NP-MRD: Showing NP-Card for Tournefolic acid A (NP0080920)

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Record Information

Version

2.0

Created at

2022-04-29 01:53:41 UTC

Updated at

2022-04-29 01:53:41 UTC

NP-MRD ID

NP0080920

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tournefolic acid A

Description

TOURNEFOLIC ACID A, also known as tournefolate a, belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. Tournefolic acid A is found in Tournefortia sarmentosa. Tournefolic acid A was first documented in 2015 (PMID: 25728025). Based on a literature review very few articles have been published on TOURNEFOLIC ACID A.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
    6.5599    1.8883   -1.1081 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3641    1.5171   -1.1915 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8667    1.2316   -2.4429 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4903    1.3777   -0.0284 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2414    0.9889   -0.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3736    0.8502    1.0275 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7458    1.1026    2.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8666    0.9529    3.4065 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5826    0.5388    3.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3115    0.3830    4.2405 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2169    0.2882    1.8747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9320   -0.1102    1.4073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8988   -0.2412    0.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0562   -0.6752   -0.6765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0159   -0.8107   -2.0485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0972   -1.2194   -2.8017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3002   -1.5171   -2.1814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3701   -1.9258   -2.9663 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3636   -1.3891   -0.8149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5586   -1.6838   -0.1889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2752   -0.9801   -0.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3565    0.0949   -0.3128 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0637    0.4316    0.8252 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5811    0.2936   -2.7124 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9385    1.6158    0.9217 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8940    0.7746   -1.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7702    1.4324    2.5051 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2254    1.1692    4.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2556    0.0839    4.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0762   -0.5796   -2.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0428   -1.3188   -3.8775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2693   -2.1613   -2.6234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7030   -1.6193    0.8158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3293   -0.8807    0.9965 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7180    0.0969   -1.3100 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6 23  2  0
 23 22  1  0
 22 13  2  0
 13 12  1  0
 12 11  1  0
 11  9  2  0
  9 10  1  0
  9  8  1  0
  8  7  2  0
 13 14  1  0
 14 21  2  0
 21 19  1  0
 19 20  1  0
 19 17  2  0
 17 18  1  0
 17 16  1  0
 16 15  2  0
  7  6  1  0
 15 14  1  0
 11 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
 22 35  1  0
 10 29  1  0
  8 28  1  0
  7 27  1  0
 21 34  1  0
 20 33  1  0
 18 32  1  0
 16 31  1  0
 15 30  1  0
M  END


  Mrv1652304292203532D          

 23 25  0  0  0  0            999 V2000
    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
    1.9233    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
    2.6378    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    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    0.8555    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
   -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
   -2.6462    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    0.0940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.7771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2089   -1.7771    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
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  4 10  1  0  0  0  0
  9 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
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 14 17  1  0  0  0  0
 13 18  1  0  0  0  0
  3 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
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0080920

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)\C=C\C1=C2C=C(OC2=C(O)C=C1)C1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H12O6/c18-12-4-2-10(7-14(12)20)15-8-11-9(3-6-16(21)22)1-5-13(19)17(11)23-15/h1-8,18-20H,(H,21,22)/b6-3+

> <INCHI_KEY>
KSKIGSUQYGWNAK-ZZXKWVIFSA-N

> <FORMULA>
C17H12O6

> <MOLECULAR_WEIGHT>
312.277

> <EXACT_MASS>
312.063388106

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
31.533718201622282

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-[2-(3,4-dihydroxyphenyl)-7-hydroxy-1-benzofuran-4-yl]prop-2-enoic acid

> <ALOGPS_LOGP>
2.87

> <JCHEM_LOGP>
2.9517401813333333

> <ALOGPS_LOGS>
-3.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.589392613658352

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8551642751675996

> <JCHEM_PKA_STRONGEST_BASIC>
-2.962439633352974

> <JCHEM_POLAR_SURFACE_AREA>
111.13000000000001

> <JCHEM_REFRACTIVITY>
82.8574

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.38e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-[2-(3,4-dihydroxyphenyl)-7-hydroxy-1-benzofuran-4-yl]prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.924   5.923   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       2.126   4.089   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   1.597   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.320   2.843   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.090   1.509   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.630   1.509   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.400   2.843   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.630   4.177   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.090   4.177   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.940   2.843   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -3.400   0.175   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.924  -0.237   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.590  -1.007   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.590  -2.547   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.924  -3.317   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.257  -3.317   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9    4                                                       
CONECT   11    9   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17   14                                                            
CONECT   18   13                                                            
CONECT   19    3   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Value	Source
TOURNEFOLate a	Generator
7-Hydroxy-2-(3,4-dihydroxyphenyl)-4-(1E-propenoyl-3-Oic acid)benofuran	MeSH

Chemical Formula

C₁₇H₁₂O₆

Average Mass

312.2770 Da

Monoisotopic Mass

312.06339 Da

IUPAC Name

(2E)-3-[2-(3,4-dihydroxyphenyl)-7-hydroxy-1-benzofuran-4-yl]prop-2-enoic acid

Traditional Name

(2E)-3-[2-(3,4-dihydroxyphenyl)-7-hydroxy-1-benzofuran-4-yl]prop-2-enoic acid

CAS Registry Number

Not Available

SMILES

OC(=O)\C=C\C1=C2C=C(OC2=C(O)C=C1)C1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C17H12O6/c18-12-4-2-10(7-14(12)20)15-8-11-9(3-6-16(21)22)1-5-13(19)17(11)23-15/h1-8,18-20H,(H,21,22)/b6-3+

InChI Key

KSKIGSUQYGWNAK-ZZXKWVIFSA-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
Tournefortia sarmentosa	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
Coumaric acid or derivatives
Coumaric acid
Cinnamic acid or derivatives
Cinnamic acid
Benzofuran
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Furan
Heteroaromatic compound
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	2.87	ALOGPS
logP	2.95	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	3.86	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	111.13 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	82.86 m³·mol⁻¹	ChemAxon
Polarizability	31.53 Å³	ChemAxon
Number of Rings	3	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

C00046468

Chemspider ID

8578660

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10403222

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hsieh JF, Lin WJ, Huang KF, Liao JH, Don MJ, Shen CC, Shiao YJ, Li WT: Antioxidant activity and inhibition of alpha-glucosidase by hydroxyl-functionalized 2-arylbenzo[b]furans. Eur J Med Chem. 2015 Mar 26;93:443-51. doi: 10.1016/j.ejmech.2015.02.024. Epub 2015 Feb 16. [PubMed:25728025 ]

Showing NP-Card for Tournefolic acid A (NP0080920)

MOL for NP0080920 (Tournefolic acid A)

3D MOL for NP0080920 (Tournefolic acid A)

3D SDF for NP0080920 (Tournefolic acid A)

3D-SDF for NP0080920 (Tournefolic acid A)

PDB for NP0080920 (Tournefolic acid A)

3D PDB for NP0080920 (Tournefolic acid A)

SMILES for NP0080920 (Tournefolic acid A)

INCHI for NP0080920 (Tournefolic acid A)

Structure for NP0080920 (Tournefolic acid A)

3D Structure for NP0080920 (Tournefolic acid A)