NP-MRD: Showing NP-Card for 4-[3-methyl-5-(prop-1-en-1-yl)-1-benzofuran-2-yl]phenol (NP0308932)

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Record Information

Version

2.0

Created at

2022-09-11 03:07:03 UTC

Updated at

2022-09-11 03:07:04 UTC

NP-MRD ID

NP0308932

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[3-methyl-5-(prop-1-en-1-yl)-1-benzofuran-2-yl]phenol

Description

AC1MHDNV belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. 4-[3-methyl-5-(prop-1-en-1-yl)-1-benzofuran-2-yl]phenol is found in Daphniphyllum angustifolium, Krameria bicolor, Krameria erecta, Krameria lappacea, Piper aequale and Piper regnellii. AC1MHDNV is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
   -6.1545    0.2118    0.1776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4688   -0.3827   -0.9891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2170   -0.5395   -1.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0436   -0.1959   -0.5004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0486    0.4186    0.7286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8614    0.7206    1.3950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6735    0.3797    0.7757 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5438    0.5373    1.1550 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4242    0.0688    0.2641 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8638    0.1419    0.4866 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7525   -0.3200   -0.4386 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1208   -0.2189   -0.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5508    0.3331    1.0393 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9068    0.4471    1.3553 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6551    0.8012    1.9768 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3239    0.7003    1.6900 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7094   -0.4335   -0.7779 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1833   -1.0717   -2.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6396   -0.2299   -0.4419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7943   -0.5192   -1.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9793    1.2903    0.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9753   -0.3941    1.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2925    0.0697    0.0221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1502   -0.7766   -1.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0279   -1.0389   -2.2451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9898    0.6805    1.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9241    1.1943    2.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5049   -0.7578   -1.3810 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8416   -0.5867   -0.8849 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3481   -0.3332    1.8515 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9950    1.2308    2.9023 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6133    1.0730    2.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2436   -1.3902   -2.5870 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7003   -0.4220   -2.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6968   -2.0468   -1.8643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7373   -0.9990   -2.0381 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
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 20  4  1  0
 16 10  1  0
 19  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  5 26  1  0
  6 27  1  0
 18 33  1  0
 18 34  1  0
 18 35  1  0
 20 36  1  0
 11 28  1  0
 12 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
M  END


  Mrv1533004241503432D          

 20 22  0  0  0  0            999 V2000
    5.4957    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    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    0.6979    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
    1.1387    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  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  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  2  0  0  0  0
  4 13  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 14 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0308932

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC=CC1=CC=C2OC(=C(C)C2=C1)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O2/c1-3-4-13-5-10-17-16(11-13)12(2)18(20-17)14-6-8-15(19)9-7-14/h3-11,19H,1-2H3

> <INCHI_KEY>
KNFUWJAIDVAYOV-UHFFFAOYSA-N

> <FORMULA>
C18H16O2

> <MOLECULAR_WEIGHT>
264.324

> <EXACT_MASS>
264.115029755

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
30.960139568927396

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[3-methyl-5-(prop-1-en-1-yl)-1-benzofuran-2-yl]phenol

> <ALOGPS_LOGP>
5.52

> <JCHEM_LOGP>
5.032788832666667

> <ALOGPS_LOGS>
-4.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.448548240248753

> <JCHEM_PKA_STRONGEST_BASIC>
-2.813716893984161

> <JCHEM_POLAR_SURFACE_AREA>
33.370000000000005

> <JCHEM_REFRACTIVITY>
82.2947

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.10e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[3-methyl-5-(prop-1-en-1-yl)-1-benzofuran-2-yl]phenol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      10.259   4.383   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.650   5.553   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.320   2.843   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.090   1.509   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.630   1.509   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.400   2.843   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -4.940   2.843   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.630   4.177   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.090   4.177   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    7   13                                                  
CONECT   13   12    4                                                       
CONECT   14    9   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   14                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₆O₂

Average Mass

264.3240 Da

Monoisotopic Mass

264.11503 Da

IUPAC Name

4-[3-methyl-5-(prop-1-en-1-yl)-1-benzofuran-2-yl]phenol

Traditional Name

4-[3-methyl-5-(prop-1-en-1-yl)-1-benzofuran-2-yl]phenol

CAS Registry Number

Not Available

SMILES

CC=CC1=CC=C2OC(=C(C)C2=C1)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C18H16O2/c1-3-4-13-5-10-17-16(11-13)12(2)18(20-17)14-6-8-15(19)9-7-14/h3-11,19H,1-2H3

InChI Key

KNFUWJAIDVAYOV-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Daphniphyllum angustifolium	LOTUS Database	35616633
Krameria bicolor	LOTUS Database	35616633
Krameria erecta	LOTUS Database	35616633
Krameria lappacea	LOTUS Database	35616633
Piper aequale	LOTUS Database	35616633
Piper regnellii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
Neolignan skeleton
2-phenylbenzofuran
Phenylbenzofuran
Benzofuran
Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Furan
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	5.52	ALOGPS
logP	5.03	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	9.45	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	33.37 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	82.29 m³·mol⁻¹	ChemAxon
Polarizability	30.96 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3001232

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-[3-methyl-5-(prop-1-en-1-yl)-1-benzofuran-2-yl]phenol (NP0308932)

MOL for NP0308932 (4-[3-methyl-5-(prop-1-en-1-yl)-1-benzofuran-2-yl]phenol)

3D MOL for NP0308932 (4-[3-methyl-5-(prop-1-en-1-yl)-1-benzofuran-2-yl]phenol)

3D SDF for NP0308932 (4-[3-methyl-5-(prop-1-en-1-yl)-1-benzofuran-2-yl]phenol)

3D-SDF for NP0308932 (4-[3-methyl-5-(prop-1-en-1-yl)-1-benzofuran-2-yl]phenol)

PDB for NP0308932 (4-[3-methyl-5-(prop-1-en-1-yl)-1-benzofuran-2-yl]phenol)

3D PDB for NP0308932 (4-[3-methyl-5-(prop-1-en-1-yl)-1-benzofuran-2-yl]phenol)

SMILES for NP0308932 (4-[3-methyl-5-(prop-1-en-1-yl)-1-benzofuran-2-yl]phenol)

INCHI for NP0308932 (4-[3-methyl-5-(prop-1-en-1-yl)-1-benzofuran-2-yl]phenol)

Structure for NP0308932 (4-[3-methyl-5-(prop-1-en-1-yl)-1-benzofuran-2-yl]phenol)

3D Structure for NP0308932 (4-[3-methyl-5-(prop-1-en-1-yl)-1-benzofuran-2-yl]phenol)