NP-MRD: Showing NP-Card for 2-[2-(1,3-dimethyl-2-methylidenecyclohexyl)ethyl]-8-methoxy-2-methylchromene-5,6-diol (NP0217312)

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Record Information

Version

2.0

Created at

2022-09-05 17:37:29 UTC

Updated at

2022-09-05 17:37:30 UTC

NP-MRD ID

NP0217312

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[2-(1,3-dimethyl-2-methylidenecyclohexyl)ethyl]-8-methoxy-2-methylchromene-5,6-diol

Description

2-[2-(1,3-Dimethyl-2-methylidenecyclohexyl)ethyl]-8-methoxy-2-methyl-2H-chromene-5,6-diol belongs to the class of organic compounds known as 1-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 1-position. 2-[2-(1,3-dimethyl-2-methylidenecyclohexyl)ethyl]-8-methoxy-2-methylchromene-5,6-diol is found in Dactylospongia metachromia. 2-[2-(1,3-Dimethyl-2-methylidenecyclohexyl)ethyl]-8-methoxy-2-methyl-2H-chromene-5,6-diol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004261505232D          

 26 28  0  0  0  0            999 V2000
    2.1434   -2.8875    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
    1.4289   -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 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
    2.8579    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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3848   -1.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8545   -2.0127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3242   -2.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6064   -3.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7939   -3.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3209   -3.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0353   -3.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0353   -4.2450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3209   -4.6575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3209   -5.4825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6064   -4.2450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8919   -4.6575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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  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
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 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
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  2  0  0  0  0
 12 25  1  0  0  0  0
 25 26  1  0  0  0  0
  3 26  1  0  0  0  0
  9 26  2  0  0  0  0
M  END


  Mrv1533004261505232D          

 26 28  0  0  0  0            999 V2000
    2.1434   -2.8875    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
    1.4289   -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 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
    2.8579    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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3848   -1.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8545   -2.0127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3242   -2.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6064   -3.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7939   -3.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3209   -3.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0353   -3.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0353   -4.2450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3209   -4.6575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3209   -5.4825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6064   -4.2450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8919   -4.6575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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  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
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 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
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  2  0  0  0  0
 12 25  1  0  0  0  0
 25 26  1  0  0  0  0
  3 26  1  0  0  0  0
  9 26  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0217312

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C(O)C2=C1OC(C)(CCC1(C)CCCC(C)C1=C)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O4/c1-14-7-6-9-21(3,15(14)2)11-12-22(4)10-8-16-19(24)17(23)13-18(25-5)20(16)26-22/h8,10,13-14,23-24H,2,6-7,9,11-12H2,1,3-5H3

> <INCHI_KEY>
WMSMWNWYHIYDCT-UHFFFAOYSA-N

> <FORMULA>
C22H30O4

> <MOLECULAR_WEIGHT>
358.478

> <EXACT_MASS>
358.214409446

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
40.21701325193726

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[2-(1,3-dimethyl-2-methylidenecyclohexyl)ethyl]-8-methoxy-2-methyl-2H-chromene-5,6-diol

> <ALOGPS_LOGP>
5.44

> <JCHEM_LOGP>
5.2041657243333335

> <ALOGPS_LOGS>
-4.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.950315528363117

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.682230387864529

> <JCHEM_PKA_STRONGEST_BASIC>
-4.628197484394366

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
104.50159999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.44e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[2-(1,3-dimethyl-2-methylidenecyclohexyl)ethyl]-8-methoxy-2-methylchromene-5,6-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667  -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       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.185  -2.043   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.195  -3.757   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.205  -4.937   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.732  -6.384   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.215  -6.651   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.066  -5.614   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.399  -6.384   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.399  -7.924   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.066  -8.694   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.066 -10.234   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.732  -7.924   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.398  -8.694   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   26                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   26                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   25                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   23                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   16   24                                                  
CONECT   24   23                                                            
CONECT   25   12   26                                                       
CONECT   26   25    3    9                                                  
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₀O₄

Average Mass

358.4780 Da

Monoisotopic Mass

358.21441 Da

IUPAC Name

2-[2-(1,3-dimethyl-2-methylidenecyclohexyl)ethyl]-8-methoxy-2-methyl-2H-chromene-5,6-diol

Traditional Name

2-[2-(1,3-dimethyl-2-methylidenecyclohexyl)ethyl]-8-methoxy-2-methylchromene-5,6-diol

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C(O)C2=C1OC(C)(CCC1(C)CCCC(C)C1=C)C=C2

InChI Identifier

InChI=1S/C22H30O4/c1-14-7-6-9-21(3,15(14)2)11-12-22(4)10-8-16-19(24)17(23)13-18(25-5)20(16)26-22/h8,10,13-14,23-24H,2,6-7,9,11-12H2,1,3-5H3

InChI Key

WMSMWNWYHIYDCT-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Dactylospongia metachromia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-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 1-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

1-benzopyrans

Alternative Parents

Substituents

1-benzopyran
Phenol ether
Anisole
1-hydroxy-2-unsubstituted benzenoid
Phenol
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	5.44	ALOGPS
logP	5.2	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	9.68	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	104.5 m³·mol⁻¹	ChemAxon
Polarizability	40.22 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

85406416

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-[2-(1,3-dimethyl-2-methylidenecyclohexyl)ethyl]-8-methoxy-2-methylchromene-5,6-diol (NP0217312)

MOL for NP0217312 (2-[2-(1,3-dimethyl-2-methylidenecyclohexyl)ethyl]-8-methoxy-2-methylchromene-5,6-diol)

3D MOL for NP0217312 (2-[2-(1,3-dimethyl-2-methylidenecyclohexyl)ethyl]-8-methoxy-2-methylchromene-5,6-diol)

3D SDF for NP0217312 (2-[2-(1,3-dimethyl-2-methylidenecyclohexyl)ethyl]-8-methoxy-2-methylchromene-5,6-diol)

3D-SDF for NP0217312 (2-[2-(1,3-dimethyl-2-methylidenecyclohexyl)ethyl]-8-methoxy-2-methylchromene-5,6-diol)

PDB for NP0217312 (2-[2-(1,3-dimethyl-2-methylidenecyclohexyl)ethyl]-8-methoxy-2-methylchromene-5,6-diol)

3D PDB for NP0217312 (2-[2-(1,3-dimethyl-2-methylidenecyclohexyl)ethyl]-8-methoxy-2-methylchromene-5,6-diol)

SMILES for NP0217312 (2-[2-(1,3-dimethyl-2-methylidenecyclohexyl)ethyl]-8-methoxy-2-methylchromene-5,6-diol)

INCHI for NP0217312 (2-[2-(1,3-dimethyl-2-methylidenecyclohexyl)ethyl]-8-methoxy-2-methylchromene-5,6-diol)

Structure for NP0217312 (2-[2-(1,3-dimethyl-2-methylidenecyclohexyl)ethyl]-8-methoxy-2-methylchromene-5,6-diol)

3D Structure for NP0217312 (2-[2-(1,3-dimethyl-2-methylidenecyclohexyl)ethyl]-8-methoxy-2-methylchromene-5,6-diol)