NP-MRD: Showing NP-Card for 3,6,8-trihydroxy-3,5,7-trimethyl-4h-2-benzopyran-1-one (NP0190457)

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Record Information

Version

2.0

Created at

2022-09-04 07:07:43 UTC

Updated at

2022-09-04 07:07:43 UTC

NP-MRD ID

NP0190457

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,6,8-trihydroxy-3,5,7-trimethyl-4h-2-benzopyran-1-one

Description

Sclerotinin B belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 3,6,8-trihydroxy-3,5,7-trimethyl-4h-2-benzopyran-1-one is found in Penicillium citrinum. Sclerotinin B is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004191523582D          

 17 18  0  0  0  0            999 V2000
    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
    0.0000    0.0000    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
    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    0.0000    0.0000 C   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
    3.8545    0.3627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3848   -0.5558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  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
  9 11  1  0  0  0  0
  9 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
  7 15  1  0  0  0  0
 15 16  2  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0190457

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(O)C(C)=C2CC(C)(O)OC(=O)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C12H14O5/c1-5-7-4-12(3,16)17-11(15)8(7)10(14)6(2)9(5)13/h13-14,16H,4H2,1-3H3

> <INCHI_KEY>
GWCJDGBOQAPHGT-UHFFFAOYSA-N

> <FORMULA>
C12H14O5

> <MOLECULAR_WEIGHT>
238.239

> <EXACT_MASS>
238.084123551

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
23.688996731086817

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,6,8-trihydroxy-3,5,7-trimethyl-3,4-dihydro-1H-2-benzopyran-1-one

> <ALOGPS_LOGP>
0.89

> <JCHEM_LOGP>
2.541460739666667

> <ALOGPS_LOGS>
-1.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.000001057504539

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.234127760471111

> <JCHEM_PKA_STRONGEST_BASIC>
-3.939489506230781

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
61.59920000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.57e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,6,8-trihydroxy-3,5,7-trimethyl-4H-2-benzopyran-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.195   0.677   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.185  -1.037   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    7   16                                                  
CONECT   16   15    2   17                                                  
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₁₄O₅

Average Mass

238.2390 Da

Monoisotopic Mass

238.08412 Da

IUPAC Name

3,6,8-trihydroxy-3,5,7-trimethyl-3,4-dihydro-1H-2-benzopyran-1-one

Traditional Name

3,6,8-trihydroxy-3,5,7-trimethyl-4H-2-benzopyran-1-one

CAS Registry Number

Not Available

SMILES

CC1=C(O)C(C)=C2CC(C)(O)OC(=O)C2=C1O

InChI Identifier

InChI=1S/C12H14O5/c1-5-7-4-12(3,16)17-11(15)8(7)10(14)6(2)9(5)13/h13-14,16H,4H2,1-3H3

InChI Key

GWCJDGBOQAPHGT-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Penicillium citrinum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Hydroxybenzoic acid derivatives

Alternative Parents

Substituents

Dihydroxybenzoic acid
Benzopyran
Isochromane
2-benzopyran
Vinylogous acid
Carboxylic acid ester
Hemiacetal
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
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
logP	0.89	ALOGPS
logP	2.54	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	9.23	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	61.6 m³·mol⁻¹	ChemAxon
Polarizability	23.69 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

12315415

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,6,8-trihydroxy-3,5,7-trimethyl-4h-2-benzopyran-1-one (NP0190457)

MOL for NP0190457 (3,6,8-trihydroxy-3,5,7-trimethyl-4h-2-benzopyran-1-one)

3D MOL for NP0190457 (3,6,8-trihydroxy-3,5,7-trimethyl-4h-2-benzopyran-1-one)

3D SDF for NP0190457 (3,6,8-trihydroxy-3,5,7-trimethyl-4h-2-benzopyran-1-one)

3D-SDF for NP0190457 (3,6,8-trihydroxy-3,5,7-trimethyl-4h-2-benzopyran-1-one)

PDB for NP0190457 (3,6,8-trihydroxy-3,5,7-trimethyl-4h-2-benzopyran-1-one)

3D PDB for NP0190457 (3,6,8-trihydroxy-3,5,7-trimethyl-4h-2-benzopyran-1-one)

SMILES for NP0190457 (3,6,8-trihydroxy-3,5,7-trimethyl-4h-2-benzopyran-1-one)

INCHI for NP0190457 (3,6,8-trihydroxy-3,5,7-trimethyl-4h-2-benzopyran-1-one)

Structure for NP0190457 (3,6,8-trihydroxy-3,5,7-trimethyl-4h-2-benzopyran-1-one)

3D Structure for NP0190457 (3,6,8-trihydroxy-3,5,7-trimethyl-4h-2-benzopyran-1-one)