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Showing NP-Card for {2-[(benzenesulfinyl)methyl]-3-phenylcyclopropyl}benzene (NP0223688)

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Record Information
Version2.0
Created at2022-09-06 01:51:34 UTC
Updated at2022-09-06 01:51:34 UTC
NP-MRD IDNP0223688
Secondary Accession NumbersNone
Natural Product Identification
Common Name{2-[(benzenesulfinyl)methyl]-3-phenylcyclopropyl}benzene
Description(2,3-Diphenylcyclopropyl)methyl phenyl sulfoxide belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. It was first documented in 2014 (PMID: 25518943). A sulfoxide in which the S atom is substituted by a phenyl and (2,3-diphenylcyclopropyl)methyl group (2,3-diphenylcyclopropyl)methyl phenyl sulfoxide is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0223688 ({2-[(benzenesulfinyl)methyl]-3-phenylcyclopropyl}benzene)


  Mrv1652303231707192D          

 24 27  0  0  0  0            999 V2000
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559   -3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849   -3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849   -4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559   -4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   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  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 24  1  0  0  0  0
M  END
Download

3D MOL for NP0223688 ({2-[(benzenesulfinyl)methyl]-3-phenylcyclopropyl}benzene)

Download
3D SDF for NP0223688 ({2-[(benzenesulfinyl)methyl]-3-phenylcyclopropyl}benzene)

  Mrv1652303231707192D          

 24 27  0  0  0  0            999 V2000
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559   -3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849   -3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849   -4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559   -4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   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  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0223688

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=S(CC1C(C1C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H20OS/c23-24(19-14-8-3-9-15-19)16-20-21(17-10-4-1-5-11-17)22(20)18-12-6-2-7-13-18/h1-15,20-22H,16H2

> <INCHI_KEY>
MVULGCSHGFLUBH-UHFFFAOYSA-N

> <FORMULA>
C22H20OS

> <MOLECULAR_WEIGHT>
332.46

> <EXACT_MASS>
332.123486438

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
37.646866981140946

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{2-[(benzenesulfinyl)methyl]-3-phenylcyclopropyl}benzene

> <ALOGPS_LOGP>
4.13

> <JCHEM_LOGP>
4.481073083333335

> <ALOGPS_LOGS>
-4.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.52445371478961

> <JCHEM_PKA_STRONGEST_BASIC>
-8.161752810784368

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
101.62100000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.06e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{2-[(benzenesulfinyl)methyl]-3-phenylcyclopropyl}benzene

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0223688 ({2-[(benzenesulfinyl)methyl]-3-phenylcyclopropyl}benzene)
Download
PDB for NP0223688 ({2-[(benzenesulfinyl)methyl]-3-phenylcyclopropyl}benzene)
HEADER    PROTEIN                                 23-MAR-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-MAR-17         0                                  
HETATM    1  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    2  S   UNK     0       1.334  -2.310   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.437  -5.954   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.897  -5.954   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.564  -6.724   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.564  -8.264   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.770  -9.034   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.104  -8.264   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.104  -6.724   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.770  -5.954   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.771  -6.724   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.105  -5.954   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.438  -6.724   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.438  -8.264   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.105  -9.034   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.771  -8.264   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4    6   13                                                  
CONECT    6    5    4    7                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13    5   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19    2   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   19                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

Download
3D PDB for NP0223688 ({2-[(benzenesulfinyl)methyl]-3-phenylcyclopropyl}benzene)
Download
SMILES for NP0223688 ({2-[(benzenesulfinyl)methyl]-3-phenylcyclopropyl}benzene)
O=S(CC1C(C1C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1
Download
INCHI for NP0223688 ({2-[(benzenesulfinyl)methyl]-3-phenylcyclopropyl}benzene)
InChI=1S/C22H20OS/c23-24(19-14-8-3-9-15-19)16-20-21(17-10-4-1-5-11-17)22(20)18-12-6-2-7-13-18/h1-15,20-22H,16H2
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View in JSmol
Synonyms
ValueSource
1,1'-{3-[(phenylsulfinyl)methyl]cyclopropane-1,2-diyl}dibenzeneChEBI
1,1'-{3-[(phenylsulphinyl)methyl]cyclopropane-1,2-diyl}dibenzeneGenerator
(2,3-Diphenylcyclopropyl)methyl phenyl sulphoxideGenerator
Chemical FormulaC22H20OS
Average Mass332.4600 Da
Monoisotopic Mass332.12349 Da
IUPAC Name{2-[(benzenesulfinyl)methyl]-3-phenylcyclopropyl}benzene
Traditional Name{2-[(benzenesulfinyl)methyl]-3-phenylcyclopropyl}benzene
CAS Registry NumberNot Available
SMILES
O=S(CC1C(C1C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C22H20OS/c23-24(19-14-8-3-9-15-19)16-20-21(17-10-4-1-5-11-17)22(20)18-12-6-2-7-13-18/h1-15,20-22H,16H2
InChI KeyMVULGCSHGFLUBH-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups  to a phenyl ring lead to stilbenoids.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassStilbenes  
Sub ClassNot Available
Direct ParentStilbenes  
Alternative Parents
Substituents
  • Stilbene
    • 

  • Phenyl sulfoxide
    • 

  • Benzenoid
    • 

  • Monocyclic benzene moiety
    • 

  • Sulfoxide
    • 

  • Sulfinyl compound
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organosulfur compound
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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
logP4.13ALOGPS
logP4.48ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)19.52ChemAxon
pKa (Strongest Basic)-8.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity101.62 m³·mol⁻¹ChemAxon
Polarizability37.65 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0062791  
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 Compound562543  
PDB IDNot Available
ChEBI ID84273  
Good Scents IDNot Available
References
General References
  1. Vermeersch KA, Wang L, McDonald JF, Styczynski MP: Distinct metabolic responses of an ovarian cancer stem cell line. BMC Syst Biol. 2014 Dec 18;8:134. doi: 10.1186/s12918-014-0134-y. [PubMed:25518943  ] 
  2. LOTUS database [Link]