NP-MRD: Showing NP-Card for (2s,3s)-4-[(1e)-3-[(1r)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid (NP0315884)

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Record Information

Version

2.0

Created at

2022-09-11 14:44:15 UTC

Updated at

2022-09-11 14:44:15 UTC

NP-MRD ID

NP0315884

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3s)-4-[(1e)-3-[(1r)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid

Description

(2S,3S)-4-[(1E)-3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. (2s,3s)-4-[(1e)-3-[(1r)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid is found in Lithospermum erythrorhizon. These are phenylpropanoids containing the 2-phenylbenzofuran moiety (2S,3S)-4-[(1E)-3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

6441498
  Mrv0541 02271202152D          

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M  END

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M  END

6441498
  Mrv0541 02271202152D          

 39 42  0  0  1  0            999 V2000
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 25 29  2  0  0  0  0
 26 28  2  0  0  0  0
 27 28  1  0  0  0  0
 29 32  1  0  0  0  0
 30 31  1  0  0  0  0
 30 35  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 36  1  0  0  0  0
 34 37  1  0  0  0  0
 36 38  2  0  0  0  0
 37 39  2  0  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0315884

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)[C@@H](CC1=CC(O)=C(O)C=C1)OC(=O)\C=C\C1=C2[C@@H]([C@H](OC2=C(O)C=C1)C1=CC(O)=C(O)C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H22O12/c28-15-5-1-12(9-18(15)31)10-20(26(34)35)38-21(33)8-4-13-2-7-17(30)25-22(13)23(27(36)37)24(39-25)14-3-6-16(29)19(32)11-14/h1-9,11,20,23-24,28-32H,10H2,(H,34,35)(H,36,37)/b8-4+/t20-,23+,24-/m1/s1

> <INCHI_KEY>
UJZQBMQZMKFSRV-RGKBJLTCSA-N

> <FORMULA>
C27H22O12

> <MOLECULAR_WEIGHT>
538.4564

> <EXACT_MASS>
538.111126168

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
52.02282582882846

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S)-4-[(1E)-3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid

> <ALOGPS_LOGP>
3.58

> <JCHEM_LOGP>
3.745670360666667

> <ALOGPS_LOGS>
-4.41

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.5260959383237664

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.8912268468586144

> <JCHEM_PKA_STRONGEST_BASIC>
-5.107138389221203

> <JCHEM_POLAR_SURFACE_AREA>
211.27999999999997

> <JCHEM_REFRACTIVITY>
133.0725

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.10e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S)-4-[(1E)-3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 6441498                                           
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  O   UNK     0      11.206  -7.014   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      13.191  -2.754   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       8.415  -8.855   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      10.656  -1.926   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      16.725  -8.442   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       5.747   0.385   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      18.265  -5.775   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       8.415   0.385   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       7.081   4.235   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       8.415   1.925   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       7.081   7.315   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       4.414   8.855   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      11.206  -4.536   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.105  -5.775   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.748  -5.005   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.748  -6.545   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.645  -5.775   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.415  -4.235   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.684  -3.072   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.415  -7.315   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.081  -5.005   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.415  -7.109   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.415  -4.442   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.081  -6.545   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.415  -2.695   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      15.955  -7.109   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.955  -4.442   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      16.725  -5.775   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.081  -1.925   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.747   1.925   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.414   2.695   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.081  -0.385   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.414   4.235   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.747   5.005   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.081   2.695   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.080   5.005   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.747   6.545   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       3.080   6.545   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.414   7.315   0.000  0.00  0.00           C+0
CONECT    1   14   16                                                       
CONECT    2   19                                                            
CONECT    3   20                                                            
CONECT    4   19                                                            
CONECT    5   26                                                            
CONECT    6   30   32                                                       
CONECT    7   28                                                            
CONECT    8   32                                                            
CONECT    9   35                                                            
CONECT   10   35                                                            
CONECT   11   37                                                            
CONECT   12   39                                                            
CONECT   13   14   15   19                                                  
CONECT   14    1   13   17                                                  
CONECT   15   13   16   18                                                  
CONECT   16    1   15   20                                                  
CONECT   17   14   22   23                                                  
CONECT   18   15   21   25                                                  
CONECT   19    2    4   13                                                  
CONECT   20    3   16   24                                                  
CONECT   21   18   24                                                       
CONECT   22   17   26                                                       
CONECT   23   17   27                                                       
CONECT   24   20   21                                                       
CONECT   25   18   29                                                       
CONECT   26    5   22   28                                                  
CONECT   27   23   28                                                       
CONECT   28    7   26   27                                                  
CONECT   29   25   32                                                       
CONECT   30    6   31   35                                                  
CONECT   31   30   33                                                       
CONECT   32    6    8   29                                                  
CONECT   33   31   34   36                                                  
CONECT   34   33   37                                                       
CONECT   35    9   10   30                                                  
CONECT   36   33   38                                                       
CONECT   37   11   34   39                                                  
CONECT   38   36   39                                                       
CONECT   39   12   37   38                                                  
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Value	Source
(2S,3S)-4-[(1E)-3-[(1R)-1-Carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylate	Generator
Lithospermate	Generator
4-(3-(1-Carboxy-2-(3,4-dihydroxyphenyl)ethoxy)-3-oxo-1-propenyl)-2-(3,4-dihydroxyphenyl)-2,3-dihydro-7-hydroxy-3-benzofurancarboxylic acid	MeSH
Monardic acid a	MeSH

Chemical Formula

C₂₇H₂₂O₁₂

Average Mass

538.4564 Da

Monoisotopic Mass

538.11113 Da

IUPAC Name

(2S,3S)-4-[(1E)-3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid

Traditional Name

(2S,3S)-4-[(1E)-3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC(=O)[C@@H](CC1=CC(O)=C(O)C=C1)OC(=O)\C=C\C1=C2[C@@H]([C@H](OC2=C(O)C=C1)C1=CC(O)=C(O)C=C1)C(O)=O

InChI Identifier

InChI=1S/C27H22O12/c28-15-5-1-12(9-18(15)31)10-20(26(34)35)38-21(33)8-4-13-2-7-17(30)25-22(13)23(27(36)37)24(39-25)14-3-6-16(29)19(32)11-14/h1-9,11,20,23-24,28-32H,10H2,(H,34,35)(H,36,37)/b8-4+/t20-,23+,24-/m1/s1

InChI Key

UJZQBMQZMKFSRV-RGKBJLTCSA-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
Lithospermum erythrorhizon	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
Coumaric acid or derivatives
3-phenylpropanoic-acid
Tricarboxylic acid or derivatives
Coumaran
Catechol
Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acid ester
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Ether
Carboxylic acid
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Organic oxygen compound
Organic oxide
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	3.58	ALOGPS
logP	3.75	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	2.89	ChemAxon
pKa (Strongest Basic)	-5.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	211.28 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	133.07 m³·mol⁻¹	ChemAxon
Polarizability	52.02 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

6441498

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3s)-4-[(1e)-3-[(1r)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid (NP0315884)

MOL for NP0315884 ((2s,3s)-4-[(1e)-3-[(1r)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid)

3D MOL for NP0315884 ((2s,3s)-4-[(1e)-3-[(1r)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid)

3D SDF for NP0315884 ((2s,3s)-4-[(1e)-3-[(1r)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid)

3D-SDF for NP0315884 ((2s,3s)-4-[(1e)-3-[(1r)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid)

PDB for NP0315884 ((2s,3s)-4-[(1e)-3-[(1r)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid)

3D PDB for NP0315884 ((2s,3s)-4-[(1e)-3-[(1r)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid)

SMILES for NP0315884 ((2s,3s)-4-[(1e)-3-[(1r)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid)

INCHI for NP0315884 ((2s,3s)-4-[(1e)-3-[(1r)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid)

Structure for NP0315884 ((2s,3s)-4-[(1e)-3-[(1r)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid)

3D Structure for NP0315884 ((2s,3s)-4-[(1e)-3-[(1r)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid)