NP-MRD: Showing NP-Card for Triptolide (NP0052059)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-27 23:14:15 UTC

Updated at

2022-04-27 23:14:15 UTC

NP-MRD ID

NP0052059

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Triptolide

Description

Triptolide belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms. Cys342 of XPB was identified as the residue that undergoes covalent modification by the 12,13-epoxide group of triptolide, and the XPB-C342T mutant rendered the T7115 cell line nearly completely resistant to triptolide. Several putative target proteins of triptolide have been reported, including polycystin-2, ADAM10, DCTPP1, TAB1, and XPB. Triptolide is an extremely weak basic (essentially neutral) compound (based on its pKa). Its Phase II clinical trials are expected to conclude in February 2019. In a preclinical mouse model of pancreatic cancer, it was "even more effective than gemcitabine". The level of resistance conferred by the C342T mutation is about 100-fold higher than the most triptolide-resistant mutants previously identified. Consequently, a synthetic water-soluble prodrug, minnelide, is being studied clinically instead. Triptolide is a diterpenoid epoxide which is produced by the thunder god vine, Tripterygium wilfordii. However, no triptolide-resistant mutations were found in polycystin-2, ADAM10, DCTPP1 and TAB1. Water-soluble prodrugs Minnelide is a more water-soluble synthetic analog of triptolide which is converted to triptolide in vivo. Triptolide is found in Tripterygium hypoglaucum and Tripterygium wilfordii . Glutriptolide, a glucose conjugate of triptolide with better solubility and lower toxicity, did not inhibit XPB activity in vitro, but exhibited tumor control in vivo, which is likely due to sustained stepwise release of active triptolide within cancer cells.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652310201623122D          

 26 32  0  0  1  0            999 V2000
    0.6371   -2.4627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4310   -2.6871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6336   -3.4868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0222   -2.1117    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2466   -1.3178    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4469   -1.5204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0464   -1.1152    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6217   -1.7065    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8461   -0.9126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4214   -1.5039    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6458   -0.7100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4456   -0.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0209   -1.0986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7965   -1.8925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9968   -2.0951    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7724   -2.8890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9726   -3.0917    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3973   -2.5004    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5976   -2.7030    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3732   -3.4969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1729   -3.2943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4822   -2.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1304   -1.8409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8453   -1.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3040   -0.3810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3035   -0.6873    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
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  7  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 15 14  1  6  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  1  0  0  0  0
  4 19  1  0  0  0  0
 19 20  1  6  0  0  0
 18 21  1  6  0  0  0
 17 21  1  6  0  0  0
 14 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 13 24  1  0  0  0  0
 24 25  2  0  0  0  0
 10 26  1  6  0  0  0
M  END

     RDKit          3D

 50 56  0  0  0  0  0  0  0  0999 V2000
    4.8460    0.6636    1.5626 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2707   -0.2143    0.4978 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9008    0.2089   -0.8333 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7662   -0.0837    0.3882 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2838    1.2327    0.0738 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9816    0.5680    1.3114 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5699    0.1702    1.5628 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4728   -1.2831    1.7606 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0449   -0.7453    0.6153 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5076   -0.6367    0.3703 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9933   -1.7260   -0.5730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3124   -0.7267    1.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7776   -0.6232    1.3649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0963    0.2694    0.2156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1925    0.9663   -0.4315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8989    1.9244   -1.3057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2156    1.4197   -1.4198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3927    0.5319   -0.3838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5071    0.0399   -0.0305 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7487    0.7380   -0.2333 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9452    1.0043   -1.4487 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3262    0.2424   -1.5650 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0979   -1.1467   -1.8563 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6837   -0.7486   -0.6791 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1107   -1.1438   -0.4343 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1928   -2.3519    0.2751 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9236    0.4690    1.6463 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7007    1.7274    1.2741 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3205    0.5041    2.5287 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5557   -1.2754    0.6381 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3042    1.0091   -1.3178 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9035    0.6461   -0.6181 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0188   -0.6417   -1.5162 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4291    1.1706    2.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0438    0.7506    2.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2824   -2.5787   -0.6040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9602   -2.1754   -0.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2225   -1.3175   -1.5766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0057    0.1003    2.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1337   -1.6771    2.1841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2481   -0.1360    2.2618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2886   -1.6073    1.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4164    2.0599   -2.2930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9640    2.8905   -0.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4248    1.4678    0.5657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8104    2.1086   -1.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5802    0.7273   -2.3412 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0835    0.7388   -2.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6270   -1.2715   -1.4084 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6443   -2.2393    1.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  4  2  1  0
  4  5  1  6
  5  6  1  0
  6  7  1  0
  7  8  1  0
  9  8  1  1
  9 24  1  0
 24 23  1  6
 23 22  1  0
 22 21  1  0
 21 20  1  0
 20 15  1  0
 15 14  2  0
 14 13  1  0
 13 12  1  0
 12 10  1  0
 10 11  1  6
 14 18  1  0
 18 19  2  0
 18 17  1  0
 17 16  1  0
 24 25  1  0
 25 26  1  0
  6  4  1  0
  9  7  1  0
 10  9  1  0
 25  4  1  0
 22 24  1  0
 10 20  1  0
 16 15  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  1
  3 31  1  0
  3 32  1  0
  3 33  1  0
  6 34  1  1
  7 35  1  1
 22 48  1  6
 21 46  1  0
 21 47  1  0
 20 45  1  1
 13 41  1  0
 13 42  1  0
 12 39  1  0
 12 40  1  0
 11 36  1  0
 11 37  1  0
 11 38  1  0
 16 43  1  0
 16 44  1  0
 25 49  1  6
 26 50  1  0
M  END


  Mrv1652310201623122D          

 26 32  0  0  1  0            999 V2000
    0.6371   -2.4627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4310   -2.6871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6336   -3.4868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0222   -2.1117    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2466   -1.3178    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4469   -1.5204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0464   -1.1152    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6217   -1.7065    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8461   -0.9126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4214   -1.5039    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6458   -0.7100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4456   -0.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0209   -1.0986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7965   -1.8925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9968   -2.0951    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7724   -2.8890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9726   -3.0917    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3973   -2.5004    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5976   -2.7030    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3732   -3.4969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1729   -3.2943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4822   -2.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1304   -1.8409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8453   -1.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3040   -0.3810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3035   -0.6873    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
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  7  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 15 14  1  6  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  1  0  0  0  0
  4 19  1  0  0  0  0
 19 20  1  6  0  0  0
 18 21  1  6  0  0  0
 17 21  1  6  0  0  0
 14 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 13 24  1  0  0  0  0
 24 25  2  0  0  0  0
 10 26  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0052059

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@]12O[C@H]1[C@@H]1O[C@]11[C@]3(O[C@H]3C[C@H]3C4=C(CC[C@]13C)C(=O)OC4)[C@@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O6/c1-8(2)18-13(25-18)14-20(26-14)17(3)5-4-9-10(7-23-15(9)21)11(17)6-12-19(20,24-12)16(18)22/h8,11-14,16,22H,4-7H2,1-3H3/t11-,12-,13-,14-,16+,17-,18-,19+,20+/m0/s1

> <INCHI_KEY>
DFBIRQPKNDILPW-CIVMWXNOSA-N

> <FORMULA>
C20H24O6

> <MOLECULAR_WEIGHT>
360.406

> <EXACT_MASS>
360.157288493

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
37.144387451074806

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,4S,5S,7R,8R,9S,11S,13S)-8-hydroxy-1-methyl-7-(propan-2-yl)-3,6,10,16-tetraoxaheptacyclo[11.7.0.0^{2,4}.0^{2,9}.0^{5,7}.0^{9,11}.0^{14,18}]icos-14(18)-en-17-one

> <ALOGPS_LOGP>
1.22

> <JCHEM_LOGP>
1.3276725586666664

> <ALOGPS_LOGS>
-2.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.30460978611875

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.54275367923714

> <JCHEM_PKA_STRONGEST_BASIC>
-3.79249501560952

> <JCHEM_POLAR_SURFACE_AREA>
84.12

> <JCHEM_REFRACTIVITY>
87.26059999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.86e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,4S,5S,7R,8R,9S,11S,13S)-8-hydroxy-7-isopropyl-1-methyl-3,6,10,16-tetraoxaheptacyclo[11.7.0.0^{2,4}.0^{2,9}.0^{5,7}.0^{9,11}.0^{14,18}]icos-14(18)-en-17-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-OCT-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-OCT-16         0                                  
HETATM    1  C   UNK     0       1.189  -4.597   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.671  -5.016   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.049  -6.509   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.775  -3.942   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.194  -2.460   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.701  -2.838   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.687  -2.082   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.761  -3.185   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       7.179  -1.703   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.253  -2.807   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.672  -1.325   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.165  -0.947   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.239  -2.051   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.820  -3.533   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.327  -3.911   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.908  -5.393   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.416  -5.771   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.342  -4.667   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.849  -5.046   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.430  -6.528   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.923  -6.149   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      12.100  -4.389   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      13.310  -3.436   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      12.778  -1.991   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      13.634  -0.711   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.033  -1.283   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6   19                                             
CONECT    5    4    6    7                                                  
CONECT    6    5    4                                                       
CONECT    7    5    8    9                                                  
CONECT    8    7    9   10   18                                             
CONECT    9    8    7                                                       
CONECT   10    8   11   15   26                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   24                                                  
CONECT   14   13   15   22                                                  
CONECT   15   14   10   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17    8   19   21                                             
CONECT   19   18    4   20                                                  
CONECT   20   19                                                            
CONECT   21   18   17                                                       
CONECT   22   14   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   13   25                                                  
CONECT   25   24                                                            
CONECT   26   10                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄O₆

Average Mass

360.4060 Da

Monoisotopic Mass

360.15729 Da

IUPAC Name

(1S,2S,4S,5S,7R,8R,9S,11S,13S)-8-hydroxy-1-methyl-7-(propan-2-yl)-3,6,10,16-tetraoxaheptacyclo[11.7.0.0^{2,4}.0^{2,9}.0^{5,7}.0^{9,11}.0^{14,18}]icos-14(18)-en-17-one

Traditional Name

(1S,2S,4S,5S,7R,8R,9S,11S,13S)-8-hydroxy-7-isopropyl-1-methyl-3,6,10,16-tetraoxaheptacyclo[11.7.0.0^{2,4}.0^{2,9}.0^{5,7}.0^{9,11}.0^{14,18}]icos-14(18)-en-17-one

CAS Registry Number

Not Available

SMILES

CC(C)[C@]12O[C@H]1[C@@H]1O[C@]11[C@]3(O[C@H]3C[C@H]3C4=C(CC[C@]13C)C(=O)OC4)[C@@H]2O

InChI Identifier

InChI=1S/C20H24O6/c1-8(2)18-13(25-18)14-20(26-14)17(3)5-4-9-10(7-23-15(9)21)11(17)6-12-19(20,24-12)16(18)22/h8,11-14,16,22H,4-7H2,1-3H3/t11-,12-,13-,14-,16+,17-,18-,19+,20+/m0/s1

InChI Key

DFBIRQPKNDILPW-CIVMWXNOSA-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
Tripterygium hypoglaucum	Plant	KNApSAcK
Tripterygium wilfordii	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxepanes

Sub Class

Not Available

Direct Parent

Oxepanes

Alternative Parents

Substituents

Oxepane
2-furanone
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Secondary alcohol
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organooxygen compound
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

oxacycle (CHEBI:9747 )
Diterpenoids (C20) (C09204 )

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	1.22	ALOGPS
logP	1.33	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	12.54	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	84.12 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	87.26 m³·mol⁻¹	ChemAxon
Polarizability	37.14 Å³	ChemAxon
Number of Rings	7	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

DB12025

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00003494

Chemspider ID

Not Available

KEGG Compound ID

C09204

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Triptolide

METLIN ID

Not Available

PubChem Compound

107985

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Triptolide (NP0052059)

MOL for NP0052059 (Triptolide)

3D MOL for NP0052059 (Triptolide)

3D SDF for NP0052059 (Triptolide)

3D-SDF for NP0052059 (Triptolide)

PDB for NP0052059 (Triptolide)

3D PDB for NP0052059 (Triptolide)

SMILES for NP0052059 (Triptolide)

INCHI for NP0052059 (Triptolide)

Structure for NP0052059 (Triptolide)

3D Structure for NP0052059 (Triptolide)