NP-MRD: Showing NP-Card for 2-hydroxyethyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate (NP0184852)

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Record Information

Version

1.0

Created at

2022-09-04 00:05:11 UTC

Updated at

2022-09-04 00:05:11 UTC

NP-MRD ID

NP0184852

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-hydroxyethyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate

Description

Ariscucurbin B belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid. 2-hydroxyethyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate is found in Aristolochia cucurbitifolia and Calocedrus formosana. It was first documented in 2022 (PMID: 36057430). Based on a literature review a significant number of articles have been published on Ariscucurbin B (PMID: 36057416) (PMID: 36057403) (PMID: 36057355) (PMID: 36057350).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042202052D          

 15 15  0  0  0  0            999 V2000
    0.0000   -1.6500    0.0000 O   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   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   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
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    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
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    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  2  0  0  0  0
  5 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0184852

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCCOC(=O)\C=C\C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H12O4/c12-7-8-15-11(14)6-3-9-1-4-10(13)5-2-9/h1-6,12-13H,7-8H2/b6-3+

> <INCHI_KEY>
RBPFUQFYWYCYPN-ZZXKWVIFSA-N

> <FORMULA>
C11H12O4

> <MOLECULAR_WEIGHT>
208.213

> <EXACT_MASS>
208.073558866

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
21.34386339451015

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
1.5216463156666664

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.095937865658996

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.398645721318836

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7568371589533465

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
56.10220000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    5                                                       
CONECT   12    2   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₂O₄

Average Mass

208.2130 Da

Monoisotopic Mass

208.07356 Da

IUPAC Name

2-hydroxyethyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

Traditional Name

2-hydroxyethyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

OCCOC(=O)\C=C\C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C11H12O4/c12-7-8-15-11(14)6-3-9-1-4-10(13)5-2-9/h1-6,12-13H,7-8H2/b6-3+

InChI Key

RBPFUQFYWYCYPN-ZZXKWVIFSA-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
Aristolochia cucurbitifolia	LOTUS Database	35616633
Calocedrus formosana	LOTUS Database	35616633

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
Styrene
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen 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	1.52	ChemAxon
pKa (Strongest Acidic)	9.4	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	56.1 m³·mol⁻¹	ChemAxon
Polarizability	21.34 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

8663970

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10488567

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Delahunt A, Conway MC, Callaghan SL, O'Brien EC, Geraghty AA, O'Reilly SL, McDonnell CM, Mehegan J, McAuliffe FM: Maternal dietary quality during pregnancy and child appetitive traits at 5-years-old: Findings from the ROLO longitudinal birth cohort study. Appetite. 2022 Aug 31;179:106291. doi: 10.1016/j.appet.2022.106291. [PubMed:36057430 ]
Oliveira FADS, de Holanda MV, Lima LB, Dantas MB, Duarte IO, de Castro LGZ, de Oliveira LLB, Paier CRK, Moreira-Nunes CFA, Lima NCB, Melo VMM, Montenegro RC: Genomic Surveillance: Circulating lineages and genomic variation of SARS-CoV-2 in early pandemic in Ceara state, Northeast Brazil. Virus Res. 2022 Aug 31:198908. doi: 10.1016/j.virusres.2022.198908. [PubMed:36057416 ]
Marszalek-Grabska M, Zakrocka I, Budzynska B, Marciniak S, Kaszubska K, Lemieszek MK, Winiarczyk S, Kotlinska JH, Rzeski W, Turski WA: Binge-like mephedrone treatment induces memory impairment concomitant with brain kynurenic acid reduction in mice. Toxicol Appl Pharmacol. 2022 Aug 31;454:116216. doi: 10.1016/j.taap.2022.116216. [PubMed:36057403 ]
Rajivgandhi G, Ramachandran G, Chackaravarthi G, Maruthupandy M, Quero F, Chelliah CK, Manoharan N, Alharbi NS, Kadaikunnan S, Khaled JM, Li WJ: Metal tolerance and biosorption of Pb ions by Bacillus cereus RMN 1 (MK521259) isolated from metal contaminated sites. Chemosphere. 2022 Aug 31;308(Pt 1):136270. doi: 10.1016/j.chemosphere.2022.136270. [PubMed:36057355 ]
Saravanan S, Carolin C F, Kumar PS, Chitra B, Rangasamy G: Biodegradation of textile dye Rhodamine-B by Brevundimonas diminuta and screening of their breakdown metabolites. Chemosphere. 2022 Aug 31;308(Pt 1):136266. doi: 10.1016/j.chemosphere.2022.136266. [PubMed:36057350 ]
LOTUS database [Link]

Showing NP-Card for 2-hydroxyethyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate (NP0184852)

MOL for NP0184852 (2-hydroxyethyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D MOL for NP0184852 (2-hydroxyethyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D SDF for NP0184852 (2-hydroxyethyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D-SDF for NP0184852 (2-hydroxyethyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

PDB for NP0184852 (2-hydroxyethyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D PDB for NP0184852 (2-hydroxyethyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

SMILES for NP0184852 (2-hydroxyethyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

INCHI for NP0184852 (2-hydroxyethyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

Structure for NP0184852 (2-hydroxyethyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D Structure for NP0184852 (2-hydroxyethyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)