NP-MRD: Showing NP-Card for Wortmannin (NP0066300)

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Record Information

Version

2.0

Created at

2022-04-28 10:34:28 UTC

Updated at

2022-04-28 10:34:29 UTC

NP-MRD ID

NP0066300

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Wortmannin

Description

Wortmannin belongs to the class of organic compounds known as oxasteroids and derivatives. These are steroid derivatives where a carbon atom of the steroid is replaced by an oxygen atom. Wortmannin is found in Myrothecium roridum and Penicillium wortmannii. Wortmannin was first documented in 2012 (PMID: 22003059). Wortmannin is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 22056625) (PMID: 22524784).

Structure

MOL 3D MOL SDF PDB SMILES InChI

KWT
  Mrv0541 02241213502D          

 34 38  0  0  0  0            999 V2000
   -1.1719    0.4412    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8844    0.8537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4594    0.8537    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1719   -0.3838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8844    1.6787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5991    2.0908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1719    2.0912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4594    1.6787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8719    2.9484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2585    2.0912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9710    1.6787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0469    2.9484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6857    2.0908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9710    0.8537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4560   -0.7980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2580   -0.3846    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4550   -1.6230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2570    0.4404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6859    0.4421    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4588    0.0287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9729   -0.7963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6869   -0.3829    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7741   -1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4718   -0.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4702    0.6980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9560    0.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7277   -1.4212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2600   -2.0346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1690   -2.0363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8864   -0.7963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6008   -0.3838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6778    0.1496    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3172   -0.2839    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7463    1.0229    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  1  0  0  0
  1 32  1  6  0  0  0
  2  5  1  0  0  0  0
  3  8  1  0  0  0  0
  3 18  1  0  0  0  0
  3 20  1  6  0  0  0
  4 30  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  8 10  2  0  0  0  0
  9 12  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  2  0  0  0  0
 11 14  1  0  0  0  0
 14 18  2  0  0  0  0
 14 19  1  0  0  0  0
 16 15  1  1  0  0  0
 15 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 21  1  0  0  0  0
 16 33  1  6  0  0  0
 17 28  2  0  0  0  0
 17 29  1  0  0  0  0
 19 22  1  0  0  0  0
 19 25  1  0  0  0  0
 19 34  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  2  0  0  0  0
 25 26  1  0  0  0  0
 30 31  1  0  0  0  0
M  END

     RDKit          3D

 55 59  0  0  0  0  0  0  0  0999 V2000
    4.2069   -0.1669    1.8635 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5305   -0.1367    0.6431 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7105    0.9978    0.6322 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9326    1.1405   -0.6271 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9096    1.2347   -1.7106 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5651    0.0797   -2.1254 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6706    0.0794   -2.7251 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9140   -1.1765   -1.8367 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2161   -2.5242   -1.9751 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2419   -3.2380   -1.4325 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3111   -2.4288   -0.9424 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7038   -1.1586   -1.1865 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9608    0.0788   -0.9375 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3717    0.4255   -2.3604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2236   -0.1396   -0.1069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6800   -1.3759    0.1572 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0651   -2.6014   -0.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3760   -3.7499    0.0132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9249   -1.6114    0.8536 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8543   -2.6436    0.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1750   -2.2871    0.9910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9808   -0.9072    1.5347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6459   -0.4045    2.3822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8150   -0.3953    0.7713 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1861   -0.0547   -0.6498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0171    0.6641    1.4763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9456    1.0345    0.4102 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2355    2.1292    0.8445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5489    3.4267    0.4180 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1794    4.6247    0.8529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5078    3.5124   -0.3741 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5187   -0.2176    2.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7977   -1.1111    1.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8907    0.6973    1.8894 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1082    0.9347    1.5410 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3838    1.8850    0.7739 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4671    2.1267   -0.6717 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1194   -2.8893   -2.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1276    1.4056   -2.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3093   -0.4124   -2.5916 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2341    0.4066   -3.0612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7809   -1.8352    1.9422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6015   -3.6931    0.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9577   -2.4801   -0.7897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9836   -2.2927    0.2359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3741   -2.9999    1.7947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3538   -0.2427   -1.3379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5797    0.9546   -0.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0378   -0.7608   -0.8987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5579    1.5869    1.6762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5562    0.1883    2.3587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6480    1.4143   -0.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1636    4.3928    1.3065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4580    5.1240    1.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2700    5.3904    0.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  6
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 27 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 11  1  0
 11 12  2  0
 12  8  1  0
  8  9  2  0
  9 10  1  0
  8  6  1  0
  6  7  2  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  4 13  1  0
 13 14  1  6
 24 19  1  0
 13 15  1  0
 16 19  1  0
 10 11  1  0
 13 12  1  0
 19 42  1  1
 20 43  1  0
 20 44  1  0
 21 45  1  0
 21 46  1  0
 25 47  1  0
 25 48  1  0
 25 49  1  0
 26 50  1  0
 26 51  1  0
 27 52  1  6
 30 53  1  0
 30 54  1  0
 30 55  1  0
  9 38  1  0
  4 37  1  1
  3 35  1  0
  3 36  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
 14 39  1  0
 14 40  1  0
 14 41  1  0
M  END

KWT
  Mrv0541 02241213502D          

 34 38  0  0  0  0            999 V2000
   -1.1719    0.4412    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8844    0.8537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4594    0.8537    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1719   -0.3838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8844    1.6787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5991    2.0908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1719    2.0912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4594    1.6787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8719    2.9484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2585    2.0912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9710    1.6787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0469    2.9484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6857    2.0908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9710    0.8537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4560   -0.7980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2580   -0.3846    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4550   -1.6230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2570    0.4404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6859    0.4421    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4588    0.0287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9729   -0.7963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6869   -0.3829    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7741   -1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4718   -0.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4702    0.6980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9560    0.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7277   -1.4212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2600   -2.0346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1690   -2.0363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8864   -0.7963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6008   -0.3838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6778    0.1496    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3172   -0.2839    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7463    1.0229    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  1  0  0  0
  1 32  1  6  0  0  0
  2  5  1  0  0  0  0
  3  8  1  0  0  0  0
  3 18  1  0  0  0  0
  3 20  1  6  0  0  0
  4 30  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  8 10  2  0  0  0  0
  9 12  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  2  0  0  0  0
 11 14  1  0  0  0  0
 14 18  2  0  0  0  0
 14 19  1  0  0  0  0
 16 15  1  1  0  0  0
 15 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 21  1  0  0  0  0
 16 33  1  6  0  0  0
 17 28  2  0  0  0  0
 17 29  1  0  0  0  0
 19 22  1  0  0  0  0
 19 25  1  0  0  0  0
 19 34  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  2  0  0  0  0
 25 26  1  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0066300

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CCC(=O)[C@@]1(C)C[C@@]([H])(OC(C)=O)C1=C2C(=O)C2=C3C(=CO2)C(=O)O[C@]([H])(COC)[C@]13C

> <INCHI_IDENTIFIER>
InChI=1S/C23H24O8/c1-10(24)30-13-7-22(2)12(5-6-14(22)25)16-18(13)23(3)15(9-28-4)31-21(27)11-8-29-20(17(11)23)19(16)26/h8,12-13,15H,5-7,9H2,1-4H3/t12-,13+,15+,22-,23-/m0/s1

> <INCHI_KEY>
QDLHCMPXEPAAMD-QAIWCSMKSA-N

> <FORMULA>
C23H24O8

> <MOLECULAR_WEIGHT>
428.4319

> <EXACT_MASS>
428.147117744

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
42.988465027248495

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3R,5S,9R,18S)-18-(methoxymethyl)-1,5-dimethyl-6,11,16-trioxo-13,17-dioxapentacyclo[10.6.1.0²,¹⁰.0⁵,⁹.0¹⁵,¹⁹]nonadeca-2(10),12(19),14-trien-3-yl acetate

> <ALOGPS_LOGP>
2.31

> <JCHEM_LOGP>
1.4426177013333334

> <ALOGPS_LOGS>
-3.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.667613949704254

> <JCHEM_PKA_STRONGEST_BASIC>
-4.104431049145731

> <JCHEM_POLAR_SURFACE_AREA>
109.11

> <JCHEM_REFRACTIVITY>
106.8572

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.21e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
wortmannin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: KWT                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.188   0.824   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.518   1.594   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.858   1.594   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.188  -0.716   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.518   3.134   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -4.852   3.903   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.188   3.904   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.858   3.134   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.628   5.504   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.483   3.904   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.813   3.134   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.088   5.504   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       3.147   3.903   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.813   1.594   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.851  -1.490   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.482  -0.718   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.849  -3.030   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.480   0.822   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.147   0.825   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.856   0.054   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.816  -1.486   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.149  -0.715   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.312  -2.246   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.614  -1.189   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.611   1.303   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.518   0.058   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.092  -2.653   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       0.485  -3.798   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -2.182  -3.801   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -3.521  -1.486   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -4.855  -0.716   0.000  0.00  0.00           C+0
HETATM   32  H   UNK     0      -3.132   0.279   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.592  -0.530   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.260   1.909   0.000  0.00  0.00           H+0
CONECT    1    2    3    4   32                                             
CONECT    2    1    5                                                       
CONECT    3    1    8   18   20                                             
CONECT    4    1   30                                                       
CONECT    5    2    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    3    7   10                                                  
CONECT    9    7   12                                                       
CONECT   10    8   11   12                                                  
CONECT   11   10   13   14                                                  
CONECT   12    9   10                                                       
CONECT   13   11                                                            
CONECT   14   11   18   19                                                  
CONECT   15   16   17                                                       
CONECT   16   15   18   21   33                                             
CONECT   17   15   28   29                                                  
CONECT   18    3   14   16                                                  
CONECT   19   14   22   25   34                                             
CONECT   20    3                                                            
CONECT   21   16   22                                                       
CONECT   22   19   21   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   26   27                                                  
CONECT   25   19   26                                                       
CONECT   26   24   25                                                       
CONECT   27   24                                                            
CONECT   28   17                                                            
CONECT   29   17                                                            
CONECT   30    4   31                                                       
CONECT   31   30                                                            
CONECT   32    1                                                            
CONECT   33   16                                                            
CONECT   34   19                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Value	Source
Wartmannin	ChEBI
(1S,6BR,9As,11R,11BR)-9a,11b-dimethyl-1-[(methyloxy)methyl]-3,6,9-trioxo-1,6,6b,7,8,9,9a,10,11,11b-decahydro-3H-furo[4,3,2-de]indeno[4,5-H][2]benzopyran-11-yl acetic acid	Generator
MS-54	MeSH
MS 54	MeSH
Wortmannin	MeSH

Chemical Formula

C₂₃H₂₄O₈

Average Mass

428.4319 Da

Monoisotopic Mass

428.14712 Da

IUPAC Name

(1R,3R,5S,9R,18S)-18-(methoxymethyl)-1,5-dimethyl-6,11,16-trioxo-13,17-dioxapentacyclo[10.6.1.0²,¹⁰.0⁵,⁹.0¹⁵,¹⁹]nonadeca-2(10),12(19),14-trien-3-yl acetate

Traditional Name

wortmannin

CAS Registry Number

Not Available

SMILES

[H][C@@]12CCC(=O)[C@@]1(C)C[C@@]([H])(OC(C)=O)C1=C2C(=O)C2=C3C(=CO2)C(=O)O[C@]([H])(COC)[C@]13C

InChI Identifier

InChI=1S/C23H24O8/c1-10(24)30-13-7-22(2)12(5-6-14(22)25)16-18(13)23(3)15(9-28-4)31-21(27)11-8-29-20(17(11)23)19(16)26/h8,12-13,15H,5-7,9H2,1-4H3/t12-,13+,15+,22-,23-/m0/s1

InChI Key

QDLHCMPXEPAAMD-QAIWCSMKSA-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
Myrothecium roridum	Fungi	KNApSAcK
Talaromyces wortmannii	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxasteroids and derivatives. These are steroid derivatives where a carbon atom of the steroid is replaced by an oxygen atom.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Oxasteroids and derivatives

Direct Parent

Oxasteroids and derivatives

Alternative Parents

Substituents

2-oxasteroid
Naphthopyran
Naphthofuran
Naphthalene
Furoic acid ester
Furopyran
Furoic acid or derivatives
Aryl ketone
Dicarboxylic acid or derivatives
Pyran
Furan
Heteroaromatic compound
Carboxylic acid ester
Ketone
Lactone
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

cyclic ketone (CHEBI:52289 )
organic heteropentacyclic compound (CHEBI:52289 )
acetate ester (CHEBI:52289 )
delta-lactone (CHEBI:52289 )

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	2.31	ALOGPS
logP	1.44	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	19.67	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	109.11 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	106.86 m³·mol⁻¹	ChemAxon
Polarizability	42.99 Å³	ChemAxon
Number of Rings	5	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

DB08059

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00023672

Chemspider ID

Not Available

KEGG Compound ID

C15181

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Wortmannin

METLIN ID

Not Available

PubChem Compound

312145

PDB ID

Not Available

ChEBI ID

52289

Good Scents ID

Not Available

References

General References

Chatterjee S, Browning EA, Hong N, DeBolt K, Sorokina EM, Liu W, Birnbaum MJ, Fisher AB: Membrane depolarization is the trigger for PI3K/Akt activation and leads to the generation of ROS. Am J Physiol Heart Circ Physiol. 2012 Jan 1;302(1):H105-14. doi: 10.1152/ajpheart.00298.2011. Epub 2011 Oct 14. [PubMed:22003059 ]
Kim SH, Jang YW, Hwang P, Kim HJ, Han GY, Kim CW: The reno-protective effect of a phosphoinositide 3-kinase inhibitor wortmannin on streptozotocin-induced proteinuric renal disease rats. Exp Mol Med. 2012 Jan 31;44(1):45-51. doi: 10.3858/emm.2012.44.1.004. [PubMed:22056625 ]
Takac T, Pechan T, Samajova O, Ovecka M, Richter H, Eck C, Niehaus K, Samaj J: Wortmannin treatment induces changes in Arabidopsis root proteome and post-Golgi compartments. J Proteome Res. 2012 Jun 1;11(6):3127-42. doi: 10.1021/pr201111n. Epub 2012 May 10. [PubMed:22524784 ]

Showing NP-Card for Wortmannin (NP0066300)

MOL for NP0066300 (Wortmannin)

3D MOL for NP0066300 (Wortmannin)

3D SDF for NP0066300 (Wortmannin)

3D-SDF for NP0066300 (Wortmannin)

PDB for NP0066300 (Wortmannin)

3D PDB for NP0066300 (Wortmannin)

SMILES for NP0066300 (Wortmannin)

INCHI for NP0066300 (Wortmannin)

Structure for NP0066300 (Wortmannin)

3D Structure for NP0066300 (Wortmannin)