name5-[5-(furan-3-yl)-2-methylpent-1-en-1-yl]-3-[3-(furan-3-yl)propylidene]oxolan-2-one
CAS Registry NumberNot Available
SMILES
CC(CCCC1=COC=C1)=CC1CC(=CCCC2=COC=C2)C(=O)O1
InChI Identifier
InChI=1S/C21H24O4/c1-16(4-2-5-17-8-10-23-14-17)12-20-13-19(21(22)25-20)7-3-6-18-9-11-24-15-18/h7-12,14-15,20H,2-6,13H2,1H3
InChI KeyYHLJEGITRQRPJZ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Spongia agaricinaLOTUS Database
Spongia officinalisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassLactones  
Sub ClassGamma butyrolactones  
Direct ParentGamma butyrolactones  
Alternative Parents
Substituents
  • Gamma butyrolactone
    • 

  • Furan
    • 

  • Oxolane
    • 

  • Enoate ester
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Heteroaromatic compound
    • 

  • Carboxylic acid ester
    • 

  • Carboxylic acid derivative
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Oxacycle
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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
logP4.95ALOGPS
logP5.41ChemAxon
logS-4.7ALOGPS
pKa (Strongest Basic)-2.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.58 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity97.37 m³·mol⁻¹ChemAxon
Polarizability37.51 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
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 Compound317399  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]