NP-MRD: Showing NP-Card for 3-hydroxy-N-methylwelwitindolinone C isonitrile (NP0001605)

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Record Information

Version

2.0

Created at

2020-09-23 01:58:20 UTC

Updated at

2021-08-10 02:55:37 UTC

NP-MRD ID

NP0001605

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-hydroxy-N-methylwelwitindolinone C isonitrile

Provided By

NPAtlas

Description

3-hydroxy-N-methylwelwitindolinone C isonitrile is found in Fischerella sp. 3-hydroxy-N-methylwelwitindolinone C isonitrile was first documented in 1999 (PMID: 10217710). Based on a literature review very few articles have been published on (2S,3S,6R,8S)-4-chloro-3-ethenyl-8-hydroxy-2-isocyano-3,7,7,10-tetramethyl-10-azatetracyclo[6.6.1.1²,⁶.0¹¹,¹⁵]Hexadeca-1(15),4,11,13-tetraene-9,16-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117433D          

 49 52  0  0  0  0            999 V2000
    3.0047   -1.5209   -2.6777 C   0  5  0  0  0  3  0  0  0  0  0  0
    2.3473   -0.9906   -1.8732 N   0  3  0  0  0  4  0  0  0  0  0  0
    1.5407   -0.3519   -0.9005 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1075    0.9408   -1.5314 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2693    1.1913   -2.7062 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4601    1.9321   -0.6653 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0724    2.0167    0.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9921    1.1618    1.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8444    1.3638    2.6022 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4120   -0.0282    0.2589 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7807    0.3585   -0.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5789   -1.1389    1.2095 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7650   -1.3733    1.7325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0257    1.6982   -0.4471 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6771    1.4995   -1.7878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5744    2.9624    0.1788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2765    0.5678    0.4969 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6420    0.8153    1.7309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7083    0.4563    0.7890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5391    1.3391    1.1085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0559   -0.9143    0.6471 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3420   -1.4972    0.9681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9231   -1.6062    0.1372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8121   -2.9354   -0.2273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6180   -3.3434   -0.7761 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4492   -2.4542   -0.9627 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3324   -1.1362   -0.5977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8719   -0.7429   -0.0459 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5416    2.9297   -1.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7506    2.8003    1.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6385    0.9726   -1.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3250   -0.5678   -0.5292 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3528    0.9498    0.4001 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7362   -1.7491    1.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6384   -0.7774    1.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8218    0.4273   -2.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0535    2.0227   -2.5663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6714    2.0016   -1.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6391    3.1284   -0.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9370    3.8086   -0.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4946   -2.4663    0.4354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1593   -0.7831    0.6715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4095   -1.6461    2.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6436   -3.6425   -0.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5304   -4.3851   -1.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3574   -2.8563   -1.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
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 12 13  2  3  0  0  0
  6 14  1  0  0  0  0
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 24 25  2  0  0  0  0
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 27 28  1  0  0  0  0
 10  3  1  0  0  0  0
 28 17  1  0  0  0  0
 27  3  1  0  0  0  0
 28 23  2  0  0  0  0
  6 29  1  6  0  0  0
  7 30  1  0  0  0  0
 11 31  1  0  0  0  0
 11 32  1  0  0  0  0
 11 33  1  0  0  0  0
 12 34  1  0  0  0  0
 13 35  1  0  0  0  0
 13 36  1  0  0  0  0
 15 37  1  0  0  0  0
 15 38  1  0  0  0  0
 15 39  1  0  0  0  0
 16 40  1  0  0  0  0
 16 41  1  0  0  0  0
 16 42  1  0  0  0  0
 18 43  1  0  0  0  0
 22 44  1  0  0  0  0
 22 45  1  0  0  0  0
 22 46  1  0  0  0  0
 24 47  1  0  0  0  0
 25 48  1  0  0  0  0
 26 49  1  0  0  0  0
M  CHG  2   1  -1   2   1
M  END

     RDKit          3D

 49 52  0  0  0  0  0  0  0  0999 V2000
    3.0047   -1.5209   -2.6777 C   0  0  0  0  0  3  0  0  0  0  0  0
    2.3473   -0.9906   -1.8732 N   0  0  0  0  0  4  0  0  0  0  0  0
    1.5407   -0.3519   -0.9005 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1075    0.9408   -1.5314 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2693    1.1913   -2.7062 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4601    1.9321   -0.6653 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0724    2.0167    0.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9921    1.1618    1.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8444    1.3638    2.6022 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4120   -0.0282    0.2589 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7807    0.3585   -0.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5789   -1.1389    1.2095 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7650   -1.3733    1.7325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0257    1.6982   -0.4471 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6771    1.4995   -1.7878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5744    2.9624    0.1788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2765    0.5678    0.4969 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6420    0.8153    1.7309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7083    0.4563    0.7890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5391    1.3391    1.1085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0559   -0.9143    0.6471 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3420   -1.4972    0.9681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9231   -1.6062    0.1372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8121   -2.9354   -0.2273 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4492   -2.4542   -0.9627 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3324   -1.1362   -0.5977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8719   -0.7429   -0.0459 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5416    2.9297   -1.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7506    2.8003    1.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6385    0.9726   -1.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3250   -0.5678   -0.5292 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3528    0.9498    0.4001 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7362   -1.7491    1.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9463   -2.1883    2.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6384   -0.7774    1.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0535    2.0227   -2.5663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6714    2.0016   -1.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9370    3.8086   -0.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5521    2.8489    1.2947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2650    0.9018    2.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4946   -2.4663    0.4354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1593   -0.7831    0.6715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4095   -1.6461    2.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6436   -3.6425   -0.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5304   -4.3851   -1.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3574   -2.8563   -1.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  3  2  1  6
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  1  1
 12 13  2  3
  6 14  1  0
 14 15  1  6
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 14 17  1  0
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 17 19  1  0
 19 20  2  0
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 10  3  1  0
 28 17  1  0
 27  3  1  0
 28 23  2  0
  6 29  1  6
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M  CHG  2   1  -1   2   1
M  END


  Mrv1652306242117433D          

 49 52  0  0  0  0            999 V2000
    3.0047   -1.5209   -2.6777 C   0  5  0  0  0  3  0  0  0  0  0  0
    2.3473   -0.9906   -1.8732 N   0  3  0  0  0  4  0  0  0  0  0  0
    1.5407   -0.3519   -0.9005 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1075    0.9408   -1.5314 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2693    1.1913   -2.7062 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4601    1.9321   -0.6653 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0724    2.0167    0.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9921    1.1618    1.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8444    1.3638    2.6022 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4120   -0.0282    0.2589 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7807    0.3585   -0.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5789   -1.1389    1.2095 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7650   -1.3733    1.7325 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6771    1.4995   -1.7878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5744    2.9624    0.1788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2765    0.5678    0.4969 C   0  0  1  0  0  0  0  0  0  0  0  0
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    3.9463   -2.1883    2.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9370    3.8086   -0.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5521    2.8489    1.2947 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4095   -1.6461    2.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6436   -3.6425   -0.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5304   -4.3851   -1.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3574   -2.8563   -1.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  1  0  0  0
 12 13  2  3  0  0  0
  6 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 10  3  1  0  0  0  0
 28 17  1  0  0  0  0
 27  3  1  0  0  0  0
 28 23  2  0  0  0  0
  6 29  1  6  0  0  0
  7 30  1  0  0  0  0
 11 31  1  0  0  0  0
 11 32  1  0  0  0  0
 11 33  1  0  0  0  0
 12 34  1  0  0  0  0
 13 35  1  0  0  0  0
 13 36  1  0  0  0  0
 15 37  1  0  0  0  0
 15 38  1  0  0  0  0
 15 39  1  0  0  0  0
 16 40  1  0  0  0  0
 16 41  1  0  0  0  0
 16 42  1  0  0  0  0
 18 43  1  0  0  0  0
 22 44  1  0  0  0  0
 22 45  1  0  0  0  0
 22 46  1  0  0  0  0
 24 47  1  0  0  0  0
 25 48  1  0  0  0  0
 26 49  1  0  0  0  0
M  CHG  2   1  -1   2   1
M  END
> <DATABASE_ID>
NP0001605

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]12C(=O)N(C3=C1C(=C([H])C([H])=C3[H])[C@@]1([N+]#[C-])C(=O)[C@]([H])(C([H])=C(Cl)[C@]1(C([H])=C([H])[H])C([H])([H])[H])C2(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H21ClN2O3/c1-7-20(4)15(23)11-13-17(26)21(20,24-5)12-9-8-10-14-16(12)22(28,19(13,2)3)18(27)25(14)6/h7-11,13,28H,1H2,2-4,6H3/t13-,20+,21+,22-/m0/s1

> <INCHI_KEY>
GFNPBZSGZFQTJA-WOHBTAIZSA-N

> <FORMULA>
C22H21ClN2O3

> <MOLECULAR_WEIGHT>
396.87

> <EXACT_MASS>
396.1240702

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
39.97969373286039

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S,6R,8S)-4-chloro-3-ethenyl-8-hydroxy-2-isocyano-3,7,7,10-tetramethyl-10-azatetracyclo[6.6.1.1^{2,6}.0^{11,15}]hexadeca-1(14),4,11(15),12-tetraene-9,16-dione

> <ALOGPS_LOGP>
3.63

> <JCHEM_LOGP>
0.8722202374573891

> <ALOGPS_LOGS>
-4.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
11.749695593556117

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.089837108026938

> <JCHEM_PKA_STRONGEST_BASIC>
-4.350807809263849

> <JCHEM_POLAR_SURFACE_AREA>
61.97

> <JCHEM_REFRACTIVITY>
116.5731

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.89e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,6R,8S)-4-chloro-3-ethenyl-8-hydroxy-2-isocyano-3,7,7,10-tetramethyl-10-azatetracyclo[6.6.1.1^{2,6}.0^{11,15}]hexadeca-1(14),4,11(15),12-tetraene-9,16-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 49 52  0  0  0  0  0  0  0  0999 V2000
    3.0047   -1.5209   -2.6777 C   0  0  0  0  0  3  0  0  0  0  0  0
    2.3473   -0.9906   -1.8732 N   0  0  0  0  0  4  0  0  0  0  0  0
    1.5407   -0.3519   -0.9005 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1075    0.9408   -1.5314 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2693    1.1913   -2.7062 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4601    1.9321   -0.6653 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0724    2.0167    0.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9921    1.1618    1.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8444    1.3638    2.6022 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4120   -0.0282    0.2589 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7807    0.3585   -0.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5789   -1.1389    1.2095 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7650   -1.3733    1.7325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0257    1.6982   -0.4471 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6771    1.4995   -1.7878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5744    2.9624    0.1788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2765    0.5678    0.4969 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6420    0.8153    1.7309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7083    0.4563    0.7890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5391    1.3391    1.1085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0559   -0.9143    0.6471 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3420   -1.4972    0.9681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9231   -1.6062    0.1372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8121   -2.9354   -0.2273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6180   -3.3434   -0.7761 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4492   -2.4542   -0.9627 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3324   -1.1362   -0.5977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8719   -0.7429   -0.0459 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5416    2.9297   -1.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7506    2.8003    1.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6385    0.9726   -1.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3250   -0.5678   -0.5292 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3528    0.9498    0.4001 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7362   -1.7491    1.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9463   -2.1883    2.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6384   -0.7774    1.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8218    0.4273   -2.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0535    2.0227   -2.5663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6714    2.0016   -1.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6391    3.1284   -0.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9370    3.8086   -0.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5521    2.8489    1.2947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2650    0.9018    2.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4946   -2.4663    0.4354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1593   -0.7831    0.6715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4095   -1.6461    2.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6436   -3.6425   -0.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5304   -4.3851   -1.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3574   -2.8563   -1.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  3  2  1  6
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  1  1
 12 13  2  3
  6 14  1  0
 14 15  1  6
 14 16  1  0
 14 17  1  0
 17 18  1  1
 17 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 10  3  1  0
 28 17  1  0
 27  3  1  0
 28 23  2  0
  6 29  1  6
  7 30  1  0
 11 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
 18 43  1  0
 22 44  1  0
 22 45  1  0
 22 46  1  0
 24 47  1  0
 25 48  1  0
 26 49  1  0
M  CHG  2   1  -1   2   1
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       3.005  -1.521  -2.678  0.00  0.00           C-1
HETATM    2  N   UNK     0       2.347  -0.991  -1.873  0.00  0.00           N+1
HETATM    3  C   UNK     0       1.541  -0.352  -0.901  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.107   0.941  -1.531  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.269   1.191  -2.706  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.460   1.932  -0.665  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.072   2.017   0.671  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.992   1.162   1.051  0.00  0.00           C+0
HETATM    9 Cl   UNK     0       2.844   1.364   2.602  0.00  0.00          Cl+0
HETATM   10  C   UNK     0       2.412  -0.028   0.259  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.781   0.359  -0.341  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.579  -1.139   1.210  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.765  -1.373   1.732  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.026   1.698  -0.447  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.677   1.500  -1.788  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.574   2.962   0.179  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.276   0.568   0.497  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.642   0.815   1.731  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.708   0.456   0.789  0.00  0.00           C+0
HETATM   20  O   UNK     0      -3.539   1.339   1.109  0.00  0.00           O+0
HETATM   21  N   UNK     0      -3.056  -0.914   0.647  0.00  0.00           N+0
HETATM   22  C   UNK     0      -4.342  -1.497   0.968  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.923  -1.606   0.137  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.812  -2.935  -0.227  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.618  -3.343  -0.776  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.449  -2.454  -0.963  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.332  -1.136  -0.598  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.872  -0.743  -0.046  0.00  0.00           C+0
HETATM   29  H   UNK     0       0.542   2.930  -1.144  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.751   2.800   1.341  0.00  0.00           H+0
HETATM   31  H   UNK     0       3.639   0.973  -1.251  0.00  0.00           H+0
HETATM   32  H   UNK     0       4.325  -0.568  -0.529  0.00  0.00           H+0
HETATM   33  H   UNK     0       4.353   0.950   0.400  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.736  -1.749   1.470  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.946  -2.188   2.447  0.00  0.00           H+0
HETATM   36  H   UNK     0       4.638  -0.777   1.492  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.822   0.427  -2.036  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.054   2.023  -2.566  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.671   2.002  -1.838  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.639   3.128  -0.086  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.937   3.809  -0.123  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.552   2.849   1.295  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.265   0.902   2.476  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.495  -2.466   0.435  0.00  0.00           H+0
HETATM   45  H   UNK     0      -5.159  -0.783   0.672  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.410  -1.646   2.056  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.644  -3.643  -0.086  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.530  -4.385  -1.062  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.357  -2.856  -1.404  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10   27                                             
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   14   29                                             
CONECT    7    6    8   30                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12    3                                             
CONECT   11   10   31   32   33                                             
CONECT   12   10   13   34                                                  
CONECT   13   12   35   36                                                  
CONECT   14    6   15   16   17                                             
CONECT   15   14   37   38   39                                             
CONECT   16   14   40   41   42                                             
CONECT   17   14   18   19   28                                             
CONECT   18   17   43                                                       
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21   44   45   46                                             
CONECT   23   21   24   28                                                  
CONECT   24   23   25   47                                                  
CONECT   25   24   26   48                                                  
CONECT   26   25   27   49                                                  
CONECT   27   26   28    3                                                  
CONECT   28   27   17   23                                                  
CONECT   29    6                                                            
CONECT   30    7                                                            
CONECT   31   11                                                            
CONECT   32   11                                                            
CONECT   33   11                                                            
CONECT   34   12                                                            
CONECT   35   13                                                            
CONECT   36   13                                                            
CONECT   37   15                                                            
CONECT   38   15                                                            
CONECT   39   15                                                            
CONECT   40   16                                                            
CONECT   41   16                                                            
CONECT   42   16                                                            
CONECT   43   18                                                            
CONECT   44   22                                                            
CONECT   45   22                                                            
CONECT   46   22                                                            
CONECT   47   24                                                            
CONECT   48   25                                                            
CONECT   49   26                                                            
MASTER        0    0    0    0    0    0    0    0   49    0  104    0
END

RDKit          3D

49 52  0  0  0  0  0  0  0  0999 V2000
    3.0047   -1.5209   -2.6777 C   0  0  0  0  0  3  0  0  0  0  0  0
    2.3473   -0.9906   -1.8732 N   0  0  0  0  0  4  0  0  0  0  0  0
    1.5407   -0.3519   -0.9005 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1075    0.9408   -1.5314 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2693    1.1913   -2.7062 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4601    1.9321   -0.6653 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0724    2.0167    0.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9921    1.1618    1.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8444    1.3638    2.6022 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4120   -0.0282    0.2589 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7807    0.3585   -0.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5789   -1.1389    1.2095 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7650   -1.3733    1.7325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0257    1.6982   -0.4471 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6771    1.4995   -1.7878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5744    2.9624    0.1788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2765    0.5678    0.4969 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6420    0.8153    1.7309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7083    0.4563    0.7890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5391    1.3391    1.1085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0559   -0.9143    0.6471 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3420   -1.4972    0.9681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9231   -1.6062    0.1372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8121   -2.9354   -0.2273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6180   -3.3434   -0.7761 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4492   -2.4542   -0.9627 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3324   -1.1362   -0.5977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8719   -0.7429   -0.0459 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5416    2.9297   -1.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7506    2.8003    1.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6385    0.9726   -1.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3250   -0.5678   -0.5292 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3528    0.9498    0.4001 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7362   -1.7491    1.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9463   -2.1883    2.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6384   -0.7774    1.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8218    0.4273   -2.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0535    2.0227   -2.5663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6714    2.0016   -1.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6391    3.1284   -0.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9370    3.8086   -0.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5521    2.8489    1.2947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2650    0.9018    2.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4946   -2.4663    0.4354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1593   -0.7831    0.6715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4095   -1.6461    2.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6436   -3.6425   -0.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5304   -4.3851   -1.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3574   -2.8563   -1.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  3  2  1  6
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  1  1
 12 13  2  3
  6 14  1  0
 14 15  1  6
 14 16  1  0
 14 17  1  0
 17 18  1  1
 17 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 10  3  1  0
 28 17  1  0
 27  3  1  0
 28 23  2  0
  6 29  1  6
  7 30  1  0
 11 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
 18 43  1  0
 22 44  1  0
 22 45  1  0
 22 46  1  0
 24 47  1  0
 25 48  1  0
 26 49  1  0
M  CHG  2   1  -1   2   1
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₂H₂₁ClN₂O₃

Average Mass

396.8700 Da

Monoisotopic Mass

396.12407 Da

IUPAC Name

(2S,3S,6R,8S)-4-chloro-3-ethenyl-8-hydroxy-2-isocyano-3,7,7,10-tetramethyl-10-azatetracyclo[6.6.1.1^{2,6}.0^{11,15}]hexadeca-1(14),4,11(15),12-tetraene-9,16-dione

Traditional Name

(2S,3S,6R,8S)-4-chloro-3-ethenyl-8-hydroxy-2-isocyano-3,7,7,10-tetramethyl-10-azatetracyclo[6.6.1.1^{2,6}.0^{11,15}]hexadeca-1(14),4,11(15),12-tetraene-9,16-dione

CAS Registry Number

Not Available

SMILES

[H]O[C@]12C(=O)N(C3=C1C(=C([H])C([H])=C3[H])[C@@]1([N+]#[C-])C(=O)[C@]([H])(C([H])=C(Cl)[C@]1(C([H])=C([H])[H])C([H])([H])[H])C2(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C22H21ClN2O3/c1-7-20(4)15(23)11-13-17(26)21(20,24-5)12-9-8-10-14-16(12)22(28,19(13,2)3)18(27)25(14)6/h7-11,13,28H,1H2,2-4,6H3/t13-,20+,21+,22-/m0/s1

InChI Key

GFNPBZSGZFQTJA-WOHBTAIZSA-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
Fischerella sp.	NPAtlas	10217710

Chemical Taxonomy

Classification

Not classified

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	3.63	ALOGPS
logP	0.87	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	9.09	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	61.97 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	116.57 m³·mol⁻¹	ChemAxon
Polarizability	39.98 Å³	ChemAxon
Number of Rings	4	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

NPAtlas ID

NPA000795

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8962270

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10786957

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Jimenez JI, Huber U, Moore RE, Patterson GM: Oxidized welwitindolinones from terrestrial fischerella spp J Nat Prod. 1999 Apr;62(4):569-72. doi: 10.1021/np980485t. [PubMed:10217710 ]

Showing NP-Card for 3-hydroxy-N-methylwelwitindolinone C isonitrile (NP0001605)

MOL for NP0001605 (3-hydroxy-N-methylwelwitindolinone C isonitrile)

3D MOL for NP0001605 (3-hydroxy-N-methylwelwitindolinone C isonitrile)

3D SDF for NP0001605 (3-hydroxy-N-methylwelwitindolinone C isonitrile)

3D-SDF for NP0001605 (3-hydroxy-N-methylwelwitindolinone C isonitrile)

PDB for NP0001605 (3-hydroxy-N-methylwelwitindolinone C isonitrile)

3D PDB for NP0001605 (3-hydroxy-N-methylwelwitindolinone C isonitrile)

SMILES for NP0001605 (3-hydroxy-N-methylwelwitindolinone C isonitrile)

INCHI for NP0001605 (3-hydroxy-N-methylwelwitindolinone C isonitrile)

Structure for NP0001605 (3-hydroxy-N-methylwelwitindolinone C isonitrile)

3D Structure for NP0001605 (3-hydroxy-N-methylwelwitindolinone C isonitrile)