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Showing NP-Card for indene (NP0194584)

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Record Information
Version2.0
Created at2022-09-04 12:15:59 UTC
Updated at2022-09-04 12:15:59 UTC
NP-MRD IDNP0194584
Secondary Accession NumbersNone
Natural Product Identification
Common Nameindene
DescriptionIndene, also known as inden or indonaphthene, belongs to the class of organic compounds known as indenes and isoindenes. Indenes and isoindenes are compounds containing an indene moiety(which consists of a cyclopentadiene fused to a benzene ring), or a isoindene moiety (which consists of a cyclopentadiene fused to cyclohexadiene ring). The principal industrial use of indene is in the production of indene/coumarone thermoplastic resins. Indene is an extremely weak acidic (essentially neutral) compound (based on its pKa). Indene is a potentially toxic compound. It is composed of a benzene ring fused with a cyclopentene ring. This aromatic liquid is colorless although samples often are pale yellow. indene is found in Terminalia chebula, Tuber borchii and Vaccinium macrocarpon. indene was first documented in 2014 (PMID: 24804069). Indene is a flammable polycyclic hydrocarbon (PMID: 24217495).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0194584 (indene)


  Mrv0541 02231216282D          

  9 10  0  0  0  0            999 V2000
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  1  9  1  0  0  0  0
  4  9  1  0  0  0  0
M  END
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3D MOL for NP0194584 (indene)

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3D SDF for NP0194584 (indene)

  Mrv0541 02231216282D          

  9 10  0  0  0  0            999 V2000
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  1  9  1  0  0  0  0
  4  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0194584

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C1C=CC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C9H8/c1-2-5-9-7-3-6-8(9)4-1/h1-6H,7H2

> <INCHI_KEY>
YBYIRNPNPLQARY-UHFFFAOYSA-N

> <FORMULA>
C9H8

> <MOLECULAR_WEIGHT>
116.1598

> <EXACT_MASS>
116.062600256

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
13.3810167737891

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1H-indene

> <ALOGPS_LOGP>
3.04

> <JCHEM_LOGP>
2.7017097003333337

> <ALOGPS_LOGS>
-3.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.11316497402911

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
40.0558

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.68e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
indene

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0194584 (indene)
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PDB for NP0194584 (indene)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2    9                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    1    4                                                  
MASTER        0    0    0    0    0    0    0    0    9    0   20    0
END

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3D PDB for NP0194584 (indene)
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SMILES for NP0194584 (indene)
C1C=CC2=CC=CC=C12
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INCHI for NP0194584 (indene)
InChI=1S/C9H8/c1-2-5-9-7-3-6-8(9)4-1/h1-6H,7H2
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View in JSmol
Synonyms
ValueSource
IndenChEBI
IndonaphtheneChEBI
Chemical FormulaC9H8
Average Mass116.1598 Da
Monoisotopic Mass116.06260 Da
IUPAC Name1H-indene
Traditional Nameindene
CAS Registry NumberNot Available
SMILES
C1C=CC2=CC=CC=C12
InChI Identifier
InChI=1S/C9H8/c1-2-5-9-7-3-6-8(9)4-1/h1-6H,7H2
InChI KeyYBYIRNPNPLQARY-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Terminalia chebulaLOTUS Database
Tuber borchiiLOTUS Database
Vaccinium macrocarponLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indenes and isoindenes. Indenes and isoindenes are compounds containing an indene moiety(which consists of a cyclopentadiene fused to a benzene ring), or a isoindene moiety (which consists of a cyclopentadiene fused to cyclohexadiene ring).
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassIndenes and isoindenes  
Sub ClassNot Available
Direct ParentIndenes and isoindenes  
Alternative Parents
Substituents
  • Indene
    • 

  • Aromatic hydrocarbon
    • 

  • Polycyclic hydrocarbon
    • 

  • Cyclic olefin
    • 

  • Unsaturated hydrocarbon
    • 

  • Olefin
    • 

  • Hydrocarbon
    • 

  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic 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
logP3.04ALOGPS
logP2.7ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)19.11ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity40.06 m³·mol⁻¹ChemAxon
Polarizability13.38 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 IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIndene  
METLIN IDNot Available
PubChem Compound7219  
PDB IDNot Available
ChEBI ID41921  
Good Scents IDNot Available
References
General References
  1. Eshiet ER, Zhu J, Anderson TA, Smith EE: Chemical characterization of Brickellia cavanillesii (Asteraceae) using gas chromatographic methods. Food Sci Nutr. 2014 Mar;2(2):105-13. doi: 10.1002/fsn3.52. Epub 2013 Dec 27. [PubMed:24804069  ] 
  2. Chai Z, Hua D, Li K, Chu J, Yang G: A novel chiral yttrium complex with a tridentate linked amido-indenyl ligand for intramolecular hydroamination. Chem Commun (Camb). 2014 Jan 7;50(2):177-9. doi: 10.1039/c3cc47006g. [PubMed:24217495  ] 
  3. LOTUS database [Link]