NP-MRD: Showing NP-Card for (1s,2s,4r,7e,9s,11s)-9-hydroxy-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradec-7-en-13-one (NP0291749)

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Record Information

Version

1.0

Created at

2022-09-09 22:57:21 UTC

Updated at

2022-09-09 22:57:22 UTC

NP-MRD ID

NP0291749

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,4r,7e,9s,11s)-9-hydroxy-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradec-7-en-13-one

Description

9Beta-hydroxyparthenolide 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. (1s,2s,4r,7e,9s,11s)-9-hydroxy-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradec-7-en-13-one is found in Anthemis cupaniana and Anvillea garcinii. It was first documented in 2014 (PMID: 24998377). Based on a literature review a significant number of articles have been published on 9beta-hydroxyparthenolide (PMID: 34199475) (PMID: 32283756) (PMID: 27919107) (PMID: 25647341).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
    3.4413    1.6603   -0.1418 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9133    0.4980   -0.4126 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6872   -0.7106   -0.7372 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9154   -0.6756   -1.0753 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8479   -1.8034   -0.6031 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6726   -1.3225    0.0836 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5028    0.0115   -0.4825 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6511    0.9255    0.3466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2855    1.7624   -0.4818 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3323    3.0488   -0.5225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6688    1.8608    0.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1409    3.3174    0.1793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4705    0.8823    0.3918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3573   -0.5563    0.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5257   -1.2556   -0.6164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6668   -2.3300   -0.0176 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5469   -3.4158    0.6144 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1420   -2.8400   -1.1638 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6584   -2.3612    0.0784 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9129    2.5698    0.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5381    1.7888   -0.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0364   -1.1942    1.1473 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2699    0.0572   -1.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1046    0.3439    1.1374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3231    1.5767    0.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2617    1.5032   -1.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6214    3.3189    0.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3779    3.7790    0.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0747    3.8185   -0.7865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0972    3.3706    0.6873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4664    1.2482    0.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9202   -0.8490    1.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3908   -1.0367    0.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2732   -1.8549   -1.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0526   -0.6576   -1.3790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4804   -3.5489    0.0770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9853   -4.3914    0.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6385   -3.2434    1.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1109   -3.2946    0.5786 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  1
 16 18  1  0
 18 19  1  0
 19  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  2  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 19 16  1  0
  7  6  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
 19 39  1  1
  6 22  1  1
  1 20  1  0
  1 21  1  0
  7 23  1  6
  8 24  1  0
  8 25  1  0
  9 26  1  6
 10 27  1  0
M  END


  Mrv1652309102200572D          

 19 21  0  0  1  0            999 V2000
    5.0951   -1.6841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3518   -1.3260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2047   -0.5142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7749    0.0820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3871   -0.4034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0291   -1.1466    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6253   -1.7168    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7725   -2.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4144   -3.2718    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8052   -3.9984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5969   -3.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4497   -2.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8703   -3.5518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2741   -2.9816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1269   -2.1698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4850   -1.4266    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6835   -1.2308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5098   -0.6019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2115   -1.0357    0.0000 C   0  0  1  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  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  2  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 19 18  1  1  0  0  0
  6 19  1  0  0  0  0
 16 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0291749

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C1=C/CC[C@@]2(C)O[C@H]2[C@H]2OC(=O)C(=C)[C@@H]2C[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-8-5-4-6-15(3)13(19-15)12-10(7-11(8)16)9(2)14(17)18-12/h5,10-13,16H,2,4,6-7H2,1,3H3/b8-5+/t10-,11-,12-,13-,15+/m0/s1

> <INCHI_KEY>
RZUCCKARTVHQBW-MPFAERRBSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.321

> <EXACT_MASS>
264.136159124

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
27.693198482904865

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,4R,7E,9S,11S)-9-hydroxy-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.0^{2,4}]tetradec-7-en-13-one

> <JCHEM_LOGP>
1.8404815313333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.602904780791715

> <JCHEM_PKA_STRONGEST_BASIC>
-2.972489448881703

> <JCHEM_POLAR_SURFACE_AREA>
59.06

> <JCHEM_REFRACTIVITY>
70.0684

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,4R,7E,9S,11S)-9-hydroxy-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.0^{2,4}]tetradec-7-en-13-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       9.511  -3.144   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.123  -2.475   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.849  -0.960   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.913   0.153   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       6.323  -0.753   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.654  -2.140   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.767  -3.205   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.042  -4.720   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.374  -6.107   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.103  -7.464   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.847  -5.900   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.573  -4.385   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.491  -6.630   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.378  -5.566   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.104  -4.050   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.772  -2.663   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.276  -2.298   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.818  -1.124   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.128  -1.933   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18    6   16                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Value	Source
9b-Hydroxyparthenolide	Generator
9Β-hydroxyparthenolide	Generator
9-Hydroxyparthenolide	MeSH
9alpha-Hydroxyparthenolide	MeSH

Chemical Formula

C₁₅H₂₀O₄

Average Mass

264.3210 Da

Monoisotopic Mass

264.13616 Da

IUPAC Name

(1S,2S,4R,7E,9S,11S)-9-hydroxy-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.0^{2,4}]tetradec-7-en-13-one

Traditional Name

(1S,2S,4R,7E,9S,11S)-9-hydroxy-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.0^{2,4}]tetradec-7-en-13-one

CAS Registry Number

Not Available

SMILES

C\C1=C/CC[C@@]2(C)O[C@H]2[C@H]2OC(=O)C(=C)[C@@H]2C[C@@H]1O

InChI Identifier

InChI=1S/C15H20O4/c1-8-5-4-6-15(3)13(19-15)12-10(7-11(8)16)9(2)14(17)18-12/h5,10-13,16H,2,4,6-7H2,1,3H3/b8-5+/t10-,11-,12-,13-,15+/m0/s1

InChI Key

RZUCCKARTVHQBW-MPFAERRBSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anthemis cupaniana	LOTUS Database	35616633
Anvillea garcinii	LOTUS Database	35616633

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Germacrane sesquiterpenoid
Sesquiterpenoid
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Oxolane
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Alcohol
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.84	ChemAxon
pKa (Strongest Acidic)	14.6	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59.06 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	70.07 m³·mol⁻¹	ChemAxon
Polarizability	27.69 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00045198

Chemspider ID

16737368

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14466188

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Aati HY, Perveen S, Orfali R, Al-Taweel AM, Peng J, Tabassum S, Abdel-Kader MS, Yusufoglu HS, Taglialatela-Scafati O: Phytochemical Analysis of Anvillea garcinii Leaves: Identification of Garcinamines F-H and Their Antiproliferative Activities. Plants (Basel). 2021 Jun 2;10(6). pii: plants10061130. doi: 10.3390/plants10061130. [PubMed:34199475 ]
Perveen S, Alqahtani J, Orfali R, Aati HY, Al-Taweel AM, Ibrahim TA, Khan A, Yusufoglu HS, Abdel-Kader MS, Taglialatela-Scafati O: Antibacterial and Antifungal Sesquiterpenoids from Aerial Parts of Anvillea garcinii. Molecules. 2020 Apr 9;25(7). pii: molecules25071730. doi: 10.3390/molecules25071730. [PubMed:32283756 ]
El Bouakher A, Jismy B, Allouchi H, Duverger E, Barkaoui L, El Hakmaoui A, Daniellou R, Guillaumet G, Akssira M: Synthetic Modification of 9alpha- and 9beta-Hydroxyparthenolide by Heck or Acylation Reactions and Evaluation of Cytotoxic Activities. Planta Med. 2017 May;83(7):661-671. doi: 10.1055/s-0042-119864. Epub 2016 Dec 5. [PubMed:27919107 ]
Destandau E, Boukhris MA, Zubrzycki S, Akssira M, Rhaffari LE, Elfakir C: Centrifugal partition chromatography elution gradient for isolation of sesquiterpene lactones and flavonoids from Anvillea radiata. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Mar 15;985:29-37. doi: 10.1016/j.jchromb.2015.01.019. Epub 2015 Jan 21. [PubMed:25647341 ]
Moumou M, El Bouakher A, Allouchi H, El Hakmaoui A, Benharref A, Mathieu V, Guillaumet G, Akssira M: Synthesis and biological evaluation of 9alpha- and 9beta-hydroxyamino-parthenolides as novel anticancer agents. Bioorg Med Chem Lett. 2014 Aug 15;24(16):4014-8. doi: 10.1016/j.bmcl.2014.06.019. Epub 2014 Jun 14. [PubMed:24998377 ]
LOTUS database [Link]

Showing NP-Card for (1s,2s,4r,7e,9s,11s)-9-hydroxy-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradec-7-en-13-one (NP0291749)

MOL for NP0291749 ((1s,2s,4r,7e,9s,11s)-9-hydroxy-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradec-7-en-13-one)

3D MOL for NP0291749 ((1s,2s,4r,7e,9s,11s)-9-hydroxy-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradec-7-en-13-one)

3D SDF for NP0291749 ((1s,2s,4r,7e,9s,11s)-9-hydroxy-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradec-7-en-13-one)

3D-SDF for NP0291749 ((1s,2s,4r,7e,9s,11s)-9-hydroxy-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradec-7-en-13-one)

PDB for NP0291749 ((1s,2s,4r,7e,9s,11s)-9-hydroxy-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradec-7-en-13-one)

3D PDB for NP0291749 ((1s,2s,4r,7e,9s,11s)-9-hydroxy-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradec-7-en-13-one)

SMILES for NP0291749 ((1s,2s,4r,7e,9s,11s)-9-hydroxy-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradec-7-en-13-one)

INCHI for NP0291749 ((1s,2s,4r,7e,9s,11s)-9-hydroxy-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradec-7-en-13-one)

Structure for NP0291749 ((1s,2s,4r,7e,9s,11s)-9-hydroxy-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradec-7-en-13-one)

3D Structure for NP0291749 ((1s,2s,4r,7e,9s,11s)-9-hydroxy-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradec-7-en-13-one)