NP-MRD: Showing NP-Card for Thiersindole C (NP0004894)

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Record Information

Version

2.0

Created at

2020-12-09 02:17:44 UTC

Updated at

2021-07-15 16:50:28 UTC

NP-MRD ID

NP0004894

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Thiersindole C

Provided By

NPAtlas

Description

(1S,2S,5R,6S)-5-[(1H-indol-3-yl)methyl]-1,5,6-trimethyl-1-(4-methylpent-3-en-1-yl)-1,2,3,4,5,6,7,8-octahydronaphthalen-2-ol belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. Thiersindole C is found in Penicillium thiersii. Based on a literature review very few articles have been published on (1S,2S,5R,6S)-5-[(1H-indol-3-yl)methyl]-1,5,6-trimethyl-1-(4-methylpent-3-en-1-yl)-1,2,3,4,5,6,7,8-octahydronaphthalen-2-ol.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118093D          

 69 72  0  0  0  0            999 V2000
   -6.0646    2.4467   -0.3726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1606    1.0030   -0.0890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4203    0.2700   -0.4441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1242    0.3729    0.4834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9109    1.1154    0.8228 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6506    0.7630    0.1498 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0868   -0.5923    0.2810 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0024   -1.6280   -0.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7960   -0.6289   -0.5103 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3369   -1.0725    0.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3627   -2.1649    1.0231 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9583   -2.2268    1.7717 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6587   -0.8915    1.7091 C   0  0  2  0  0  0  0  0  0  0  0  0
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    1.6815   -0.5165   -0.3949 C   0  0  2  0  0  0  0  0  0  0  0  0
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    5.5175    1.6425    0.5302 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4134    1.2262   -1.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6054   -1.5941   -2.6259 H   0  0  0  0  0  0  0  0  0  0  0  0
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  4  5  1  0  0  0  0
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 29 67  1  0  0  0  0
 30 68  1  0  0  0  0
 30 69  1  0  0  0  0
M  END

     RDKit          3D

 69 72  0  0  0  0  0  0  0  0999 V2000
   -6.0646    2.4467   -0.3726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1606    1.0030   -0.0890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4203    0.2700   -0.4441 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306242118093D          

 69 72  0  0  0  0            999 V2000
   -6.0646    2.4467   -0.3726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1606    1.0030   -0.0890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4203    0.2700   -0.4441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1242    0.3729    0.4834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9109    1.1154    0.8228 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6506    0.7630    0.1498 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0868   -0.5923    0.2810 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0024   -1.6280   -0.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7960   -0.6289   -0.5103 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3369   -1.0725    0.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3627   -2.1649    1.0231 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9583   -2.2268    1.7717 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -2.7004   -0.8803    2.5945 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6815   -0.5165   -0.3949 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5792   -1.7195   -0.5203 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0694    0.4211    0.6934 C   0  0  1  0  0  0  0  0  0  0  0  0
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    3.5258    2.3907    0.0610 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8351    2.7056    0.0477 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5175    1.6425    0.5302 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8716    1.4622    0.7283 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3715    0.2987    1.2463 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4690   -0.6891    1.5639 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1134   -0.5160    1.3683 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6036    0.6548    0.8454 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6168    0.1352   -1.7529 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9100   -0.0656   -2.5221 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5152   -0.4905   -2.5714 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.9353   -0.0973    1.9857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4556   -0.4550    3.4477 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6494   -2.2488    0.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6002   -1.4727   -0.8499 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1364   -2.4746   -1.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2575    1.1932    0.8742 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0224   -0.1786    1.6594 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1918    3.6310   -0.2904 H   0  0  0  0  0  0  0  0  0  0  0  0
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    8.4136    0.1461    1.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8186   -1.6221    1.9750 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4134    1.2262   -1.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8966    0.5808   -3.4419 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0627   -1.1161   -2.8269 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7826    0.2558   -1.9140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6054   -1.5941   -2.6259 H   0  0  0  0  0  0  0  0  0  0  0  0
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 30  9  1  0  0  0  0
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 30 68  1  0  0  0  0
 30 69  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004894

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])C([H])([H])C([H])([H])C2=C(C([H])([H])C([H])([H])[C@]([H])(C([H])([H])[H])[C@@]2(C([H])([H])[H])C([H])([H])C2=C([H])N([H])C3=C([H])C([H])=C([H])C([H])=C23)[C@]1(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C28H39NO/c1-19(2)9-8-16-27(4)23-13-12-20(3)28(5,24(23)14-15-26(27)30)17-21-18-29-25-11-7-6-10-22(21)25/h6-7,9-11,18,20,26,29-30H,8,12-17H2,1-5H3/t20-,26-,27-,28+/m0/s1

> <INCHI_KEY>
OCYNSSRIJRLWML-QGQKXLEHSA-N

> <FORMULA>
C28H39NO

> <MOLECULAR_WEIGHT>
405.626

> <EXACT_MASS>
405.30316488

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
49.94867451585518

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,5R,6S)-5-[(1H-indol-3-yl)methyl]-1,5,6-trimethyl-1-(4-methylpent-3-en-1-yl)-1,2,3,4,5,6,7,8-octahydronaphthalen-2-ol

> <ALOGPS_LOGP>
7.10

> <JCHEM_LOGP>
6.784813671666665

> <ALOGPS_LOGS>
-6.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.77128524894027

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.20705987560497

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7118398321135259

> <JCHEM_POLAR_SURFACE_AREA>
36.019999999999996

> <JCHEM_REFRACTIVITY>
128.38299999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.66e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5R,6S)-5-(1H-indol-3-ylmethyl)-1,5,6-trimethyl-1-(4-methylpent-3-en-1-yl)-2,3,4,6,7,8-hexahydronaphthalen-2-ol

> <JCHEM_VEBER_RULE>
1

$$$$

     RDKit          3D

 69 72  0  0  0  0  0  0  0  0999 V2000
   -6.0646    2.4467   -0.3726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1606    1.0030   -0.0890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4203    0.2700   -0.4441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1242    0.3729    0.4834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9109    1.1154    0.8228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6506    0.7630    0.1498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0868   -0.5923    0.2810 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0024   -1.6280   -0.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7960   -0.6289   -0.5103 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3369   -1.0725    0.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3627   -2.1649    1.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9583   -2.2268    1.7717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6587   -0.8915    1.7091 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7004   -0.8803    2.5945 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6815   -0.5165   -0.3949 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5792   -1.7195   -0.5203 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0694    0.4211    0.6934 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3483    1.1117    0.5549 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5258    2.3907    0.0610 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8351    2.7056    0.0477 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5175    1.6425    0.5302 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8716    1.4622    0.7283 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3715    0.2987    1.2463 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4690   -0.6891    1.5639 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1134   -0.5160    1.3683 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6036    0.6548    0.8454 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6168    0.1352   -1.7529 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9100   -0.0656   -2.5221 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5152   -0.4905   -2.5714 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4636   -2.3847   -0.9009 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1391   -2.0100    1.7956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5898   -3.1288    0.5164 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6002   -1.4727   -0.8499 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1364   -2.4746   -1.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1918    3.6310   -0.2904 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5770    2.2463    0.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4136    0.1461    1.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8186   -1.6221    1.9750 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4553   -1.3342    1.6467 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4134    1.2262   -1.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8966    0.5808   -3.4419 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0627   -1.1161   -2.8269 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7826    0.2558   -1.9140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6054   -1.5941   -2.6259 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5132   -0.0818   -3.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8900    0.9597   -1.9278 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  7  6  1  1
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  9 10  2  0
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 11 12  1  0
 12 13  1  0
 13 14  1  0
 10 15  1  0
 15 16  1  6
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 18 19  2  0
 19 20  1  0
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 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
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 15 27  1  0
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 27 29  1  0
 29 30  1  0
 13  7  1  0
 26 18  1  0
 30  9  1  0
 26 21  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  8 42  1  0
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 11 45  1  0
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 29 67  1  0
 30 68  1  0
 30 69  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      -6.065   2.447  -0.373  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.161   1.003  -0.089  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.420   0.270  -0.444  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.124   0.373   0.483  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.911   1.115   0.823  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.651   0.763   0.150  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.087  -0.592   0.281  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.002  -1.628  -0.267  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.796  -0.629  -0.510  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.337  -1.073   0.002  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.363  -2.165   1.023  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.958  -2.227   1.772  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.659  -0.892   1.709  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.700  -0.880   2.595  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.682  -0.517  -0.395  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.579  -1.720  -0.520  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.069   0.421   0.693  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.348   1.112   0.555  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.526   2.391   0.061  0.00  0.00           C+0
HETATM   20  N   UNK     0       4.835   2.706   0.048  0.00  0.00           N+0
HETATM   21  C   UNK     0       5.518   1.643   0.530  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.872   1.462   0.728  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.372   0.299   1.246  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.469  -0.689   1.564  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.113  -0.516   1.368  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.604   0.655   0.845  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.617   0.135  -1.753  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.910  -0.066  -2.522  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.515  -0.491  -2.571  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.803  -0.144  -1.919  0.00  0.00           C+0
HETATM   31  H   UNK     0      -6.995   2.794  -0.895  0.00  0.00           H+0
HETATM   32  H   UNK     0      -5.209   2.610  -1.060  0.00  0.00           H+0
HETATM   33  H   UNK     0      -5.938   3.062   0.554  0.00  0.00           H+0
HETATM   34  H   UNK     0      -7.223  -0.749  -0.819  0.00  0.00           H+0
HETATM   35  H   UNK     0      -8.073   0.192   0.467  0.00  0.00           H+0
HETATM   36  H   UNK     0      -7.965   0.879  -1.187  0.00  0.00           H+0
HETATM   37  H   UNK     0      -5.289  -0.683   0.671  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.102   2.209   0.579  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.838   1.087   1.947  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.855   1.501   0.429  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.832   0.927  -0.964  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.700  -1.143  -0.978  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.488  -2.162   0.563  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.464  -2.385  -0.901  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.139  -2.010   1.796  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.590  -3.129   0.516  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.825  -2.526   2.832  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.569  -3.002   1.297  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.935  -0.097   1.986  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.456  -0.455   3.448  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.649  -2.249   0.448  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.600  -1.473  -0.850  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.136  -2.475  -1.221  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.258   1.193   0.874  0.00  0.00           H+0
HETATM   55  H   UNK     0       2.022  -0.179   1.659  0.00  0.00           H+0
HETATM   56  H   UNK     0       2.727   3.052  -0.271  0.00  0.00           H+0
HETATM   57  H   UNK     0       5.192   3.631  -0.290  0.00  0.00           H+0
HETATM   58  H   UNK     0       7.577   2.246   0.475  0.00  0.00           H+0
HETATM   59  H   UNK     0       8.414   0.146   1.404  0.00  0.00           H+0
HETATM   60  H   UNK     0       6.819  -1.622   1.975  0.00  0.00           H+0
HETATM   61  H   UNK     0       4.455  -1.334   1.647  0.00  0.00           H+0
HETATM   62  H   UNK     0       1.413   1.226  -1.704  0.00  0.00           H+0
HETATM   63  H   UNK     0       2.897   0.581  -3.442  0.00  0.00           H+0
HETATM   64  H   UNK     0       3.063  -1.116  -2.827  0.00  0.00           H+0
HETATM   65  H   UNK     0       3.783   0.256  -1.914  0.00  0.00           H+0
HETATM   66  H   UNK     0       0.605  -1.594  -2.626  0.00  0.00           H+0
HETATM   67  H   UNK     0       0.513  -0.082  -3.589  0.00  0.00           H+0
HETATM   68  H   UNK     0      -1.599  -0.656  -2.489  0.00  0.00           H+0
HETATM   69  H   UNK     0      -0.890   0.960  -1.928  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2    1    3    4                                                  
CONECT    3    2   34   35   36                                             
CONECT    4    2    5   37                                                  
CONECT    5    4    6   38   39                                             
CONECT    6    5    7   40   41                                             
CONECT    7    6    8    9   13                                             
CONECT    8    7   42   43   44                                             
CONECT    9    7   10   30                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10   12   45   46                                             
CONECT   12   11   13   47   48                                             
CONECT   13   12   14    7   49                                             
CONECT   14   13   50                                                       
CONECT   15   10   16   17   27                                             
CONECT   16   15   51   52   53                                             
CONECT   17   15   18   54   55                                             
CONECT   18   17   19   26                                                  
CONECT   19   18   20   56                                                  
CONECT   20   19   21   57                                                  
CONECT   21   20   22   26                                                  
CONECT   22   21   23   58                                                  
CONECT   23   22   24   59                                                  
CONECT   24   23   25   60                                                  
CONECT   25   24   26   61                                                  
CONECT   26   25   18   21                                                  
CONECT   27   15   28   29   62                                             
CONECT   28   27   63   64   65                                             
CONECT   29   27   30   66   67                                             
CONECT   30   29    9   68   69                                             
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    3                                                            
CONECT   35    3                                                            
CONECT   36    3                                                            
CONECT   37    4                                                            
CONECT   38    5                                                            
CONECT   39    5                                                            
CONECT   40    6                                                            
CONECT   41    6                                                            
CONECT   42    8                                                            
CONECT   43    8                                                            
CONECT   44    8                                                            
CONECT   45   11                                                            
CONECT   46   11                                                            
CONECT   47   12                                                            
CONECT   48   12                                                            
CONECT   49   13                                                            
CONECT   50   14                                                            
CONECT   51   16                                                            
CONECT   52   16                                                            
CONECT   53   16                                                            
CONECT   54   17                                                            
CONECT   55   17                                                            
CONECT   56   19                                                            
CONECT   57   20                                                            
CONECT   58   22                                                            
CONECT   59   23                                                            
CONECT   60   24                                                            
CONECT   61   25                                                            
CONECT   62   27                                                            
CONECT   63   28                                                            
CONECT   64   28                                                            
CONECT   65   28                                                            
CONECT   66   29                                                            
CONECT   67   29                                                            
CONECT   68   30                                                            
CONECT   69   30                                                            
MASTER        0    0    0    0    0    0    0    0   69    0  144    0
END

RDKit          3D

69 72  0  0  0  0  0  0  0  0999 V2000
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    0.3627   -2.1649    1.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9583   -2.2268    1.7717 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.7004   -0.8803    2.5945 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6815   -0.5165   -0.3949 C   0  0  2  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  1  0
  2  4  2  3
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 30 68  1  0
 30 69  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₈H₃₉NO

Average Mass

405.6260 Da

Monoisotopic Mass

405.30316 Da

IUPAC Name

(1S,2S,5R,6S)-5-[(1H-indol-3-yl)methyl]-1,5,6-trimethyl-1-(4-methylpent-3-en-1-yl)-1,2,3,4,5,6,7,8-octahydronaphthalen-2-ol

Traditional Name

(1S,2S,5R,6S)-5-(1H-indol-3-ylmethyl)-1,5,6-trimethyl-1-(4-methylpent-3-en-1-yl)-2,3,4,6,7,8-hexahydronaphthalen-2-ol

CAS Registry Number

Not Available

SMILES

C[C@H]1CCC2=C(CC[C@H](O)[C@@]2(C)CCC=C(C)C)[C@]1(C)CC1=CNC2=CC=CC=C12

InChI Identifier

InChI=1S/C28H39NO/c1-19(2)9-8-16-27(4)23-13-12-20(3)28(5,24(23)14-15-26(27)30)17-21-18-29-25-11-7-6-10-22(21)25/h6-7,9-11,18,20,26,29-30H,8,12-17H2,1-5H3/t20-,26-,27-,28+/m0/s1

InChI Key

OCYNSSRIJRLWML-QGQKXLEHSA-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
Penicillium thiersii	NPAtlas	14510604

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Secondary alcohol
Azacycle
Organic nitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Alcohol
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	7.1	ALOGPS
logP	6.78	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	17.21	ChemAxon
pKa (Strongest Basic)	-0.71	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	36.02 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	128.38 m³·mol⁻¹	ChemAxon
Polarizability	49.95 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA014688

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9233745

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11058587

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Thiersindole C (NP0004894)

MOL for NP0004894 (Thiersindole C)

3D MOL for NP0004894 (Thiersindole C)

3D SDF for NP0004894 (Thiersindole C)

3D-SDF for NP0004894 (Thiersindole C)

PDB for NP0004894 (Thiersindole C)

3D PDB for NP0004894 (Thiersindole C)

SMILES for NP0004894 (Thiersindole C)

INCHI for NP0004894 (Thiersindole C)

Structure for NP0004894 (Thiersindole C)

3D Structure for NP0004894 (Thiersindole C)