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Showing NP-Card for Cyclohexanones (NP0338437)

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Record Information
Version2.0
Created at2024-09-11 15:28:47 UTC
Updated at2024-09-11 15:28:47 UTC
NP-MRD IDNP0338437
Secondary Accession NumbersNone
Natural Product Identification
Common NameCyclohexanones
Description Cyclohexanones was first documented in 2023 (PMID: 38038403). Based on a literature review a significant number of articles have been published on Cyclohexanones (PMID: 39161707) (PMID: 39106109) (PMID: 38856301) (PMID: 38809603) (PMID: 38773694) (PMID: 38711202).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0338437 (Cyclohexanones)


  Mrv2104 05262318012D          

 16 16  0  0  0  0            999 V2000
    2.0070    0.4943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1945    0.6376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6642    0.0056    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1482    0.1488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9607    0.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4910    0.6376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2088    1.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3964    1.5561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1339    0.9241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9464    1.0673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1482   -0.6762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5192   -1.1611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2643   -1.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5607   -1.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8157   -1.1611    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.2463    0.0000    0.0000 Cl  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
  5  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
  4  9  1  0  0  0  0
  9 10  2  0  0  0  0
  4 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 11 15  1  0  0  0  0
M  END
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3D MOL for NP0338437 (Cyclohexanones)

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3D SDF for NP0338437 (Cyclohexanones)

  Mrv2104 05262318012D          

 16 16  0  0  0  0            999 V2000
    2.0070    0.4943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1945    0.6376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6642    0.0056    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1482    0.1488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9607    0.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4910    0.6376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2088    1.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3964    1.5561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1339    0.9241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9464    1.0673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1482   -0.6762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5192   -1.1611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2643   -1.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5607   -1.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8157   -1.1611    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.2463    0.0000    0.0000 Cl  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
  5  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
  4  9  1  0  0  0  0
  9 10  2  0  0  0  0
  4 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 11 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0338437

> <DATABASE_NAME>
NP-MRD

> <SMILES>
Cl.CCNC1(CCCCC1=O)C1=CC=CS1

> <INCHI_IDENTIFIER>
InChI=1/C12H17NOS.ClH/c1-2-13-12(11-7-5-9-15-11)8-4-3-6-10(12)14;/h5,7,9,13H,2-4,6,8H2,1H3;1H

> <INCHI_KEY>
ZUYKJZQOPXDNOK-UHFFFAOYNA-N

> <FORMULA>
C12H18ClNOS

> <MOLECULAR_WEIGHT>
259.79

> <EXACT_MASS>
259.0797631

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
24.650021020193055

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(ethylamino)-2-(thiophen-2-yl)cyclohexan-1-one hydrochloride

> <JCHEM_LOGP>
3.0129473173333325

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.71228517064502

> <JCHEM_PKA_STRONGEST_BASIC>
7.908283519263563

> <JCHEM_POLAR_SURFACE_AREA>
29.1

> <JCHEM_REFRACTIVITY>
62.3875

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
tiletamine hydrochloride

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0338437 (Cyclohexanones)
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PDB for NP0338437 (Cyclohexanones)
HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0       3.746   0.923   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.230   1.190   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       1.240   0.010   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -0.277   0.278   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.793   0.010   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.783   1.190   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.256   2.637   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.740   2.905   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.250   1.725   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.767   1.992   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.277  -1.262   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.969  -2.167   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.493  -3.632   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.047  -3.632   0.000  0.00  0.00           C+0
HETATM   15  S   UNK     0      -1.523  -2.167   0.000  0.00  0.00           S+0
HETATM   16 Cl   UNK     0       7.926   0.000   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9   11                                             
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4   10                                                  
CONECT   10    9                                                            
CONECT   11    4   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   11                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

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3D PDB for NP0338437 (Cyclohexanones)
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SMILES for NP0338437 (Cyclohexanones)
Cl.CCNC1(CCCCC1=O)C1=CC=CS1
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INCHI for NP0338437 (Cyclohexanones)
InChI=1/C12H17NOS.ClH/c1-2-13-12(11-7-5-9-15-11)8-4-3-6-10(12)14;/h5,7,9,13H,2-4,6,8H2,1H3;1H
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View in JSmol
SynonymsNot Available
Chemical FormulaC12H18ClNOS
Average Mass259.7900 Da
Monoisotopic Mass259.07976 Da
IUPAC Name2-(ethylamino)-2-(thiophen-2-yl)cyclohexan-1-one hydrochloride
Traditional Nametiletamine hydrochloride
CAS Registry NumberNot Available
SMILES
Cl.CCNC1(CCCCC1=O)C1=CC=CS1
InChI Identifier
InChI=1/C12H17NOS.ClH/c1-2-13-12(11-7-5-9-15-11)8-4-3-6-10(12)14;/h5,7,9,13H,2-4,6,8H2,1H3;1H
InChI KeyZUYKJZQOPXDNOK-UHFFFAOYNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
ClassificationNot classified
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.01ChemAxon
pKa (Strongest Acidic)19.71ChemAxon
pKa (Strongest Basic)7.91ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.1 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity62.39 m³·mol⁻¹ChemAxon
Polarizability24.65 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCyclohexanone  
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Nair D, Tiwari A, Laha B, Namboothiri INN: Diastereoselective synthesis of highly substituted cyclohexanones and tetrahydrochromene-4-ones via conjugate addition of curcumins to arylidenemalonates. Beilstein J Org Chem. 2024 Aug 15;20:2016-2023. doi: 10.3762/bjoc.20.177.  eCollection 2024. [PubMed:39161707  ] 
  2. Chen J, Qi S, Wang Z, Hu L, Liu J, Huang G, Peng Y, Fang Z, Wu Q, Hu Y, Guo K: Ene-Reductase-Catalyzed Aromatization of Simple Cyclohexanones to Phenols. Angew Chem Int Ed Engl. 2024 Aug 6:e202408359. doi: 10.1002/anie.202408359. [PubMed:39106109  ] 
  3. Kattula B, Munakala A, Kashyap R, Nallamilli T, Nagendla NK, Naza S, Mudiam MKR, Chegondi R, Addlagatta A: Strategic enzymatic enantioselective desymmetrization of prochiral cyclohexa-2,5-dienones. Chem Commun (Camb). 2024 Jun 25;60(52):6647-6650. doi: 10.1039/d4cc02181a. [PubMed:38856301  ] 
  4. Zhao L, Weng Y, Zhou X, Wu G: Aminoselenation and Dehydroaromatization of Cyclohexanones with Anilines and Diselenides. Org Lett. 2024 Jun 7;26(22):4835-4839. doi: 10.1021/acs.orglett.4c01799. Epub  2024 May 29. [PubMed:38809603  ] 
  5. Zhao Y, Zhang J, Zhang J, Zhang Z, Liu R: Iodine-Catalyzed Cyclization of o-Nitrothiophenols with Cyclohexanones to Phenothiazines. J Org Chem. 2024 Jun 7;89(11):7478-7484. doi: 10.1021/acs.joc.4c00039. Epub 2024  May 21. [PubMed:38773694  ] 
  6. Ying M, Wang K, Yan W, Pu M, Lin L: Stable Axially Chiral Cyclohexylidenes from Catalytic Asymmetric Knoevenagel Condensation. Chemistry. 2024 Jul 11;30(39):e202401243. doi: 10.1002/chem.202401243. Epub 2024  Jun 14. [PubMed:38711202  ] 
  7. Xu B, Liu X, Deng L, Shang Y, Jie X, Su W: Dehydrogenative synthesis of N-functionalized 2-aminophenols from cyclohexanones and amines: Molecular complexities via one-shot assembly. Sci Adv. 2024 May 3;10(18):eadn7656. doi: 10.1126/sciadv.adn7656. Epub 2024 May  1. [PubMed:38691610  ] 
  8. Miki K, Maeda K, Matsubara R, Hayashi M: Synthesis of 2-(Pyridin-2-yl)phenols and 2-(Pyridin-2-yl)anilines. J Org Chem. 2024 Apr 19;89(8):5797-5810. doi: 10.1021/acs.joc.4c00423. Epub 2024  Apr 2. [PubMed:38563078  ] 
  9. Kitzinger KM, Giordano MT, de Jesus Cruz P, Johnson JS: Diastereoselective (3 + 3)-Annulations of Trisubstituted Michael Acceptors for Access to Polyfunctional Cyclohexanones. J Org Chem. 2024 Apr 19;89(8):5878-5882. doi: 10.1021/acs.joc.4c00157. Epub 2024  Mar 19. [PubMed:38501591  ] 
  10. Bickelhaupt FM, Fernandez I: What defines electrophilicity in carbonyl compounds. Chem Sci. 2024 Feb 6;15(11):3980-3987. doi: 10.1039/d3sc05595g. eCollection 2024  Mar 13. [PubMed:38487236  ] 
  11. Essman JZ, Jacobsen EN: Enantioselective Potassium-Catalyzed Wittig Olefinations. J Am Chem Soc. 2024 Mar 20;146(11):7165-7172. doi: 10.1021/jacs.4c00564. Epub  2024 Mar 7. [PubMed:38451542  ] 
  12. Nemcovicova I, Lopusna K, Stibraniova I, Benedetti F, Berti F, Felluga F, Drioli S, Vidali M, Katrlik J, Pazitna L, Holazova A, Blahutova J, Lenhartova S, Slavikova M, Klempa B, Ondrejovic M, Chmelova D, Legerska B, Miertus S, Klacsova M, Uhrikova D, Kerti L, Frecer V: Identification and evaluation of antiviral activity of novel compounds targeting SARS-CoV-2 virus by enzymatic and antiviral assays, and computational analysis. J Enzyme Inhib Med Chem. 2024 Dec;39(1):2301772. doi:  10.1080/14756366.2024.2301772. Epub 2024 Jan 14. [PubMed:38221792  ] 
  13. Zou H, Wang Z, Guo D, Zhang L, Wang S, Zhu X: Synthesis and catalytic activity of tetradentate beta-diketiminato rare-earth metal monoalkyl complexes in tandem Oppenauer oxidation and cross-aldol condensation. Dalton Trans. 2023 Dec 19;53(1):267-275. doi: 10.1039/d3dt03374k. [PubMed:38038403  ] 
  14. Zheng J, Tao F, Shen X, Yang Z, Zhang J, Chen Y, Liu X, Qi Y, Luo H: Rapid Construction of Vinyl Indomorphans by Rhenium Catalysis. Org Lett. 2023 Dec 1;25(47):8457-8462. doi: 10.1021/acs.orglett.3c03367. Epub  2023 Nov 17. [PubMed:37976044  ] 
  15. Chen F, Geng H, Li C, Wang J, Guo B, Tang L, Yang YY: Aerobic Dehydrogenative Aromatization in the Preparation of 4-Aminoquinoline Derivatives by Synergistic Pd/Cu Catalysis. J Org Chem. 2023 Nov 17;88(22):15589-15596. doi: 10.1021/acs.joc.3c01400. Epub  2023 Nov 6. [PubMed:37931324  ]