NP-MRD: Showing NP-Card for 3,4-Dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-ol (NP0337048)

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Record Information

Version

2.0

Created at

2024-09-11 09:02:52 UTC

Updated at

2024-09-11 09:02:52 UTC

NP-MRD ID

NP0337048

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4-Dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-ol

Description

3,4-Dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-ol, also known as PMHC or 2,2,5,7,8-pentamethyl-benz[b]dihydropyran-6-ol, belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. 3,4-Dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-ol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3,4-Dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-ol has been detected, but not quantified in, fats and oils. This could make 3,4-dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-ol a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061311422D          

 16 17  0  0  0  0            999 V2000
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    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
    0.6165    0.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1468    1.6002    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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    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
    3.5724   -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
    4.2868    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   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
  7  6  1  0  0  0  0
  8  1  1  0  0  0  0
  9  2  1  0  0  0  0
  9  8  1  0  0  0  0
 10  3  1  0  0  0  0
 11  6  1  0  0  0  0
 11 10  2  0  0  0  0
 12  8  2  0  0  0  0
 12 10  1  0  0  0  0
 13  9  2  0  0  0  0
 13 11  1  0  0  0  0
 14  4  1  0  0  0  0
 14  5  1  0  0  0  0
 14  7  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 16 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0337048

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(O)C(C)=C2CCC(C)(C)OC2=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C14H20O2/c1-8-9(2)13-11(10(3)12(8)15)6-7-14(4,5)16-13/h15H,6-7H2,1-5H3

> <INCHI_KEY>
SEBPXHSZHLFWRL-UHFFFAOYSA-N

> <FORMULA>
C14H20O2

> <MOLECULAR_WEIGHT>
220.3074

> <EXACT_MASS>
220.146329884

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
25.844265682599502

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,2,5,7,8-pentamethyl-3,4-dihydro-2H-1-benzopyran-6-ol

> <ALOGPS_LOGP>
4.06

> <JCHEM_LOGP>
4.233882261

> <ALOGPS_LOGS>
-2.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.80311762365108

> <JCHEM_PKA_STRONGEST_BASIC>
-4.8512640634228195

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
66.59330000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.59e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,2,5,7,8-pentamethyl-3,4-dihydro-1-benzopyran-6-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.151   1.273   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.141   2.987   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   1.540   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       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4   14                                                            
CONECT    5   14                                                            
CONECT    6    7   11                                                       
CONECT    7    6   14                                                       
CONECT    8    1    9   12                                                  
CONECT    9    2    8   13                                                  
CONECT   10    3   11   12                                                  
CONECT   11    6   10   13                                                  
CONECT   12    8   10   15                                                  
CONECT   13    9   11   16                                                  
CONECT   14    4    5    7   16                                             
CONECT   15   12                                                            
CONECT   16   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
2,2,5,7,8-Pentamethyl-benz[b]dihydropyran-6-ol	HMDB
3,4-Dihydro-6-hydroxy-2,2,5,7,8-pentamethyl-2H-1-benzopyran	HMDB
PMHC	HMDB
PMHCR	HMDB

Chemical Formula

C₁₄H₂₀O₂

Average Mass

220.3074 Da

Monoisotopic Mass

220.14633 Da

IUPAC Name

2,2,5,7,8-pentamethyl-3,4-dihydro-2H-1-benzopyran-6-ol

Traditional Name

2,2,5,7,8-pentamethyl-3,4-dihydro-1-benzopyran-6-ol

CAS Registry Number

Not Available

SMILES

CC1=C(O)C(C)=C2CCC(C)(C)OC2=C1C

InChI Identifier

InChI=1S/C14H20O2/c1-8-9(2)13-11(10(3)12(8)15)6-7-14(4,5)16-13/h15H,6-7H2,1-5H3

InChI Key

SEBPXHSZHLFWRL-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 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

2,2-dimethyl-1-benzopyrans

Alternative Parents

Substituents

2,2-dimethyl-1-benzopyran
Alkyl aryl ether
Benzenoid
Oxacycle
Ether
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
logP	4.06	ALOGPS
logP	4.23	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	10.8	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	66.59 m³·mol⁻¹	ChemAxon
Polarizability	25.84 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0040217

DrugBank ID

DB13111

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB019929

KNApSAcK ID

Not Available

Chemspider ID

89875

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

99479

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3,4-Dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-ol (NP0337048)

MOL for NP0337048 (3,4-Dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-ol)

3D MOL for NP0337048 (3,4-Dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-ol)

3D SDF for NP0337048 (3,4-Dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-ol)

3D-SDF for NP0337048 (3,4-Dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-ol)

PDB for NP0337048 (3,4-Dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-ol)

3D PDB for NP0337048 (3,4-Dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-ol)

SMILES for NP0337048 (3,4-Dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-ol)

INCHI for NP0337048 (3,4-Dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-ol)

Structure for NP0337048 (3,4-Dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-ol)

3D Structure for NP0337048 (3,4-Dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-ol)