NP-MRD: Showing NP-Card for Neoraufurane (NP0056832)

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Record Information

Version

2.0

Created at

2022-04-28 02:28:26 UTC

Updated at

2022-04-28 02:28:26 UTC

NP-MRD ID

NP0056832

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Neoraufurane

Description

Neoraufurane belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. Thus, neoraufurane is considered to be a flavonoid lipid molecule. Neoraufurane is found in Neorautanenia amboensis and Neorautanenia edulis. Neoraufurane is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 46  0  0  0  0  0  0  0  0999 V2000
   -1.0256    3.4219    0.9779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9739    2.5563   -0.1498 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9558    1.1774   -0.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1703    0.5183   -0.0042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1561   -0.8514    0.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9285   -1.5118    0.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2748   -0.8527    0.2072 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5089   -1.2613    0.2878 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3559   -0.2341    0.2230 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7952   -0.4129    0.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3601   -1.6748    0.4254 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7183   -1.8812    0.4919 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5615   -0.8012    0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9214   -0.9568    0.4840 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0441    0.4896    0.2854 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6596    0.6447    0.2227 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2162    1.9448    0.0878 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5909    0.8984    0.0922 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2483    0.5189    0.0802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3446   -1.5313    0.1432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6052   -0.9245    0.0436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3991   -1.3664    1.2765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2951   -1.5588   -1.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5783    0.5330   -0.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4416    1.2151   -0.1126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3977    4.4170    0.6094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0097    3.5324    1.4094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7054    3.0384    1.7654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9396   -2.5937    0.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6835   -2.5068    0.4782 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1449   -2.8632    0.5970 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3819   -0.9321    1.3877 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7060    1.3276    0.2316 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8081    2.7565    0.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9393    1.8980    0.0124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4924   -1.3130    1.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0603   -2.3681    1.5553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1498   -0.6708    2.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5325   -1.6883   -1.9666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1436   -0.9272   -1.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6277   -2.5612   -0.8666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5233    1.0515   -0.1701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4626    2.3038   -0.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 19  2  0
 19 18  1  0
 18  9  2  0
  9  8  1  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  4 25  1  0
 25 24  2  0
 24 21  1  0
 21 22  1  0
 21 23  1  0
 21 20  1  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
 16 17  1  0
  4  3  1  0
 16 10  1  0
  7 19  1  0
 20  5  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 18 35  1  0
  6 29  1  0
 25 43  1  0
 24 42  1  0
 22 36  1  0
 22 37  1  0
 22 38  1  0
 23 39  1  0
 23 40  1  0
 23 41  1  0
 11 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  0
 17 34  1  0
M  END


  Mrv1533004261504482D          

 25 28  0  0  0  0            999 V2000
    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 O   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
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3082   -2.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7779   -3.1232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 O   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   -2.7604    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
    1.8532   -2.6029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -1.2680    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
    0.5433   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1308   -2.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6942   -2.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1067   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9317   -1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6942   -1.2210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1308   -1.2210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5433   -0.5065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  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
  3 17  2  0  0  0  0
 13 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 18 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0056832

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C=C(OC2=CC2=C1C=CC(C)(C)O2)C1=CC=C(O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O5/c1-20(2)7-6-13-18(25-20)10-17-14(19(13)23-3)9-16(24-17)12-5-4-11(21)8-15(12)22/h4-10,21-22H,1-3H3

> <INCHI_KEY>
LROKNLVNTRTDCU-UHFFFAOYSA-N

> <FORMULA>
C20H18O5

> <MOLECULAR_WEIGHT>
338.359

> <EXACT_MASS>
338.11542368

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
36.75766625400422

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{4-methoxy-7,7-dimethyl-7H-furo[3,2-g]chromen-2-yl}benzene-1,3-diol

> <ALOGPS_LOGP>
4.13

> <JCHEM_LOGP>
3.8354171953333327

> <ALOGPS_LOGS>
-3.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.883089460763802

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.43406216002178

> <JCHEM_PKA_STRONGEST_BASIC>
-2.819242225545214

> <JCHEM_POLAR_SURFACE_AREA>
72.06

> <JCHEM_REFRACTIVITY>
94.7312

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.73e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
neoraufurane

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.258  -0.533   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.775  -4.115   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.785  -5.830   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.925  -5.153   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.258  -5.153   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  O   UNK     0       3.459  -4.859   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.554  -3.613   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.459  -2.367   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.014  -3.613   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.244  -4.947   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.296  -4.947   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.066  -3.613   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.606  -3.613   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.296  -2.279   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.244  -2.279   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.014  -0.945   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11                                                       
CONECT   11   10    4   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16    3   13                                                  
CONECT   18   15   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   18   25                                                  
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₁₈O₅

Average Mass

338.3590 Da

Monoisotopic Mass

338.11542 Da

IUPAC Name

4-{4-methoxy-7,7-dimethyl-7H-furo[3,2-g]chromen-2-yl}benzene-1,3-diol

Traditional Name

neoraufurane

CAS Registry Number

Not Available

SMILES

COC1=C2C=C(OC2=CC2=C1C=CC(C)(C)O2)C1=CC=C(O)C=C1O

InChI Identifier

InChI=1S/C20H18O5/c1-20(2)7-6-13-18(25-20)10-17-14(19(13)23-3)9-16(24-17)12-5-4-11(21)8-15(12)22/h4-10,21-22H,1-3H3

InChI Key

LROKNLVNTRTDCU-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, 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
Neorautanenia amboensis	LOTUS Database	35616633
Neorautanenia edulis	Plant	KNApSAcK

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
2-phenylbenzofuran
Phenylbenzofuran
2,2-dimethyl-1-benzopyran
Benzopyran
1-benzopyran
Benzofuran
Anisole
Phenol ether
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Furan
Heteroaromatic compound
Ether
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Other Flavonoids (LMPK12160047 )

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	4.13	ALOGPS
logP	3.84	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	8.43	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	72.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	94.73 m³·mol⁻¹	ChemAxon
Polarizability	36.76 Å³	ChemAxon
Number of Rings	4	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

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

44260112

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Neoraufurane (NP0056832)

MOL for NP0056832 (Neoraufurane)

3D MOL for NP0056832 (Neoraufurane)

3D SDF for NP0056832 (Neoraufurane)

3D-SDF for NP0056832 (Neoraufurane)

PDB for NP0056832 (Neoraufurane)

3D PDB for NP0056832 (Neoraufurane)

SMILES for NP0056832 (Neoraufurane)

INCHI for NP0056832 (Neoraufurane)

Structure for NP0056832 (Neoraufurane)

3D Structure for NP0056832 (Neoraufurane)