NP-MRD: Showing NP-Card for 4-hydroxy-4-methyl-5-oxooxolan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate (NP0228209)

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Record Information

Version

2.0

Created at

2022-09-06 07:46:20 UTC

Updated at

2022-09-06 07:46:20 UTC

NP-MRD ID

NP0228209

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-hydroxy-4-methyl-5-oxooxolan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate

Description

4-Hydroxy-4-methyl-5-oxooxolan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate 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. 4-hydroxy-4-methyl-5-oxooxolan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate is found in Bidens pilosa. 4-Hydroxy-4-methyl-5-oxooxolan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 36  0  0  0  0  0  0  0  0999 V2000
   -3.9174   -0.5550   -1.7622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8034   -0.3897   -0.2834 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3059   -1.5667    0.2683 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0971   -0.1085    0.3842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2048   -0.6044    0.0860 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8948    0.7994    1.4038 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4937    1.1107    1.4942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9948    0.8163    0.1271 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6276    0.6625   -0.0021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7910    1.4058   -0.8038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3083    2.3112   -1.4861 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6578    1.1587   -0.8681 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2368    0.2302   -0.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6484   -0.0256   -0.2273 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4810    0.7159   -1.0264 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8565    0.4532   -1.0632 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4158   -0.5550   -0.3005 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7834   -0.7940   -0.3562 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5865   -1.3015    0.5022 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1712   -2.3116    1.2616 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2467   -1.0318    0.5262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9262   -0.3812   -2.2270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2130   -1.6198   -1.9722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7083    0.1088   -2.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9955   -2.0576    0.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4001    2.1833    1.7863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0940    0.4503    2.2811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3115    1.6589   -0.5395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2202    1.7914   -1.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6356   -0.4060    0.4865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1417    1.5179   -1.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4546    1.0621   -1.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3647   -0.2263   -0.9572 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5761   -2.8738    1.8607 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6108   -1.6279    1.1621 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  1
  2  8  1  0
  8  7  1  0
  7  6  1  0
  6  4  1  0
  4  5  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  2  0
  4  2  1  0
 21 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  8 28  1  6
  7 26  1  0
  7 27  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 18 33  1  0
 20 34  1  0
 21 35  1  0
M  END


  Mrv1533004171512172D          

 21 22  0  0  0  0            999 V2000
    2.6954   -3.0994    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
    1.5914   -3.0994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8109   -4.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559   -4.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -4.9820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4760   -4.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6914   -3.9425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5955   -3.9425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7670   -3.1355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1539   -2.5835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5516   -2.8806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7231   -2.0736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5078   -1.8187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6793   -1.0117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4639   -0.7568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0770   -1.3088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8616   -1.0538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9055   -2.1158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5186   -2.6678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1209   -2.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12 10  1  4  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 14 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0228209

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(O)C(COC1=O)OC(=O)C=CC1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H14O7/c1-14(19)11(7-20-13(14)18)21-12(17)5-3-8-2-4-9(15)10(16)6-8/h2-6,11,15-16,19H,7H2,1H3

> <INCHI_KEY>
OPURFTKJCNDEDB-UHFFFAOYSA-N

> <FORMULA>
C14H14O7

> <MOLECULAR_WEIGHT>
294.259

> <EXACT_MASS>
294.073952791

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
27.873277340122314

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-4-methyl-5-oxooxolan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
1.38

> <JCHEM_LOGP>
1.3749226586666667

> <ALOGPS_LOGS>
-2.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.521793356200464

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.20665815091748

> <JCHEM_PKA_STRONGEST_BASIC>
-4.3050143536720435

> <JCHEM_POLAR_SURFACE_AREA>
113.29000000000002

> <JCHEM_REFRACTIVITY>
71.09660000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.80e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-4-methyl-5-oxooxolan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       5.031  -5.786   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.971  -5.786   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       5.247  -7.835   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.771  -9.300   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.231  -9.300   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.755  -7.835   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.291  -7.359   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       6.712  -7.359   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.032  -5.853   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.887  -4.822   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.496  -5.377   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.817  -3.871   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.281  -3.395   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.601  -1.888   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.066  -1.413   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.210  -2.443   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      14.675  -1.967   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      12.890  -3.949   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      14.035  -4.980   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      11.426  -4.425   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    7                                             
CONECT    3    2                                                            
CONECT    4    2    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7                                                            
CONECT    9    4   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   14                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Value	Source
4-Hydroxy-4-methyl-5-oxooxolan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₁₄H₁₄O₇

Average Mass

294.2590 Da

Monoisotopic Mass

294.07395 Da

IUPAC Name

4-hydroxy-4-methyl-5-oxooxolan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

4-hydroxy-4-methyl-5-oxooxolan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

CC1(O)C(COC1=O)OC(=O)C=CC1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C14H14O7/c1-14(19)11(7-20-13(14)18)21-12(17)5-3-8-2-4-9(15)10(16)6-8/h2-6,11,15-16,19H,7H2,1H3

InChI Key

OPURFTKJCNDEDB-UHFFFAOYSA-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
Bidens pilosa	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
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Fatty acyl
Dicarboxylic acid or derivatives
Benzenoid
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Organic oxygen compound
Alcohol
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	1.38	ALOGPS
logP	1.37	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	71.1 m³·mol⁻¹	ChemAxon
Polarizability	27.87 Å³	ChemAxon
Number of Rings	2	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

85405748

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-hydroxy-4-methyl-5-oxooxolan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate (NP0228209)

MOL for NP0228209 (4-hydroxy-4-methyl-5-oxooxolan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D MOL for NP0228209 (4-hydroxy-4-methyl-5-oxooxolan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D SDF for NP0228209 (4-hydroxy-4-methyl-5-oxooxolan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D-SDF for NP0228209 (4-hydroxy-4-methyl-5-oxooxolan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate)

PDB for NP0228209 (4-hydroxy-4-methyl-5-oxooxolan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D PDB for NP0228209 (4-hydroxy-4-methyl-5-oxooxolan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate)

SMILES for NP0228209 (4-hydroxy-4-methyl-5-oxooxolan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate)

INCHI for NP0228209 (4-hydroxy-4-methyl-5-oxooxolan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate)

Structure for NP0228209 (4-hydroxy-4-methyl-5-oxooxolan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D Structure for NP0228209 (4-hydroxy-4-methyl-5-oxooxolan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate)