NP-MRD: Showing NP-Card for Salvianolic acid I (NP0075756)

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Record Information

Version

2.0

Created at

2022-04-28 20:59:46 UTC

Updated at

2022-04-28 20:59:46 UTC

NP-MRD ID

NP0075756

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Salvianolic acid I

Description

2-{4-[(1E)-3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3-(3,4-dihydroxyphenyl)prop-2-enoic acid belongs to the class of organic compounds known as phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid. Salvianolic acid I is found in Salvia cavaleriei and Salvia officinalis . Based on a literature review very few articles have been published on 2-{4-[(1E)-3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3-(3,4-dihydroxyphenyl)prop-2-enoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282222592D          

 39 41  0  0  1  0            999 V2000
    8.5737   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.2881   -7.8375    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
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  3 38  1  0  0  0  0
  2 39  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282222592D          

 39 41  0  0  1  0            999 V2000
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  2 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0075756

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H22O12/c28-17-5-1-15(10-19(17)30)12-23(26(34)35)38-22-7-3-14(9-21(22)32)4-8-25(33)39-24(27(36)37)13-16-2-6-18(29)20(31)11-16/h1-12,24,28-32H,13H2,(H,34,35)(H,36,37)/b8-4+,23-12+/t24-/m1/s1

> <INCHI_KEY>
MZSGWZGPESCJAN-MOBFUUNNSA-N

> <FORMULA>
C27H22O12

> <MOLECULAR_WEIGHT>
538.461

> <EXACT_MASS>
538.111126148

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
51.63775369141022

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-2-{4-[(1E)-3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3-(3,4-dihydroxyphenyl)prop-2-enoic acid

> <ALOGPS_LOGP>
4.02

> <JCHEM_LOGP>
4.148596226666665

> <ALOGPS_LOGS>
-4.95

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.1759479963353527

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.2808362913859304

> <JCHEM_PKA_STRONGEST_BASIC>
-5.147684883799841

> <JCHEM_POLAR_SURFACE_AREA>
211.27999999999997

> <JCHEM_REFRACTIVITY>
136.16020000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.01e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-2-{4-[(1E)-3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3-(3,4-dihydroxyphenyl)prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      16.004 -12.320   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.004 -13.860   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.670 -14.630   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.337 -13.860   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.337 -12.320   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.003 -11.550   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      10.669  -9.240   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      12.003  -6.930   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      13.337  -7.700   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      14.670 -10.010   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      14.670 -16.170   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      17.338 -14.630   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   39                                                  
CONECT    3    2    4   38                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   35                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   34                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20   17   21                                                       
CONECT   21   20   22   31                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27   23                                                       
CONECT   29   26                                                            
CONECT   30   25                                                            
CONECT   31   21   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   16                                                            
CONECT   35    8   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38    3                                                            
CONECT   39    2                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   82    0
END

View in JSmol

Synonyms

Value	Source
2-{4-[(1E)-3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3-(3,4-dihydroxyphenyl)prop-2-enoate	Generator

Chemical Formula

C₂₇H₂₂O₁₂

Average Mass

538.4610 Da

Monoisotopic Mass

538.11113 Da

IUPAC Name

(2E)-2-{4-[(1E)-3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3-(3,4-dihydroxyphenyl)prop-2-enoic acid

Traditional Name

(2E)-2-{4-[(1E)-3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3-(3,4-dihydroxyphenyl)prop-2-enoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C27H22O12/c28-17-5-1-15(10-19(17)30)12-23(26(34)35)38-22-7-3-14(9-21(22)32)4-8-25(33)39-24(27(36)37)13-16-2-6-18(29)20(31)11-16/h1-12,24,28-32H,13H2,(H,34,35)(H,36,37)/b8-4+,23-12+/t24-/m1/s1

InChI Key

MZSGWZGPESCJAN-MOBFUUNNSA-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
Salvia cavaleriei	Plant	KNApSAcK
Salvia officinalis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylpyruvic acid derivatives

Direct Parent

Phenylpyruvic acid derivatives

Alternative Parents

Substituents

Cinnamic acid ester
Enol-phenylpyruvate
Hydroxycinnamic acid or derivatives
Hydroxycinnamic acid
Coumaric acid or derivatives
Cinnamic acid or derivatives
Cinnamic acid
3-phenylpropanoic-acid
Phenoxyacetate
Tricarboxylic acid or derivatives
Phenoxy compound
Styrene
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acid ester
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	4.02	ALOGPS
logP	4.15	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	2.28	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	11	ChemAxon
Refractivity	136.16 m³·mol⁻¹	ChemAxon
Polarizability	51.64 Å³	ChemAxon
Number of Rings	3	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

107447123

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162890634

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Salvianolic acid I (NP0075756)

MOL for NP0075756 (Salvianolic acid I)

3D MOL for NP0075756 (Salvianolic acid I)

3D SDF for NP0075756 (Salvianolic acid I)

3D-SDF for NP0075756 (Salvianolic acid I)

PDB for NP0075756 (Salvianolic acid I)

3D PDB for NP0075756 (Salvianolic acid I)

SMILES for NP0075756 (Salvianolic acid I)

INCHI for NP0075756 (Salvianolic acid I)

Structure for NP0075756 (Salvianolic acid I)

3D Structure for NP0075756 (Salvianolic acid I)