NP-MRD: Showing NP-Card for Hymenoxon (NP0051913)

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Record Information

Version

2.0

Created at

2022-04-27 23:06:59 UTC

Updated at

2022-04-27 23:06:59 UTC

NP-MRD ID

NP0051913

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Hymenoxon

Description

Hymenoxon, also known as hymenovin, belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms. Hymenoxon is found in Baileya multiradiata, Dugaldia hoopesii, Hymenoxys lemmonii, Hymenoxys odorata, Hymenoxys richardsonii and Psilostrophe gnaphalodes. Hymenoxon was first documented in 1984 (PMID: 6711966). Based on a literature review a significant number of articles have been published on Hymenoxon (PMID: 1609486) (PMID: 2802343) (PMID: 2532610) (PMID: 3343693) (PMID: 2852991) (PMID: 4089888).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
    3.0909   -1.9826    0.5929 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9075   -0.8265   -0.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7578    0.3456    0.1780 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7902    0.5005    0.8924 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2418    1.3827   -0.6091 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8277    1.1001   -0.6496 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3764    1.2840    0.7850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0864    1.5015    0.8173 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3380    2.9782    0.4727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8598    0.6986   -0.1812 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3266    0.7863    0.2629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2387    0.1943   -0.7787 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0893   -0.7445   -0.1786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4307   -0.5281   -1.6667 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7198   -1.4467   -0.8850 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3182   -2.4764   -1.7096 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5119   -0.7578   -0.2153 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4581   -1.3567    1.1856 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6542   -1.1083   -1.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8849   -0.3645   -0.9778 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4303   -2.8295    0.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9011   -2.1510    1.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2998    1.7170   -1.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8698    2.2399    1.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7859    0.4892    1.3998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4888    1.3998    1.8662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2197    3.1095   -0.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5448    3.3780   -0.0928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4304    3.5982    1.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7824    1.1157   -1.1835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3771    0.1580    1.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6052    1.7993    0.5641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8564    0.9423   -1.2900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9240   -0.7769    0.8118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4162   -1.8497   -0.1462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0384   -3.1676   -1.7538 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2651   -2.1721    1.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2560   -0.6206    1.9660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4460   -1.8232    1.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8717   -2.2012   -0.8590 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3006   -1.1253   -2.1354 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4174   -0.4097   -1.9790 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  2 20  1  0
 20 19  1  0
 19 17  1  0
 17 18  1  1
 17 15  1  0
 15 16  1  0
 15 14  1  0
 14 12  1  0
 12 13  1  0
 12 11  1  0
 11 10  1  0
 10  8  1  0
 20  6  1  0
 10 17  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
  8 26  1  1
  7 24  1  0
  7 25  1  0
  6 23  1  6
  1 21  1  0
  1 22  1  0
 20 42  1  6
 19 40  1  0
 19 41  1  0
 18 37  1  0
 18 38  1  0
 18 39  1  0
 15 35  1  1
 16 36  1  0
 12 33  1  6
 13 34  1  0
 11 31  1  0
 11 32  1  0
 10 30  1  6
M  END


  Mrv1652304282201072D          

 20 22  0  0  1  0            999 V2000
    3.4829    2.3555    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3084    1.5491    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5691    1.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8219    1.5325    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6293    2.3347    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1364    2.9855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9614    2.9947    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3110    3.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8068    2.3995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4911    1.6373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3111    1.4448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1184    1.1015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0537    0.2790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9194    0.9948    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7050    1.2468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8795    2.0531    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2685    2.6074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6651    2.3051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7448    0.1885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1945    0.7320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  1  0  0  0
  5  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  4 12  1  6  0  0  0
 12 13  2  0  0  0  0
  2 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  1 17  1  6  0  0  0
 16 18  1  6  0  0  0
 14 19  1  1  0  0  0
  2 20  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0051913

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@H]2OC(=O)C(=C)[C@H]2C[C@]2(C)[C@H](O)O[C@@H](O)C[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O5/c1-7-4-11-9(8(2)13(17)19-11)6-15(3)10(7)5-12(16)20-14(15)18/h7,9-12,14,16,18H,2,4-6H2,1,3H3/t7-,9-,10+,11-,12-,14-,15+/m1/s1

> <INCHI_KEY>
PYINVOHSOZSEPB-DKGLCQEFSA-N

> <FORMULA>
C15H22O5

> <MOLECULAR_WEIGHT>
282.336

> <EXACT_MASS>
282.146723808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
29.26263767850385

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3R,7R,9R,10S,12R,14R)-12,14-dihydroxy-1,9-dimethyl-4-methylidene-6,13-dioxatricyclo[8.4.0.0^{3,7}]tetradecan-5-one

> <ALOGPS_LOGP>
0.77

> <JCHEM_LOGP>
1.6564514853333328

> <ALOGPS_LOGS>
-1.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.606169835795757

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.77723897353768

> <JCHEM_PKA_STRONGEST_BASIC>
-3.936407149184972

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
70.58560000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.11e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,7R,9R,10S,12R,14R)-12,14-dihydroxy-1,9-dimethyl-4-methylidene-6,13-dioxatricyclo[8.4.0.0^{3,7}]tetradecan-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       6.501   4.397   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.176   2.892   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.796   2.208   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.401   2.861   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.041   4.358   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.988   5.573   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.528   5.590   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.181   6.985   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.506   4.479   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.917   3.056   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.581   2.697   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.088   2.056   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.967   0.521   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.316   1.857   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.783   2.327   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.108   3.832   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.968   4.867   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.575   4.303   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.990   0.352   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.963   1.366   0.000  0.00  0.00           C+0
CONECT    1    2    7   17                                                  
CONECT    2    1    3   14   20                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   12                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    1    8                                                  
CONECT    8    7                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    4   13                                                  
CONECT   13   12                                                            
CONECT   14    2   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16    1                                                       
CONECT   18   16                                                            
CONECT   19   14                                                            
CONECT   20    2                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
Hymenovin	MeSH
Hymenovin, (3ar-(3aalpha,4abeta,5alpha,7beta,8aalpha,9alpha,10aalpha))-isomer	MeSH
Hymenoxone	MeSH

Chemical Formula

C₁₅H₂₂O₅

Average Mass

282.3360 Da

Monoisotopic Mass

282.14672 Da

IUPAC Name

(1S,3R,7R,9R,10S,12R,14R)-12,14-dihydroxy-1,9-dimethyl-4-methylidene-6,13-dioxatricyclo[8.4.0.0^{3,7}]tetradecan-5-one

Traditional Name

(1S,3R,7R,9R,10S,12R,14R)-12,14-dihydroxy-1,9-dimethyl-4-methylidene-6,13-dioxatricyclo[8.4.0.0^{3,7}]tetradecan-5-one

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@H]2OC(=O)C(=C)[C@H]2C[C@]2(C)[C@H](O)O[C@@H](O)C[C@@H]12

InChI Identifier

InChI=1S/C15H22O5/c1-7-4-11-9(8(2)13(17)19-11)6-15(3)10(7)5-12(16)20-14(15)18/h7,9-12,14,16,18H,2,4-6H2,1,3H3/t7-,9-,10+,11-,12-,14-,15+/m1/s1

InChI Key

PYINVOHSOZSEPB-DKGLCQEFSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Baileya multiradiata	LOTUS Database	35616633
Dugaldia hoopesii	Plant	KNApSAcK
Hymenoxys lemmonii	Plant	KNApSAcK
Hymenoxys odorata	Plant	KNApSAcK
Hymenoxys richardsonii	Plant	KNApSAcK
Psilostrophe gnaphalodes	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxanes

Sub Class

Not Available

Direct Parent

Oxanes

Alternative Parents

Substituents

Gamma butyrolactone
Oxane
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Hemiacetal
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Carbonyl group
Organic oxide
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

oxanes (CHEBI:5826 )
pseudoguaianolide (C09482 )

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	0.77	ALOGPS
logP	1.66	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	11.78	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	70.59 m³·mol⁻¹	ChemAxon
Polarizability	29.26 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

C00003304

Chemspider ID

38569

KEGG Compound ID

C09482

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

42295

PDB ID

Not Available

ChEBI ID

5826

Good Scents ID

Not Available

References

General References

Post LO, Bailey EM: The effect of dietary supplements on chronic bitterweed (Hymenoxys odorata) poisoning in sheep. Vet Hum Toxicol. 1992 Jun;34(3):209-13. [PubMed:1609486 ]
Calhoun MC, Baldwin BC Jr, Kuhlmann SW, Kim HL: Experimental prevention of bitterweed (Hymenoxys odorata) poisoning of sheep. Am J Vet Res. 1989 Sep;50(9):1642-6. [PubMed:2802343 ]
Narasimham TR, Kim HL, Safe SH: Effects of sesquiterpene lactones on mitochondrial oxidative phosphorylation. Gen Pharmacol. 1989;20(5):681-7. doi: 10.1016/0306-3623(89)90107-9. [PubMed:2532610 ]
Merrill JC, Kim HL, Safe S, Murray CA, Hayes MA: Role of glutathione in the toxicity of the sesquiterpene lactones hymenoxon and helenalin. J Toxicol Environ Health. 1988;23(2):159-69. doi: 10.1080/15287398809531103. [PubMed:3343693 ]
Sylvia VL, Kim HL, Norman JO, Busbee DL: The sesquiterpene lactone hymenoxon acts as a bifunctional alkylating agent. Cell Biol Toxicol. 1987 Mar;3(1):39-49. doi: 10.1007/BF00117824. [PubMed:2852991 ]
Sylvia VL, Joe CO, Stipanovic RD, Kim HL, Busbee DL: Alkylation of deoxyguanosine by the sesquiterpene lactone hymenoxon. Toxicol Lett. 1985 Dec;29(2-3):69-76. doi: 10.1016/0378-4274(85)90026-8. [PubMed:4089888 ]
Merrill J, Kim H, Safe S: Hymenoxon: biologic and toxic effects. Biochem Pharmacol. 1985 Sep 15;34(18):3383-6. doi: 10.1016/0006-2952(85)90363-6. [PubMed:4038346 ]
Bowers DE Jr, Jones DH, Sampson HW, Dunlap MK: Acute exposure to hymenoxon: electron microscopic study of the mouse liver. Am J Vet Res. 1984 Feb;45(2):383-6. [PubMed:6711966 ]
Roberts AJ, Camp BJ: In vivo effects of hymenoxon on glucose metabolism in rat brain. Vet Hum Toxicol. 1984 Feb;26(1):1-4. [PubMed:6702094 ]
Roberts AJ, Camp BJ: In vitro effects of hymenoxon on phosphofructokinase. Vet Hum Toxicol. 1984 Feb;26(1):5-10. [PubMed:6230792 ]

Showing NP-Card for Hymenoxon (NP0051913)

MOL for NP0051913 (Hymenoxon)

3D MOL for NP0051913 (Hymenoxon)

3D SDF for NP0051913 (Hymenoxon)

3D-SDF for NP0051913 (Hymenoxon)

PDB for NP0051913 (Hymenoxon)

3D PDB for NP0051913 (Hymenoxon)

SMILES for NP0051913 (Hymenoxon)

INCHI for NP0051913 (Hymenoxon)

Structure for NP0051913 (Hymenoxon)

3D Structure for NP0051913 (Hymenoxon)