NP-MRD: Showing NP-Card for (1r,2s)-1-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}propane-1,2,3-tricarboxylic acid (NP0245338)

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Record Information

Version

2.0

Created at

2022-09-07 06:23:00 UTC

Updated at

2022-09-07 06:23:00 UTC

NP-MRD ID

NP0245338

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s)-1-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}propane-1,2,3-tricarboxylic acid

Description

(1r,2s)-1-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}propane-1,2,3-tricarboxylic acid is found in Ananas comosus. Based on a literature review very few articles have been published on ZINC13536425.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 38  0  0  0  0  0  0  0  0999 V2000
   -2.6042    0.3538   -2.7566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4581   -0.1357   -1.6025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2642   -0.7823   -1.3514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5520    0.0250   -0.6607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3243   -0.3004    0.7564 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5946   -0.3339    1.4936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7625    0.3292    2.5284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6639   -1.1183    1.0562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2943    0.4685    1.5022 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9680    0.3231    0.9761 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0455   -0.2477    1.7098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2731   -0.6394    2.8686 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3998   -0.3955    1.1936 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7649    0.0109    0.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1038   -0.1139   -0.5594 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1489   -0.6929    0.1248 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4286   -0.8120   -0.4243 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6882   -0.3414   -1.6991 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9383   -0.4335   -2.2933 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6415    0.2344   -2.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3799    0.3516   -1.8322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5282    1.9133    1.5835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5808    2.6917    1.2167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6712    2.5557    2.0169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9192   -1.5450   -1.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3803   -0.6617   -1.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0205    1.0452   -0.8116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9665   -1.3899    0.7789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6272   -0.8322    1.1539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2643    0.0610    2.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1506   -0.8654    1.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0072    0.4883   -0.6150 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0195   -1.0845    1.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2498   -1.2655    0.1102 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6665    0.2390   -2.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8323    0.6092   -3.3796 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5656    0.8093   -2.3803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3134    2.9801    1.3822 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  1  0
  5  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
  9 22  1  0
 22 24  1  0
 22 23  2  0
  5  6  1  0
  6  8  1  0
  6  7  2  0
 21 15  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  6
  9 30  1  1
 13 31  1  0
 14 32  1  0
 16 33  1  0
 17 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
 24 38  1  0
  8 29  1  0
M  END


  Mrv1652309072208232D          

 24 24  0  0  1  0            999 V2000
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -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
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    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
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 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
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 15 21  1  0  0  0  0
  9 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0245338

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O9/c16-9-4-1-8(2-5-9)3-6-12(19)24-13(15(22)23)10(14(20)21)7-11(17)18/h1-6,10,13,16H,7H2,(H,17,18)(H,20,21)(H,22,23)/b6-3+/t10-,13+/m0/s1

> <INCHI_KEY>
LRJBKCVWTWKWRX-JLBMVGGZSA-N

> <FORMULA>
C15H14O9

> <MOLECULAR_WEIGHT>
338.268

> <EXACT_MASS>
338.063782031

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
31.070710336940856

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S)-1-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}propane-1,2,3-tricarboxylic acid

> <JCHEM_LOGP>
1.2839971466666664

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
4.705628761839802

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.204346688743764

> <JCHEM_PKA_STRONGEST_BASIC>
-5.954733364493795

> <JCHEM_POLAR_SURFACE_AREA>
158.43

> <JCHEM_REFRACTIVITY>
77.26469999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S)-1-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}propane-1,2,3-tricarboxylic 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       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.001 -11.550   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.002 -12.320   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       5.335 -12.320   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       9.336 -10.010   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.004  -9.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.338 -10.010   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.338 -11.550   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      18.672 -12.320   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      16.004 -12.320   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5   10   22                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   15                                                       
CONECT   22    9   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₄O₉

Average Mass

338.2680 Da

Monoisotopic Mass

338.06378 Da

IUPAC Name

(1R,2S)-1-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}propane-1,2,3-tricarboxylic acid

Traditional Name

(1R,2S)-1-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}propane-1,2,3-tricarboxylic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H14O9/c16-9-4-1-8(2-5-9)3-6-12(19)24-13(15(22)23)10(14(20)21)7-11(17)18/h1-6,10,13,16H,7H2,(H,17,18)(H,20,21)(H,22,23)/b6-3+/t10-,13+/m0/s1

InChI Key

LRJBKCVWTWKWRX-JLBMVGGZSA-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
Ananas comosus	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	1.28	ChemAxon
pKa (Strongest Acidic)	3.2	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	158.43 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	77.26 m³·mol⁻¹	ChemAxon
Polarizability	31.07 Å³	ChemAxon
Number of Rings	1	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

124351363

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s)-1-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}propane-1,2,3-tricarboxylic acid (NP0245338)

MOL for NP0245338 ((1r,2s)-1-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}propane-1,2,3-tricarboxylic acid)

3D MOL for NP0245338 ((1r,2s)-1-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}propane-1,2,3-tricarboxylic acid)

3D SDF for NP0245338 ((1r,2s)-1-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}propane-1,2,3-tricarboxylic acid)

3D-SDF for NP0245338 ((1r,2s)-1-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}propane-1,2,3-tricarboxylic acid)

PDB for NP0245338 ((1r,2s)-1-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}propane-1,2,3-tricarboxylic acid)

3D PDB for NP0245338 ((1r,2s)-1-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}propane-1,2,3-tricarboxylic acid)

SMILES for NP0245338 ((1r,2s)-1-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}propane-1,2,3-tricarboxylic acid)

INCHI for NP0245338 ((1r,2s)-1-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}propane-1,2,3-tricarboxylic acid)

Structure for NP0245338 ((1r,2s)-1-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}propane-1,2,3-tricarboxylic acid)

3D Structure for NP0245338 ((1r,2s)-1-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}propane-1,2,3-tricarboxylic acid)