NP-MRD: Showing NP-Card for 3a,5,5-trimethyl-6-(3-oxobutyl)-tetrahydro-2h-pentalen-1-one (NP0281696)

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Record Information

Version

2.0

Created at

2022-09-09 08:12:01 UTC

Updated at

2022-09-09 08:12:02 UTC

NP-MRD ID

NP0281696

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3a,5,5-trimethyl-6-(3-oxobutyl)-tetrahydro-2h-pentalen-1-one

Description

Hexahydro-3a,5,5-trimethyl-6-(3-oxobutyl)-1(2h)-pentalenone belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. 3a,5,5-trimethyl-6-(3-oxobutyl)-tetrahydro-2h-pentalen-1-one is found in Artemisia chamaemelifolia. Hexahydro-3a,5,5-trimethyl-6-(3-oxobutyl)-1(2h)-pentalenone is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 42  0  0  0  0  0  0  0  0999 V2000
    4.8804    0.7768   -1.1041 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6964    0.8740   -0.1928 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7452    1.6464    0.7492 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4762    0.0754   -0.3876 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4694    0.4011    0.6939 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2273   -0.4193    0.4855 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4332   -0.1617   -0.8482 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5980   -1.4015   -1.6539 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2575   -2.2609   -1.7750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9298   -1.4672   -2.2935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7277   -0.4166   -1.5987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8612    0.2189   -0.5696 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9764    1.7140   -0.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1225   -0.3306    0.7859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7951   -0.2943    1.5397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7347   -1.5009    2.4645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8019    0.9891    2.3065 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5112    0.4098   -2.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6450    0.0934   -0.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2752    1.8063   -1.2307 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0535    0.2260   -1.4080 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7820   -0.9971   -0.3572 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9217    0.0604    1.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2979    1.4781    0.7683 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5866   -1.4911    0.4381 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0592    0.6488   -1.4211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8834   -1.2691   -3.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4116   -2.4721   -2.1576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0914    0.3587   -2.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6300   -0.8235   -1.0812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8045    2.1390   -0.0804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9957    2.1894   -0.4747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2163    1.9460   -1.7409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3908   -1.4102    0.6770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9188    0.2145    1.3386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2210   -2.0576    2.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7417   -1.2339    3.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5422   -2.2210    2.1809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4254    1.7853    1.8515 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1961    1.3999    2.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2697    0.7772    3.3039 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  1
 12 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15  6  1  0
 12  7  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  6
  7 26  1  6
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 17 41  1  0
M  END


  Mrv1533004171504152D          

 17 18  0  0  0  0            999 V2000
   -0.8543    2.3248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0473    2.1533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5047    2.7664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2076    1.3686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0146    1.1971    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
    2.0542    0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8388    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0937    1.1971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3237   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8388   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695   -0.9224    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
    0.0659   -0.6599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0659    0.1501    0.0000 C   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 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
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0281696

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)CCC1C2C(=O)CCC2(C)CC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O2/c1-10(16)5-6-11-13-12(17)7-8-15(13,4)9-14(11,2)3/h11,13H,5-9H2,1-4H3

> <INCHI_KEY>
GTUMAHOVZNSHNI-UHFFFAOYSA-N

> <FORMULA>
C15H24O2

> <MOLECULAR_WEIGHT>
236.355

> <EXACT_MASS>
236.177630013

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
27.525741542282336

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3a,5,5-trimethyl-6-(3-oxobutyl)-octahydropentalen-1-one

> <ALOGPS_LOGP>
2.53

> <JCHEM_LOGP>
2.9271272569999995

> <ALOGPS_LOGS>
-3.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.46390110373691

> <JCHEM_PKA_STRONGEST_BASIC>
-7.041086996201352

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
68.0342

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.60e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3a,5,5-trimethyl-6-(3-oxobutyl)-tetrahydro-2H-pentalen-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      -1.595   4.340   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.088   4.019   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.942   5.164   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.388   2.555   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.894   2.235   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.834   0.294   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.299   0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.775   2.235   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.204  -0.476   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.299  -1.722   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.834  -1.246   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.834  -2.786   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.370  -1.722   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.123  -1.232   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.123   0.280   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7   13   14                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14    6   16   17                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄O₂

Average Mass

236.3550 Da

Monoisotopic Mass

236.17763 Da

IUPAC Name

3a,5,5-trimethyl-6-(3-oxobutyl)-octahydropentalen-1-one

Traditional Name

3a,5,5-trimethyl-6-(3-oxobutyl)-tetrahydro-2H-pentalen-1-one

CAS Registry Number

Not Available

SMILES

CC(=O)CCC1C2C(=O)CCC2(C)CC1(C)C

InChI Identifier

InChI=1S/C15H24O2/c1-10(16)5-6-11-13-12(17)7-8-15(13,4)9-14(11,2)3/h11,13H,5-9H2,1-4H3

InChI Key

GTUMAHOVZNSHNI-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Artemisia chamaemelifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Ketones

Alternative Parents

Substituents

Ketone
Organic oxide
Hydrocarbon derivative
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	2.53	ALOGPS
logP	2.93	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	19.46	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	68.03 m³·mol⁻¹	ChemAxon
Polarizability	27.53 Å³	ChemAxon
Number of Rings	2	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

129682005

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3a,5,5-trimethyl-6-(3-oxobutyl)-tetrahydro-2h-pentalen-1-one (NP0281696)

MOL for NP0281696 (3a,5,5-trimethyl-6-(3-oxobutyl)-tetrahydro-2h-pentalen-1-one)

3D MOL for NP0281696 (3a,5,5-trimethyl-6-(3-oxobutyl)-tetrahydro-2h-pentalen-1-one)

3D SDF for NP0281696 (3a,5,5-trimethyl-6-(3-oxobutyl)-tetrahydro-2h-pentalen-1-one)

3D-SDF for NP0281696 (3a,5,5-trimethyl-6-(3-oxobutyl)-tetrahydro-2h-pentalen-1-one)

PDB for NP0281696 (3a,5,5-trimethyl-6-(3-oxobutyl)-tetrahydro-2h-pentalen-1-one)

3D PDB for NP0281696 (3a,5,5-trimethyl-6-(3-oxobutyl)-tetrahydro-2h-pentalen-1-one)

SMILES for NP0281696 (3a,5,5-trimethyl-6-(3-oxobutyl)-tetrahydro-2h-pentalen-1-one)

INCHI for NP0281696 (3a,5,5-trimethyl-6-(3-oxobutyl)-tetrahydro-2h-pentalen-1-one)

Structure for NP0281696 (3a,5,5-trimethyl-6-(3-oxobutyl)-tetrahydro-2h-pentalen-1-one)

3D Structure for NP0281696 (3a,5,5-trimethyl-6-(3-oxobutyl)-tetrahydro-2h-pentalen-1-one)