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Showing NP-Card for 1-[(1s,2s,5s,6s)-5,6-dihydroxy-2-[(1e)-prop-1-en-1-yl]cyclohex-3-en-1-yl]-1-hydroxypropan-2-one (NP0282296)

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Record Information
Version2.0
Created at2022-09-09 09:04:41 UTC
Updated at2022-09-09 09:04:41 UTC
NP-MRD IDNP0282296
Secondary Accession NumbersNone
Natural Product Identification
Common Name1-[(1s,2s,5s,6s)-5,6-dihydroxy-2-[(1e)-prop-1-en-1-yl]cyclohex-3-en-1-yl]-1-hydroxypropan-2-one
DescriptionArthropsatriol B belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups. 1-[(1s,2s,5s,6s)-5,6-dihydroxy-2-[(1e)-prop-1-en-1-yl]cyclohex-3-en-1-yl]-1-hydroxypropan-2-one is found in Arthropsis truncata. Based on a literature review very few articles have been published on Arthropsatriol B.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0282296 (1-[(1s,2s,5s,6s)-5,6-dihydroxy-2-[(1e)-prop-1-en-1-yl]cyclohex-3-en-1-yl]-1-hydroxypropan-2-one)


  Mrv1652309092211042D          

 16 16  0  0  1  0            999 V2000
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  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
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   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  1  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
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  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    1.2375    0.0000 O   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  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
M  END
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3D MOL for NP0282296 (1-[(1s,2s,5s,6s)-5,6-dihydroxy-2-[(1e)-prop-1-en-1-yl]cyclohex-3-en-1-yl]-1-hydroxypropan-2-one)

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3D SDF for NP0282296 (1-[(1s,2s,5s,6s)-5,6-dihydroxy-2-[(1e)-prop-1-en-1-yl]cyclohex-3-en-1-yl]-1-hydroxypropan-2-one)

  Mrv1652309092211042D          

 16 16  0  0  1  0            999 V2000
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  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
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   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  1  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
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  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    1.2375    0.0000 O   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  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0282296

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H18O4/c1-3-4-8-5-6-9(14)12(16)10(8)11(15)7(2)13/h3-6,8-12,14-16H,1-2H3/b4-3+/t8-,9-,10+,11?,12+/m0/s1

> <INCHI_KEY>
ZUVDWANJVVXNTN-HSCVWOFMSA-N

> <FORMULA>
C12H18O4

> <MOLECULAR_WEIGHT>
226.272

> <EXACT_MASS>
226.12050906

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
23.740822358096274

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(1S,2S,5S,6S)-5,6-dihydroxy-2-[(1E)-prop-1-en-1-yl]cyclohex-3-en-1-yl]-1-hydroxypropan-2-one

> <JCHEM_LOGP>
-0.19657351566666692

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.683902985127883

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.916144663749904

> <JCHEM_PKA_STRONGEST_BASIC>
-3.312784824424172

> <JCHEM_POLAR_SURFACE_AREA>
77.75999999999999

> <JCHEM_REFRACTIVITY>
62.1493

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1-[(1S,2S,5S,6S)-5,6-dihydroxy-2-[(1E)-prop-1-en-1-yl]cyclohex-3-en-1-yl]-1-hydroxypropan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0282296 (1-[(1s,2s,5s,6s)-5,6-dihydroxy-2-[(1e)-prop-1-en-1-yl]cyclohex-3-en-1-yl]-1-hydroxypropan-2-one)
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PDB for NP0282296 (1-[(1s,2s,5s,6s)-5,6-dihydroxy-2-[(1e)-prop-1-en-1-yl]cyclohex-3-en-1-yl]-1-hydroxypropan-2-one)
HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    4   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

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3D PDB for NP0282296 (1-[(1s,2s,5s,6s)-5,6-dihydroxy-2-[(1e)-prop-1-en-1-yl]cyclohex-3-en-1-yl]-1-hydroxypropan-2-one)
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SMILES for NP0282296 (1-[(1s,2s,5s,6s)-5,6-dihydroxy-2-[(1e)-prop-1-en-1-yl]cyclohex-3-en-1-yl]-1-hydroxypropan-2-one)
C\C=C\[C@H]1C=C[C@H](O)[C@@H](O)[C@H]1C(O)C(C)=O
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INCHI for NP0282296 (1-[(1s,2s,5s,6s)-5,6-dihydroxy-2-[(1e)-prop-1-en-1-yl]cyclohex-3-en-1-yl]-1-hydroxypropan-2-one)
InChI=1S/C12H18O4/c1-3-4-8-5-6-9(14)12(16)10(8)11(15)7(2)13/h3-6,8-12,14-16H,1-2H3/b4-3+/t8-,9-,10+,11?,12+/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC12H18O4
Average Mass226.2720 Da
Monoisotopic Mass226.12051 Da
IUPAC Name1-[(1S,2S,5S,6S)-5,6-dihydroxy-2-[(1E)-prop-1-en-1-yl]cyclohex-3-en-1-yl]-1-hydroxypropan-2-one
Traditional Name1-[(1S,2S,5S,6S)-5,6-dihydroxy-2-[(1E)-prop-1-en-1-yl]cyclohex-3-en-1-yl]-1-hydroxypropan-2-one
CAS Registry NumberNot Available
SMILES
C\C=C\[C@H]1C=C[C@H](O)[C@@H](O)[C@H]1C(O)C(C)=O
InChI Identifier
InChI=1S/C12H18O4/c1-3-4-8-5-6-9(14)12(16)10(8)11(15)7(2)13/h3-6,8-12,14-16H,1-2H3/b4-3+/t8-,9-,10+,11?,12+/m0/s1
InChI KeyZUVDWANJVVXNTN-HSCVWOFMSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Arthropsis truncataLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentAcyloins  
Alternative Parents
Substituents
  • Acyloin
    • 

  • Alpha-hydroxy ketone
    • 

  • Secondary alcohol
    • 

  • Ketone
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Alcohol
    • 

  • 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
logP-0.2ChemAxon
pKa (Strongest Acidic)12.92ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity62.15 m³·mol⁻¹ChemAxon
Polarizability23.74 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID78436267  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound139583157  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]