NP-MRD: Showing NP-Card for (2s,3s,4s)-5-[(1s,2s,3r,4s,6r,9s,12e)-12-(bromomethylidene)-4-hydroxy-3,6,9-trimethyltetracyclo[6.6.1.0²,⁶.0¹¹,¹⁵]pentadeca-7,11(15)-dien-3-yl]-2-methylpentane-1,2,3,4-tetrol (NP0204913)

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Record Information

Version

2.0

Created at

2022-09-05 00:42:37 UTC

Updated at

2022-09-05 00:42:37 UTC

NP-MRD ID

NP0204913

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3s,4s)-5-[(1s,2s,3r,4s,6r,9s,12e)-12-(bromomethylidene)-4-hydroxy-3,6,9-trimethyltetracyclo[6.6.1.0²,⁶.0¹¹,¹⁵]pentadeca-7,11(15)-dien-3-yl]-2-methylpentane-1,2,3,4-tetrol

Description

Neomangicol B belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open. Based on a literature review very few articles have been published on Neomangicol B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052202422D          

 31 34  0  0  1  0            999 V2000
    0.0960   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509   -0.2549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1340    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6507   -0.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3491   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8340    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6590    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3491    1.0799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0635    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0135    1.8336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4984    2.5011    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3189    2.4148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1629    3.2547    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3424    3.3410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6478    3.9222    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9804    4.4071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3152    3.4372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1327    4.5896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7972    5.3433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7486    1.3770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5771    2.1840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925    2.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1794    1.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6053    2.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7768    2.9488    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  1  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 13  1  6  0  0  0
  8 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26  5  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  4 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
M  END

     RDKit          3D

 68 71  0  0  0  0  0  0  0  0999 V2000
   -5.9482   -1.6135    0.9084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1818   -0.7251   -0.0127 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3334    0.7488    0.3707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9660    1.3122    0.3625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1281    0.3918   -0.0770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7129   -0.9149    0.0744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8700   -1.9035    0.2289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4343   -1.6790    0.2682 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0180   -2.1801    1.6860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8403   -2.6781   -0.7238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5822   -2.1543   -0.7853 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2801   -2.6436    0.2869 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4073   -0.6315   -0.7428 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4178   -0.2093   -2.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5637   -0.0587   -0.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9138   -0.2308   -0.6178 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3366   -1.5177   -0.8140 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9028    0.3828    0.3934 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5334    1.6831    0.6366 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3203    0.2446   -0.1144 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2284    0.8040    0.9605 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5850   -1.0866   -0.3237 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5517    1.0551   -1.3724 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2866    2.4034   -1.1706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8638   -0.3523   -0.0067 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7865    0.6146   -0.6406 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5207    2.0576   -0.5326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9902    2.7476    0.7298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4714    2.6389    0.7472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2688    3.6132    1.0693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5904    5.3472    1.5711 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -6.3846   -2.4349    0.3203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3500   -2.0445    1.7300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8190   -1.0152    1.3057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4757   -0.8929   -1.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7638    0.7768    1.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9903    1.2781   -0.3465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2470   -2.9057    0.3289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8512   -1.9808    2.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1599   -1.6027    2.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612   -3.2643    1.6731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9062   -3.7027   -0.3786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3598   -2.5849   -1.6932 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0288   -2.5202   -1.7136 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7048   -3.5036    0.1497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4140   -0.7147   -2.6995 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3428   -0.6875   -2.6287 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5159    0.8514   -2.3602 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4383    1.0579    0.1335 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6528   -0.4326    1.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0588    0.4157   -1.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6143   -1.7413   -1.7264 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8115   -0.1980    1.3128 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0299    1.7827    1.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6799    1.6128    1.4815 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3931    0.0018    1.7264 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1818    1.1828    0.5426 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7926   -1.5110    0.5433 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9851    0.6538   -2.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6297    0.9642   -1.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4474    2.6914   -0.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5990    0.0973    1.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8430    0.3731   -1.7343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1565    2.5552   -1.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5006    2.3859   -0.8229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5670    2.2834    1.6417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6850    3.8099    0.6356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3586    3.4974    1.0716 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 26 25  1  0
 25  8  1  0
  8  9  1  1
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  6
 20 23  1  0
 23 24  1  0
  8  7  1  0
  7  6  2  0
  6  2  1  0
 29  4  1  0
 13 25  1  0
  6  5  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  6
  3 36  1  0
  3 37  1  0
 26 63  1  6
 27 64  1  0
 27 65  1  0
 28 66  1  0
 28 67  1  0
 30 68  1  0
 25 62  1  1
  9 39  1  0
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  6
 12 45  1  0
 14 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  0
 15 50  1  0
 16 51  1  6
 17 52  1  0
 18 53  1  1
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 21 55  1  0
 21 56  1  0
 21 57  1  0
 22 58  1  0
 23 59  1  0
 23 60  1  0
 24 61  1  0
  7 38  1  0
M  END


  Mrv1652309052202422D          

 31 34  0  0  1  0            999 V2000
    0.0960   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509   -0.2549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1340    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6507   -0.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3491   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8340    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6590    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3491    1.0799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0635    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0135    1.8336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4984    2.5011    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3189    2.4148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1629    3.2547    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3424    3.3410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6478    3.9222    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9804    4.4071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3152    3.4372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1327    4.5896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7972    5.3433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7486    1.3770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5771    2.1840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925    2.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1794    1.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6053    2.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7768    2.9488    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
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 20 22  1  1  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 13  1  6  0  0  0
  8 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26  5  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  4 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0204913

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CC2=C3[C@@H](CC\C2=C/Br)[C@H]2[C@](C)(C[C@H](O)[C@]2(C)C[C@H](O)[C@H](O)[C@@](C)(O)CO)C=C13

> <INCHI_IDENTIFIER>
InChI=1S/C25H37BrO5/c1-13-7-16-14(11-26)5-6-15-20(16)17(13)8-23(2)10-19(29)24(3,21(15)23)9-18(28)22(30)25(4,31)12-27/h8,11,13,15,18-19,21-22,27-31H,5-7,9-10,12H2,1-4H3/b14-11+/t13-,15+,18-,19-,21-,22-,23-,24-,25-/m0/s1

> <INCHI_KEY>
YYAQDQSNICELJC-SXVQFVPVSA-N

> <FORMULA>
C25H37BrO5

> <MOLECULAR_WEIGHT>
497.47

> <EXACT_MASS>
496.182437

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
51.02997079082958

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4S)-5-[(1S,2S,3R,4S,6R,9S,12E)-12-(bromomethylidene)-4-hydroxy-3,6,9-trimethyltetracyclo[6.6.1.0^{2,6}.0^{11,15}]pentadeca-7,11(15)-dien-3-yl]-2-methylpentane-1,2,3,4-tetrol

> <JCHEM_LOGP>
1.2393000853333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.888340499810013

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.768693131671768

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9440485981125573

> <JCHEM_POLAR_SURFACE_AREA>
101.15

> <JCHEM_REFRACTIVITY>
125.29139999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S)-5-[(1S,2S,3R,4S,6R,9S,12E)-12-(bromomethylidene)-4-hydroxy-3,6,9-trimethyltetracyclo[6.6.1.0^{2,6}.0^{11,15}]pentadeca-7,11(15)-dien-3-yl]-2-methylpentane-1,2,3,4-tetrol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       0.179  -1.941   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.655  -0.476   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.250   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.655   2.016   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.120   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.120  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.453  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.787  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.948  -1.532   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.252  -0.476   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.157   0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.697   0.770   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.252   2.016   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.585   2.786   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.625   3.423   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.530   4.669   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.062   4.508   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.904   6.075   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.372   6.236   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.809   7.321   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.563   8.227   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.055   6.416   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.714   8.567   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.088   9.974   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.264   2.570   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.944   4.077   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.479   4.553   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.335   3.522   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.130   3.998   0.000  0.00  0.00           C+0
HETATM   31 Br   UNK     0      -1.450   5.504   0.000  0.00  0.00          Br+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   29                                                  
CONECT    5    4    6   26                                                  
CONECT    6    5    2    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10   25                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15   25                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20   24                                                       
CONECT   24   23                                                            
CONECT   25   13    8   26                                                  
CONECT   26   25    5   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28    4   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₇BrO₅

Average Mass

497.4700 Da

Monoisotopic Mass

496.18244 Da

IUPAC Name

(2S,3S,4S)-5-[(1S,2S,3R,4S,6R,9S,12E)-12-(bromomethylidene)-4-hydroxy-3,6,9-trimethyltetracyclo[6.6.1.0^{2,6}.0^{11,15}]pentadeca-7,11(15)-dien-3-yl]-2-methylpentane-1,2,3,4-tetrol

Traditional Name

(2S,3S,4S)-5-[(1S,2S,3R,4S,6R,9S,12E)-12-(bromomethylidene)-4-hydroxy-3,6,9-trimethyltetracyclo[6.6.1.0^{2,6}.0^{11,15}]pentadeca-7,11(15)-dien-3-yl]-2-methylpentane-1,2,3,4-tetrol

CAS Registry Number

Not Available

SMILES

C[C@H]1CC2=C3[C@@H](CC\C2=C/Br)[C@H]2[C@](C)(C[C@H](O)[C@]2(C)C[C@H](O)[C@H](O)[C@@](C)(O)CO)C=C13

InChI Identifier

InChI=1S/C25H37BrO5/c1-13-7-16-14(11-26)5-6-15-20(16)17(13)8-23(2)10-19(29)24(3,21(15)23)9-18(28)22(30)25(4,31)12-27/h8,11,13,15,18-19,21-22,27-31H,5-7,9-10,12H2,1-4H3/b14-11+/t13-,15+,18-,19-,21-,22-,23-,24-,25-/m0/s1

InChI Key

YYAQDQSNICELJC-SXVQFVPVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Iridoids and derivatives

Alternative Parents

Substituents

11-noriridane monoterpenoid
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
Bromoalkene
Haloalkene
Vinyl halide
Vinyl bromide
Polyol
Alcohol
Primary alcohol
Organooxygen compound
Organobromide
Organohalogen compound
Hydrocarbon derivative
Organic oxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	1.24	ChemAxon
pKa (Strongest Acidic)	12.77	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	101.15 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	125.29 m³·mol⁻¹	ChemAxon
Polarizability	51.03 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	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

8181641

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10006061

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3s,4s)-5-[(1s,2s,3r,4s,6r,9s,12e)-12-(bromomethylidene)-4-hydroxy-3,6,9-trimethyltetracyclo[6.6.1.0²,⁶.0¹¹,¹⁵]pentadeca-7,11(15)-dien-3-yl]-2-methylpentane-1,2,3,4-tetrol (NP0204913)

MOL for NP0204913 ((2s,3s,4s)-5-[(1s,2s,3r,4s,6r,9s,12e)-12-(bromomethylidene)-4-hydroxy-3,6,9-trimethyltetracyclo[6.6.1.0²,⁶.0¹¹,¹⁵]pentadeca-7,11(15)-dien-3-yl]-2-methylpentane-1,2,3,4-tetrol)

3D MOL for NP0204913 ((2s,3s,4s)-5-[(1s,2s,3r,4s,6r,9s,12e)-12-(bromomethylidene)-4-hydroxy-3,6,9-trimethyltetracyclo[6.6.1.0²,⁶.0¹¹,¹⁵]pentadeca-7,11(15)-dien-3-yl]-2-methylpentane-1,2,3,4-tetrol)

3D SDF for NP0204913 ((2s,3s,4s)-5-[(1s,2s,3r,4s,6r,9s,12e)-12-(bromomethylidene)-4-hydroxy-3,6,9-trimethyltetracyclo[6.6.1.0²,⁶.0¹¹,¹⁵]pentadeca-7,11(15)-dien-3-yl]-2-methylpentane-1,2,3,4-tetrol)

3D-SDF for NP0204913 ((2s,3s,4s)-5-[(1s,2s,3r,4s,6r,9s,12e)-12-(bromomethylidene)-4-hydroxy-3,6,9-trimethyltetracyclo[6.6.1.0²,⁶.0¹¹,¹⁵]pentadeca-7,11(15)-dien-3-yl]-2-methylpentane-1,2,3,4-tetrol)

PDB for NP0204913 ((2s,3s,4s)-5-[(1s,2s,3r,4s,6r,9s,12e)-12-(bromomethylidene)-4-hydroxy-3,6,9-trimethyltetracyclo[6.6.1.0²,⁶.0¹¹,¹⁵]pentadeca-7,11(15)-dien-3-yl]-2-methylpentane-1,2,3,4-tetrol)

3D PDB for NP0204913 ((2s,3s,4s)-5-[(1s,2s,3r,4s,6r,9s,12e)-12-(bromomethylidene)-4-hydroxy-3,6,9-trimethyltetracyclo[6.6.1.0²,⁶.0¹¹,¹⁵]pentadeca-7,11(15)-dien-3-yl]-2-methylpentane-1,2,3,4-tetrol)

SMILES for NP0204913 ((2s,3s,4s)-5-[(1s,2s,3r,4s,6r,9s,12e)-12-(bromomethylidene)-4-hydroxy-3,6,9-trimethyltetracyclo[6.6.1.0²,⁶.0¹¹,¹⁵]pentadeca-7,11(15)-dien-3-yl]-2-methylpentane-1,2,3,4-tetrol)

INCHI for NP0204913 ((2s,3s,4s)-5-[(1s,2s,3r,4s,6r,9s,12e)-12-(bromomethylidene)-4-hydroxy-3,6,9-trimethyltetracyclo[6.6.1.0²,⁶.0¹¹,¹⁵]pentadeca-7,11(15)-dien-3-yl]-2-methylpentane-1,2,3,4-tetrol)

Structure for NP0204913 ((2s,3s,4s)-5-[(1s,2s,3r,4s,6r,9s,12e)-12-(bromomethylidene)-4-hydroxy-3,6,9-trimethyltetracyclo[6.6.1.0²,⁶.0¹¹,¹⁵]pentadeca-7,11(15)-dien-3-yl]-2-methylpentane-1,2,3,4-tetrol)

3D Structure for NP0204913 ((2s,3s,4s)-5-[(1s,2s,3r,4s,6r,9s,12e)-12-(bromomethylidene)-4-hydroxy-3,6,9-trimethyltetracyclo[6.6.1.0²,⁶.0¹¹,¹⁵]pentadeca-7,11(15)-dien-3-yl]-2-methylpentane-1,2,3,4-tetrol)