NP-MRD: Showing NP-Card for methyl 5-hydroxy-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-4h,4ah,5h,7h,7ah-furo[3,4-b]pyran-3-carboxylate (NP0207030)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-05 03:28:57 UTC

Updated at

2022-09-05 03:28:57 UTC

NP-MRD ID

NP0207030

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 5-hydroxy-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-4h,4ah,5h,7h,7ah-furo[3,4-b]pyran-3-carboxylate

Description

Methyl 5-hydroxy-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-4H,4aH,5H,7H,7aH-furo[3,4-b]pyran-3-carboxylate belongs to the class of organic compounds known as tyrosols and derivatives. Tyrosols and derivatives are compounds containing a hydroxyethyl group attached to the C4 carbon of a phenol group. methyl 5-hydroxy-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-4h,4ah,5h,7h,7ah-furo[3,4-b]pyran-3-carboxylate is found in Ligustrum vulgare. Based on a literature review very few articles have been published on methyl 5-hydroxy-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-4H,4aH,5H,7H,7aH-furo[3,4-b]pyran-3-carboxylate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052205292D          

 27 29  0  0  0  0            999 V2000
    2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   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
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6131   -0.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2775    0.4807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5429    0.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0950    1.0076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3428   -1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 21 27  1  0  0  0  0
M  END


  Mrv1652309052205292D          

 27 29  0  0  0  0            999 V2000
    2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   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
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6131   -0.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2775    0.4807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5429    0.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0950    1.0076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3428   -1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 21 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0207030

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=COC2COC(O)C2C1CC(=O)OCCC1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H22O8/c1-24-18(22)14-9-26-15-10-27-19(23)17(15)13(14)8-16(21)25-7-6-11-2-4-12(20)5-3-11/h2-5,9,13,15,17,19-20,23H,6-8,10H2,1H3

> <INCHI_KEY>
DWZAHHHTINRSFL-UHFFFAOYSA-N

> <FORMULA>
C19H22O8

> <MOLECULAR_WEIGHT>
378.377

> <EXACT_MASS>
378.131467668

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
37.891287951536114

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 5-hydroxy-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-4H,4aH,5H,7H,7aH-furo[3,4-b]pyran-3-carboxylate

> <JCHEM_LOGP>
1.310152241

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.080554053731777

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.502588736423693

> <JCHEM_PKA_STRONGEST_BASIC>
-4.076269651659197

> <JCHEM_POLAR_SURFACE_AREA>
111.52000000000001

> <JCHEM_REFRACTIVITY>
92.52550000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl 5-hydroxy-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-4H,4aH,5H,7H,7aH-furo[3,4-b]pyran-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       5.335  -6.160   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.144  -0.510   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.518   0.897   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.013   0.736   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.044   1.881   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.240  -2.786   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.669  -1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.337  -1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      14.670  -3.850   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      12.003  -3.850   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    8   14                                                  
CONECT   14   13    5   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   21                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Value	Source
Methyl 5-hydroxy-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-4H,4ah,5H,7H,7ah-furo[3,4-b]pyran-3-carboxylic acid	Generator

Chemical Formula

C₁₉H₂₂O₈

Average Mass

378.3770 Da

Monoisotopic Mass

378.13147 Da

IUPAC Name

methyl 5-hydroxy-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-4H,4aH,5H,7H,7aH-furo[3,4-b]pyran-3-carboxylate

Traditional Name

methyl 5-hydroxy-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-4H,4aH,5H,7H,7aH-furo[3,4-b]pyran-3-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=COC2COC(O)C2C1CC(=O)OCCC1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C19H22O8/c1-24-18(22)14-9-26-15-10-27-19(23)17(15)13(14)8-16(21)25-7-6-11-2-4-12(20)5-3-11/h2-5,9,13,15,17,19-20,23H,6-8,10H2,1H3

InChI Key

DWZAHHHTINRSFL-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ligustrum vulgare	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tyrosols and derivatives. Tyrosols and derivatives are compounds containing a hydroxyethyl group attached to the C4 carbon of a phenol group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

Tyrosols and derivatives

Direct Parent

Tyrosols and derivatives

Alternative Parents

Substituents

Tyrosol derivative
Furopyran
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Pyran
Furan
Tetrahydrofuran
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous ester
Hemiacetal
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	1.31	ChemAxon
pKa (Strongest Acidic)	9.5	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	111.52 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	92.53 m³·mol⁻¹	ChemAxon
Polarizability	37.89 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

163189641

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 5-hydroxy-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-4h,4ah,5h,7h,7ah-furo[3,4-b]pyran-3-carboxylate (NP0207030)

MOL for NP0207030 (methyl 5-hydroxy-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-4h,4ah,5h,7h,7ah-furo[3,4-b]pyran-3-carboxylate)

3D MOL for NP0207030 (methyl 5-hydroxy-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-4h,4ah,5h,7h,7ah-furo[3,4-b]pyran-3-carboxylate)

3D SDF for NP0207030 (methyl 5-hydroxy-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-4h,4ah,5h,7h,7ah-furo[3,4-b]pyran-3-carboxylate)

3D-SDF for NP0207030 (methyl 5-hydroxy-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-4h,4ah,5h,7h,7ah-furo[3,4-b]pyran-3-carboxylate)

PDB for NP0207030 (methyl 5-hydroxy-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-4h,4ah,5h,7h,7ah-furo[3,4-b]pyran-3-carboxylate)

3D PDB for NP0207030 (methyl 5-hydroxy-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-4h,4ah,5h,7h,7ah-furo[3,4-b]pyran-3-carboxylate)

SMILES for NP0207030 (methyl 5-hydroxy-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-4h,4ah,5h,7h,7ah-furo[3,4-b]pyran-3-carboxylate)

INCHI for NP0207030 (methyl 5-hydroxy-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-4h,4ah,5h,7h,7ah-furo[3,4-b]pyran-3-carboxylate)

Structure for NP0207030 (methyl 5-hydroxy-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-4h,4ah,5h,7h,7ah-furo[3,4-b]pyran-3-carboxylate)

3D Structure for NP0207030 (methyl 5-hydroxy-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-4h,4ah,5h,7h,7ah-furo[3,4-b]pyran-3-carboxylate)