NP-MRD: Showing NP-Card for [(1r,2r)-2-acetyl-1-isopropylcyclopropyl]acetic acid (NP0159409)

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Record Information

Version

2.0

Created at

2022-09-02 17:09:38 UTC

Updated at

2022-09-02 17:09:38 UTC

NP-MRD ID

NP0159409

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1r,2r)-2-acetyl-1-isopropylcyclopropyl]acetic acid

Description

Secothujene 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. [(1r,2r)-2-acetyl-1-isopropylcyclopropyl]acetic acid is found in Achillea fragrantissima, Artemisia herba-alba and Cotula cinerea. Based on a literature review very few articles have been published on Secothujene.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 29  0  0  0  0  0  0  0  0999 V2000
    3.5860    0.1592    1.5233 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3275    0.6730    0.9013 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2144    1.8857    0.9254 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3684   -0.2651    0.3368 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8789    0.1548   -1.0623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0710   -0.0157    0.1257 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7619    1.2135    0.5722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8519    1.7267   -0.2750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0829    1.5302   -0.0597 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5810    2.4988   -1.4220 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9127   -1.2622   -0.0260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9801   -1.0814   -1.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4436   -1.7383    1.3128 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4625    0.4778    0.8902 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6927    0.4699    2.5776 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6128   -0.9634    1.5258 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6840   -1.3493    0.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9440   -0.6092   -1.8356 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0709    1.1949   -1.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2496    1.0173    1.5803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0867    2.0659    0.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9317    3.2672   -1.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2543   -2.1094   -0.3936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0165   -1.9652   -1.7678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0261   -1.1073   -0.6141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8258   -0.2233   -1.7265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5176   -1.4596    1.3900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4081   -2.8447    1.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8407   -1.3408    2.1506 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
 11 13  1  0
  6 11  1  6
  6  7  1  0
  7  8  1  0
  8 10  1  0
  8  9  2  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  4  6  1  0
 12 24  1  0
 12 25  1  0
 12 26  1  0
 11 23  1  0
 13 27  1  0
 13 28  1  0
 13 29  1  0
  7 20  1  0
  7 21  1  0
 10 22  1  0
  5 18  1  0
  5 19  1  0
  4 17  1  6
  1 14  1  0
  1 15  1  0
  1 16  1  0
M  END


  Mrv1652309022219092D          

 13 13  0  0  1  0            999 V2000
    1.3651   -1.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3651   -0.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0796    0.1743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6507    0.1743    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1743    0.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2382    0.8888    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2350    1.5646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0569    1.4927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4056    0.7450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5301    2.1685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7114    1.5646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3627    2.3123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5332    1.4927    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
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  6 11  1  1  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0159409

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@]1(CC(O)=O)C[C@H]1C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H16O3/c1-6(2)10(5-9(12)13)4-8(10)7(3)11/h6,8H,4-5H2,1-3H3,(H,12,13)/t8-,10+/m0/s1

> <INCHI_KEY>
KHQMPLDSNBIPLK-WCBMZHEXSA-N

> <FORMULA>
C10H16O3

> <MOLECULAR_WEIGHT>
184.235

> <EXACT_MASS>
184.109944375

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
19.703335085850366

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1R,2R)-2-acetyl-1-(propan-2-yl)cyclopropyl]acetic acid

> <ALOGPS_LOGP>
1.42

> <JCHEM_LOGP>
1.3290569086666673

> <ALOGPS_LOGS>
-1.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.397089798980186

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.634612763903225

> <JCHEM_PKA_STRONGEST_BASIC>
-7.357983288997314

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
48.033699999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.38e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,2R)-2-acetyl-1-isopropylcyclopropyl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       2.548  -1.985   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.548  -0.445   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.882   0.325   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.215   0.325   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.325   0.325   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.445   1.659   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.439   2.921   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.973   2.786   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.624   1.391   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -2.856   4.048   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.328   2.921   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.677   4.316   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.862   2.786   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4    6                                                       
CONECT    6    5    4    7   11                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    6   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₀H₁₆O₃

Average Mass

184.2350 Da

Monoisotopic Mass

184.10994 Da

IUPAC Name

2-[(1R,2R)-2-acetyl-1-(propan-2-yl)cyclopropyl]acetic acid

Traditional Name

[(1R,2R)-2-acetyl-1-isopropylcyclopropyl]acetic acid

CAS Registry Number

Not Available

SMILES

CC(C)[C@]1(CC(O)=O)C[C@H]1C(C)=O

InChI Identifier

InChI=1S/C10H16O3/c1-6(2)10(5-9(12)13)4-8(10)7(3)11/h6,8H,4-5H2,1-3H3,(H,12,13)/t8-,10+/m0/s1

InChI Key

KHQMPLDSNBIPLK-WCBMZHEXSA-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
Achillea fragrantissima	LOTUS Database	35616633
Artemisia herba-alba	LOTUS Database	35616633
Cotula cinerea	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
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
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	1.42	ALOGPS
logP	1.33	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	4.63	ChemAxon
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	48.03 m³·mol⁻¹	ChemAxon
Polarizability	19.7 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

110557770

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12444318

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(1r,2r)-2-acetyl-1-isopropylcyclopropyl]acetic acid (NP0159409)

MOL for NP0159409 ([(1r,2r)-2-acetyl-1-isopropylcyclopropyl]acetic acid)

3D MOL for NP0159409 ([(1r,2r)-2-acetyl-1-isopropylcyclopropyl]acetic acid)

3D SDF for NP0159409 ([(1r,2r)-2-acetyl-1-isopropylcyclopropyl]acetic acid)

3D-SDF for NP0159409 ([(1r,2r)-2-acetyl-1-isopropylcyclopropyl]acetic acid)

PDB for NP0159409 ([(1r,2r)-2-acetyl-1-isopropylcyclopropyl]acetic acid)

3D PDB for NP0159409 ([(1r,2r)-2-acetyl-1-isopropylcyclopropyl]acetic acid)

SMILES for NP0159409 ([(1r,2r)-2-acetyl-1-isopropylcyclopropyl]acetic acid)

INCHI for NP0159409 ([(1r,2r)-2-acetyl-1-isopropylcyclopropyl]acetic acid)

Structure for NP0159409 ([(1r,2r)-2-acetyl-1-isopropylcyclopropyl]acetic acid)

3D Structure for NP0159409 ([(1r,2r)-2-acetyl-1-isopropylcyclopropyl]acetic acid)