NP-MRD: Showing NP-Card for 8-chloro-6,7-dihydroxy-5-methoxy-2,2-dimethyl-5,6,7,8-tetrahydro-3h-1-benzopyran-4-one (NP0225174)

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Record Information

Version

2.0

Created at

2022-09-06 03:49:12 UTC

Updated at

2022-09-06 03:49:13 UTC

NP-MRD ID

NP0225174

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-chloro-6,7-dihydroxy-5-methoxy-2,2-dimethyl-5,6,7,8-tetrahydro-3h-1-benzopyran-4-one

Description

8-Chloro-6,7-dihydroxy-5-methoxy-2,2-dimethyl-3,4,5,6,7,8-hexahydro-2H-1-benzopyran-4-one belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. Based on a literature review very few articles have been published on 8-chloro-6,7-dihydroxy-5-methoxy-2,2-dimethyl-3,4,5,6,7,8-hexahydro-2H-1-benzopyran-4-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062205492D          

 18 19  0  0  0  0            999 V2000
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   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
    2.4256    0.3627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9559   -0.5558    0.0000 C   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
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 Cl  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   -0.0000    0.0000 O   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   -1.6500    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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  2  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
  3 17  1  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0225174

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1C(O)C(O)C(Cl)C2=C1C(=O)CC(C)(C)O2

> <INCHI_IDENTIFIER>
InChI=1S/C12H17ClO5/c1-12(2)4-5(14)6-10(18-12)7(13)8(15)9(16)11(6)17-3/h7-9,11,15-16H,4H2,1-3H3

> <INCHI_KEY>
DEZSZDHQEFMIGP-UHFFFAOYSA-N

> <FORMULA>
C12H17ClO5

> <MOLECULAR_WEIGHT>
276.71

> <EXACT_MASS>
276.0764513

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
26.852675067686917

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-chloro-6,7-dihydroxy-5-methoxy-2,2-dimethyl-3,4,5,6,7,8-hexahydro-2H-1-benzopyran-4-one

> <JCHEM_LOGP>
-0.1542523993333338

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.13513133100734

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.702896984187802

> <JCHEM_PKA_STRONGEST_BASIC>
-3.641464166741522

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
65.3619

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
8-chloro-6,7-dihydroxy-5-methoxy-2,2-dimethyl-5,6,7,8-tetrahydro-3H-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.528   0.677   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.518  -1.037   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   14 Cl   UNK     0       0.000   1.540   0.000  0.00  0.00          Cl+0
HETATM   15  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11                                                       
CONECT   11   10    4   12                                                  
CONECT   12   11                                                            
CONECT   13    5   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    3   18                                                  
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₁₇ClO₅

Average Mass

276.7100 Da

Monoisotopic Mass

276.07645 Da

IUPAC Name

8-chloro-6,7-dihydroxy-5-methoxy-2,2-dimethyl-3,4,5,6,7,8-hexahydro-2H-1-benzopyran-4-one

Traditional Name

8-chloro-6,7-dihydroxy-5-methoxy-2,2-dimethyl-5,6,7,8-tetrahydro-3H-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

COC1C(O)C(O)C(Cl)C2=C1C(=O)CC(C)(C)O2

InChI Identifier

InChI=1S/C12H17ClO5/c1-12(2)4-5(14)6-10(18-12)7(13)8(15)9(16)11(6)17-3/h7-9,11,15-16H,4H2,1-3H3

InChI Key

DEZSZDHQEFMIGP-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 benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

Not Available

Direct Parent

Benzopyrans

Alternative Parents

Substituents

Benzopyran
Dihydropyranone
Cyclitol or derivatives
Vinylogous ester
1,2-diol
Chlorohydrin
Secondary alcohol
Halohydrin
Ketone
Oxacycle
Dialkyl ether
Ether
Organooxygen compound
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Alkyl halide
Alkyl chloride
Organochloride
Organohalogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	-0.15	ChemAxon
pKa (Strongest Acidic)	12.7	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	65.36 m³·mol⁻¹	ChemAxon
Polarizability	26.85 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

162866986

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 8-chloro-6,7-dihydroxy-5-methoxy-2,2-dimethyl-5,6,7,8-tetrahydro-3h-1-benzopyran-4-one (NP0225174)

MOL for NP0225174 (8-chloro-6,7-dihydroxy-5-methoxy-2,2-dimethyl-5,6,7,8-tetrahydro-3h-1-benzopyran-4-one)

3D MOL for NP0225174 (8-chloro-6,7-dihydroxy-5-methoxy-2,2-dimethyl-5,6,7,8-tetrahydro-3h-1-benzopyran-4-one)

3D SDF for NP0225174 (8-chloro-6,7-dihydroxy-5-methoxy-2,2-dimethyl-5,6,7,8-tetrahydro-3h-1-benzopyran-4-one)

3D-SDF for NP0225174 (8-chloro-6,7-dihydroxy-5-methoxy-2,2-dimethyl-5,6,7,8-tetrahydro-3h-1-benzopyran-4-one)

PDB for NP0225174 (8-chloro-6,7-dihydroxy-5-methoxy-2,2-dimethyl-5,6,7,8-tetrahydro-3h-1-benzopyran-4-one)

3D PDB for NP0225174 (8-chloro-6,7-dihydroxy-5-methoxy-2,2-dimethyl-5,6,7,8-tetrahydro-3h-1-benzopyran-4-one)

SMILES for NP0225174 (8-chloro-6,7-dihydroxy-5-methoxy-2,2-dimethyl-5,6,7,8-tetrahydro-3h-1-benzopyran-4-one)

INCHI for NP0225174 (8-chloro-6,7-dihydroxy-5-methoxy-2,2-dimethyl-5,6,7,8-tetrahydro-3h-1-benzopyran-4-one)

Structure for NP0225174 (8-chloro-6,7-dihydroxy-5-methoxy-2,2-dimethyl-5,6,7,8-tetrahydro-3h-1-benzopyran-4-one)

3D Structure for NP0225174 (8-chloro-6,7-dihydroxy-5-methoxy-2,2-dimethyl-5,6,7,8-tetrahydro-3h-1-benzopyran-4-one)