NP-MRD: Showing NP-Card for 2,3-dihydroxypropyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate (NP0172318)

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Record Information

Version

2.0

Created at

2022-09-03 09:12:08 UTC

Updated at

2022-09-03 09:12:09 UTC

NP-MRD ID

NP0172318

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,3-dihydroxypropyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Description

1-O-Caffeoylglycerol belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. 2,3-dihydroxypropyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate is found in Ananas comosus and Populus euphratica. Based on a literature review very few articles have been published on 1-O-Caffeoylglycerol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 32  0  0  0  0  0  0  0  0999 V2000
    1.8396   -2.4609    0.1918 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2908   -1.3688    0.3929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1316   -1.2345    0.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7925   -0.1166    0.2990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2146    0.0996    0.0457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0115   -0.9054   -0.4297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3483   -0.6941   -0.6654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8801    0.5529   -0.4147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2320    0.7934   -0.6451 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1070    1.5918    0.0654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6594    2.8492    0.3145 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7885    1.3388    0.2846 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0030   -0.3009    0.8681 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3732   -0.3508    1.1588 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2105   -0.7053   -0.0566 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5431   -0.7399    0.2850 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9943    0.3291   -1.1582 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3735    1.5920   -0.7475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7130   -2.0890   -0.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2095    0.7348    0.6812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6334   -1.8816   -0.6345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9839   -1.5109   -1.0491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8227    0.0548   -0.9957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0669    3.5748    0.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1422    2.1232    0.6611 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6316   -0.9859    2.0046 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6821    0.6956    1.4507 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9456   -1.6994   -0.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7596   -1.6569    0.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9132    0.3825   -1.4184 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5284   -0.0038   -2.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6486    1.9922   -0.1882 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17 15  1  0
 15 16  1  0
 15 14  1  0
 14 13  1  0
 13  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 12  5  1  0
 18 32  1  0
 17 30  1  0
 17 31  1  0
 15 28  1  6
 16 29  1  0
 14 26  1  0
 14 27  1  0
  3 19  1  0
  4 20  1  0
  6 21  1  0
  7 22  1  0
  9 23  1  0
 11 24  1  0
 12 25  1  0
M  END


  Mrv1652309032211122D          

 18 18  0  0  0  0            999 V2000
    1.4289   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    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
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  5 12  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0172318

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC(O)COC(=O)\C=C\C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H14O6/c13-6-9(14)7-18-12(17)4-2-8-1-3-10(15)11(16)5-8/h1-5,9,13-16H,6-7H2/b4-2+

> <INCHI_KEY>
NOHROAYVCRHDHO-DUXPYHPUSA-N

> <FORMULA>
C12H14O6

> <MOLECULAR_WEIGHT>
254.238

> <EXACT_MASS>
254.079038171

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
25.06039680998581

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,3-dihydroxypropyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
0.05

> <JCHEM_LOGP>
0.587746052

> <ALOGPS_LOGS>
-2.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.571667359475253

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.20861859947946

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9686917101118624

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
64.04560000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.13e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,3-dihydroxypropyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  O   UNK     0       2.667  -6.160   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001  -3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -5.335  -1.540   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.001  -3.850   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.336  -3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    5                                                       
CONECT   13    2   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₁₄O₆

Average Mass

254.2380 Da

Monoisotopic Mass

254.07904 Da

IUPAC Name

2,3-dihydroxypropyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

2,3-dihydroxypropyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

OCC(O)COC(=O)\C=C\C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C12H14O6/c13-6-9(14)7-18-12(17)4-2-8-1-3-10(15)11(16)5-8/h1-5,9,13-16H,6-7H2/b4-2+

InChI Key

NOHROAYVCRHDHO-DUXPYHPUSA-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
Populus euphratica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Coumaric acid or derivatives
Cinnamic acid ester
Monoacylglycerol
Styrene
Monoradylglycerol
Catechol
1-acyl-sn-glycerol
Glycerolipid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
1-hydroxy-4-unsubstituted benzenoid
Phenol
Benzenoid
Fatty acyl
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
1,2-diol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Primary alcohol
Organooxygen compound
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	0.05	ALOGPS
logP	0.59	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	64.05 m³·mol⁻¹	ChemAxon
Polarizability	25.06 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

4474881

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5315606

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,3-dihydroxypropyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate (NP0172318)

MOL for NP0172318 (2,3-dihydroxypropyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D MOL for NP0172318 (2,3-dihydroxypropyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D SDF for NP0172318 (2,3-dihydroxypropyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D-SDF for NP0172318 (2,3-dihydroxypropyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

PDB for NP0172318 (2,3-dihydroxypropyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D PDB for NP0172318 (2,3-dihydroxypropyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

SMILES for NP0172318 (2,3-dihydroxypropyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

INCHI for NP0172318 (2,3-dihydroxypropyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

Structure for NP0172318 (2,3-dihydroxypropyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D Structure for NP0172318 (2,3-dihydroxypropyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)