NP-MRD: Showing NP-Card for 11-Hydroxy-11-methylethyl-6,10-dimethylspiro[4.5]-dec-6-en-8-one (NP0047039)

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Record Information

Version

2.0

Created at

2022-03-17 20:33:36 UTC

Updated at

2022-03-17 20:33:36 UTC

NP-MRD ID

NP0047039

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11-Hydroxy-11-methylethyl-6,10-dimethylspiro[4.5]-dec-6-en-8-one

Description

(4R,5S,7R,11R)-11,12-Dihydroxy-1(10)-spirovetiven-2-one belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units (4R,5S,7R,11R)-11,12-Dihydroxy-1(10)-spirovetiven-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (4R,5S,7R,11R)-11,12-Dihydroxy-1(10)-spirovetiven-2-one has been detected, but not quantified in, potato. 11-Hydroxy-11-methylethyl-6,10-dimethylspiro[4.5]-dec-6-en-8-one is found in Hyoscyamus albus and Boeremia foveata. This could make (4R,5S,7R,11R)-11,12-dihydroxy-1(10)-spirovetiven-2-one a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307002D          

 18 19  0  0  0  0            999 V2000
    1.2695    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1825    1.9774    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
    0.7846   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5070    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5070   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3349    1.7948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6820    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6820   -0.3020    0.0000 C   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
    2.9195    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6674    1.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0886    1.4593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7445    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1524    0.6425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
 10  1  1  0  0  0  0
 10  6  2  0  0  0  0
 11  2  1  0  0  0  0
 11  7  1  0  0  0  0
 12  4  1  0  0  0  0
 12  8  1  0  0  0  0
 13  6  1  0  0  0  0
 13  7  1  0  0  0  0
 14  3  1  0  0  0  0
 14  9  1  0  0  0  0
 14 12  1  0  0  0  0
 15  5  1  0  0  0  0
 15  8  1  0  0  0  0
 15 10  1  0  0  0  0
 15 11  1  0  0  0  0
 16  9  1  0  0  0  0
 17 13  2  0  0  0  0
 18 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047039

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CC(=O)C=C(C)C11CCC(C1)C(C)(O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O3/c1-10-6-13(17)7-11(2)15(10)5-4-12(8-15)14(3,18)9-16/h6,11-12,16,18H,4-5,7-9H2,1-3H3

> <INCHI_KEY>
FWLWCLDHPUPCHO-UHFFFAOYSA-N

> <FORMULA>
C15H24O3

> <MOLECULAR_WEIGHT>
252.3493

> <EXACT_MASS>
252.172544634

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.38116160295177

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(1,2-dihydroxypropan-2-yl)-6,10-dimethylspiro[4.5]dec-6-en-8-one

> <ALOGPS_LOGP>
1.51

> <JCHEM_LOGP>
1.6074117019999996

> <ALOGPS_LOGS>
-2.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.380421067342184

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.871938151544466

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0715469852006088

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
71.59579999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.75e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(1,2-dihydroxypropan-2-yl)-6,10-dimethylspiro[4.5]dec-6-en-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.370   3.437   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.370  -1.897   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.341   3.691   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  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.680   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.680  -0.564   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.465   2.016   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.492   3.350   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.140   2.104   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.140  -0.564   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.450   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.246   2.445   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.899   2.724   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       6.990   0.770   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.151   1.199   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   11                                                            
CONECT    3   14                                                            
CONECT    4    5   12                                                       
CONECT    5    4   15                                                       
CONECT    6   10   13                                                       
CONECT    7   11   13                                                       
CONECT    8   12   15                                                       
CONECT    9   14   16                                                       
CONECT   10    1    6   15                                                  
CONECT   11    2    7   15                                                  
CONECT   12    4    8   14                                                  
CONECT   13    6    7   17                                                  
CONECT   14    3    9   12   18                                             
CONECT   15    5    8   10   11                                             
CONECT   16    9                                                            
CONECT   17   13                                                            
CONECT   18   14                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄O₃

Average Mass

252.3493 Da

Monoisotopic Mass

252.17254 Da

IUPAC Name

2-(1,2-dihydroxypropan-2-yl)-6,10-dimethylspiro[4.5]dec-6-en-8-one

Traditional Name

2-(1,2-dihydroxypropan-2-yl)-6,10-dimethylspiro[4.5]dec-6-en-8-one

CAS Registry Number

Not Available

SMILES

CC1CC(=O)C=C(C)C11CCC(C1)C(C)(O)CO

InChI Identifier

InChI=1S/C15H24O3/c1-10-6-13(17)7-11(2)15(10)5-4-12(8-15)14(3,18)9-16/h6,11-12,16,18H,4-5,7-9H2,1-3H3

InChI Key

FWLWCLDHPUPCHO-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Hyoscyamus albus	LOTUS Database	35616633
Phoma exigua var. foveata	LOTUS Database	35616633
Solanum tuberosum	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...

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

Spirovetivane-type sesquiterpenoid
Sesquiterpenoid
Cyclohexenone
Tertiary alcohol
Cyclic ketone
Ketone
1,2-diol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
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	1.51	ALOGPS
logP	1.61	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	13.87	ChemAxon
pKa (Strongest Basic)	-3.1	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	71.6 m³·mol⁻¹	ChemAxon
Polarizability	28.38 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

HMDB0033149

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011262

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

73810597

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 11-Hydroxy-11-methylethyl-6,10-dimethylspiro[4.5]-dec-6-en-8-one (NP0047039)

MOL for NP0047039 (11-Hydroxy-11-methylethyl-6,10-dimethylspiro[4.5]-dec-6-en-8-one)

3D MOL for NP0047039 (11-Hydroxy-11-methylethyl-6,10-dimethylspiro[4.5]-dec-6-en-8-one)

3D SDF for NP0047039 (11-Hydroxy-11-methylethyl-6,10-dimethylspiro[4.5]-dec-6-en-8-one)

3D-SDF for NP0047039 (11-Hydroxy-11-methylethyl-6,10-dimethylspiro[4.5]-dec-6-en-8-one)

PDB for NP0047039 (11-Hydroxy-11-methylethyl-6,10-dimethylspiro[4.5]-dec-6-en-8-one)

3D PDB for NP0047039 (11-Hydroxy-11-methylethyl-6,10-dimethylspiro[4.5]-dec-6-en-8-one)

SMILES for NP0047039 (11-Hydroxy-11-methylethyl-6,10-dimethylspiro[4.5]-dec-6-en-8-one)

INCHI for NP0047039 (11-Hydroxy-11-methylethyl-6,10-dimethylspiro[4.5]-dec-6-en-8-one)

Structure for NP0047039 (11-Hydroxy-11-methylethyl-6,10-dimethylspiro[4.5]-dec-6-en-8-one)

3D Structure for NP0047039 (11-Hydroxy-11-methylethyl-6,10-dimethylspiro[4.5]-dec-6-en-8-one)