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Showing NP-Card for (3e)-4-[(1r,4s)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]but-3-en-2-one (NP0317562)

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Record Information
Version2.0
Created at2022-09-11 17:31:27 UTC
Updated at2022-09-11 17:31:27 UTC
NP-MRD IDNP0317562
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3e)-4-[(1r,4s)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]but-3-en-2-one
Description(1R,4S)-1-(3-Oxo-1-butenyl)-2,6,6-trimethyl-4-hydroxy-2-cyclohexene belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (3e)-4-[(1r,4s)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]but-3-en-2-one is found in Tagetes erecta. Based on a literature review very few articles have been published on (1R,4S)-1-(3-Oxo-1-butenyl)-2,6,6-trimethyl-4-hydroxy-2-cyclohexene.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0317562 ((3e)-4-[(1r,4s)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]but-3-en-2-one)


  Mrv1652309112219312D          

 15 15  0  0  1  0            999 V2000
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    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
    2.1434    2.0625    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
    1.4289    0.8250    0.0000 C   0  0  1  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
    2.1434   -0.4125    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  1  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3272    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1018    1.9659    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  2  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
M  END
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3D MOL for NP0317562 ((3e)-4-[(1r,4s)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]but-3-en-2-one)

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3D SDF for NP0317562 ((3e)-4-[(1r,4s)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]but-3-en-2-one)

  Mrv1652309112219312D          

 15 15  0  0  1  0            999 V2000
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    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
    2.1434    2.0625    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
    1.4289    0.8250    0.0000 C   0  0  1  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
    2.1434   -0.4125    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  1  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3272    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1018    1.9659    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  2  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0317562

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)\C=C\[C@H]1C(C)=C[C@@H](O)CC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C13H20O2/c1-9-7-11(15)8-13(3,4)12(9)6-5-10(2)14/h5-7,11-12,15H,8H2,1-4H3/b6-5+/t11-,12+/m1/s1

> <INCHI_KEY>
FDSNVAKZRJLMJN-AIIUZBJTSA-N

> <FORMULA>
C13H20O2

> <MOLECULAR_WEIGHT>
208.301

> <EXACT_MASS>
208.146329884

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
24.104250036080636

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3E)-4-[(1R,4S)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]but-3-en-2-one

> <JCHEM_LOGP>
2.088470428

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.830484481331627

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.217272336537686

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3914321684010935

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
63.6042

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3E)-4-[(1R,4S)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]but-3-en-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0317562 ((3e)-4-[(1r,4s)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]but-3-en-2-one)
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PDB for NP0317562 ((3e)-4-[(1r,4s)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]but-3-en-2-one)
HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.611   3.670   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.057   3.670   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   13                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    6   14   15                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

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3D PDB for NP0317562 ((3e)-4-[(1r,4s)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]but-3-en-2-one)
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SMILES for NP0317562 ((3e)-4-[(1r,4s)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]but-3-en-2-one)
CC(=O)\C=C\[C@H]1C(C)=C[C@@H](O)CC1(C)C
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INCHI for NP0317562 ((3e)-4-[(1r,4s)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]but-3-en-2-one)
InChI=1S/C13H20O2/c1-9-7-11(15)8-13(3,4)12(9)6-5-10(2)14/h5-7,11-12,15H,8H2,1-4H3/b6-5+/t11-,12+/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC13H20O2
Average Mass208.3010 Da
Monoisotopic Mass208.14633 Da
IUPAC Name(3E)-4-[(1R,4S)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]but-3-en-2-one
Traditional Name(3E)-4-[(1R,4S)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]but-3-en-2-one
CAS Registry NumberNot Available
SMILES
CC(=O)\C=C\[C@H]1C(C)=C[C@@H](O)CC1(C)C
InChI Identifier
InChI=1S/C13H20O2/c1-9-7-11(15)8-13(3,4)12(9)6-5-10(2)14/h5-7,11-12,15H,8H2,1-4H3/b6-5+/t11-,12+/m1/s1
InChI KeyFDSNVAKZRJLMJN-AIIUZBJTSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
African marigoldLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassSesquiterpenoids  
Direct ParentSesquiterpenoids  
Alternative Parents
Substituents
  • Sesquiterpenoid
    • 

  • Megastigmane sesquiterpenoid
    • 

  • Cyclofarsesane sesquiterpenoid
    • 

  • Ionone derivative
    • 

  • Acryloyl-group
    • 

  • Enone
    • 

  • Alpha,beta-unsaturated ketone
    • 

  • Secondary alcohol
    • 

  • Ketone
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
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
logP2.09ChemAxon
pKa (Strongest Acidic)18.22ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity63.6 m³·mol⁻¹ChemAxon
Polarizability24.1 ųChemAxon
Number of Rings1ChemAxon
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 LinkNot Available
METLIN IDNot Available
PubChem Compound59904349  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]