NP-MRD: Showing NP-Card for (1's,2'r,4's,7'r,9'r,10'r,11's)-4',11'-bis(acetyloxy)-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate (NP0197743)

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Record Information

Version

2.0

Created at

2022-09-04 16:03:53 UTC

Updated at

2022-09-04 16:03:53 UTC

NP-MRD ID

NP0197743

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1's,2'r,4's,7'r,9'r,10'r,11's)-4',11'-bis(acetyloxy)-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate

Description

SCHEMBL19971591 belongs to the class of organic compounds known as trichothecenes. These are sesquiterpene mycotoxins structurally characterized by the presence of an epoxide ring and a benzopyran derivative with a variant number of hydroxyl, acetyl, or other substituents. The most important structural features causing the biological activities of trichothecenes are the 12,13-epoxy ring, the presence of hydroxyl or acetyl groups at appropriate positions on the trichothecene nucleus and the structure and position of the side-chain. Based on a literature review very few articles have been published on SCHEMBL19971591.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042218032D          

 30 33  0  0  1  0            999 V2000
    3.9220   -1.5741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2475   -1.0990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4989   -1.4457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3216   -0.2774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6471    0.1976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7212    1.0193    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3584    0.4952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1308    0.7849    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7680    0.2608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5404    0.5505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1775    0.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6757    1.3644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2661    1.5988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0386    1.8885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6290    2.1229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8566    1.8331    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3047    2.4463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4811    2.3972    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0061    1.7227    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1923    1.8580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2373    0.9307    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6241    0.3788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1605    0.6339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7737    0.0820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3319    1.4409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0006    0.6177    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0498   -0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5184    1.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9482    0.8463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7170    1.6383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
  6 16  1  0  0  0  0
 16 17  1  6  0  0  0
 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 21 26  1  0  0  0  0
  6 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 18 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 30  1  0  0  0  0
M  END

     RDKit          3D

 58 61  0  0  0  0  0  0  0  0999 V2000
   -0.6480    4.2751    3.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0486    2.9674    2.9828 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5984    2.5703    4.0314 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0905    2.2108    1.8454 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7203    0.9791    1.7450 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6376    0.3195    0.3816 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4346   -0.9712    0.5881 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9623   -1.6007   -0.6270 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1274   -2.3686   -0.2656 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2718   -3.6929   -0.5303 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5070   -4.3976   -0.1195 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3807   -4.3315   -1.1155 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4606   -0.6611   -1.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3420   -1.1964   -2.7830 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1446    0.5899   -1.6087 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3128    1.2227   -0.5930 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4525    2.0882   -1.2519 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6805    1.5039   -1.7619 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8209    1.9832   -0.8448 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6597    3.2813   -0.4396 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8340    0.9620    0.2661 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0907    0.2621    0.0827 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0342    0.1968    1.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3297   -0.5113    0.9398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7338    0.7821    2.1841 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7537   -0.0393   -0.0469 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2151   -1.3621    0.5111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7841    0.0317   -1.5433 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9969   -0.5918   -2.2184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6703   -0.9504   -2.4186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3954    4.3590    2.1862 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1291    5.0546    2.8305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0978    4.3976    4.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8157    1.1674    1.9571 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4263    0.2567    2.5411 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8267   -1.6465    1.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3256   -0.7263    1.2437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3004   -2.3388   -1.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6736   -5.2599   -0.8128 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4051   -3.7356   -0.1671 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3852   -4.8341    0.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3679   -0.4352   -3.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3475   -1.2939   -2.3337 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9823   -2.1765   -3.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5357    1.2478   -2.3980 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0064    1.9180   -0.0197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9095    1.8014   -2.7976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7410    1.9620   -1.4822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5129    3.7000   -0.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8706    1.3458    1.2711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8197   -0.1560    0.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1336   -1.6015    0.8701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9207   -0.3458    1.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1196   -1.2853    1.6199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3040   -1.4451    0.3326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7592   -2.2435    0.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5160    0.0011   -2.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6677   -1.2387   -1.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  6  5  1  1
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  8 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 21 26  1  0
 26 27  1  6
 26 28  1  0
 28 29  1  0
 29 30  1  0
 16  6  1  0
 28 18  1  0
 28 30  1  6
 26  6  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  5 34  1  0
  5 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  6
 11 39  1  0
 11 40  1  0
 11 41  1  0
 14 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  0
 16 46  1  1
 18 47  1  6
 19 48  1  6
 20 49  1  0
 21 50  1  1
 24 51  1  0
 24 52  1  0
 24 53  1  0
 27 54  1  0
 27 55  1  0
 27 56  1  0
 29 57  1  0
 29 58  1  0
M  END


  Mrv1652309042218032D          

 30 33  0  0  1  0            999 V2000
    3.9220   -1.5741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2475   -1.0990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4989   -1.4457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3216   -0.2774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6471    0.1976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7212    1.0193    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3584    0.4952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1308    0.7849    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7680    0.2608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5404    0.5505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1775    0.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6757    1.3644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2661    1.5988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0386    1.8885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6290    2.1229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8566    1.8331    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3047    2.4463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4811    2.3972    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0061    1.7227    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1923    1.8580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2373    0.9307    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6241    0.3788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1605    0.6339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7737    0.0820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3319    1.4409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0006    0.6177    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0498   -0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5184    1.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9482    0.8463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7170    1.6383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
  6 16  1  0  0  0  0
 16 17  1  6  0  0  0
 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 21 26  1  0  0  0  0
  6 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 18 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0197743

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@]12C[C@H](OC(C)=O)C(C)=C[C@H]1O[C@@H]1[C@H](O)[C@@H](OC(C)=O)[C@@]2(C)C11CO1

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O9/c1-10-6-15-20(8-26-11(2)22,7-14(10)28-12(3)23)19(5)17(29-13(4)24)16(25)18(30-15)21(19)9-27-21/h6,14-18,25H,7-9H2,1-5H3/t14-,15+,16+,17+,18+,19+,20+,21?/m0/s1

> <INCHI_KEY>
BIQPSTSCCIEMEI-NCHBFNGESA-N

> <FORMULA>
C21H28O9

> <MOLECULAR_WEIGHT>
424.446

> <EXACT_MASS>
424.173332482

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
42.350109390743064

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1'S,2'R,4'S,7'R,9'R,10'R,11'S)-4',11'-bis(acetyloxy)-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-2'-yl]methyl acetate

> <JCHEM_LOGP>
-0.4126860513333325

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.072305054496212

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6419737691633562

> <JCHEM_POLAR_SURFACE_AREA>
120.89000000000001

> <JCHEM_REFRACTIVITY>
99.7667

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,2'R,4'S,7'R,9'R,10'R,11'S)-4',11'-bis(acetyloxy)-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-2'-ylmethyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       7.321  -2.938   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.062  -2.052   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.665  -2.699   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.200  -0.518   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.941   0.369   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.080   1.903   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.269   0.924   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.711   1.465   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.900   0.487   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.342   1.028   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.531   0.049   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      10.595   2.547   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.963   2.984   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.405   3.525   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.774   3.963   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.332   3.422   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.302   4.567   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.765   4.475   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.878   3.216   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.359   3.468   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.310   1.737   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.165   0.707   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.300   1.183   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.444   0.153   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.619   2.690   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.734   1.153   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.826  -0.384   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.834   2.693   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.770   1.580   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.338   3.058   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   16   26                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    8   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15    6   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   28                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   21    6   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   18   29   30                                             
CONECT   29   28   30                                                       
CONECT   30   29   28                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₈O₉

Average Mass

424.4460 Da

Monoisotopic Mass

424.17333 Da

IUPAC Name

[(1'S,2'R,4'S,7'R,9'R,10'R,11'S)-4',11'-bis(acetyloxy)-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-2'-yl]methyl acetate

Traditional Name

(1'S,2'R,4'S,7'R,9'R,10'R,11'S)-4',11'-bis(acetyloxy)-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-2'-ylmethyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@]12C[C@H](OC(C)=O)C(C)=C[C@H]1O[C@@H]1[C@H](O)[C@@H](OC(C)=O)[C@@]2(C)C11CO1

InChI Identifier

InChI=1S/C21H28O9/c1-10-6-15-20(8-26-11(2)22,7-14(10)28-12(3)23)19(5)17(29-13(4)24)16(25)18(30-15)21(19)9-27-21/h6,14-18,25H,7-9H2,1-5H3/t14-,15+,16+,17+,18+,19+,20+,21?/m0/s1

InChI Key

BIQPSTSCCIEMEI-NCHBFNGESA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trichothecenes. These are sesquiterpene mycotoxins structurally characterized by the presence of an epoxide ring and a benzopyran derivative with a variant number of hydroxyl, acetyl, or other substituents. The most important structural features causing the biological activities of trichothecenes are the 12,13-epoxy ring, the presence of hydroxyl or acetyl groups at appropriate positions on the trichothecene nucleus and the structure and position of the side-chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Trichothecenes

Alternative Parents

Substituents

Trichothecene skeleton
Tricarboxylic acid or derivatives
Oxepane
Oxane
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Alcohol
Carbonyl group
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	-0.41	ChemAxon
pKa (Strongest Acidic)	13.07	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	120.89 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	99.77 m³·mol⁻¹	ChemAxon
Polarizability	42.35 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2299348

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3035020

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1's,2'r,4's,7'r,9'r,10'r,11's)-4',11'-bis(acetyloxy)-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate (NP0197743)

MOL for NP0197743 ((1's,2'r,4's,7'r,9'r,10'r,11's)-4',11'-bis(acetyloxy)-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate)

3D MOL for NP0197743 ((1's,2'r,4's,7'r,9'r,10'r,11's)-4',11'-bis(acetyloxy)-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate)

3D SDF for NP0197743 ((1's,2'r,4's,7'r,9'r,10'r,11's)-4',11'-bis(acetyloxy)-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate)

3D-SDF for NP0197743 ((1's,2'r,4's,7'r,9'r,10'r,11's)-4',11'-bis(acetyloxy)-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate)

PDB for NP0197743 ((1's,2'r,4's,7'r,9'r,10'r,11's)-4',11'-bis(acetyloxy)-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate)

3D PDB for NP0197743 ((1's,2'r,4's,7'r,9'r,10'r,11's)-4',11'-bis(acetyloxy)-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate)

SMILES for NP0197743 ((1's,2'r,4's,7'r,9'r,10'r,11's)-4',11'-bis(acetyloxy)-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate)

INCHI for NP0197743 ((1's,2'r,4's,7'r,9'r,10'r,11's)-4',11'-bis(acetyloxy)-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate)

Structure for NP0197743 ((1's,2'r,4's,7'r,9'r,10'r,11's)-4',11'-bis(acetyloxy)-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate)

3D Structure for NP0197743 ((1's,2'r,4's,7'r,9'r,10'r,11's)-4',11'-bis(acetyloxy)-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate)