NP-MRD: Showing NP-Card for methyl 3,5-dihydroxy-2-(2-hydroxyethyl)-7-methyl-4-oxo-2h-furo[2,3-b]chromene-3-carboxylate (NP0188588)

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Record Information

Version

2.0

Created at

2022-09-04 04:56:50 UTC

Updated at

2022-09-04 04:56:50 UTC

NP-MRD ID

NP0188588

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 3,5-dihydroxy-2-(2-hydroxyethyl)-7-methyl-4-oxo-2h-furo[2,3-b]chromene-3-carboxylate

Description

Methyl 3,5-dihydroxy-2-(2-hydroxyethyl)-7-methyl-4-oxo-2H,3H,4H-furo[2,3-b]chromene-3-carboxylate belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). Methyl 3,5-dihydroxy-2-(2-hydroxyethyl)-7-methyl-4-oxo-2H,3H,4H-furo[2,3-b]chromene-3-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004231514132D          

 24 26  0  0  0  0            999 V2000
    5.7859   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0714   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3069   -1.0086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1274    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9524    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3649    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1899    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425    1.0799    0.0000 O   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
    2.8579    0.0000    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
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   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
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   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
   -0.7145    1.2375    0.0000 C   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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   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  1  0  0  0  0
  5  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
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 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  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  0  0  0  0
 12 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0188588

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1(O)C(CCO)OC2=C1C(=O)C1=C(O)C=C(C)C=C1O2

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O8/c1-7-5-8(18)11-9(6-7)23-14-12(13(11)19)16(21,15(20)22-2)10(24-14)3-4-17/h5-6,10,17-18,21H,3-4H2,1-2H3

> <INCHI_KEY>
NOVKWPGSOIBVFB-UHFFFAOYSA-N

> <FORMULA>
C16H16O8

> <MOLECULAR_WEIGHT>
336.296

> <EXACT_MASS>
336.084517475

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
33.14799577951396

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 3,5-dihydroxy-2-(2-hydroxyethyl)-7-methyl-4-oxo-2H,3H,4H-furo[2,3-b]chromene-3-carboxylate

> <ALOGPS_LOGP>
0.77

> <JCHEM_LOGP>
1.0628163533333335

> <ALOGPS_LOGS>
-2.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.534403612370104

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.406621134776145

> <JCHEM_PKA_STRONGEST_BASIC>
-2.4129171269312923

> <JCHEM_POLAR_SURFACE_AREA>
122.52000000000001

> <JCHEM_REFRACTIVITY>
89.8943

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.99e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 3,5-dihydroxy-2-(2-hydroxyethyl)-7-methyl-4-oxo-2H-furo[2,3-b]chromene-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0      10.800  -1.246   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.467  -0.476   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.133  -1.246   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.133  -2.786   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.799  -0.476   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.173  -1.883   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       7.705   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.245   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.015   2.104   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      11.555   2.104   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       6.799   2.016   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7   13                                             
CONECT    6    5                                                            
CONECT    7    5    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    7   12                                                       
CONECT   12   11   13   24                                                  
CONECT   13   12    5   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   23                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   16   24                                                  
CONECT   24   23   12                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
Methyl 3,5-dihydroxy-2-(2-hydroxyethyl)-7-methyl-4-oxo-2H,3H,4H-furo[2,3-b]chromene-3-carboxylic acid	Generator

Chemical Formula

C₁₆H₁₆O₈

Average Mass

336.2960 Da

Monoisotopic Mass

336.08452 Da

IUPAC Name

methyl 3,5-dihydroxy-2-(2-hydroxyethyl)-7-methyl-4-oxo-2H,3H,4H-furo[2,3-b]chromene-3-carboxylate

Traditional Name

methyl 3,5-dihydroxy-2-(2-hydroxyethyl)-7-methyl-4-oxo-2H-furo[2,3-b]chromene-3-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1(O)C(CCO)OC2=C1C(=O)C1=C(O)C=C(C)C=C1O2

InChI Identifier

InChI=1S/C16H16O8/c1-7-5-8(18)11-9(6-7)23-14-12(13(11)19)16(21,15(20)22-2)10(24-14)3-4-17/h5-6,10,17-18,21H,3-4H2,1-2H3

InChI Key

NOVKWPGSOIBVFB-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Not Available

Direct Parent

Coumarins and derivatives

Alternative Parents

Substituents

Chromone
Coumarin
Benzopyran
1-benzopyran
Furopyran
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Benzenoid
Pyran
Methyl ester
Heteroaromatic compound
Tertiary alcohol
Vinylogous ester
Vinylogous acid
Furan
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Ether
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organooxygen compound
Alcohol
Primary alcohol
Carbonyl group
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	0.77	ALOGPS
logP	1.06	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	7.41	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	122.52 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	89.89 m³·mol⁻¹	ChemAxon
Polarizability	33.15 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	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 3,5-dihydroxy-2-(2-hydroxyethyl)-7-methyl-4-oxo-2h-furo[2,3-b]chromene-3-carboxylate (NP0188588)

MOL for NP0188588 (methyl 3,5-dihydroxy-2-(2-hydroxyethyl)-7-methyl-4-oxo-2h-furo[2,3-b]chromene-3-carboxylate)

3D MOL for NP0188588 (methyl 3,5-dihydroxy-2-(2-hydroxyethyl)-7-methyl-4-oxo-2h-furo[2,3-b]chromene-3-carboxylate)

3D SDF for NP0188588 (methyl 3,5-dihydroxy-2-(2-hydroxyethyl)-7-methyl-4-oxo-2h-furo[2,3-b]chromene-3-carboxylate)

3D-SDF for NP0188588 (methyl 3,5-dihydroxy-2-(2-hydroxyethyl)-7-methyl-4-oxo-2h-furo[2,3-b]chromene-3-carboxylate)

PDB for NP0188588 (methyl 3,5-dihydroxy-2-(2-hydroxyethyl)-7-methyl-4-oxo-2h-furo[2,3-b]chromene-3-carboxylate)

3D PDB for NP0188588 (methyl 3,5-dihydroxy-2-(2-hydroxyethyl)-7-methyl-4-oxo-2h-furo[2,3-b]chromene-3-carboxylate)

SMILES for NP0188588 (methyl 3,5-dihydroxy-2-(2-hydroxyethyl)-7-methyl-4-oxo-2h-furo[2,3-b]chromene-3-carboxylate)

INCHI for NP0188588 (methyl 3,5-dihydroxy-2-(2-hydroxyethyl)-7-methyl-4-oxo-2h-furo[2,3-b]chromene-3-carboxylate)

Structure for NP0188588 (methyl 3,5-dihydroxy-2-(2-hydroxyethyl)-7-methyl-4-oxo-2h-furo[2,3-b]chromene-3-carboxylate)

3D Structure for NP0188588 (methyl 3,5-dihydroxy-2-(2-hydroxyethyl)-7-methyl-4-oxo-2h-furo[2,3-b]chromene-3-carboxylate)