NP-MRD: Showing NP-Card for [(1s,3r,4s)-6,8-dihydroxy-3,4,5-trimethyl-3,4-dihydro-1h-2-benzopyran-1-yl]acetic acid (NP0304499)

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Record Information

Version

1.0

Created at

2022-09-10 19:38:05 UTC

Updated at

2022-09-10 19:38:05 UTC

NP-MRD ID

NP0304499

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1s,3r,4s)-6,8-dihydroxy-3,4,5-trimethyl-3,4-dihydro-1h-2-benzopyran-1-yl]acetic acid

Description

2-[(1S,3R,4S)-6,8-dihydroxy-3,4,5-trimethyl-3,4-dihydro-1H-2-benzopyran-1-yl]acetic acid 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. Based on a literature review very few articles have been published on 2-[(1S,3R,4S)-6,8-dihydroxy-3,4,5-trimethyl-3,4-dihydro-1H-2-benzopyran-1-yl]acetic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309102221382D          

 19 20  0  0  1  0            999 V2000
    0.0000    0.8250    0.0000 C   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
   -0.7145   -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
    0.0000   -1.6500    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
    0.7145   -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 C   0  0  2  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  1  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
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   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
  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  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0304499

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1O[C@@H](CC(O)=O)C2=C([C@@H]1C)C(C)=C(O)C=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C14H18O5/c1-6-8(3)19-11(5-12(17)18)14-10(16)4-9(15)7(2)13(6)14/h4,6,8,11,15-16H,5H2,1-3H3,(H,17,18)/t6-,8-,11+/m1/s1

> <INCHI_KEY>
MVYNCALKQXJGNE-HLEGCSNESA-N

> <FORMULA>
C14H18O5

> <MOLECULAR_WEIGHT>
266.293

> <EXACT_MASS>
266.11542368

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
27.239098023139626

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1S,3R,4S)-6,8-dihydroxy-3,4,5-trimethyl-3,4-dihydro-1H-2-benzopyran-1-yl]acetic acid

> <JCHEM_LOGP>
2.3515127703333336

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.382306133208276

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.02265928422851

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2046794957032

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
69.28229999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,3R,4S)-6,8-dihydroxy-3,4,5-trimethyl-3,4-dihydro-1H-2-benzopyran-1-yl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -0.000   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      -2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   15                                                  
CONECT    9    8    2   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14    8   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Value	Source
2-[(1S,3R,4S)-6,8-Dihydroxy-3,4,5-trimethyl-3,4-dihydro-1H-2-benzopyran-1-yl]acetate	Generator

Chemical Formula

C₁₄H₁₈O₅

Average Mass

266.2930 Da

Monoisotopic Mass

266.11542 Da

IUPAC Name

2-[(1S,3R,4S)-6,8-dihydroxy-3,4,5-trimethyl-3,4-dihydro-1H-2-benzopyran-1-yl]acetic acid

Traditional Name

[(1S,3R,4S)-6,8-dihydroxy-3,4,5-trimethyl-3,4-dihydro-1H-2-benzopyran-1-yl]acetic acid

CAS Registry Number

Not Available

SMILES

C[C@H]1O[C@@H](CC(O)=O)C2=C([C@@H]1C)C(C)=C(O)C=C2O

InChI Identifier

InChI=1S/C14H18O5/c1-6-8(3)19-11(5-12(17)18)14-10(16)4-9(15)7(2)13(6)14/h4,6,8,11,15-16H,5H2,1-3H3,(H,17,18)/t6-,8-,11+/m1/s1

InChI Key

MVYNCALKQXJGNE-HLEGCSNESA-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-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
Benzenoid
Oxacycle
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	2.35	ChemAxon
pKa (Strongest Acidic)	4.02	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	69.28 m³·mol⁻¹	ChemAxon
Polarizability	27.24 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

71048815

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

146683967

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(1s,3r,4s)-6,8-dihydroxy-3,4,5-trimethyl-3,4-dihydro-1h-2-benzopyran-1-yl]acetic acid (NP0304499)

MOL for NP0304499 ([(1s,3r,4s)-6,8-dihydroxy-3,4,5-trimethyl-3,4-dihydro-1h-2-benzopyran-1-yl]acetic acid)

3D MOL for NP0304499 ([(1s,3r,4s)-6,8-dihydroxy-3,4,5-trimethyl-3,4-dihydro-1h-2-benzopyran-1-yl]acetic acid)

3D SDF for NP0304499 ([(1s,3r,4s)-6,8-dihydroxy-3,4,5-trimethyl-3,4-dihydro-1h-2-benzopyran-1-yl]acetic acid)

3D-SDF for NP0304499 ([(1s,3r,4s)-6,8-dihydroxy-3,4,5-trimethyl-3,4-dihydro-1h-2-benzopyran-1-yl]acetic acid)

PDB for NP0304499 ([(1s,3r,4s)-6,8-dihydroxy-3,4,5-trimethyl-3,4-dihydro-1h-2-benzopyran-1-yl]acetic acid)

3D PDB for NP0304499 ([(1s,3r,4s)-6,8-dihydroxy-3,4,5-trimethyl-3,4-dihydro-1h-2-benzopyran-1-yl]acetic acid)

SMILES for NP0304499 ([(1s,3r,4s)-6,8-dihydroxy-3,4,5-trimethyl-3,4-dihydro-1h-2-benzopyran-1-yl]acetic acid)

INCHI for NP0304499 ([(1s,3r,4s)-6,8-dihydroxy-3,4,5-trimethyl-3,4-dihydro-1h-2-benzopyran-1-yl]acetic acid)

Structure for NP0304499 ([(1s,3r,4s)-6,8-dihydroxy-3,4,5-trimethyl-3,4-dihydro-1h-2-benzopyran-1-yl]acetic acid)

3D Structure for NP0304499 ([(1s,3r,4s)-6,8-dihydroxy-3,4,5-trimethyl-3,4-dihydro-1h-2-benzopyran-1-yl]acetic acid)