NP-MRD: Showing NP-Card for 3-hydroxy-N-methylwelwitindolinone C isothiocyanate (NP0001606)

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Record Information

Version

2.0

Created at

2020-09-23 01:58:22 UTC

Updated at

2021-08-10 02:55:37 UTC

NP-MRD ID

NP0001606

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-hydroxy-N-methylwelwitindolinone C isothiocyanate

Provided By

NPAtlas

Description

(2S,3S,6R,8S)-4-chloro-3-ethenyl-8-hydroxy-2-isothiocyanato-3,7,7,10-tetramethyl-10-azatetracyclo[6.6.1.1²,⁶.0¹¹,¹⁵]Hexadeca-1(15),4,11,13-tetraene-9,16-dione 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. 3-hydroxy-N-methylwelwitindolinone C isothiocyanate is found in Fischerella sp. 3-hydroxy-N-methylwelwitindolinone C isothiocyanate 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-isothiocyanato-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          

 50 53  0  0  0  0            999 V2000
    3.4514    0.4157   -1.9566 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4193    0.5755   -1.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3158   -0.2481    0.0656 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7183   -0.5382    0.5948 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7516   -1.5543   -0.3473 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3268   -2.1603   -1.9229 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.9100   -2.3208    0.2792 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1587   -1.7667    1.4545 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8292   -0.5949    2.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8660   -0.4174    3.1920 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4781    0.3989    1.1042 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1789    1.3382    1.9522 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3689    1.7334    1.7852 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4742    2.8891    1.4914 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.3395    1.1542    0.4810 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5952    2.4981    0.4485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3171    3.4194   -0.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8120   -0.4665   -0.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8118   -2.9049    0.6431 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2502   -0.3030   -1.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  3  0  0  0
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  7 36  1  0  0  0  0
  8 37  1  1  0  0  0
 16 38  1  0  0  0  0
 17 39  1  0  0  0  0
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 22 41  1  0  0  0  0
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 29 48  1  0  0  0  0
 29 49  1  0  0  0  0
 29 50  1  0  0  0  0
M  END

     RDKit          3D

 50 53  0  0  0  0  0  0  0  0999 V2000
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    4.4742    2.8891    1.4914 S   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5952    2.4981    0.4485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3171    3.4194   -0.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8730    0.6857    0.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8049   -1.2477   -1.2966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8120   -0.4665   -0.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2235    1.4809   -1.3631 C   0  0  0  0  0  0  0  0  0  0  0  0
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  3  2  1  6
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M  END


  Mrv1652306242117433D          

 50 53  0  0  0  0            999 V2000
    3.4514    0.4157   -1.9566 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4193    0.5755   -1.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3158   -0.2481    0.0656 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7183   -0.5382    0.5948 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7516   -1.5543   -0.3473 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9100   -2.3208    0.2792 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1587   -1.7667    1.4545 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8292   -0.5949    2.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8660   -0.4174    3.1920 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4781    0.3989    1.1042 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1789    1.3382    1.9522 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3689    1.7334    1.7852 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4742    2.8891    1.4914 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.3395    1.1542    0.4810 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5952    2.4981    0.4485 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8049   -1.2477   -1.2966 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6913   -0.6771    1.6714 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3955    0.2068    0.1879 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0284   -1.6106    2.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2762    0.0271    2.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5130   -1.1901    3.1796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8871   -3.0196    0.8936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2050   -3.7064    1.1371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6312   -3.0286   -0.4444 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  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  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  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
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 11  3  1  0  0  0  0
 20 15  1  0  0  0  0
 27  8  1  0  0  0  0
 25 19  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  2 32  1  0  0  0  0
  4 33  1  0  0  0  0
  4 34  1  0  0  0  0
  4 35  1  0  0  0  0
  7 36  1  0  0  0  0
  8 37  1  1  0  0  0
 16 38  1  0  0  0  0
 17 39  1  0  0  0  0
 18 40  1  0  0  0  0
 22 41  1  0  0  0  0
 26 42  1  0  0  0  0
 26 43  1  0  0  0  0
 26 44  1  0  0  0  0
 28 45  1  0  0  0  0
 28 46  1  0  0  0  0
 28 47  1  0  0  0  0
 29 48  1  0  0  0  0
 29 49  1  0  0  0  0
 29 50  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001606

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]12C(=O)N(C3=C1C(=C([H])C([H])=C3[H])[C@@]1(N=C=S)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/C22H21ClN2O3S/c1-6-20(4)15(23)10-13-17(26)21(20,24-11-29)12-8-7-9-14-16(12)22(28,19(13,2)3)18(27)25(14)5/h6-10,13,28H,1H2,2-5H3/t13-,20+,21+,22-/m0/s1

> <INCHI_KEY>
VDNAFECSPBXWIH-WOHBTAIZSA-N

> <FORMULA>
C22H21ClN2O3S

> <MOLECULAR_WEIGHT>
428.93

> <EXACT_MASS>
428.0961414

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
42.84244158756172

> <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-isothiocyanato-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>
3.72

> <JCHEM_LOGP>
3.9002792946666682

> <ALOGPS_LOGS>
-5.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.895086480240938

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.812468294696

> <JCHEM_PKA_STRONGEST_BASIC>
-4.329994219211607

> <JCHEM_POLAR_SURFACE_AREA>
69.96999999999998

> <JCHEM_REFRACTIVITY>
116.39059999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.88e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,6R,8S)-4-chloro-3-ethenyl-8-hydroxy-2-isothiocyanato-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

 50 53  0  0  0  0  0  0  0  0999 V2000
    3.4514    0.4157   -1.9566 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4193    0.5755   -1.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3158   -0.2481    0.0656 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7183   -0.5382    0.5948 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7516   -1.5543   -0.3473 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3268   -2.1603   -1.9229 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.9100   -2.3208    0.2792 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1587   -1.7667    1.4545 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8292   -0.5949    2.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8660   -0.4174    3.1920 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4781    0.3989    1.1042 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1789    1.3382    1.9522 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3689    1.7334    1.7852 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4742    2.8891    1.4914 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.3395    1.1542    0.4810 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5952    2.4981    0.4485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3171    3.4194   -0.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5220    2.9540   -0.5032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7951    1.5816   -0.4740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8730    0.6857    0.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4058   -0.6537   -0.1504 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8049   -1.2477   -1.2966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8120   -0.4665   -0.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6819   -1.3803   -0.5498 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0046    0.9243   -0.8164 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2235    1.4809   -1.3631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2800   -1.5451    1.0357 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0721   -1.0656    2.2253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8118   -2.9049    0.6431 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2502   -0.3030   -1.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5844    0.9995   -2.8781 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6674    1.2975   -1.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6913   -0.6771    1.6714 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3955    0.2068    0.1879 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0706   -1.5284    0.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7288   -3.3643   -0.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1436   -2.5619    2.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5243    2.9310    0.7999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0916    4.4900   -0.0571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2660    3.6344   -0.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1591   -0.7783   -2.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9711    1.6812   -0.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6273    0.8475   -2.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9781    2.4686   -1.8235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0284   -1.6106    2.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2762    0.0271    2.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5130   -1.1901    3.1796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8871   -3.0196    0.8936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2050   -3.7064    1.1371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6312   -3.0286   -0.4444 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  3  2  1  6
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  1
 12 13  2  0
 13 14  2  0
 11 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  6
 21 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 21 27  1  0
 27 28  1  1
 27 29  1  0
 11  3  1  0
 20 15  1  0
 27  8  1  0
 25 19  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  4 33  1  0
  4 34  1  0
  4 35  1  0
  7 36  1  0
  8 37  1  1
 16 38  1  0
 17 39  1  0
 18 40  1  0
 22 41  1  0
 26 42  1  0
 26 43  1  0
 26 44  1  0
 28 45  1  0
 28 46  1  0
 28 47  1  0
 29 48  1  0
 29 49  1  0
 29 50  1  0
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       3.451   0.416  -1.957  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.419   0.576  -1.151  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.316  -0.248   0.066  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.718  -0.538   0.595  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.752  -1.554  -0.347  0.00  0.00           C+0
HETATM    6 Cl   UNK     0       2.327  -2.160  -1.923  0.00  0.00          Cl+0
HETATM    7  C   UNK     0       0.910  -2.321   0.279  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.159  -1.767   1.454  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.829  -0.595   2.007  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.866  -0.417   3.192  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.478   0.399   1.104  0.00  0.00           C+0
HETATM   12  N   UNK     0       2.179   1.338   1.952  0.00  0.00           N+0
HETATM   13  C   UNK     0       3.369   1.733   1.785  0.00  0.00           C+0
HETATM   14  S   UNK     0       4.474   2.889   1.491  0.00  0.00           S+0
HETATM   15  C   UNK     0       0.340   1.154   0.481  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.595   2.498   0.449  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.317   3.419  -0.039  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.522   2.954  -0.503  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.795   1.582  -0.474  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.873   0.686   0.010  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.406  -0.654  -0.150  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.805  -1.248  -1.297  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.812  -0.467  -0.515  0.00  0.00           C+0
HETATM   24  O   UNK     0      -3.682  -1.380  -0.550  0.00  0.00           O+0
HETATM   25  N   UNK     0      -3.005   0.924  -0.816  0.00  0.00           N+0
HETATM   26  C   UNK     0      -4.223   1.481  -1.363  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.280  -1.545   1.036  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.072  -1.066   2.225  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.812  -2.905   0.643  0.00  0.00           C+0
HETATM   30  H   UNK     0       4.250  -0.303  -1.775  0.00  0.00           H+0
HETATM   31  H   UNK     0       3.584   1.000  -2.878  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.667   1.298  -1.389  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.691  -0.677   1.671  0.00  0.00           H+0
HETATM   34  H   UNK     0       4.396   0.207   0.188  0.00  0.00           H+0
HETATM   35  H   UNK     0       4.071  -1.528   0.173  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.729  -3.364  -0.023  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.144  -2.562   2.217  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.524   2.931   0.800  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.092   4.490  -0.057  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.266   3.634  -0.893  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.159  -0.778  -2.097  0.00  0.00           H+0
HETATM   42  H   UNK     0      -4.971   1.681  -0.567  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.627   0.848  -2.174  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.978   2.469  -1.823  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.028  -1.611   2.360  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.276   0.027   2.139  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.513  -1.190   3.180  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.887  -3.020   0.894  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.205  -3.706   1.137  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.631  -3.029  -0.444  0.00  0.00           H+0
CONECT    1    2   30   31                                                  
CONECT    2    1    3   32                                                  
CONECT    3    2    4    5   11                                             
CONECT    4    3   33   34   35                                             
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   36                                                  
CONECT    8    7    9   27   37                                             
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   15    3                                             
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   11   16   20                                                  
CONECT   16   15   17   38                                                  
CONECT   17   16   18   39                                                  
CONECT   18   17   19   40                                                  
CONECT   19   18   20   25                                                  
CONECT   20   19   21   15                                                  
CONECT   21   20   22   23   27                                             
CONECT   22   21   41                                                       
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   19                                                  
CONECT   26   25   42   43   44                                             
CONECT   27   21   28   29    8                                             
CONECT   28   27   45   46   47                                             
CONECT   29   27   48   49   50                                             
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    2                                                            
CONECT   33    4                                                            
CONECT   34    4                                                            
CONECT   35    4                                                            
CONECT   36    7                                                            
CONECT   37    8                                                            
CONECT   38   16                                                            
CONECT   39   17                                                            
CONECT   40   18                                                            
CONECT   41   22                                                            
CONECT   42   26                                                            
CONECT   43   26                                                            
CONECT   44   26                                                            
CONECT   45   28                                                            
CONECT   46   28                                                            
CONECT   47   28                                                            
CONECT   48   29                                                            
CONECT   49   29                                                            
CONECT   50   29                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  106    0
END

RDKit          3D

50 53  0  0  0  0  0  0  0  0999 V2000
    3.4514    0.4157   -1.9566 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4193    0.5755   -1.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3158   -0.2481    0.0656 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7183   -0.5382    0.5948 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7516   -1.5543   -0.3473 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3268   -2.1603   -1.9229 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.9100   -2.3208    0.2792 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1587   -1.7667    1.4545 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8292   -0.5949    2.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8660   -0.4174    3.1920 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4781    0.3989    1.1042 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1789    1.3382    1.9522 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3689    1.7334    1.7852 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4742    2.8891    1.4914 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.3395    1.1542    0.4810 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5952    2.4981    0.4485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3171    3.4194   -0.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5220    2.9540   -0.5032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7951    1.5816   -0.4740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8730    0.6857    0.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4058   -0.6537   -0.1504 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8049   -1.2477   -1.2966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8120   -0.4665   -0.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6819   -1.3803   -0.5498 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0046    0.9243   -0.8164 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2235    1.4809   -1.3631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2800   -1.5451    1.0357 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0721   -1.0656    2.2253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8118   -2.9049    0.6431 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2502   -0.3030   -1.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5844    0.9995   -2.8781 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6674    1.2975   -1.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6913   -0.6771    1.6714 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3955    0.2068    0.1879 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0706   -1.5284    0.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7288   -3.3643   -0.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1436   -2.5619    2.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5243    2.9310    0.7999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0916    4.4900   -0.0571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2660    3.6344   -0.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1591   -0.7783   -2.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9711    1.6812   -0.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6273    0.8475   -2.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9781    2.4686   -1.8235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0284   -1.6106    2.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2762    0.0271    2.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5130   -1.1901    3.1796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8871   -3.0196    0.8936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2050   -3.7064    1.1371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6312   -3.0286   -0.4444 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  3  2  1  6
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  1
 12 13  2  0
 13 14  2  0
 11 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  6
 21 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 21 27  1  0
 27 28  1  1
 27 29  1  0
 11  3  1  0
 20 15  1  0
 27  8  1  0
 25 19  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  4 33  1  0
  4 34  1  0
  4 35  1  0
  7 36  1  0
  8 37  1  1
 16 38  1  0
 17 39  1  0
 18 40  1  0
 22 41  1  0
 26 42  1  0
 26 43  1  0
 26 44  1  0
 28 45  1  0
 28 46  1  0
 28 47  1  0
 29 48  1  0
 29 49  1  0
 29 50  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
3-Hydroxy-N-methylwelwitindolinone C isothiocyanic acid	Generator

Chemical Formula

C₂₂H₂₁ClN₂O₃S

Average Mass

428.9300 Da

Monoisotopic Mass

428.09614 Da

IUPAC Name

(2S,3S,6R,8S)-4-chloro-3-ethenyl-8-hydroxy-2-isothiocyanato-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-isothiocyanato-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=S)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/C22H21ClN2O3S/c1-6-20(4)15(23)10-13-17(26)21(20,24-11-29)12-8-7-9-14-16(12)22(28,19(13,2)3)18(27)25(14)5/h6-10,13,28H,1H2,2-5H3/t13-,20+,21+,22-/m0/s1

InChI Key

VDNAFECSPBXWIH-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

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 alcohol
Tertiary carboxylic acid amide
Carboxamide group
Isothiocyanate
Ketone
Lactam
Propargyl-type 1,3-dipolar organic compound
Azacycle
Vinyl halide
Vinyl chloride
Chloroalkene
Haloalkene
Organic 1,3-dipolar compound
Carboxylic acid derivative
Hydrocarbon derivative
Organonitrogen compound
Organochloride
Organohalogen compound
Alcohol
Carbonyl group
Organic nitrogen compound
Organooxygen 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	3.72	ALOGPS
logP	3.9	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	10.81	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	69.97 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	116.39 m³·mol⁻¹	ChemAxon
Polarizability	42.84 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

NPA019682

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8987793

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10812488

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 isothiocyanate (NP0001606)

MOL for NP0001606 (3-hydroxy-N-methylwelwitindolinone C isothiocyanate)

3D MOL for NP0001606 (3-hydroxy-N-methylwelwitindolinone C isothiocyanate)

3D SDF for NP0001606 (3-hydroxy-N-methylwelwitindolinone C isothiocyanate)

3D-SDF for NP0001606 (3-hydroxy-N-methylwelwitindolinone C isothiocyanate)

PDB for NP0001606 (3-hydroxy-N-methylwelwitindolinone C isothiocyanate)

3D PDB for NP0001606 (3-hydroxy-N-methylwelwitindolinone C isothiocyanate)

SMILES for NP0001606 (3-hydroxy-N-methylwelwitindolinone C isothiocyanate)

INCHI for NP0001606 (3-hydroxy-N-methylwelwitindolinone C isothiocyanate)

Structure for NP0001606 (3-hydroxy-N-methylwelwitindolinone C isothiocyanate)

3D Structure for NP0001606 (3-hydroxy-N-methylwelwitindolinone C isothiocyanate)