NP-MRD: Showing NP-Card for 4'-methylpinosylvin (NP0074352)

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Record Information

Version

2.0

Created at

2022-04-28 19:31:24 UTC

Updated at

2022-04-28 19:31:24 UTC

NP-MRD ID

NP0074352

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4'-methylpinosylvin

Description

4'-Methylpinosylvin 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. 4'-methylpinosylvin is found in Stemona aphylla, Stemona burkillii, Stemona cf. pierrei, Stemona cf.pierrei, Stemona cochinchinensis, Stemona collinsae, Stemona curtisii, Stemona involuta, Stemona japonica , Stemona kerrii, Stemona parviflora, Stemona phyllantha, Stemona pierrei and Stemona sessilifolia . 4'-methylpinosylvin was first documented in 2002 (PMID: 12088422). Based on a literature review very few articles have been published on 4'-methylpinosylvin (PMID: 14697275).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 32  0  0  0  0  0  0  0  0999 V2000
   -5.0890   -0.6690   -0.6317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6635   -0.3835   -0.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2682    0.4407    0.7085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2798    1.0237    1.4762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9381    0.6776    0.9640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9305    0.0864    0.1861 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4487    0.3807    0.5124 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4429   -0.1227   -0.1545 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8497    0.1508    0.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7989   -0.4527   -0.6470 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1479   -0.2560   -0.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5714    0.5654    0.5794 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6455    1.1844    1.3900 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2958    0.9617    1.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3719   -0.7283   -0.8267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7079   -0.9730   -1.0919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0078   -1.8254   -2.1568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7046    0.0538   -0.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2393   -0.4866   -1.7359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3158   -1.7277   -0.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0050    1.6345    2.2373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6247    1.3219    1.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6836    1.0515    1.3507 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2066   -0.7895   -0.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5189   -1.1147   -1.4728 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8914   -0.7311   -1.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6396    0.7196    0.7392 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9934    1.8205    2.1809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5935    1.4458    1.7862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6244   -1.2050   -1.4519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9572   -2.0539   -2.4142 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  6 15  1  0
 15 16  2  0
 16 17  1  0
 16  2  1  0
 14  9  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  5 22  1  0
  7 23  1  0
  8 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
M  END


  Mrv1652304282221312D          

 17 18  0  0  0  0            999 V2000
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  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
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
  3 15  1  0  0  0  0
  2 16  1  0  0  0  0
  1 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0074352

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(O)C=C(\C=C\C2=CC=CC=C2)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O2/c1-11-14(16)9-13(10-15(11)17)8-7-12-5-3-2-4-6-12/h2-10,16-17H,1H3/b8-7+

> <INCHI_KEY>
OCNRSGCLTQHHRD-BQYQJAHWSA-N

> <FORMULA>
C15H14O2

> <MOLECULAR_WEIGHT>
226.275

> <EXACT_MASS>
226.099379691

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
25.659848108398283

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methyl-5-[(E)-2-phenylethenyl]benzene-1,3-diol

> <ALOGPS_LOGP>
3.61

> <JCHEM_LOGP>
4.219377597333333

> <ALOGPS_LOGS>
-3.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.403455597611456

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.06184308028717

> <JCHEM_PKA_STRONGEST_BASIC>
-6.158694884364967

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
70.51580000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.50e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methyl-5-[(E)-2-phenylethenyl]benzene-1,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2    6   17                                                  
CONECT    2    1    3   16                                                  
CONECT    3    2    4   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
CONECT   15    3                                                            
CONECT   16    2                                                            
CONECT   17    1                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₄O₂

Average Mass

226.2750 Da

Monoisotopic Mass

226.09938 Da

IUPAC Name

2-methyl-5-[(E)-2-phenylethenyl]benzene-1,3-diol

Traditional Name

2-methyl-5-[(E)-2-phenylethenyl]benzene-1,3-diol

CAS Registry Number

Not Available

SMILES

CC1=C(O)C=C(\C=C\C2=CC=CC=C2)C=C1O

InChI Identifier

InChI=1S/C15H14O2/c1-11-14(16)9-13(10-15(11)17)8-7-12-5-3-2-4-6-12/h2-10,16-17H,1H3/b8-7+

InChI Key

OCNRSGCLTQHHRD-BQYQJAHWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Stemona aphylla	Plant	KNApSAcK
Stemona burkillii	Plant	KNApSAcK
Stemona cf. pierrei	Plant	KNApSAcK
Stemona cf.pierrei	Plant	KNApSAcK
Stemona cochinchinensis	Plant	KNApSAcK
Stemona collinsiae	Plant	KNApSAcK
Stemona curtisii	Plant	KNApSAcK
Stemona involuta	Plant	KNApSAcK
Stemona japonica	Plant	KNApSAcK
Stemona kerrii	Plant	KNApSAcK
Stemona parviflora	Plant	KNApSAcK
Stemona phyllantha	Plant	KNApSAcK
Stemona pierrei	Plant	KNApSAcK
Stemona sessilifolia	Plant	KNApSAcK

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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Styrene
Resorcinol
O-cresol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Toluene
Phenol
Benzenoid
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.61	ALOGPS
logP	4.22	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	9.06	ChemAxon
pKa (Strongest Basic)	-6.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	70.52 m³·mol⁻¹	ChemAxon
Polarizability	25.66 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00035502

Chemspider ID

23339833

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44566996

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kostecki K, Engelmeier D, Pacher T, Hofer O, Vajrodaya S, Greger H: Dihydrophenanthrenes and other antifungal stilbenoids from Stemona cf. pierrei. Phytochemistry. 2004 Jan;65(1):99-106. doi: 10.1016/j.phytochem.2003.09.015. [PubMed:14697275 ]
Pacher T, Seger C, Engelmeier D, Vajrodaya S, Hofer O, Greger H: Antifungal stilbenoids from Stemona collinsae. J Nat Prod. 2002 Jun;65(6):820-7. doi: 10.1021/np0105073. [PubMed:12088422 ]

Showing NP-Card for 4'-methylpinosylvin (NP0074352)

MOL for NP0074352 (4'-methylpinosylvin)

3D MOL for NP0074352 (4'-methylpinosylvin)

3D SDF for NP0074352 (4'-methylpinosylvin)

3D-SDF for NP0074352 (4'-methylpinosylvin)

PDB for NP0074352 (4'-methylpinosylvin)

3D PDB for NP0074352 (4'-methylpinosylvin)

SMILES for NP0074352 (4'-methylpinosylvin)

INCHI for NP0074352 (4'-methylpinosylvin)

Structure for NP0074352 (4'-methylpinosylvin)

3D Structure for NP0074352 (4'-methylpinosylvin)