NP-MRD: Showing NP-Card for (2s,3s,6r,8r)-4-chloro-3-ethenyl-2-isothiocyanato-3,7,7,10-tetramethyl-10-azatetracyclo[6.6.1.1²,⁶.0¹¹,¹⁵]hexadeca-1(14),4,11(15),12-tetraene-9,16-dione (NP0177404)

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Record Information

Version

1.0

Created at

2022-09-03 15:14:22 UTC

Updated at

2022-09-03 15:14:22 UTC

NP-MRD ID

NP0177404

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3s,6r,8r)-4-chloro-3-ethenyl-2-isothiocyanato-3,7,7,10-tetramethyl-10-azatetracyclo[6.6.1.1²,⁶.0¹¹,¹⁵]hexadeca-1(14),4,11(15),12-tetraene-9,16-dione

Description

N-Methylwelwitindolinone C isothiocyanate, also known as N-me-wc-NCS, belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. (2s,3s,6r,8r)-4-chloro-3-ethenyl-2-isothiocyanato-3,7,7,10-tetramethyl-10-azatetracyclo[6.6.1.1²,⁶.0¹¹,¹⁵]hexadeca-1(14),4,11(15),12-tetraene-9,16-dione is found in Fischerella major. It was first documented in 2012 (PMID: 22830424). Based on a literature review a significant number of articles have been published on N-Methylwelwitindolinone C isothiocyanate (PMID: 29386433) (PMID: 26214342) (PMID: 24677572) (PMID: 23976796).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032217142D          

 28 31  0  0  1  0            999 V2000
    4.2127   -0.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3793    0.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7629    1.0769    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3628    0.3555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4681    1.5838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2347    1.2788    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.3092    2.4087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5278    2.6827    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1122    1.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3658    2.3341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8801    1.3364    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6501    0.5441    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8489    0.3471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0478    0.1502    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9777    1.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3231    1.0276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5209    1.2802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3306    2.0856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9098    2.6606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6852    2.4218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1429    3.1436    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6589    3.7931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8834    4.5870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8889    3.4863    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2003    3.9407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9428    3.2562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8150    4.0713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5295    3.8362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  2  0  0  0  0
 13 14  2  0  0  0  0
 11 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 26  1  0  0  0  0
  8 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
M  END

     RDKit          3D

 49 52  0  0  0  0  0  0  0  0999 V2000
    3.9652   -1.5810    1.2111 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8996   -1.6227    0.4440 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3401   -0.3864   -0.1109 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4563    0.3149   -0.8799 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9374    0.5698    0.9500 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3364    0.1964    2.6322 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2997    1.6656    0.5916 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5109    1.8199   -0.6606 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8168    0.7250   -1.6282 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7438    0.9318   -2.8195 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2047   -0.5937   -1.0463 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6440   -1.5164   -2.0750 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2849   -1.0151   -3.0578 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8099   -0.7967   -4.5626 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0149   -1.1736   -0.4500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1825   -2.5286   -0.7342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2582   -3.2605   -0.2974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2309   -2.6441    0.4592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1031   -1.3057    0.7618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0183   -0.6030    0.3142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1278    0.7850    0.8312 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4397    0.8562    1.4674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0068    1.8660    1.9341 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0030   -0.4488    1.4790 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2347   -0.8368    2.0901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9507    1.8125   -0.2323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8747    1.5789   -1.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2274    3.1749    0.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4366   -2.4541    1.6583 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4295   -0.6300    1.4324 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4383   -2.5662    0.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9857    1.0573   -1.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1032   -0.3958   -1.4127 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0866    0.8183   -0.1089 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3479    2.5234    1.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7414    2.8229   -1.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5950   -3.0089   -1.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3580   -4.3120   -0.5352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1043   -3.2053    0.8228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3748    0.9570    1.6477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2507   -0.6177    3.1958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3965   -1.9328    1.9795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1220   -0.3382    1.6627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8997    2.5089   -2.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8866    1.4022   -0.9868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5109    0.7796   -2.0577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0991    3.1484    1.4920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2412    3.5329    0.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4973    3.9261    0.0087 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 24  1  0
 24 22  1  0
 22 23  2  0
 22 21  1  0
 21 20  1  0
 20 19  2  0
 19 18  1  0
 18 17  2  0
 17 16  1  0
 16 15  2  0
 15 11  1  0
 11 12  1  6
 12 13  2  0
 13 14  2  0
 11  9  1  0
  9 10  2  0
  9  8  1  0
  8  7  1  0
  7  5  2  0
  5  6  1  0
  5  3  1  0
  3  4  1  0
  3  2  1  1
  2  1  2  3
  8 26  1  0
 26 27  1  0
 26 28  1  0
 19 24  1  0
  3 11  1  0
 26 21  1  0
 15 20  1  0
 25 41  1  0
 25 42  1  0
 25 43  1  0
 21 40  1  1
 18 39  1  0
 17 38  1  0
 16 37  1  0
  8 36  1  6
  7 35  1  0
  4 32  1  0
  4 33  1  0
  4 34  1  0
  2 31  1  0
  1 29  1  0
  1 30  1  0
 27 44  1  0
 27 45  1  0
 27 46  1  0
 28 47  1  0
 28 48  1  0
 28 49  1  0
M  END


  Mrv1652309032217142D          

 28 31  0  0  1  0            999 V2000
    4.2127   -0.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3793    0.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7629    1.0769    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3628    0.3555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4681    1.5838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2347    1.2788    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.3092    2.4087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5278    2.6827    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1122    1.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3658    2.3341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8801    1.3364    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6501    0.5441    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8489    0.3471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0478    0.1502    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9777    1.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3231    1.0276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5209    1.2802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3306    2.0856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9098    2.6606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6852    2.4218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1429    3.1436    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6589    3.7931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8834    4.5870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8889    3.4863    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2003    3.9407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9428    3.2562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8150    4.0713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5295    3.8362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  2  0  0  0  0
 13 14  2  0  0  0  0
 11 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 26  1  0  0  0  0
  8 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0177404

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(=O)[C@H]2C3=C1C=CC=C3[C@@]1(N=C=S)C(=O)[C@H](C=C(Cl)[C@@]1(C)C=C)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C22H21ClN2O2S/c1-6-21(4)15(23)10-13-18(26)22(21,24-11-28)12-8-7-9-14-16(12)17(20(13,2)3)19(27)25(14)5/h6-10,13,17H,1H2,2-5H3/t13-,17+,21+,22+/m0/s1

> <INCHI_KEY>
ULCGNHFUBLOLRR-YLBNWIERSA-N

> <FORMULA>
C22H21ClN2O2S

> <MOLECULAR_WEIGHT>
412.93

> <EXACT_MASS>
412.1012268

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
42.12268252741859

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S,6R,8R)-4-chloro-3-ethenyl-2-isothiocyanato-3,7,7,10-tetramethyl-10-azatetracyclo[6.6.1.1^{2,6}.0^{11,15}]hexadeca-1(15),4,11,13-tetraene-9,16-dione

> <JCHEM_LOGP>
4.491796957666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.693749808873775

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.971905417121862

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4038239656124287

> <JCHEM_POLAR_SURFACE_AREA>
49.74

> <JCHEM_REFRACTIVITY>
115.14459999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,6R,8R)-4-chloro-3-ethenyl-2-isothiocyanato-3,7,7,10-tetramethyl-10-azatetracyclo[6.6.1.1^{2,6}.0^{11,15}]hexadeca-1(15),4,11,13-tetraene-9,16-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       7.864  -0.521   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.175   0.987   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.024   2.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.277   0.664   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.340   2.956   0.000  0.00  0.00           C+0
HETATM    6 Cl   UNK     0       9.771   2.387   0.000  0.00  0.00          Cl+0
HETATM    7  C   UNK     0       8.044   4.496   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.585   5.008   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.809   3.701   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.416   4.357   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.376   2.495   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       4.947   1.016   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       3.451   0.648   0.000  0.00  0.00           C+0
HETATM   14  S   UNK     0       1.956   0.280   0.000  0.00  0.00           S+0
HETATM   15  C   UNK     0       3.692   2.978   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.470   1.918   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.972   2.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.617   3.893   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.698   4.967   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.146   4.521   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.000   5.868   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.097   7.080   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.516   8.562   0.000  0.00  0.00           O+0
HETATM   24  N   UNK     0       1.659   6.508   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       0.374   7.356   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.493   6.078   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.255   7.600   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.588   7.161   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   11                                             
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   26                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    3   12   15                                             
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   11   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   15   21                                                  
CONECT   21   20   22   26                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   19   25                                                  
CONECT   25   24                                                            
CONECT   26   21    8   27   28                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Value	Source
N-Methylwelwitindolinone C isothiocyanic acid	Generator
N-Me-wc-NCS	MeSH

Chemical Formula

C₂₂H₂₁ClN₂O₂S

Average Mass

412.9300 Da

Monoisotopic Mass

412.10123 Da

IUPAC Name

(2S,3S,6R,8R)-4-chloro-3-ethenyl-2-isothiocyanato-3,7,7,10-tetramethyl-10-azatetracyclo[6.6.1.1^{2,6}.0^{11,15}]hexadeca-1(15),4,11,13-tetraene-9,16-dione

Traditional Name

(2S,3S,6R,8R)-4-chloro-3-ethenyl-2-isothiocyanato-3,7,7,10-tetramethyl-10-azatetracyclo[6.6.1.1^{2,6}.0^{11,15}]hexadeca-1(15),4,11,13-tetraene-9,16-dione

CAS Registry Number

Not Available

SMILES

CN1C(=O)[C@H]2C3=C1C=CC=C3[C@@]1(N=C=S)C(=O)[C@H](C=C(Cl)[C@@]1(C)C=C)C2(C)C

InChI Identifier

InChI=1S/C22H21ClN2O2S/c1-6-21(4)15(23)10-13-18(26)22(21,24-11-28)12-8-7-9-14-16(12)17(20(13,2)3)19(27)25(14)5/h6-10,13,17H,1H2,2-5H3/t13-,17+,21+,22+/m0/s1

InChI Key

ULCGNHFUBLOLRR-YLBNWIERSA-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

Species Name	Source	Reference
Fischerella major	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Not Available

Direct Parent

Indoles and derivatives

Alternative Parents

Substituents

Indole or derivatives
Cyclohexenone
Benzenoid
Tertiary carboxylic acid amide
Carboxamide group
Isothiocyanate
Ketone
Lactam
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Azacycle
Vinyl halide
Vinyl chloride
Chloroalkene
Haloalkene
Carboxylic acid derivative
Hydrocarbon derivative
Organonitrogen compound
Organochloride
Organohalogen compound
Organooxygen compound
Carbonyl group
Organic nitrogen compound
Organosulfur compound
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	4.49	ChemAxon
pKa (Strongest Acidic)	11.97	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	49.74 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	115.14 m³·mol⁻¹	ChemAxon
Polarizability	42.12 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8652217

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10476807

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Fu TH, McElroy WT, Shamszad M, Martin SF: Formal syntheses of naturally occurring welwitindolinones. Org Lett. 2012 Aug 3;14(15):3834-7. doi: 10.1021/ol301424h. Epub 2012 Jul 25. [PubMed:22830424 ]
Hatakeyama S: [Stereocontrolled Total Synthesis of Biologically Active Natural Products]. Yakugaku Zasshi. 2018;138(2):191-209. doi: 10.1248/yakushi.17-00187. [PubMed:29386433 ]
Komine K, Nomura Y, Ishihara J, Hatakeyama S: Total Synthesis of (-)-N-Methylwelwitindolinone C Isothiocyanate Based on a Pd-Catalyzed Tandem Enolate Coupling Strategy. Org Lett. 2015 Aug 7;17(15):3918-21. doi: 10.1021/acs.orglett.5b01952. Epub 2015 Jul 27. [PubMed:26214342 ]
Hillwig ML, Fuhrman HA, Ittiamornkul K, Sevco TJ, Kwak DH, Liu X: Identification and characterization of a welwitindolinone alkaloid biosynthetic gene cluster in the stigonematalean Cyanobacterium Hapalosiphon welwitschii. Chembiochem. 2014 Mar 21;15(5):665-9. doi: 10.1002/cbic.201300794. [PubMed:24677572 ]
Fu TH, McElroy WT, Shamszad M, Heidebrecht RW Jr, Gulledge B, Martin SF: Studies toward welwitindolinones: formal syntheses of N-methylwelwitindolinone C isothiocyanate and related natural products. Tetrahedron. 2013 Jul 8;69(27-28):5588-5603. doi: 10.1016/j.tet.2013.03.010. [PubMed:23976796 ]
LOTUS database [Link]

Showing NP-Card for (2s,3s,6r,8r)-4-chloro-3-ethenyl-2-isothiocyanato-3,7,7,10-tetramethyl-10-azatetracyclo[6.6.1.1²,⁶.0¹¹,¹⁵]hexadeca-1(14),4,11(15),12-tetraene-9,16-dione (NP0177404)

MOL for NP0177404 ((2s,3s,6r,8r)-4-chloro-3-ethenyl-2-isothiocyanato-3,7,7,10-tetramethyl-10-azatetracyclo[6.6.1.1²,⁶.0¹¹,¹⁵]hexadeca-1(14),4,11(15),12-tetraene-9,16-dione)

3D MOL for NP0177404 ((2s,3s,6r,8r)-4-chloro-3-ethenyl-2-isothiocyanato-3,7,7,10-tetramethyl-10-azatetracyclo[6.6.1.1²,⁶.0¹¹,¹⁵]hexadeca-1(14),4,11(15),12-tetraene-9,16-dione)

3D SDF for NP0177404 ((2s,3s,6r,8r)-4-chloro-3-ethenyl-2-isothiocyanato-3,7,7,10-tetramethyl-10-azatetracyclo[6.6.1.1²,⁶.0¹¹,¹⁵]hexadeca-1(14),4,11(15),12-tetraene-9,16-dione)

3D-SDF for NP0177404 ((2s,3s,6r,8r)-4-chloro-3-ethenyl-2-isothiocyanato-3,7,7,10-tetramethyl-10-azatetracyclo[6.6.1.1²,⁶.0¹¹,¹⁵]hexadeca-1(14),4,11(15),12-tetraene-9,16-dione)

PDB for NP0177404 ((2s,3s,6r,8r)-4-chloro-3-ethenyl-2-isothiocyanato-3,7,7,10-tetramethyl-10-azatetracyclo[6.6.1.1²,⁶.0¹¹,¹⁵]hexadeca-1(14),4,11(15),12-tetraene-9,16-dione)

3D PDB for NP0177404 ((2s,3s,6r,8r)-4-chloro-3-ethenyl-2-isothiocyanato-3,7,7,10-tetramethyl-10-azatetracyclo[6.6.1.1²,⁶.0¹¹,¹⁵]hexadeca-1(14),4,11(15),12-tetraene-9,16-dione)

SMILES for NP0177404 ((2s,3s,6r,8r)-4-chloro-3-ethenyl-2-isothiocyanato-3,7,7,10-tetramethyl-10-azatetracyclo[6.6.1.1²,⁶.0¹¹,¹⁵]hexadeca-1(14),4,11(15),12-tetraene-9,16-dione)

INCHI for NP0177404 ((2s,3s,6r,8r)-4-chloro-3-ethenyl-2-isothiocyanato-3,7,7,10-tetramethyl-10-azatetracyclo[6.6.1.1²,⁶.0¹¹,¹⁵]hexadeca-1(14),4,11(15),12-tetraene-9,16-dione)

Structure for NP0177404 ((2s,3s,6r,8r)-4-chloro-3-ethenyl-2-isothiocyanato-3,7,7,10-tetramethyl-10-azatetracyclo[6.6.1.1²,⁶.0¹¹,¹⁵]hexadeca-1(14),4,11(15),12-tetraene-9,16-dione)

3D Structure for NP0177404 ((2s,3s,6r,8r)-4-chloro-3-ethenyl-2-isothiocyanato-3,7,7,10-tetramethyl-10-azatetracyclo[6.6.1.1²,⁶.0¹¹,¹⁵]hexadeca-1(14),4,11(15),12-tetraene-9,16-dione)