NP-MRD: Showing NP-Card for 2-[(5-{[(1r,2s,4as,8as)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]methyl}-3,6-dioxocyclohexa-1,4-dien-1-yl)amino]ethanesulfonic acid (NP0281697)

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Record Information

Version

2.0

Created at

2022-09-09 08:12:06 UTC

Updated at

2022-09-09 08:12:07 UTC

NP-MRD ID

NP0281697

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Melemeleone A belongs to the class of organic compounds known as prenylquinones. These are quinones with a structure characterized by the quinone ring substituted by an prenyl side-chain. 2-[(5-{[(1r,2s,4as,8as)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]methyl}-3,6-dioxocyclohexa-1,4-dien-1-yl)amino]ethanesulfonic acid is found in Dysidea avara. Based on a literature review very few articles have been published on Melemeleone A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092210122D          

 30 32  0  0  1  0            999 V2000
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    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
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -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  2  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  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  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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8163   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0416   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4788   -3.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3033   -3.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7405   -3.7489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5650   -3.7201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3532   -4.4774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5287   -4.5061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1414   -5.2346    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5785   -5.9342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1912   -6.6626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6284   -7.3623    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0656   -8.0619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9288   -7.7995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3281   -6.9251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0915   -3.8065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2670   -3.8353    0.0000 O   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  6  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
  6 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  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  2  0  0  0  0
 25 28  1  0  0  0  0
 21 29  1  0  0  0  0
 16 29  1  0  0  0  0
 29 30  2  0  0  0  0
M  END

     RDKit          3D

 63 65  0  0  0  0  0  0  0  0999 V2000
   -6.0618    0.6398    0.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8567   -0.0358    0.9831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8040   -0.3044    2.2772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6273   -0.9756    2.8573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3293   -0.4369    2.2640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4662   -0.0310    0.8274 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6813   -0.4396    0.1426 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9015   -1.8267   -0.2962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7763    0.4329   -1.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5809    0.2600   -1.9843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2679    0.2751   -1.3397 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3240   -0.4617   -2.3059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1242   -0.2042    0.0733 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6378   -1.5921    0.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2443    0.7506    0.8257 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1170    1.0291    0.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4120    2.2727   -0.0646 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7253    2.6044   -0.4989 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0383    3.7743   -0.9394 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8435    1.6360   -0.4823 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5715    0.4375   -0.0402 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5932   -0.5907    0.0210 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5063   -0.5370    1.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5072    0.5635    1.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6049    0.3927   -0.2997 S   0  0  0  0  0  6  0  0  0  0  0  0
    6.8028    0.3116   -1.5482 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5203    1.5550   -0.3739 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4245   -1.0759   -0.1483 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2012    0.0899    0.4102 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0857   -1.1053    0.8196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5305    1.2699    1.2561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8006   -0.1369    0.1974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8461    1.3307   -0.3759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6391   -0.0330    2.9509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6740   -2.0993    2.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6270   -0.8113    3.9545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5777   -1.2221    2.4623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0300    0.4119    2.9419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5357    1.1125    0.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0268   -1.9045   -0.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4864   -2.0795   -1.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7294   -2.6353    0.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8579    1.5034   -0.8263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6798    0.1561   -1.7059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6239    1.0744   -2.7662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7356   -0.6803   -2.5894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8876    1.3407   -1.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7071   -0.4647   -1.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6568   -1.5091   -2.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4029    0.0029   -3.3203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2967   -1.9787    1.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1204   -1.8482   -0.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4800   -2.3360   -0.1421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1963    0.4675    1.9229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8208    1.7309    0.8409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6080    2.9981   -0.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8265    1.9339   -0.8236 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6324   -1.3102   -0.7115 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9431   -0.4468    2.0884 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0867   -1.5015    1.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0755    1.5812    1.1701 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1124    0.4597    2.0458 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7592   -1.7850   -0.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  7  1  0
  7  8  1  6
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  6 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 28  1  0
 25 26  2  0
 25 27  2  0
 21 29  1  0
 29 30  2  0
 13 11  1  0
 29 16  1  0
  2  7  1  0
 12 48  1  0
 12 49  1  0
 12 50  1  0
 11 47  1  1
 10 45  1  0
 10 46  1  0
  9 43  1  0
  9 44  1  0
  8 40  1  0
  8 41  1  0
  8 42  1  0
  6 39  1  1
  5 37  1  0
  5 38  1  0
  4 35  1  0
  4 36  1  0
  3 34  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
 14 51  1  0
 14 52  1  0
 14 53  1  0
 15 54  1  0
 15 55  1  0
 17 56  1  0
 20 57  1  0
 22 58  1  0
 23 59  1  0
 23 60  1  0
 24 61  1  0
 24 62  1  0
 28 63  1  0
M  END


  Mrv1652309092210122D          

 30 32  0  0  1  0            999 V2000
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    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
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -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  2  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  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  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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8163   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0416   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4788   -3.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3033   -3.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7405   -3.7489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5650   -3.7201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3532   -4.4774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5287   -4.5061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1414   -5.2346    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5785   -5.9342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1912   -6.6626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6284   -7.3623    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0656   -8.0619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9288   -7.7995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3281   -6.9251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0915   -3.8065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2670   -3.8353    0.0000 O   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  6  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
  6 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  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  2  0  0  0  0
 25 28  1  0  0  0  0
 21 29  1  0  0  0  0
 16 29  1  0  0  0  0
 29 30  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0281697

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CC[C@@]2(C)[C@@H](CCC=C2C)[C@]1(C)CC1=CC(=O)C=C(NCCS(O)(=O)=O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H33NO5S/c1-15-6-5-7-20-22(15,3)9-8-16(2)23(20,4)14-17-12-18(25)13-19(21(17)26)24-10-11-30(27,28)29/h6,12-13,16,20,24H,5,7-11,14H2,1-4H3,(H,27,28,29)/t16-,20+,22+,23+/m0/s1

> <INCHI_KEY>
PZOXNEXWCRTPSE-DQOBCGMHSA-N

> <FORMULA>
C23H33NO5S

> <MOLECULAR_WEIGHT>
435.58

> <EXACT_MASS>
435.207944341

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
46.295585258799306

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
3.5308358973333336

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.37374408204082

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.1472465077869147

> <JCHEM_PKA_STRONGEST_BASIC>
-7.747210652363037

> <JCHEM_POLAR_SURFACE_AREA>
100.53999999999999

> <JCHEM_REFRACTIVITY>
119.61749999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.390  -4.440   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.944  -4.440   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.760  -5.746   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.300  -5.692   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.116  -6.998   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.655  -6.944   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.393  -8.358   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.854  -8.411   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       2.131  -9.771   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       2.947 -11.077   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.224 -12.437   0.000  0.00  0.00           C+0
HETATM   25  S   UNK     0       3.040 -13.743   0.000  0.00  0.00           S+0
HETATM   26  O   UNK     0       3.856 -15.049   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       1.734 -14.559   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       4.346 -12.927   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.037  -7.105   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.498  -7.159   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    2    8    9                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    6   14   15                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   29                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   29                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25                                                            
CONECT   29   21   16   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₃NO₅S

Average Mass

435.5800 Da

Monoisotopic Mass

435.20794 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

C[C@H]1CC[C@@]2(C)[C@@H](CCC=C2C)[C@]1(C)CC1=CC(=O)C=C(NCCS(O)(=O)=O)C1=O

InChI Identifier

InChI=1S/C23H33NO5S/c1-15-6-5-7-20-22(15,3)9-8-16(2)23(20,4)14-17-12-18(25)13-19(21(17)26)24-10-11-30(27,28)29/h6,12-13,16,20,24H,5,7-11,14H2,1-4H3,(H,27,28,29)/t16-,20+,22+,23+/m0/s1

InChI Key

PZOXNEXWCRTPSE-DQOBCGMHSA-N

Experimental Spectra

Not Available

Predicted Spectra

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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Dysidea avara	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prenylquinones. These are quinones with a structure characterized by the quinone ring substituted by an prenyl side-chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Prenylquinones

Alternative Parents

Substituents

Prenylbenzoquinone
P-benzoquinone
Quinone
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Organosulfonic acid
Sulfonyl
Alkanesulfonic acid
Vinylogous amide
Cyclic ketone
Ketone
Secondary aliphatic amine
Enamine
Amine
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Hydrocarbon derivative
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	3.53	ChemAxon
pKa (Strongest Acidic)	-1.1	ChemAxon
pKa (Strongest Basic)	-7.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.54 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	119.62 m³·mol⁻¹	ChemAxon
Polarizability	46.3 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

8541145

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10365696

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-[(5-{[(1r,2s,4as,8as)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]methyl}-3,6-dioxocyclohexa-1,4-dien-1-yl)amino]ethanesulfonic acid (NP0281697)

MOL for NP0281697 (2-[(5-{[(1r,2s,4as,8as)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]methyl}-3,6-dioxocyclohexa-1,4-dien-1-yl)amino]ethanesulfonic acid)

3D MOL for NP0281697 (2-[(5-{[(1r,2s,4as,8as)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]methyl}-3,6-dioxocyclohexa-1,4-dien-1-yl)amino]ethanesulfonic acid)

3D SDF for NP0281697 (2-[(5-{[(1r,2s,4as,8as)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]methyl}-3,6-dioxocyclohexa-1,4-dien-1-yl)amino]ethanesulfonic acid)

3D-SDF for NP0281697 (2-[(5-{[(1r,2s,4as,8as)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]methyl}-3,6-dioxocyclohexa-1,4-dien-1-yl)amino]ethanesulfonic acid)

PDB for NP0281697 (2-[(5-{[(1r,2s,4as,8as)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]methyl}-3,6-dioxocyclohexa-1,4-dien-1-yl)amino]ethanesulfonic acid)

3D PDB for NP0281697 (2-[(5-{[(1r,2s,4as,8as)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]methyl}-3,6-dioxocyclohexa-1,4-dien-1-yl)amino]ethanesulfonic acid)

SMILES for NP0281697 (2-[(5-{[(1r,2s,4as,8as)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]methyl}-3,6-dioxocyclohexa-1,4-dien-1-yl)amino]ethanesulfonic acid)

INCHI for NP0281697 (2-[(5-{[(1r,2s,4as,8as)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]methyl}-3,6-dioxocyclohexa-1,4-dien-1-yl)amino]ethanesulfonic acid)

Structure for NP0281697 (2-[(5-{[(1r,2s,4as,8as)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]methyl}-3,6-dioxocyclohexa-1,4-dien-1-yl)amino]ethanesulfonic acid)

3D Structure for NP0281697 (2-[(5-{[(1r,2s,4as,8as)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]methyl}-3,6-dioxocyclohexa-1,4-dien-1-yl)amino]ethanesulfonic acid)