NP-MRD: Showing NP-Card for 4-(3,4-dihydroxy-2,2,6-trimethylcyclohexyl)but-3-en-2-one (NP0220626)

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Record Information

Version

2.0

Created at

2022-09-05 21:59:50 UTC

Updated at

2022-09-05 21:59:50 UTC

NP-MRD ID

NP0220626

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-(3,4-dihydroxy-2,2,6-trimethylcyclohexyl)but-3-en-2-one

Description

4-(3,4-Dihydroxy-2,2,6-trimethylcyclohexyl)but-3-en-2-one belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 4-(3,4-dihydroxy-2,2,6-trimethylcyclohexyl)but-3-en-2-one is found in Ginkgo biloba. 4-(3,4-Dihydroxy-2,2,6-trimethylcyclohexyl)but-3-en-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533005011512472D          

 16 16  0  0  0  0            999 V2000
    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
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    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
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    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 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
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  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
  2 11  1  0  0  0  0
 12 11  1  4  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0220626

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CC(O)C(O)C(C)(C)C1C=CC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H22O3/c1-8-7-11(15)12(16)13(3,4)10(8)6-5-9(2)14/h5-6,8,10-12,15-16H,7H2,1-4H3

> <INCHI_KEY>
ATKLFQNRZDAYDU-UHFFFAOYSA-N

> <FORMULA>
C13H22O3

> <MOLECULAR_WEIGHT>
226.316

> <EXACT_MASS>
226.156894568

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
25.5753122125836

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(3,4-dihydroxy-2,2,6-trimethylcyclohexyl)but-3-en-2-one

> <ALOGPS_LOGP>
1.26

> <JCHEM_LOGP>
1.4191463023333333

> <ALOGPS_LOGS>
-1.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.159478469665476

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.623352030577685

> <JCHEM_PKA_STRONGEST_BASIC>
-3.156092842359378

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
64.1157

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.49e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(3,4-dihydroxy-2,2,6-trimethylcyclohexyl)but-3-en-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 01-MAY-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-MAY-15         0                                  
HETATM    1  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   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  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.334   2.310   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       0.344   3.490   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.324   3.490   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   2.310   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       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8    2   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₂₂O₃

Average Mass

226.3160 Da

Monoisotopic Mass

226.15689 Da

IUPAC Name

4-(3,4-dihydroxy-2,2,6-trimethylcyclohexyl)but-3-en-2-one

Traditional Name

4-(3,4-dihydroxy-2,2,6-trimethylcyclohexyl)but-3-en-2-one

CAS Registry Number

Not Available

SMILES

CC1CC(O)C(O)C(C)(C)C1C=CC(C)=O

InChI Identifier

InChI=1S/C13H22O3/c1-8-7-11(15)12(16)13(3,4)10(8)6-5-9(2)14/h5-6,8,10-12,15-16H,7H2,1-4H3

InChI Key

ATKLFQNRZDAYDU-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ginkgo biloba	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Cyclofarsesane sesquiterpenoid
Megastigmane sesquiterpenoid
Sesquiterpenoid
Ionone derivative
Cyclohexanol
Acryloyl-group
Cyclic alcohol
Alpha,beta-unsaturated ketone
Enone
1,2-diol
Secondary alcohol
Ketone
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxide
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	1.26	ALOGPS
logP	1.42	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	13.62	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	64.12 m³·mol⁻¹	ChemAxon
Polarizability	25.58 Å³	ChemAxon
Number of Rings	1	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 4-(3,4-dihydroxy-2,2,6-trimethylcyclohexyl)but-3-en-2-one (NP0220626)

MOL for NP0220626 (4-(3,4-dihydroxy-2,2,6-trimethylcyclohexyl)but-3-en-2-one)

3D MOL for NP0220626 (4-(3,4-dihydroxy-2,2,6-trimethylcyclohexyl)but-3-en-2-one)

3D SDF for NP0220626 (4-(3,4-dihydroxy-2,2,6-trimethylcyclohexyl)but-3-en-2-one)

3D-SDF for NP0220626 (4-(3,4-dihydroxy-2,2,6-trimethylcyclohexyl)but-3-en-2-one)

PDB for NP0220626 (4-(3,4-dihydroxy-2,2,6-trimethylcyclohexyl)but-3-en-2-one)

3D PDB for NP0220626 (4-(3,4-dihydroxy-2,2,6-trimethylcyclohexyl)but-3-en-2-one)

SMILES for NP0220626 (4-(3,4-dihydroxy-2,2,6-trimethylcyclohexyl)but-3-en-2-one)

INCHI for NP0220626 (4-(3,4-dihydroxy-2,2,6-trimethylcyclohexyl)but-3-en-2-one)

Structure for NP0220626 (4-(3,4-dihydroxy-2,2,6-trimethylcyclohexyl)but-3-en-2-one)

3D Structure for NP0220626 (4-(3,4-dihydroxy-2,2,6-trimethylcyclohexyl)but-3-en-2-one)