NP-MRD: Showing NP-Card for (2s)-2-{[(2e)-3-{4-[(6,7-dihydroxy-2-oxochromen-3-yl)oxy]-3-hydroxyphenyl}prop-2-enoyl]oxy}-3-(3,4-dihydroxyphenyl)propanoic acid (NP0246529)

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Record Information

Version

2.0

Created at

2022-09-07 08:02:26 UTC

Updated at

2022-09-07 08:02:26 UTC

NP-MRD ID

NP0246529

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-{[(2e)-3-{4-[(6,7-dihydroxy-2-oxochromen-3-yl)oxy]-3-hydroxyphenyl}prop-2-enoyl]oxy}-3-(3,4-dihydroxyphenyl)propanoic acid

Description

(2S)-2-{[(2E)-3-{4-[(6,7-dihydroxy-2-oxo-2H-chromen-3-yl)oxy]-3-hydroxyphenyl}prop-2-enoyl]oxy}-3-(3,4-dihydroxyphenyl)propanoic acid belongs to the class of organic compounds known as 6,7-dihydroxycoumarins. These are coumarins bearing two hydroxyl groups at positions 6 and 7 of the coumarin skeleton, respectively. (2s)-2-{[(2e)-3-{4-[(6,7-dihydroxy-2-oxochromen-3-yl)oxy]-3-hydroxyphenyl}prop-2-enoyl]oxy}-3-(3,4-dihydroxyphenyl)propanoic acid is found in Salvia officinalis. Based on a literature review very few articles have been published on (2S)-2-{[(2E)-3-{4-[(6,7-dihydroxy-2-oxo-2H-chromen-3-yl)oxy]-3-hydroxyphenyl}prop-2-enoyl]oxy}-3-(3,4-dihydroxyphenyl)propanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072210022D          

 39 42  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309072210022D          

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 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 29 36  1  0  0  0  0
 27 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0246529

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)[C@H](CC1=CC=C(O)C(O)=C1)OC(=O)\C=C\C1=CC=C(OC2=CC3=CC(O)=C(O)C=C3OC2=O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H20O12/c28-16-4-1-14(8-17(16)29)9-23(26(34)35)38-25(33)6-3-13-2-5-21(20(32)7-13)37-24-11-15-10-18(30)19(31)12-22(15)39-27(24)36/h1-8,10-12,23,28-32H,9H2,(H,34,35)/b6-3+/t23-/m0/s1

> <INCHI_KEY>
FGLLLJUSIHHQKZ-DLMBFZKISA-N

> <FORMULA>
C27H20O12

> <MOLECULAR_WEIGHT>
536.445

> <EXACT_MASS>
536.095476084

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
50.732495218818976

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-{[(2E)-3-{4-[(6,7-dihydroxy-2-oxo-2H-chromen-3-yl)oxy]-3-hydroxyphenyl}prop-2-enoyl]oxy}-3-(3,4-dihydroxyphenyl)propanoic acid

> <JCHEM_LOGP>
4.067702915333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.678042418789909

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.097821265773732

> <JCHEM_PKA_STRONGEST_BASIC>
-5.147716068407907

> <JCHEM_POLAR_SURFACE_AREA>
200.27999999999997

> <JCHEM_REFRACTIVITY>
134.64890000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-{[(2E)-3-{4-[(6,7-dihydroxy-2-oxochromen-3-yl)oxy]-3-hydroxyphenyl}prop-2-enoyl]oxy}-3-(3,4-dihydroxyphenyl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  O   UNK     0      -8.002  -4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0     -10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -16.004  -4.620   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0     -17.338  -5.390   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0     -16.004  -3.080   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0     -17.338  -2.310   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0     -14.670  -2.310   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0     -10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0     -12.003  -5.390   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   26                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   25                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   23                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   21                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   12   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   10   22                                                  
CONECT   22   21                                                            
CONECT   23    8   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23    5                                                       
CONECT   26    2   27                                                       
CONECT   27   26   28   37                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   36                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   29                                                       
CONECT   37   27   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Value	Source
(2S)-2-{[(2E)-3-{4-[(6,7-dihydroxy-2-oxo-2H-chromen-3-yl)oxy]-3-hydroxyphenyl}prop-2-enoyl]oxy}-3-(3,4-dihydroxyphenyl)propanoate	Generator

Chemical Formula

C₂₇H₂₀O₁₂

Average Mass

536.4450 Da

Monoisotopic Mass

536.09548 Da

IUPAC Name

(2S)-2-{[(2E)-3-{4-[(6,7-dihydroxy-2-oxo-2H-chromen-3-yl)oxy]-3-hydroxyphenyl}prop-2-enoyl]oxy}-3-(3,4-dihydroxyphenyl)propanoic acid

Traditional Name

(2S)-2-{[(2E)-3-{4-[(6,7-dihydroxy-2-oxochromen-3-yl)oxy]-3-hydroxyphenyl}prop-2-enoyl]oxy}-3-(3,4-dihydroxyphenyl)propanoic acid

CAS Registry Number

Not Available

SMILES

OC(=O)[C@H](CC1=CC=C(O)C(O)=C1)OC(=O)\C=C\C1=CC=C(OC2=CC3=CC(O)=C(O)C=C3OC2=O)C(O)=C1

InChI Identifier

InChI=1S/C27H20O12/c28-16-4-1-14(8-17(16)29)9-23(26(34)35)38-25(33)6-3-13-2-5-21(20(32)7-13)37-24-11-15-10-18(30)19(31)12-22(15)39-27(24)36/h1-8,10-12,23,28-32H,9H2,(H,34,35)/b6-3+/t23-/m0/s1

InChI Key

FGLLLJUSIHHQKZ-DLMBFZKISA-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
Salvia officinalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6,7-dihydroxycoumarins. These are coumarins bearing two hydroxyl groups at positions 6 and 7 of the coumarin skeleton, respectively.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Hydroxycoumarins

Direct Parent

6,7-dihydroxycoumarins

Alternative Parents

Substituents

6,7-dihydroxycoumarin
7-hydroxycoumarin
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Diaryl ether
3-phenylpropanoic-acid
Benzopyran
1-benzopyran
Phenoxy compound
Catechol
Phenol ether
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Pyranone
Monocyclic benzene moiety
Fatty acyl
Dicarboxylic acid or derivatives
Pyran
Benzenoid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Heteroaromatic compound
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Ether
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Carbonyl group
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
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	4.07	ChemAxon
pKa (Strongest Acidic)	3.1	ChemAxon
pKa (Strongest Basic)	-5.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	200.28 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	134.65 m³·mol⁻¹	ChemAxon
Polarizability	50.73 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

71812273

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2-{[(2e)-3-{4-[(6,7-dihydroxy-2-oxochromen-3-yl)oxy]-3-hydroxyphenyl}prop-2-enoyl]oxy}-3-(3,4-dihydroxyphenyl)propanoic acid (NP0246529)

MOL for NP0246529 ((2s)-2-{[(2e)-3-{4-[(6,7-dihydroxy-2-oxochromen-3-yl)oxy]-3-hydroxyphenyl}prop-2-enoyl]oxy}-3-(3,4-dihydroxyphenyl)propanoic acid)

3D MOL for NP0246529 ((2s)-2-{[(2e)-3-{4-[(6,7-dihydroxy-2-oxochromen-3-yl)oxy]-3-hydroxyphenyl}prop-2-enoyl]oxy}-3-(3,4-dihydroxyphenyl)propanoic acid)

3D SDF for NP0246529 ((2s)-2-{[(2e)-3-{4-[(6,7-dihydroxy-2-oxochromen-3-yl)oxy]-3-hydroxyphenyl}prop-2-enoyl]oxy}-3-(3,4-dihydroxyphenyl)propanoic acid)

3D-SDF for NP0246529 ((2s)-2-{[(2e)-3-{4-[(6,7-dihydroxy-2-oxochromen-3-yl)oxy]-3-hydroxyphenyl}prop-2-enoyl]oxy}-3-(3,4-dihydroxyphenyl)propanoic acid)

PDB for NP0246529 ((2s)-2-{[(2e)-3-{4-[(6,7-dihydroxy-2-oxochromen-3-yl)oxy]-3-hydroxyphenyl}prop-2-enoyl]oxy}-3-(3,4-dihydroxyphenyl)propanoic acid)

3D PDB for NP0246529 ((2s)-2-{[(2e)-3-{4-[(6,7-dihydroxy-2-oxochromen-3-yl)oxy]-3-hydroxyphenyl}prop-2-enoyl]oxy}-3-(3,4-dihydroxyphenyl)propanoic acid)

SMILES for NP0246529 ((2s)-2-{[(2e)-3-{4-[(6,7-dihydroxy-2-oxochromen-3-yl)oxy]-3-hydroxyphenyl}prop-2-enoyl]oxy}-3-(3,4-dihydroxyphenyl)propanoic acid)

INCHI for NP0246529 ((2s)-2-{[(2e)-3-{4-[(6,7-dihydroxy-2-oxochromen-3-yl)oxy]-3-hydroxyphenyl}prop-2-enoyl]oxy}-3-(3,4-dihydroxyphenyl)propanoic acid)

Structure for NP0246529 ((2s)-2-{[(2e)-3-{4-[(6,7-dihydroxy-2-oxochromen-3-yl)oxy]-3-hydroxyphenyl}prop-2-enoyl]oxy}-3-(3,4-dihydroxyphenyl)propanoic acid)

3D Structure for NP0246529 ((2s)-2-{[(2e)-3-{4-[(6,7-dihydroxy-2-oxochromen-3-yl)oxy]-3-hydroxyphenyl}prop-2-enoyl]oxy}-3-(3,4-dihydroxyphenyl)propanoic acid)