Np mrd loader

Showing NP-Card for alpha-Peroxyachifolide (NP0334038)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2024-09-09 21:46:47 UTC
Updated at2024-09-09 21:46:48 UTC
NP-MRD IDNP0334038
Secondary Accession NumbersNone
Natural Product Identification
Common Namealpha-Peroxyachifolide
DescriptionConstituent of Achillea millefolium (yarrow). Alpha-Peroxyachifolide is found in herbs and spices.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0334038 (alpha-Peroxyachifolide)


  Mrv2104 05252300192D          

 32 35  0  0  1  0            999 V2000
   -1.3709    3.9928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3718    2.0521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1106    1.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6184   -0.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2206    2.3222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2542    3.1761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7548    0.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5915    1.3430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5243    2.1319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4885    2.8688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3870    0.9628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6411    1.3152    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8130    2.5499    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0753    0.7148    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2531    0.7827    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1604    3.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2822    0.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3387   -0.0634    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0428    2.2543    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7936    1.4679    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8809    3.3721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0436    4.1950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8827   -0.4213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4716   -0.0088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9260    3.0710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5267    0.0825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2471    0.8587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9031    2.6666    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3049    1.8051    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5453    2.9298    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8937    0.6100    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4770    0.5031    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2 10  1  0  0  0  0
  3 11  2  0  0  0  0
 18  4  1  1  0  0  0
 19  5  1  6  0  0  0
  6 28  1  0  0  0  0
  6 10  2  0  0  0  0
  7  8  2  0  0  0  0
 18  7  1  0  0  0  0
 20  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13  9  1  0  0  0  0
 10 16  1  0  0  0  0
 12 11  1  0  0  0  0
 11 17  1  0  0  0  0
 12 29  1  6  0  0  0
 14 12  1  0  0  0  0
 13 30  1  1  0  0  0
 19 13  1  0  0  0  0
 13 21  1  6  0  0  0
 14 31  1  1  0  0  0
 15 14  1  0  0  0  0
 14 24  1  0  0  0  0
 15 32  1  6  0  0  0
 15 18  1  0  0  0  0
 15 20  1  0  0  0  0
 16 22  2  0  0  0  0
 16 25  1  0  0  0  0
 17 23  2  0  0  0  0
 17 24  1  0  0  0  0
 18 26  1  0  0  0  0
 20 19  1  0  0  0  0
 19 25  1  1  0  0  0
 20 27  1  6  0  0  0
 26 27  1  0  0  0  0
M  END
Download

3D MOL for NP0334038 (alpha-Peroxyachifolide)

Download
3D SDF for NP0334038 (alpha-Peroxyachifolide)

  Mrv2104 05252300192D          

 32 35  0  0  1  0            999 V2000
   -1.3709    3.9928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3718    2.0521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1106    1.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6184   -0.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2206    2.3222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2542    3.1761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7548    0.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5915    1.3430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5243    2.1319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4885    2.8688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3870    0.9628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6411    1.3152    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8130    2.5499    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0753    0.7148    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2531    0.7827    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1604    3.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2822    0.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3387   -0.0634    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0428    2.2543    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7936    1.4679    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8809    3.3721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0436    4.1950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8827   -0.4213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4716   -0.0088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9260    3.0710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5267    0.0825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2471    0.8587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9031    2.6666    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3049    1.8051    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5453    2.9298    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8937    0.6100    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4770    0.5031    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2 10  1  0  0  0  0
  3 11  2  0  0  0  0
 18  4  1  1  0  0  0
 19  5  1  6  0  0  0
  6 28  1  0  0  0  0
  6 10  2  0  0  0  0
  7  8  2  0  0  0  0
 18  7  1  0  0  0  0
 20  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13  9  1  0  0  0  0
 10 16  1  0  0  0  0
 12 11  1  0  0  0  0
 11 17  1  0  0  0  0
 12 29  1  6  0  0  0
 14 12  1  0  0  0  0
 13 30  1  1  0  0  0
 19 13  1  0  0  0  0
 13 21  1  6  0  0  0
 14 31  1  1  0  0  0
 15 14  1  0  0  0  0
 14 24  1  0  0  0  0
 15 32  1  6  0  0  0
 15 18  1  0  0  0  0
 15 20  1  0  0  0  0
 16 22  2  0  0  0  0
 16 25  1  0  0  0  0
 17 23  2  0  0  0  0
 17 24  1  0  0  0  0
 18 26  1  0  0  0  0
 20 19  1  0  0  0  0
 19 25  1  1  0  0  0
 20 27  1  6  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334038

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(C)=C(/C)C(=O)O[C@@]1(C)[C@]([H])(O)C[C@@]2([H])C(=C)C(=O)O[C@]2([H])[C@@]2([H])[C@@]3(C)OO[C@@]12C=C3

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O7/c1-6-10(2)16(22)25-19(5)13(21)9-12-11(3)17(23)24-14(12)15-18(4)7-8-20(15,19)27-26-18/h6-8,12-15,21H,3,9H2,1-2,4-5H3/b10-6-/t12-,13+,14-,15-,18-,19-,20+/m0/s1

> <INCHI_KEY>
UMHHYRUGXILZJB-MFTVPULDSA-N

> <FORMULA>
C20H24O7

> <MOLECULAR_WEIGHT>
376.405

> <EXACT_MASS>
376.152203113

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
38.558046371146034

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,3R,5S,9S,10S,11S)-3-hydroxy-2,11-dimethyl-6-methylidene-7-oxo-8,12,13-trioxatetracyclo[9.2.2.0^{1,10}.0^{5,9}]pentadec-14-en-2-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_LOGP>
2.717268562000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.846819060577799

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3032013429032703

> <JCHEM_POLAR_SURFACE_AREA>
91.29

> <JCHEM_REFRACTIVITY>
94.42019999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3R,5S,9S,10S,11S)-3-hydroxy-2,11-dimethyl-6-methylidene-7-oxo-8,12,13-trioxatetracyclo[9.2.2.0^{1,10}.0^{5,9}]pentadec-14-en-2-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0334038 (alpha-Peroxyachifolide)
Download
PDB for NP0334038 (alpha-Peroxyachifolide)
HEADER    PROTEIN                                 25-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-MAY-23         0                                  
HETATM    1  C   UNK     0      -2.559   7.453   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.694   3.831   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.673   2.537   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.021  -1.567   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.412   4.335   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.341   5.929   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.276   1.040   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.971   2.507   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.712   3.980   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.912   5.355   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.322   1.797   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.930   2.455   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.384   4.760   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.874   1.334   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.339   1.461   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.299   6.306   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.127   0.270   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.499  -0.118   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.947   4.208   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.481   2.740   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.511   6.295   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.081   7.831   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       7.248  -0.786   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.614  -0.016   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       1.729   5.733   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       0.983   0.154   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       0.461   1.603   0.000  0.00  0.00           O+0
HETATM   28  H   UNK     0      -3.552   4.978   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       6.169   3.369   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       4.751   5.469   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       5.401   1.139   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.890   0.939   0.000  0.00  0.00           H+0
CONECT    1    6                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4   18                                                            
CONECT    5   19                                                            
CONECT    6    1   28   10                                                  
CONECT    7    8   18                                                       
CONECT    8    7   20                                                       
CONECT    9   12   13                                                       
CONECT   10    2    6   16                                                  
CONECT   11    3   12   17                                                  
CONECT   12    9   11   29   14                                             
CONECT   13    9   30   19   21                                             
CONECT   14   12   31   15   24                                             
CONECT   15   14   32   18   20                                             
CONECT   16   10   22   25                                                  
CONECT   17   11   23   24                                                  
CONECT   18    4    7   15   26                                             
CONECT   19    5   13   20   25                                             
CONECT   20    8   15   19   27                                             
CONECT   21   13                                                            
CONECT   22   16                                                            
CONECT   23   17                                                            
CONECT   24   14   17                                                       
CONECT   25   16   19                                                       
CONECT   26   18   27                                                       
CONECT   27   20   26                                                       
CONECT   28    6                                                            
CONECT   29   12                                                            
CONECT   30   13                                                            
CONECT   31   14                                                            
CONECT   32   15                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

Download
3D PDB for NP0334038 (alpha-Peroxyachifolide)
Download
SMILES for NP0334038 (alpha-Peroxyachifolide)
[H]\C(C)=C(/C)C(=O)O[C@@]1(C)[C@]([H])(O)C[C@@]2([H])C(=C)C(=O)O[C@]2([H])[C@@]2([H])[C@@]3(C)OO[C@@]12C=C3
Download
INCHI for NP0334038 (alpha-Peroxyachifolide)
InChI=1S/C20H24O7/c1-6-10(2)16(22)25-19(5)13(21)9-12-11(3)17(23)24-14(12)15-18(4)7-8-20(15,19)27-26-18/h6-8,12-15,21H,3,9H2,1-2,4-5H3/b10-6-/t12-,13+,14-,15-,18-,19-,20+/m0/s1
Download
View in JSmol
Synonyms
ValueSource
a-PeroxyachifolideGenerator
Α-peroxyachifolideGenerator
Chemical FormulaC20H24O7
Average Mass376.4050 Da
Monoisotopic Mass376.15220 Da
IUPAC Name(1R,2S,3R,5S,9S,10S,11S)-3-hydroxy-2,11-dimethyl-6-methylidene-7-oxo-8,12,13-trioxatetracyclo[9.2.2.0^{1,10}.0^{5,9}]pentadec-14-en-2-yl (2Z)-2-methylbut-2-enoate
Traditional Name(1R,2S,3R,5S,9S,10S,11S)-3-hydroxy-2,11-dimethyl-6-methylidene-7-oxo-8,12,13-trioxatetracyclo[9.2.2.0^{1,10}.0^{5,9}]pentadec-14-en-2-yl (2Z)-2-methylbut-2-enoate
CAS Registry NumberNot Available
SMILES
[H]\C(C)=C(/C)C(=O)O[C@@]1(C)[C@]([H])(O)C[C@@]2([H])C(=C)C(=O)O[C@]2([H])[C@@]2([H])[C@@]3(C)OO[C@@]12C=C3
InChI Identifier
InChI=1S/C20H24O7/c1-6-10(2)16(22)25-19(5)13(21)9-12-11(3)17(23)24-14(12)15-18(4)7-8-20(15,19)27-26-18/h6-8,12-15,21H,3,9H2,1-2,4-5H3/b10-6-/t12-,13+,14-,15-,18-,19-,20+/m0/s1
InChI KeyUMHHYRUGXILZJB-MFTVPULDSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassTerpene lactones  
Direct ParentGuaianolides and derivatives  
Alternative Parents
Substituents
  • Guaianolide-skeleton
    • 

  • Farsesane sesquiterpenoid
    • 

  • Sesquiterpenoid
    • 

  • Fatty alcohol ester
    • 

  • Fatty acid ester
    • 

  • Fatty acyl
    • 

  • Gamma butyrolactone
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Tetrahydrofuran
    • 

  • Cyclic alcohol
    • 

  • Ortho-dioxolane
    • 

  • Dialkyl peroxide
    • 

  • Secondary alcohol
    • 

  • Lactone
    • 

  • Carboxylic acid ester
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • 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
logP2.72ChemAxon
pKa (Strongest Acidic)13.85ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area91.29 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity94.42 m³·mol⁻¹ChemAxon
Polarizability38.56 ųChemAxon
Number of Rings4ChemAxon
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 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. Rucker G, Neugebauer M, Kiefer A: [Quantitative determination of alpha-peroxyachifolide in yarrow by HPLC with amperometric detection]. Pharmazie. 1994 Feb-Mar;49(2-3):167-9. [PubMed:8171079  ]