NP-MRD: Showing NP-Card for 4-methoxy-8,8-dimethyl-2h-[1,3]dioxolo[4,5-h]chromene (NP0249511)

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Record Information

Version

2.0

Created at

2022-09-07 12:05:05 UTC

Updated at

2022-09-07 12:05:05 UTC

NP-MRD ID

NP0249511

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-methoxy-8,8-dimethyl-2h-[1,3]dioxolo[4,5-h]chromene

Description

4-Methoxy-8,8-dimethyl-2H,8H-[1,3]dioxolo[4,5-h]chromene 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. 4-methoxy-8,8-dimethyl-2h-[1,3]dioxolo[4,5-h]chromene is found in Myriactis humilis. 4-Methoxy-8,8-dimethyl-2H,8H-[1,3]dioxolo[4,5-h]chromene is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004231519022D          

 17 19  0  0  0  0            999 V2000
    2.1072    1.2272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9318    1.2530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3664    0.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1910    0.5775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6256   -0.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4502   -0.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8849   -0.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4949   -1.5262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2785   -1.7841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3771   -2.3428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6703   -1.5520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2357   -0.8508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4111   -0.8765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8784   -1.5066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1147   -1.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1752   -0.3719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9765   -0.1753    0.0000 C   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  3 17  1  0  0  0  0
 13 17  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0249511

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(OC(C)(C)C=C2)C2=C1OCO2

> <INCHI_IDENTIFIER>
InChI=1S/C13H14O4/c1-13(2)5-4-8-6-9(14-3)11-12(10(8)17-13)16-7-15-11/h4-6H,7H2,1-3H3

> <INCHI_KEY>
GCYOSVGQZCADOK-UHFFFAOYSA-N

> <FORMULA>
C13H14O4

> <MOLECULAR_WEIGHT>
234.251

> <EXACT_MASS>
234.089208931

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
24.423886285901247

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-methoxy-8,8-dimethyl-2H,8H-[1,3]dioxolo[4,5-h]chromene

> <ALOGPS_LOGP>
2.62

> <JCHEM_LOGP>
2.3394314199999995

> <ALOGPS_LOGS>
-2.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.4149236450823945

> <JCHEM_POLAR_SURFACE_AREA>
36.92

> <JCHEM_REFRACTIVITY>
62.68150000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-methoxy-8,8-dimethyl-2H-[1,3]dioxolo[4,5-h]chromene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       3.934   2.291   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.473   2.339   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.284   1.030   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.823   1.078   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.635  -0.231   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.174  -0.183   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.985  -1.492   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.257  -2.849   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.720  -3.330   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.037  -4.373   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.718  -2.897   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.907  -1.588   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.367  -1.636   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.373  -2.812   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.947  -2.230   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.060  -0.694   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.556  -0.327   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12                                                       
CONECT   12   11    5   13                                                  
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    3   13                                                  
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₄O₄

Average Mass

234.2510 Da

Monoisotopic Mass

234.08921 Da

IUPAC Name

4-methoxy-8,8-dimethyl-2H,8H-[1,3]dioxolo[4,5-h]chromene

Traditional Name

4-methoxy-8,8-dimethyl-2H-[1,3]dioxolo[4,5-h]chromene

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(OC(C)(C)C=C2)C2=C1OCO2

InChI Identifier

InChI=1S/C13H14O4/c1-13(2)5-4-8-6-9(14-3)11-12(10(8)17-13)16-7-15-11/h4-6H,7H2,1-3H3

InChI Key

GCYOSVGQZCADOK-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Myriactis humilis	LOTUS Database	35616633

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
Benzodioxole
Anisole
Alkyl aryl ether
Benzenoid
Oxacycle
Ether
Acetal
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	2.62	ALOGPS
logP	2.34	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	36.92 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	62.68 m³·mol⁻¹	ChemAxon
Polarizability	24.42 Å³	ChemAxon
Number of Rings	3	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

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

11564904

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-methoxy-8,8-dimethyl-2h-[1,3]dioxolo[4,5-h]chromene (NP0249511)

MOL for NP0249511 (4-methoxy-8,8-dimethyl-2h-[1,3]dioxolo[4,5-h]chromene)

3D MOL for NP0249511 (4-methoxy-8,8-dimethyl-2h-[1,3]dioxolo[4,5-h]chromene)

3D SDF for NP0249511 (4-methoxy-8,8-dimethyl-2h-[1,3]dioxolo[4,5-h]chromene)

3D-SDF for NP0249511 (4-methoxy-8,8-dimethyl-2h-[1,3]dioxolo[4,5-h]chromene)

PDB for NP0249511 (4-methoxy-8,8-dimethyl-2h-[1,3]dioxolo[4,5-h]chromene)

3D PDB for NP0249511 (4-methoxy-8,8-dimethyl-2h-[1,3]dioxolo[4,5-h]chromene)

SMILES for NP0249511 (4-methoxy-8,8-dimethyl-2h-[1,3]dioxolo[4,5-h]chromene)

INCHI for NP0249511 (4-methoxy-8,8-dimethyl-2h-[1,3]dioxolo[4,5-h]chromene)

Structure for NP0249511 (4-methoxy-8,8-dimethyl-2h-[1,3]dioxolo[4,5-h]chromene)

3D Structure for NP0249511 (4-methoxy-8,8-dimethyl-2h-[1,3]dioxolo[4,5-h]chromene)