NP-MRD: Showing NP-Card for (3r)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carbaldehyde (NP0207580)

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Record Information

Version

2.0

Created at

2022-09-05 04:14:57 UTC

Updated at

2022-09-05 04:14:57 UTC

NP-MRD ID

NP0207580

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carbaldehyde

Description

CHEMBL450534 belongs to the class of organic compounds known as 2-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position. (3r)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carbaldehyde is found in Brucea javanica, Picea glauca and Theobroma grandiflorum. Based on a literature review very few articles have been published on CHEMBL450534.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052206142D          

 15 16  0  0  1  0            999 V2000
    0.0000    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  2  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
    2.1434   -0.4125    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
    2.8579    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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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
    2.1434   -1.2375    0.0000 C   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
    1.4289   -2.4750    0.0000 O   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
  2  1  1  6  0  0  0
  2  3  1  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
  6  7  2  0  0  0  0
  5  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
  4 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  2 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0207580

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC2=C(C=O)C=CC(O)=C2C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C11H10O4/c1-6-4-8-7(5-12)2-3-9(13)10(8)11(14)15-6/h2-3,5-6,13H,4H2,1H3/t6-/m1/s1

> <INCHI_KEY>
PTNGWSBREHHWFF-ZCFIWIBFSA-N

> <FORMULA>
C11H10O4

> <MOLECULAR_WEIGHT>
206.197

> <EXACT_MASS>
206.057908802

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
20.14085379718351

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-5-carbaldehyde

> <JCHEM_LOGP>
2.2921233340000002

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.512733405708455

> <JCHEM_PKA_STRONGEST_BASIC>
-5.761767226455029

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
54.37660000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carbaldehyde

> <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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   12                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    4   13                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    2                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₀O₄

Average Mass

206.1970 Da

Monoisotopic Mass

206.05791 Da

IUPAC Name

(3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-5-carbaldehyde

Traditional Name

(3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carbaldehyde

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC2=C(C=O)C=CC(O)=C2C(=O)O1

InChI Identifier

InChI=1S/C11H10O4/c1-6-4-8-7(5-12)2-3-9(13)10(8)11(14)15-6/h2-3,5-6,13H,4H2,1H3/t6-/m1/s1

InChI Key

PTNGWSBREHHWFF-ZCFIWIBFSA-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
Brucea javanica	LOTUS Database	35616633
Picea glauca	LOTUS Database	35616633
Theobroma grandiflorum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

2-benzopyrans

Direct Parent

2-benzopyrans

Alternative Parents

Substituents

2-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aryl-aldehyde
Benzenoid
Vinylogous acid
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Organic oxide
Organic oxygen compound
Organooxygen compound
Aldehyde
Hydrocarbon derivative
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	2.29	ChemAxon
pKa (Strongest Acidic)	7.51	ChemAxon
pKa (Strongest Basic)	-5.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	54.38 m³·mol⁻¹	ChemAxon
Polarizability	20.14 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

24688857

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44577733

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carbaldehyde (NP0207580)

MOL for NP0207580 ((3r)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carbaldehyde)

3D MOL for NP0207580 ((3r)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carbaldehyde)

3D SDF for NP0207580 ((3r)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carbaldehyde)

3D-SDF for NP0207580 ((3r)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carbaldehyde)

PDB for NP0207580 ((3r)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carbaldehyde)

3D PDB for NP0207580 ((3r)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carbaldehyde)

SMILES for NP0207580 ((3r)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carbaldehyde)

INCHI for NP0207580 ((3r)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carbaldehyde)

Structure for NP0207580 ((3r)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carbaldehyde)

3D Structure for NP0207580 ((3r)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carbaldehyde)