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Showing NP-Card for Hydroxypelenolide (NP0335001)

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Record Information
Version2.0
Created at2024-09-10 23:26:18 UTC
Updated at2024-09-10 23:26:18 UTC
NP-MRD IDNP0335001
Secondary Accession NumbersNone
Natural Product Identification
Common NameHydroxypelenolide
DescriptionHydroxypelenolide belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Hydroxypelenolide was first documented in 2016 (PMID: 27980595). Based on a literature review very few articles have been published on Hydroxypelenolide (PMID: 33925212).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0335001 (Hydroxypelenolide)


  Mrv2104 05262301582D          

 18 19  0  0  0  0            999 V2000
    5.6722    1.2985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0298   -2.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8558    0.8272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5668    0.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9037   -0.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2755   -0.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6124   -0.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6929   -1.9226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3809    0.5267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5070   -1.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8173    0.0031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4614   -0.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7983   -1.0170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1701   -1.2843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1279   -0.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0002   -0.8080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3561   -0.1588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3460   -1.2458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  9  1  1  0  0  0  0
  9  4  1  0  0  0  0
  9  5  2  0  0  0  0
 10  2  1  0  0  0  0
 10  8  1  0  0  0  0
 11  3  1  0  0  0  0
 12  6  1  0  0  0  0
 12 11  1  0  0  0  0
 13  7  1  0  0  0  0
 13 10  1  0  0  0  0
 14  8  1  0  0  0  0
 14 12  1  0  0  0  0
 15 11  1  0  0  0  0
 16 13  1  0  0  0  0
 17 15  2  0  0  0  0
 18 14  1  0  0  0  0
 18 15  1  0  0  0  0
M  END
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3D MOL for NP0335001 (Hydroxypelenolide)

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3D SDF for NP0335001 (Hydroxypelenolide)

  Mrv2104 05262301582D          

 18 19  0  0  0  0            999 V2000
    5.6722    1.2985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0298   -2.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8558    0.8272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5668    0.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9037   -0.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2755   -0.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6124   -0.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6929   -1.9226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3809    0.5267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5070   -1.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8173    0.0031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4614   -0.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7983   -1.0170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1701   -1.2843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1279   -0.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0002   -0.8080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3561   -0.1588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3460   -1.2458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  9  1  1  0  0  0  0
  9  4  1  0  0  0  0
  9  5  2  0  0  0  0
 10  2  1  0  0  0  0
 10  8  1  0  0  0  0
 11  3  1  0  0  0  0
 12  6  1  0  0  0  0
 12 11  1  0  0  0  0
 13  7  1  0  0  0  0
 13 10  1  0  0  0  0
 14  8  1  0  0  0  0
 14 12  1  0  0  0  0
 15 11  1  0  0  0  0
 16 13  1  0  0  0  0
 17 15  2  0  0  0  0
 18 14  1  0  0  0  0
 18 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0335001

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2CC\C(C)=C/CC(O)C(C)CC2OC1=O

> <INCHI_IDENTIFIER>
InChI=1/C15H24O3/c1-9-4-6-12-11(3)15(17)18-14(12)8-10(2)13(16)7-5-9/h5,10-14,16H,4,6-8H2,1-3H3/b9-5-

> <INCHI_KEY>
LAOQYXNUSDEVJK-UITAMQMPNA-N

> <FORMULA>
C15H24O3

> <MOLECULAR_WEIGHT>
252.354

> <EXACT_MASS>
252.172544633

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
28.567660940628773

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-hydroxy-3,6,10-trimethyl-2H,3H,3aH,4H,5H,8H,9H,10H,11H,11aH-cyclodeca[b]furan-2-one

> <JCHEM_LOGP>
2.615419166666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.895819832960512

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8443684050630713

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
71.0395

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
9-hydroxy-3,6,10-trimethyl-3H,3aH,4H,5H,8H,9H,10H,11H,11aH-cyclodeca[b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0335001 (Hydroxypelenolide)
Download
PDB for NP0335001 (Hydroxypelenolide)
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      10.588   2.424   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.389  -4.531   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.331   1.544   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.525   0.734   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.020  -0.208   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.981  -0.707   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.476  -1.649   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.893  -3.589   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.044   0.983   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.413  -3.339   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.259   0.006   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.461  -0.957   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.957  -1.898   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.918  -2.397   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.972  -0.840   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.467  -1.508   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.531  -0.296   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.379  -2.325   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4    6    9                                                       
CONECT    5    7    9                                                       
CONECT    6    4   12                                                       
CONECT    7    5   13                                                       
CONECT    8   10   14                                                       
CONECT    9    1    4    5                                                  
CONECT   10    2    8   13                                                  
CONECT   11    3   12   15                                                  
CONECT   12    6   11   14                                                  
CONECT   13    7   10   16                                                  
CONECT   14    8   12   18                                                  
CONECT   15   11   17   18                                                  
CONECT   16   13                                                            
CONECT   17   15                                                            
CONECT   18   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

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3D PDB for NP0335001 (Hydroxypelenolide)
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SMILES for NP0335001 (Hydroxypelenolide)
CC1C2CC\C(C)=C/CC(O)C(C)CC2OC1=O
Download
INCHI for NP0335001 (Hydroxypelenolide)
InChI=1/C15H24O3/c1-9-4-6-12-11(3)15(17)18-14(12)8-10(2)13(16)7-5-9/h5,10-14,16H,4,6-8H2,1-3H3/b9-5-
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View in JSmol
SynonymsNot Available
Chemical FormulaC15H24O3
Average Mass252.3540 Da
Monoisotopic Mass252.17254 Da
IUPAC Name9-hydroxy-3,6,10-trimethyl-2H,3H,3aH,4H,5H,8H,9H,10H,11H,11aH-cyclodeca[b]furan-2-one
Traditional Name9-hydroxy-3,6,10-trimethyl-3H,3aH,4H,5H,8H,9H,10H,11H,11aH-cyclodeca[b]furan-2-one
CAS Registry NumberNot Available
SMILES
CC1C2CC\C(C)=C/CC(O)C(C)CC2OC1=O
InChI Identifier
InChI=1/C15H24O3/c1-9-4-6-12-11(3)15(17)18-14(12)8-10(2)13(16)7-5-9/h5,10-14,16H,4,6-8H2,1-3H3/b9-5-
InChI KeyLAOQYXNUSDEVJK-UITAMQMPNA-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 germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassTerpene lactones  
Direct ParentGermacranolides and derivatives  
Alternative Parents
Substituents
  • Germacranolide
    • 

  • Germacrane sesquiterpenoid
    • 

  • Sesquiterpenoid
    • 

  • Gamma butyrolactone
    • 

  • Tetrahydrofuran
    • 

  • Carboxylic acid ester
    • 

  • Lactone
    • 

  • Secondary alcohol
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Alcohol
    • 

  • Carbonyl group
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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
logP2.62ChemAxon
pKa (Strongest Acidic)14.9ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity71.04 m³·mol⁻¹ChemAxon
Polarizability28.57 ųChemAxon
Number of Rings2ChemAxon
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 IDC00012209  
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 IDNot Available
Good Scents IDNot Available
References
General References
  1. Fraga BM, Diaz CE, Bailen M, Gonzalez-Coloma A: Sesquiterpene Lactones from Artemisia absinthium. Biotransformation and Rearrangement of the Insect Antifeedant 3alpha-hydroxypelenolide. Plants (Basel). 2021 Apr 28;10(5):891. doi: 10.3390/plants10050891. [PubMed:33925212  ] 
  2. de Almeida LM, de Carvalho LS, Gazolla MC, Silva Pinto PL, da Silva MP, de Moraes J, Da Silva Filho AA: Flavonoids and Sesquiterpene Lactones from Artemisia absinthium and Tanacetum parthenium against Schistosoma mansoni Worms. Evid Based Complement Alternat Med. 2016;2016:9521349. doi: 10.1155/2016/9521349.  Epub 2016 Nov 17. [PubMed:27980595  ]