NP-MRD: Showing NP-Card for 2-[(5-{[(1r,2r,4as,8as)-1,2,4a,5-tetramethyl-1,3,4,7,8,8a-hexahydronaphthalen-2-yl]methyl}-6-hydroxy-3,4-dioxocyclohexa-1,5-dien-1-yl)amino]ethanesulfonic acid (NP0311414)

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Record Information

Version

2.0

Created at

2022-09-11 07:23:23 UTC

Updated at

2022-09-11 07:23:23 UTC

NP-MRD ID

NP0311414

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(5-{[(1r,2r,4as,8as)-1,2,4a,5-tetramethyl-1,3,4,7,8,8a-hexahydronaphthalen-2-yl]methyl}-6-hydroxy-3,4-dioxocyclohexa-1,5-dien-1-yl)amino]ethanesulfonic acid

Description

Dysidine belongs to the class of organic compounds known as o-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 2-positions, respectively. 2-[(5-{[(1r,2r,4as,8as)-1,2,4a,5-tetramethyl-1,3,4,7,8,8a-hexahydronaphthalen-2-yl]methyl}-6-hydroxy-3,4-dioxocyclohexa-1,5-dien-1-yl)amino]ethanesulfonic acid was first documented in 2009 (PMID: 19262557). Based on a literature review a small amount of articles have been published on Dysidine (PMID: 33676391) (PMID: 19091557).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112209232D          

 31 33  0  0  1  0            999 V2000
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8545    0.3627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3848   -0.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6670   -1.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4795   -1.4743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0098   -0.8423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7616   -2.2495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5741   -2.3928    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1044   -1.7608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9169   -1.9040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4472   -1.2721    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.9775   -0.6401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0791   -1.8024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8152   -0.7418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2313   -2.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4189   -2.7382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8886   -3.3702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1367   -1.9630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3242   -1.8197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  2  0  0  0  0
 19 22  1  0  0  0  0
 15 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 12 26  1  0  0  0  0
 26 27  2  0  0  0  0
  9 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
  2 30  1  0  0  0  0
  6 30  1  0  0  0  0
 30 31  1  1  0  0  0
M  END

     RDKit          3D

 64 66  0  0  0  0  0  0  0  0999 V2000
   -6.0759   -0.0068   -0.0308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8668    0.7792   -0.3251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9323    1.8031   -1.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7372    2.6111   -1.4682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4797    1.8096   -1.5263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5340    0.5021   -0.7742 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1477    0.0267   -0.3589 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4799    0.9468    0.5914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2154   -1.4129    0.0429 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6852   -2.2666   -1.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0047   -1.9559    0.7016 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2982   -1.9104    0.0396 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2939   -1.1837    0.5958 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0875   -0.4780    1.7993 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6263   -1.0622    0.0393 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6349   -0.2593    0.6983 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0125   -0.3125    0.3063 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8852    0.6128    1.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4350    2.3037    0.9643 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.0368    2.5555    1.3885 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5869    2.8052   -0.4431 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5091    3.2050    1.9242 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9615   -1.6781   -1.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9873   -2.4922   -1.7754 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2845   -3.0826   -2.8343 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6370   -2.5933   -1.1799 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8464   -3.3201   -1.8318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3173   -1.5975    1.1194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6030   -0.9707    0.8111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5570    0.4467    0.2906 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3810    1.3399    1.4721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1533   -0.1715    1.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9683    0.6040   -0.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1137   -0.9712   -0.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8964    2.0755   -1.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6457    3.5027   -0.7835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9347    3.1020   -2.4679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6491    2.4769   -1.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2495    1.6460   -2.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8509   -0.2348   -1.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5478    0.0568   -1.3167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9439    1.9515    0.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4099    0.5844    1.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5732    1.1856    0.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5576   -3.3584   -0.9202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3459   -1.9501   -2.0949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8244   -2.1962   -1.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1315   -1.5507    1.7456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1481   -3.0745    0.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3499    0.4756    1.9223 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3446    0.3598    1.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4314   -1.3392    0.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1077   -0.0006   -0.7653 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7834    0.3135    2.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9593    0.5099    0.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4088    4.1606    1.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9739   -1.5464   -1.4465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4541   -2.6965    1.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8574   -1.2792    2.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1853   -0.9131    1.7791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1961   -1.5666    0.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1956    2.3874    1.2872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3788    1.3149    2.0130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6723    0.9770    2.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
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 26 12  1  0
 30  6  1  0
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  4 36  1  0
  4 37  1  0
  3 35  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
 31 62  1  0
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 18 55  1  0
 22 56  1  0
 23 57  1  0
M  END


  Mrv1652309112209232D          

 31 33  0  0  1  0            999 V2000
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8545    0.3627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3848   -0.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6670   -1.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4795   -1.4743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0098   -0.8423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7616   -2.2495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5741   -2.3928    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1044   -1.7608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9169   -1.9040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4472   -1.2721    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.9775   -0.6401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0791   -1.8024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8152   -0.7418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2313   -2.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4189   -2.7382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8886   -3.3702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1367   -1.9630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3242   -1.8197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  1  0  0  0
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 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
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M  END
> <DATABASE_ID>
NP0311414

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1[C@@H]2CCC=C(C)[C@@]2(C)CC[C@]1(C)CC1=C(O)C(NCCS(O)(=O)=O)=CC(=O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H33NO6S/c1-14-6-5-7-17-15(2)22(3,8-9-23(14,17)4)13-16-20(26)18(12-19(25)21(16)27)24-10-11-31(28,29)30/h6,12,15,17,24,26H,5,7-11,13H2,1-4H3,(H,28,29,30)/t15-,17+,22-,23-/m1/s1

> <INCHI_KEY>
JUZCKAMLAZUOHD-CIVZFWGOSA-N

> <FORMULA>
C23H33NO6S

> <MOLECULAR_WEIGHT>
451.58

> <EXACT_MASS>
451.202858961

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
48.558897093891474

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(5-{[(1R,2R,4aS,8aS)-1,2,4a,5-tetramethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-2-yl]methyl}-6-hydroxy-3,4-dioxocyclohexa-1,5-dien-1-yl)amino]ethane-1-sulfonic acid

> <JCHEM_LOGP>
3.012178216000001

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.27542294800528

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.2009126026931911

> <JCHEM_PKA_STRONGEST_BASIC>
-6.635690111042835

> <JCHEM_POLAR_SURFACE_AREA>
120.77000000000001

> <JCHEM_REFRACTIVITY>
121.58489999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-[(5-{[(1R,2R,4aS,8aS)-1,2,4a,5-tetramethyl-1,3,4,7,8,8a-hexahydronaphthalen-2-yl]methyl}-6-hydroxy-3,4-dioxocyclohexa-1,5-dien-1-yl)amino]ethanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.195   0.677   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.185  -1.037   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.712  -2.485   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.228  -2.752   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      11.218  -1.572   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      10.755  -4.199   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      12.272  -4.467   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      13.262  -3.287   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.778  -3.554   0.000  0.00  0.00           C+0
HETATM   19  S   UNK     0      15.768  -2.375   0.000  0.00  0.00           S+0
HETATM   20  O   UNK     0      16.758  -1.195   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      16.948  -3.364   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      14.588  -1.385   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.765  -5.379   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.249  -5.111   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.259  -6.291   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       7.722  -3.664   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.205  -3.397   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   30                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   30                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11   28                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   26                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19                                                            
CONECT   23   15   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   12   27                                                  
CONECT   27   26                                                            
CONECT   28    9   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29    2    6   31                                             
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₃NO₆S

Average Mass

451.5800 Da

Monoisotopic Mass

451.20286 Da

IUPAC Name

2-[(5-{[(1R,2R,4aS,8aS)-1,2,4a,5-tetramethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-2-yl]methyl}-6-hydroxy-3,4-dioxocyclohexa-1,5-dien-1-yl)amino]ethane-1-sulfonic acid

Traditional Name

2-[(5-{[(1R,2R,4aS,8aS)-1,2,4a,5-tetramethyl-1,3,4,7,8,8a-hexahydronaphthalen-2-yl]methyl}-6-hydroxy-3,4-dioxocyclohexa-1,5-dien-1-yl)amino]ethanesulfonic acid

CAS Registry Number

Not Available

SMILES

C[C@@H]1[C@@H]2CCC=C(C)[C@@]2(C)CC[C@]1(C)CC1=C(O)C(NCCS(O)(=O)=O)=CC(=O)C1=O

InChI Identifier

InChI=1S/C23H33NO6S/c1-14-6-5-7-17-15(2)22(3,8-9-23(14,17)4)13-16-20(26)18(12-19(25)21(16)27)24-10-11-31(28,29)30/h6,12,15,17,24,26H,5,7-11,13H2,1-4H3,(H,28,29,30)/t15-,17+,22-,23-/m1/s1

InChI Key

JUZCKAMLAZUOHD-CIVZFWGOSA-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 o-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 2-positions, respectively.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

O-benzoquinones

Alternative Parents

Substituents

O-benzoquinone
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Organosulfonic acid
Sulfonyl
Alkanesulfonic acid
Vinylogous acid
Vinylogous amide
Secondary amine
Secondary aliphatic amine
Enamine
Enol
Amine
Organosulfur compound
Organic nitrogen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
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	3.01	ChemAxon
pKa (Strongest Acidic)	-1.2	ChemAxon
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	120.77 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	121.58 m³·mol⁻¹	ChemAxon
Polarizability	48.56 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

8497047

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10321583

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Maurya A, Mohan S, Verma SC: Antidiabetic Potential of Naturally Occurring Sesquiterpenes: A Review. Curr Top Med Chem. 2021;21(10):851-862. doi: 10.2174/1568026621666210305102500. [PubMed:33676391 ]
Zhang Y, Li Y, Guo YW, Jiang HL, Shen X: A sesquiterpene quinone, dysidine, from the sponge Dysidea villosa, activates the insulin pathway through inhibition of PTPases. Acta Pharmacol Sin. 2009 Mar;30(3):333-45. doi: 10.1038/aps.2009.5. [PubMed:19262557 ]
Li Y, Zhang Y, Shen X, Guo YW: A novel sesquiterpene quinone from Hainan sponge Dysidea villosa. Bioorg Med Chem Lett. 2009 Jan 15;19(2):390-2. doi: 10.1016/j.bmcl.2008.11.068. Epub 2008 Nov 24. [PubMed:19091557 ]
LOTUS database [Link]

Showing NP-Card for 2-[(5-{[(1r,2r,4as,8as)-1,2,4a,5-tetramethyl-1,3,4,7,8,8a-hexahydronaphthalen-2-yl]methyl}-6-hydroxy-3,4-dioxocyclohexa-1,5-dien-1-yl)amino]ethanesulfonic acid (NP0311414)

MOL for NP0311414 (2-[(5-{[(1r,2r,4as,8as)-1,2,4a,5-tetramethyl-1,3,4,7,8,8a-hexahydronaphthalen-2-yl]methyl}-6-hydroxy-3,4-dioxocyclohexa-1,5-dien-1-yl)amino]ethanesulfonic acid)

3D MOL for NP0311414 (2-[(5-{[(1r,2r,4as,8as)-1,2,4a,5-tetramethyl-1,3,4,7,8,8a-hexahydronaphthalen-2-yl]methyl}-6-hydroxy-3,4-dioxocyclohexa-1,5-dien-1-yl)amino]ethanesulfonic acid)

3D SDF for NP0311414 (2-[(5-{[(1r,2r,4as,8as)-1,2,4a,5-tetramethyl-1,3,4,7,8,8a-hexahydronaphthalen-2-yl]methyl}-6-hydroxy-3,4-dioxocyclohexa-1,5-dien-1-yl)amino]ethanesulfonic acid)

3D-SDF for NP0311414 (2-[(5-{[(1r,2r,4as,8as)-1,2,4a,5-tetramethyl-1,3,4,7,8,8a-hexahydronaphthalen-2-yl]methyl}-6-hydroxy-3,4-dioxocyclohexa-1,5-dien-1-yl)amino]ethanesulfonic acid)

PDB for NP0311414 (2-[(5-{[(1r,2r,4as,8as)-1,2,4a,5-tetramethyl-1,3,4,7,8,8a-hexahydronaphthalen-2-yl]methyl}-6-hydroxy-3,4-dioxocyclohexa-1,5-dien-1-yl)amino]ethanesulfonic acid)

3D PDB for NP0311414 (2-[(5-{[(1r,2r,4as,8as)-1,2,4a,5-tetramethyl-1,3,4,7,8,8a-hexahydronaphthalen-2-yl]methyl}-6-hydroxy-3,4-dioxocyclohexa-1,5-dien-1-yl)amino]ethanesulfonic acid)

SMILES for NP0311414 (2-[(5-{[(1r,2r,4as,8as)-1,2,4a,5-tetramethyl-1,3,4,7,8,8a-hexahydronaphthalen-2-yl]methyl}-6-hydroxy-3,4-dioxocyclohexa-1,5-dien-1-yl)amino]ethanesulfonic acid)

INCHI for NP0311414 (2-[(5-{[(1r,2r,4as,8as)-1,2,4a,5-tetramethyl-1,3,4,7,8,8a-hexahydronaphthalen-2-yl]methyl}-6-hydroxy-3,4-dioxocyclohexa-1,5-dien-1-yl)amino]ethanesulfonic acid)

Structure for NP0311414 (2-[(5-{[(1r,2r,4as,8as)-1,2,4a,5-tetramethyl-1,3,4,7,8,8a-hexahydronaphthalen-2-yl]methyl}-6-hydroxy-3,4-dioxocyclohexa-1,5-dien-1-yl)amino]ethanesulfonic acid)

3D Structure for NP0311414 (2-[(5-{[(1r,2r,4as,8as)-1,2,4a,5-tetramethyl-1,3,4,7,8,8a-hexahydronaphthalen-2-yl]methyl}-6-hydroxy-3,4-dioxocyclohexa-1,5-dien-1-yl)amino]ethanesulfonic acid)