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Showing NP-Card for 2-[(1r,3s)-1,3-dimethyl-2-methylidenecyclopentyl]-5-methylphenol (NP0318876)

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Record Information
Version2.0
Created at2022-09-11 19:37:11 UTC
Updated at2022-09-11 19:37:12 UTC
NP-MRD IDNP0318876
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-[(1r,3s)-1,3-dimethyl-2-methylidenecyclopentyl]-5-methylphenol
DescriptionDebromoisolaurinterol belongs to the class of organic compounds known as meta cresols. These are aromatic compounds containing a meta-cresol moiety, which consists of a benzene ring bearing a methyl group and a hydroxyl group at ring positions 1 and 3, respectively. 2-[(1r,3s)-1,3-dimethyl-2-methylidenecyclopentyl]-5-methylphenol is found in Laurencia dendroidea. 2-[(1r,3s)-1,3-dimethyl-2-methylidenecyclopentyl]-5-methylphenol was first documented in 2014 (PMID: 26548986). Based on a literature review very few articles have been published on Debromoisolaurinterol.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0318876 (2-[(1r,3s)-1,3-dimethyl-2-methylidenecyclopentyl]-5-methylphenol)


  Mrv1652309112221372D          

 16 17  0  0  1  0            999 V2000
   -1.0821   -1.3771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2975   -1.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0425   -2.4167    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5275   -3.0841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7825   -2.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0374   -1.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3700   -1.1471    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7750   -0.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0350   -0.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8600   -0.4197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2650    0.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8450    1.0091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2500    1.7279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0201    1.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3849    0.2817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2099    0.2731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  6  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
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3D MOL for NP0318876 (2-[(1r,3s)-1,3-dimethyl-2-methylidenecyclopentyl]-5-methylphenol)

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3D SDF for NP0318876 (2-[(1r,3s)-1,3-dimethyl-2-methylidenecyclopentyl]-5-methylphenol)

  Mrv1652309112221372D          

 16 17  0  0  1  0            999 V2000
   -1.0821   -1.3771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2975   -1.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0425   -2.4167    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5275   -3.0841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7825   -2.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0374   -1.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3700   -1.1471    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7750   -0.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0350   -0.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8600   -0.4197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2650    0.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8450    1.0091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2500    1.7279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0201    1.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3849    0.2817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2099    0.2731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  6  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0318876

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CC[C@](C)(C1=C)C1=CC=C(C)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O/c1-10-5-6-13(14(16)9-10)15(4)8-7-11(2)12(15)3/h5-6,9,11,16H,3,7-8H2,1-2,4H3/t11-,15+/m0/s1

> <INCHI_KEY>
MGFYGXNKBXOQOU-XHDPSFHLSA-N

> <FORMULA>
C15H20O

> <MOLECULAR_WEIGHT>
216.324

> <EXACT_MASS>
216.151415264

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
25.716809955477586

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1R,3S)-1,3-dimethyl-2-methylidenecyclopentyl]-5-methylphenol

> <JCHEM_LOGP>
4.379961963333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.39230511890133

> <JCHEM_PKA_STRONGEST_BASIC>
-6.0206498978525795

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
68.0205

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-[(1R,3S)-1,3-dimethyl-2-methylidenecyclopentyl]-5-methylphenol

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0318876 (2-[(1r,3s)-1,3-dimethyl-2-methylidenecyclopentyl]-5-methylphenol)
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PDB for NP0318876 (2-[(1r,3s)-1,3-dimethyl-2-methylidenecyclopentyl]-5-methylphenol)
HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.020  -2.571   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.555  -3.046   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.079  -4.511   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.985  -5.757   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.461  -4.511   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.936  -3.046   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.691  -2.141   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.447  -0.800   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.065  -0.800   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.605  -0.783   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.361   0.558   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.577   1.884   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.333   3.225   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.037   1.868   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.719   0.526   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.258   0.510   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    2    8    9                                             
CONECT    8    7                                                            
CONECT    9    7   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14    9   16                                                  
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

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3D PDB for NP0318876 (2-[(1r,3s)-1,3-dimethyl-2-methylidenecyclopentyl]-5-methylphenol)
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SMILES for NP0318876 (2-[(1r,3s)-1,3-dimethyl-2-methylidenecyclopentyl]-5-methylphenol)
C[C@H]1CC[C@](C)(C1=C)C1=CC=C(C)C=C1O
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INCHI for NP0318876 (2-[(1r,3s)-1,3-dimethyl-2-methylidenecyclopentyl]-5-methylphenol)
InChI=1S/C15H20O/c1-10-5-6-13(14(16)9-10)15(4)8-7-11(2)12(15)3/h5-6,9,11,16H,3,7-8H2,1-2,4H3/t11-,15+/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC15H20O
Average Mass216.3240 Da
Monoisotopic Mass216.15142 Da
IUPAC Name2-[(1R,3S)-1,3-dimethyl-2-methylidenecyclopentyl]-5-methylphenol
Traditional Name2-[(1R,3S)-1,3-dimethyl-2-methylidenecyclopentyl]-5-methylphenol
CAS Registry NumberNot Available
SMILES
C[C@H]1CC[C@](C)(C1=C)C1=CC=C(C)C=C1O
InChI Identifier
InChI=1S/C15H20O/c1-10-5-6-13(14(16)9-10)15(4)8-7-11(2)12(15)3/h5-6,9,11,16H,3,7-8H2,1-2,4H3/t11-,15+/m0/s1
InChI KeyMGFYGXNKBXOQOU-XHDPSFHLSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Laurencia dendroideaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as meta cresols. These are aromatic compounds containing a meta-cresol moiety, which consists of a benzene ring bearing a methyl group and a hydroxyl group at ring positions 1 and 3, respectively.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassPhenols  
Sub ClassCresols  
Direct ParentMeta cresols  
Alternative Parents
Substituents
  • M-cresol
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Toluene
    • 

  • Monocyclic benzene moiety
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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
logP4.38ChemAxon
pKa (Strongest Acidic)9.39ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity68.02 m³·mol⁻¹ChemAxon
Polarizability25.72 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9141154  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10965943  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Zaleta-Pinet DA, Holland IP, Munoz-Ochoa M, Murillo-Alvarez JI, Sakoff JA, van Altena IA, McCluskey A: Cytotoxic compounds from Laurencia pacifica. Org Med Chem Lett. 2014 Dec;4(1):8. doi: 10.1186/s13588-014-0008-8. Epub 2014 Sep 20. [PubMed:26548986  ] 
  2. LOTUS database [Link]