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Showing NP-Card for Dehydrovomifoliol (NP0337516)

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Record Information
Version2.0
Created at2024-09-11 11:12:05 UTC
Updated at2024-09-11 11:12:05 UTC
NP-MRD IDNP0337516
Secondary Accession NumbersNone
Natural Product Identification
Common NameDehydrovomifoliol
DescriptionDehydrovomifoliol belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Dehydrovomifoliol was first documented in 2023 (PMID: 37631179). Based on a literature review a small amount of articles have been published on Dehydrovomifoliol (PMID: 38869958) (PMID: 38835269) (PMID: 38454878) (PMID: 38439740).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0337516 (Dehydrovomifoliol)


  Mrv2104 05262313442D          

 16 16  0  0  0  0            999 V2000
   -1.7848    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7848   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5004   -1.2378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0706   -1.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3564   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3591   -1.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6004    1.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0706    0.4136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5380    1.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3564    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3591    0.4136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0720    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.4136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5004    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    1.2378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3591   -0.4122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  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
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 16  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
M  END
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3D MOL for NP0337516 (Dehydrovomifoliol)

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3D SDF for NP0337516 (Dehydrovomifoliol)

  Mrv2104 05262313442D          

 16 16  0  0  0  0            999 V2000
   -1.7848    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7848   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5004   -1.2378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0706   -1.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3564   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3591   -1.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6004    1.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0706    0.4136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5380    1.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3564    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3591    0.4136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0720    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.4136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5004    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    1.2378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3591   -0.4122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  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
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 16  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0337516

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)\C=C\C1(O)C(C)=CC(=O)CC1(C)C

> <INCHI_IDENTIFIER>
InChI=1/C13H18O3/c1-9-7-11(15)8-12(3,4)13(9,16)6-5-10(2)14/h5-7,16H,8H2,1-4H3/b6-5+

> <INCHI_KEY>
JJRYPZMXNLLZFH-AATRIKPKNA-N

> <FORMULA>
C13H18O3

> <MOLECULAR_WEIGHT>
222.284

> <EXACT_MASS>
222.12559444

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
24.12364407400927

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-3,5,5-trimethyl-4-[(1E)-3-oxobut-1-en-1-yl]cyclohex-2-en-1-one

> <JCHEM_LOGP>
1.6523240710000004

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.814275656733443

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.372689942700873

> <JCHEM_PKA_STRONGEST_BASIC>
-3.510585303663095

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
63.926899999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxy-3-oxo-α-ionone

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0337516 (Dehydrovomifoliol)
Download
PDB for NP0337516 (Dehydrovomifoliol)
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      -3.332   0.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.332  -1.540   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -4.667  -2.311   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.998  -2.311   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.665  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.670  -2.311   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.987   1.954   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.998   0.772   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.004   1.954   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.665   0.001   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.670   0.772   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.001   0.001   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.334   0.772   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.667   0.001   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.334   2.311   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.670  -0.769   0.000  0.00  0.00           O+0
CONECT    1    2    8                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5                                                            
CONECT    7    8                                                            
CONECT    8    1    7    9   10                                             
CONECT    9    8                                                            
CONECT   10    5    8   11   16                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   10                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

Download
3D PDB for NP0337516 (Dehydrovomifoliol)
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SMILES for NP0337516 (Dehydrovomifoliol)
CC(=O)\C=C\C1(O)C(C)=CC(=O)CC1(C)C
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INCHI for NP0337516 (Dehydrovomifoliol)
InChI=1/C13H18O3/c1-9-7-11(15)8-12(3,4)13(9,16)6-5-10(2)14/h5-7,16H,8H2,1-4H3/b6-5+
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View in JSmol
Synonyms
ValueSource
(+/-)-6-hydroxy-3-oxo-alpha-iononeChEBI
(6Rs)-6-Hydroxy-9-apo-epsilon-carotene-3,9-dioneChEBI
6-Hydroxy-3-oxo-alpha-iononeChEBI
(+/-)-6-hydroxy-3-oxo-a-iononeGenerator
(+/-)-6-hydroxy-3-oxo-α-iononeGenerator
6-Hydroxy-3-oxo-a-iononeGenerator
6-Hydroxy-3-oxo-α-iononeGenerator
Chemical FormulaC13H18O3
Average Mass222.2840 Da
Monoisotopic Mass222.12559 Da
IUPAC Name4-hydroxy-3,5,5-trimethyl-4-[(1E)-3-oxobut-1-en-1-yl]cyclohex-2-en-1-one
Traditional Name6-hydroxy-3-oxo-α-ionone
CAS Registry NumberNot Available
SMILES
CC(=O)\C=C\C1(O)C(C)=CC(=O)CC1(C)C
InChI Identifier
InChI=1/C13H18O3/c1-9-7-11(15)8-12(3,4)13(9,16)6-5-10(2)14/h5-7,16H,8H2,1-4H3/b6-5+
InChI KeyJJRYPZMXNLLZFH-AATRIKPKNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound 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
    • 

  • Cyclohexenone
    • 

  • Acryloyl-group
    • 

  • Enone
    • 

  • Alpha,beta-unsaturated ketone
    • 

  • Tertiary alcohol
    • 

  • Ketone
    • 

  • Cyclic ketone
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Hydrocarbon derivative
    • 

  • Carbonyl group
    • 

  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
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
logP1.65ChemAxon
pKa (Strongest Acidic)13.37ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity63.93 m³·mol⁻¹ChemAxon
Polarizability24.12 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 IDC00029298  
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID18429  
Good Scents IDNot Available
References
General References
  1. Huang X, Xu N, Liu Z, Li H, Lu H, Li J: Chemical Composition of Achillea millefolium L. and Their Anti-Inflammatory Activity. Chem Biodivers. 2024 Aug;21(8):e202400946. doi: 10.1002/cbdv.202400946. Epub 2024  Jul 26. [PubMed:38869958  ] 
  2. Zhang CX, Zhang GH, Wei F, Kong GH, He Y, Li YK, Cai XH: Ionones from cigar tobacco leaves. J Asian Nat Prod Res. 2024 Sep;26(9):1033-1040. doi:  10.1080/10286020.2024.2342509. Epub 2024 Jun 5. [PubMed:38835269  ] 
  3. Nguyen TVA, Nguyen TMH, Ha TT, Nguyen TD, Bui DH: Antiplatelet and Anticoagulant Effects of Two New Phenylpropanoid Sucrose Esters and Other Secondary Metabolites from the Aerial Part of Canna edulis. Chem Biodivers. 2024 May;21(5):e202400302. doi: 10.1002/cbdv.202400302. Epub 2024  Mar 27. [PubMed:38454878  ] 
  4. Kooltheat N, Noonong K, Hanson KM, Lao-On U: Phytochemical composition of the diethyl ether extract of Artemisia lactiflora Wall. ex DC and its antimetastatic activity in human lung cancer cells. Nat Prod Res. 2024 Mar 5:1-7. doi: 10.1080/14786419.2024.2324114. [PubMed:38439740  ] 
  5. Lun TL, Tojo S, Teruya T, Kato-Noguchi H: Allelopathic Activity of the Invasive Plant Polygonum chinense Linn. and Its Allelopathic Substances. Plants (Basel). 2023 Aug 17;12(16):2968. doi: 10.3390/plants12162968. [PubMed:37631179  ]