NP-MRD: Showing NP-Card for (S)-(+)-1-(p-Hydroxy-trans-cinnamoyl)-glycerol (NP0047161)

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Record Information

Version

2.0

Created at

2022-03-17 20:35:38 UTC

Updated at

2022-03-17 20:35:38 UTC

NP-MRD ID

NP0047161

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(S)-(+)-1-(p-Hydroxy-trans-cinnamoyl)-glycerol

Description

(S)-(+)-1-(p-Hydroxy-trans-cinnamoyl)-glycerol is found in Greigia sphacelata and Populus euphratica.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241212512D          

 18 18  0  0  0  0            999 V2000
   -0.2946    0.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0091    0.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0091   -0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2946   -0.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4198   -0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4198    0.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7236   -0.7366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1343    0.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9593    0.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5427    1.4968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3677    1.4968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5427    2.3218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1927    1.4968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0177    1.4968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0177    2.3218    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0177    0.6718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8427    1.4968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2552    0.7823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  3  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  6  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047161

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C(O)(CO)COC(=O)\C=C\C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H14O5/c13-7-11(15)8-17-12(16)6-3-9-1-4-10(14)5-2-9/h1-6,11,13-15H,7-8H2/b6-3+

> <INCHI_KEY>
YUQSZTOOHLGKGG-ZZXKWVIFSA-N

> <FORMULA>
C12H14O5

> <MOLECULAR_WEIGHT>
238.2366

> <EXACT_MASS>
238.084123558

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
24.376264672362147

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.51

> <JCHEM_LOGP>
0.8913113736666671

> <ALOGPS_LOGS>
-2.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.618717314068764

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.398618185660007

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9686917101118624

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
62.06470000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.23e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.550   1.705   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.884   0.935   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.884  -0.605   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.550  -1.375   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.784  -0.605   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.784   0.935   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.217  -1.375   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.117   1.705   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.657   1.705   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.746   2.794   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.286   2.794   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       4.746   4.334   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.826   2.794   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.366   2.794   0.000  0.00  0.00           C+0
HETATM   15  H   UNK     0       9.366   4.334   0.000  0.00  0.00           H+0
HETATM   16  O   UNK     0       9.366   1.254   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      10.906   2.794   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      11.676   1.460   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    8                                                  
CONECT    7    3                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10   13                                                       
CONECT   12   10                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14   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

C₁₂H₁₄O₅

Average Mass

238.2366 Da

Monoisotopic Mass

238.08412 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

[H]C(O)(CO)COC(=O)\C=C\C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C12H14O5/c13-7-11(15)8-17-12(16)6-3-9-1-4-10(14)5-2-9/h1-6,11,13-15H,7-8H2/b6-3+

InChI Key

YUQSZTOOHLGKGG-ZZXKWVIFSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Greigia sphacelata	Plant	KNApSAcK
Populus euphratica	LOTUS Database	35616633
Zea mays L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acid esters

Alternative Parents

Substituents

Coumaric acid ester
Coumaric acid or derivatives
Cinnamic acid ester
1-acyl-sn-glycerol
Monoradylglycerol
Styrene
Monoacylglycerol
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Glycerolipid
Phenol
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
1,2-diol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Alcohol
Organooxygen compound
Primary alcohol
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	0.51	ALOGPS
logP	0.89	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	9.4	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	62.06 m³·mol⁻¹	ChemAxon
Polarizability	24.38 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

FDB007616

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

5319874

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (S)-(+)-1-(p-Hydroxy-trans-cinnamoyl)-glycerol (NP0047161)

MOL for NP0047161 ((S)-(+)-1-(p-Hydroxy-trans-cinnamoyl)-glycerol)

3D MOL for NP0047161 ((S)-(+)-1-(p-Hydroxy-trans-cinnamoyl)-glycerol)

3D SDF for NP0047161 ((S)-(+)-1-(p-Hydroxy-trans-cinnamoyl)-glycerol)

3D-SDF for NP0047161 ((S)-(+)-1-(p-Hydroxy-trans-cinnamoyl)-glycerol)

PDB for NP0047161 ((S)-(+)-1-(p-Hydroxy-trans-cinnamoyl)-glycerol)

3D PDB for NP0047161 ((S)-(+)-1-(p-Hydroxy-trans-cinnamoyl)-glycerol)

SMILES for NP0047161 ((S)-(+)-1-(p-Hydroxy-trans-cinnamoyl)-glycerol)

INCHI for NP0047161 ((S)-(+)-1-(p-Hydroxy-trans-cinnamoyl)-glycerol)

Structure for NP0047161 ((S)-(+)-1-(p-Hydroxy-trans-cinnamoyl)-glycerol)

3D Structure for NP0047161 ((S)-(+)-1-(p-Hydroxy-trans-cinnamoyl)-glycerol)