NP-MRD: Showing NP-Card for 5-(hydroxymethyl)-1,1,6-trimethyl-4,4a,8,8a-tetrahydro-3h-naphthalene-2,7-dione (NP0183385)

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Record Information

Version

2.0

Created at

2022-09-03 22:16:41 UTC

Updated at

2022-09-03 22:16:41 UTC

NP-MRD ID

NP0183385

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-(hydroxymethyl)-1,1,6-trimethyl-4,4a,8,8a-tetrahydro-3h-naphthalene-2,7-dione

Description

5-(Hydroxymethyl)-1,1,6-trimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalene-2,7-dione belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. 5-(Hydroxymethyl)-1,1,6-trimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalene-2,7-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004181502122D          

 17 18  0  0  0  0            999 V2000
    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 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    1.2375    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
    4.2868   -1.6500    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
    3.3882   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3276   -2.2820    0.0000 C   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
    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 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
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0183385

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(CO)C2CCC(=O)C(C)(C)C2CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H20O3/c1-8-10(7-15)9-4-5-13(17)14(2,3)11(9)6-12(8)16/h9,11,15H,4-7H2,1-3H3

> <INCHI_KEY>
HEMXAFWEGIYKBA-UHFFFAOYSA-N

> <FORMULA>
C14H20O3

> <MOLECULAR_WEIGHT>
236.311

> <EXACT_MASS>
236.141244504

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
26.002843927443635

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(hydroxymethyl)-1,1,6-trimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalene-2,7-dione

> <ALOGPS_LOGP>
1.78

> <JCHEM_LOGP>
1.763390833666667

> <ALOGPS_LOGS>
-2.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.863224528905487

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.092509081228314

> <JCHEM_PKA_STRONGEST_BASIC>
-2.75829248687789

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
65.96839999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.09e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-(hydroxymethyl)-1,1,6-trimethyl-4,4a,8,8a-tetrahydro-3H-naphthalene-2,7-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -0.770   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  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.325  -4.260   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.345  -4.260   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11    6   15                                                  
CONECT   15   14   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

C₁₄H₂₀O₃

Average Mass

236.3110 Da

Monoisotopic Mass

236.14124 Da

IUPAC Name

5-(hydroxymethyl)-1,1,6-trimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalene-2,7-dione

Traditional Name

5-(hydroxymethyl)-1,1,6-trimethyl-4,4a,8,8a-tetrahydro-3H-naphthalene-2,7-dione

CAS Registry Number

Not Available

SMILES

CC1=C(CO)C2CCC(=O)C(C)(C)C2CC1=O

InChI Identifier

InChI=1S/C14H20O3/c1-8-10(7-15)9-4-5-13(17)14(2,3)11(9)6-12(8)16/h9,11,15H,4-7H2,1-3H3

InChI Key

HEMXAFWEGIYKBA-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 cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Organic oxide
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	1.78	ALOGPS
logP	1.76	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	15.09	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	65.97 m³·mol⁻¹	ChemAxon
Polarizability	26 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-(hydroxymethyl)-1,1,6-trimethyl-4,4a,8,8a-tetrahydro-3h-naphthalene-2,7-dione (NP0183385)

MOL for NP0183385 (5-(hydroxymethyl)-1,1,6-trimethyl-4,4a,8,8a-tetrahydro-3h-naphthalene-2,7-dione)

3D MOL for NP0183385 (5-(hydroxymethyl)-1,1,6-trimethyl-4,4a,8,8a-tetrahydro-3h-naphthalene-2,7-dione)

3D SDF for NP0183385 (5-(hydroxymethyl)-1,1,6-trimethyl-4,4a,8,8a-tetrahydro-3h-naphthalene-2,7-dione)

3D-SDF for NP0183385 (5-(hydroxymethyl)-1,1,6-trimethyl-4,4a,8,8a-tetrahydro-3h-naphthalene-2,7-dione)

PDB for NP0183385 (5-(hydroxymethyl)-1,1,6-trimethyl-4,4a,8,8a-tetrahydro-3h-naphthalene-2,7-dione)

3D PDB for NP0183385 (5-(hydroxymethyl)-1,1,6-trimethyl-4,4a,8,8a-tetrahydro-3h-naphthalene-2,7-dione)

SMILES for NP0183385 (5-(hydroxymethyl)-1,1,6-trimethyl-4,4a,8,8a-tetrahydro-3h-naphthalene-2,7-dione)

INCHI for NP0183385 (5-(hydroxymethyl)-1,1,6-trimethyl-4,4a,8,8a-tetrahydro-3h-naphthalene-2,7-dione)

Structure for NP0183385 (5-(hydroxymethyl)-1,1,6-trimethyl-4,4a,8,8a-tetrahydro-3h-naphthalene-2,7-dione)

3D Structure for NP0183385 (5-(hydroxymethyl)-1,1,6-trimethyl-4,4a,8,8a-tetrahydro-3h-naphthalene-2,7-dione)