NP-MRD: Showing NP-Card for (3r)-5-bromo-8-hydroxy-3-methyl-3,4-dihydro-2-benzopyran-1-one (NP0280668)

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Record Information

Version

2.0

Created at

2022-09-09 06:35:29 UTC

Updated at

2022-09-09 06:35:29 UTC

NP-MRD ID

NP0280668

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r)-5-bromo-8-hydroxy-3-methyl-3,4-dihydro-2-benzopyran-1-one

Description

(R)-(-)-5-bromomellein 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)-5-bromo-8-hydroxy-3-methyl-3,4-dihydro-2-benzopyran-1-one is found in Aspergillus ochraceus. Based on a literature review very few articles have been published on (R)-(-)-5-bromomellein.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309092208352D          

 14 15  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 Br  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
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  2 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0280668

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H9BrO3/c1-5-4-6-7(11)2-3-8(12)9(6)10(13)14-5/h2-3,5,12H,4H2,1H3/t5-/m1/s1

> <INCHI_KEY>
OAKDFQHJDRFNMW-RXMQYKEDSA-N

> <FORMULA>
C10H9BrO3

> <MOLECULAR_WEIGHT>
257.083

> <EXACT_MASS>
255.973507

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
21.329344390749327

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
3.348373614666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.212433062565442

> <JCHEM_PKA_STRONGEST_BASIC>
-4.603170260472122

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
55.415400000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-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 Br   UNK     0       5.335   1.540   0.000  0.00  0.00          Br+0
HETATM    7  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    4   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    2                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₀H₉BrO₃

Average Mass

257.0830 Da

Monoisotopic Mass

255.97351 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C10H9BrO3/c1-5-4-6-7(11)2-3-8(12)9(6)10(13)14-5/h2-3,5,12H,4H2,1H3/t5-/m1/s1

InChI Key

OAKDFQHJDRFNMW-RXMQYKEDSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aspergillus ochraceus	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
4-halophenol
4-bromophenol
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aryl halide
Aryl bromide
Benzenoid
Vinylogous acid
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Organobromide
Organohalogen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
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

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

29215596

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71623280

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r)-5-bromo-8-hydroxy-3-methyl-3,4-dihydro-2-benzopyran-1-one (NP0280668)

MOL for NP0280668 ((3r)-5-bromo-8-hydroxy-3-methyl-3,4-dihydro-2-benzopyran-1-one)

3D MOL for NP0280668 ((3r)-5-bromo-8-hydroxy-3-methyl-3,4-dihydro-2-benzopyran-1-one)

3D SDF for NP0280668 ((3r)-5-bromo-8-hydroxy-3-methyl-3,4-dihydro-2-benzopyran-1-one)

3D-SDF for NP0280668 ((3r)-5-bromo-8-hydroxy-3-methyl-3,4-dihydro-2-benzopyran-1-one)

PDB for NP0280668 ((3r)-5-bromo-8-hydroxy-3-methyl-3,4-dihydro-2-benzopyran-1-one)

3D PDB for NP0280668 ((3r)-5-bromo-8-hydroxy-3-methyl-3,4-dihydro-2-benzopyran-1-one)

SMILES for NP0280668 ((3r)-5-bromo-8-hydroxy-3-methyl-3,4-dihydro-2-benzopyran-1-one)

INCHI for NP0280668 ((3r)-5-bromo-8-hydroxy-3-methyl-3,4-dihydro-2-benzopyran-1-one)

Structure for NP0280668 ((3r)-5-bromo-8-hydroxy-3-methyl-3,4-dihydro-2-benzopyran-1-one)

3D Structure for NP0280668 ((3r)-5-bromo-8-hydroxy-3-methyl-3,4-dihydro-2-benzopyran-1-one)