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Showing NP-Card for Verlotorin (NP0046782)

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Record Information
Version2.0
Created at2022-03-17 20:29:28 UTC
Updated at2022-03-17 20:29:28 UTC
NP-MRD IDNP0046782
Secondary Accession NumbersNone
Natural Product Identification
Common NameVerlotorin
DescriptionVerlotorin belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Verlotorin is found in Artemisia annua, Artemisia genipy, Artemisia umbelliformis, Laurus nobilis and Magnolia grandiflora . Verlotorin is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0046782 (Verlotorin)


  Mrv0541 02241221232D          

 19 20  0  0  0  0            999 V2000
    1.3561   -0.1588    0.0000 O   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
    2.8173    0.0031    0.0000 O   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
    4.2755   -0.3788    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
    5.3809    0.5267    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
    5.6124   -0.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1352   -1.5216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8439   -2.2935    0.0000 O   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
    4.0002   -0.8080    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
    3.6929   -1.9226    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
    2.3460   -1.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8304   -1.8899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0440    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  2  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  4 16  1  0  0  0  0
 16 17  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  2  0  0  0  0
  6 19  1  0  0  0  0
M  END
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3D MOL for NP0046782 (Verlotorin)

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3D SDF for NP0046782 (Verlotorin)

  Mrv0541 02241221232D          

 19 20  0  0  0  0            999 V2000
    1.3561   -0.1588    0.0000 O   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
    2.8173    0.0031    0.0000 O   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
    4.2755   -0.3788    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
    5.3809    0.5267    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
    5.6124   -0.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1352   -1.5216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8439   -2.2935    0.0000 O   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
    4.0002   -0.8080    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
    3.6929   -1.9226    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
    2.3460   -1.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8304   -1.8899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0440    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  2  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  4 16  1  0  0  0  0
 16 17  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  2  0  0  0  0
  6 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046782

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C1=C/C2OC(=O)C(=C)C2CCC(=C)C(CC1)OO

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-9-4-7-13(19-17)10(2)5-6-12-11(3)15(16)18-14(12)8-9/h8,12-14,17H,2-7H2,1H3/b9-8+

> <INCHI_KEY>
IXRHWRRLTANMPL-CMDGGOBGSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.3169

> <EXACT_MASS>
264.136159128

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.78249926719655

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroperoxy-10-methyl-3,6-dimethylidene-2H,3H,3aH,4H,5H,6H,7H,8H,9H,11aH-cyclodeca[b]furan-2-one

> <ALOGPS_LOGP>
2.76

> <JCHEM_LOGP>
3.0926246273333335

> <ALOGPS_LOGS>
-2.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.711276580410768

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2372876237283466

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
71.7396

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.53e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-hydroperoxy-10-methyl-3,6-dimethylidene-3aH,4H,5H,7H,8H,9H,11aH-cyclodeca[b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0046782 (Verlotorin)
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PDB for NP0046782 (Verlotorin)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       2.531  -0.296   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.972  -0.840   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.259   0.006   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       6.461  -0.957   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.981  -0.707   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.525   0.734   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.044   0.983   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.020  -0.208   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.476  -1.649   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      11.452  -2.840   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      10.909  -4.281   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.957  -1.898   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.467  -1.508   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.413  -3.339   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.893  -3.589   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.918  -2.397   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.379  -2.325   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.417  -3.528   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.549   1.925   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   16                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    4   17                                                  
CONECT   17   16    2   18                                                  
CONECT   18   17                                                            
CONECT   19    6                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

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3D PDB for NP0046782 (Verlotorin)
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SMILES for NP0046782 (Verlotorin)
C\C1=C/C2OC(=O)C(=C)C2CCC(=C)C(CC1)OO
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INCHI for NP0046782 (Verlotorin)
InChI=1S/C15H20O4/c1-9-4-7-13(19-17)10(2)5-6-12-11(3)15(16)18-14(12)8-9/h8,12-14,17H,2-7H2,1H3/b9-8+
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View in JSmol
SynonymsNot Available
Chemical FormulaC15H20O4
Average Mass264.3169 Da
Monoisotopic Mass264.13616 Da
IUPAC Name7-hydroperoxy-10-methyl-3,6-dimethylidene-2H,3H,3aH,4H,5H,6H,7H,8H,9H,11aH-cyclodeca[b]furan-2-one
Traditional Name7-hydroperoxy-10-methyl-3,6-dimethylidene-3aH,4H,5H,7H,8H,9H,11aH-cyclodeca[b]furan-2-one
CAS Registry Number31105-79-0
SMILES
C\C1=C/C2OC(=O)C(=C)C2CCC(=C)C(CC1)OO
InChI Identifier
InChI=1S/C15H20O4/c1-9-4-7-13(19-17)10(2)5-6-12-11(3)15(16)18-14(12)8-9/h8,12-14,17H,2-7H2,1H3/b9-8+
InChI KeyIXRHWRRLTANMPL-CMDGGOBGSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Artemisia annuaLOTUS Database
Artemisia genipyPlant
Artemisia umbelliformisLOTUS Database
Laurus nobilisLOTUS Database
Laurus nobilis L.FooDB
Magnolia grandifloraPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassTerpene lactones  
Direct ParentTerpene lactones  
Alternative Parents
Substituents
  • Terpene lactone
    • 

  • Germacrane sesquiterpenoid
    • 

  • Sesquiterpenoid
    • 

  • Gamma butyrolactone
    • 

  • Tetrahydrofuran
    • 

  • Enoate ester
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Hydroperoxide
    • 

  • Lactone
    • 

  • Carboxylic acid ester
    • 

  • Alkyl hydroperoxide
    • 

  • Peroxol
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Organoheterocyclic compound
    • 

  • Oxacycle
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • 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
logP2.76ALOGPS
logP3.09ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)11.71ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity71.74 m³·mol⁻¹ChemAxon
Polarizability27.78 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 IDFDB005902  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5358982  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available