NP-MRD: Showing NP-Card for (2e)-5-[(1s,4as,5r,8as)-2,5,8a-trimethyl-5-(4-methylpent-3-en-1-yl)-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-2-enoic acid (NP0273361)

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Record Information

Version

2.0

Created at

2022-09-08 20:22:07 UTC

Updated at

2022-09-08 20:22:07 UTC

NP-MRD ID

NP0273361

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-5-[(1s,4as,5r,8as)-2,5,8a-trimethyl-5-(4-methylpent-3-en-1-yl)-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-2-enoic acid

Description

Kohamaic acid A, also known as kohamaate a, belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units. (2e)-5-[(1s,4as,5r,8as)-2,5,8a-trimethyl-5-(4-methylpent-3-en-1-yl)-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-2-enoic acid was first documented in 2003 (PMID: 12758147). Based on a literature review a small amount of articles have been published on Kohamaic acid A (PMID: 19127241) (PMID: 18997393).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082222222D          

 27 28  0  0  1  0            999 V2000
   -1.0266    3.4465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4963    2.8145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3162    2.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7784    2.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2481    1.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5303    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5303    0.6320    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  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  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
    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  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
    1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  1  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  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
M  END

     RDKit          3D

 67 68  0  0  0  0  0  0  0  0999 V2000
    7.1292    0.1391    0.2252 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9730   -0.7420    0.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9473   -2.0994    0.6718 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9221   -0.3607   -0.7044 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7501   -1.2324   -0.9077 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4547   -0.8370   -0.3604 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7771    0.4157   -0.7554 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7068    1.5685   -0.3215 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5841    0.5919   -2.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2565    0.8269   -2.7877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8867    1.1181   -1.8632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7330    0.1864   -0.6325 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7218   -1.1980   -1.2275 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5039    0.6475   -0.0097 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5944    0.3424    1.4833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5039    1.1892    2.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6882    1.1942    1.4541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7784    2.1091    1.9853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9274    0.3284    0.2403 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3626   -1.0128    0.8271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5904   -0.8938    1.6660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8578   -0.6029    0.9819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0398   -0.3523    1.8406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9603   -0.5624   -0.3078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2282   -0.2647   -0.9828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3151   -0.2282   -2.2406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3556   -0.0177   -0.2458 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8627    1.2045    0.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8132   -0.0041   -0.6483 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6483   -0.1760    1.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8899   -2.2823    1.2324 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0757   -2.2453    1.3313 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9192   -2.8492   -0.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0318    0.6227   -1.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6964   -1.5829   -1.9841 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0115   -2.2170   -0.3904 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7311   -1.6975   -0.5207 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5733   -0.8994    0.7818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2180    2.0334   -1.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4507    1.2541    0.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1107    2.3711    0.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2854    1.4005   -2.6095 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0149   -0.3153   -2.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0605    0.0348   -3.5469 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2918    1.7408   -3.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7987    2.1759   -1.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8219    0.9297   -2.3868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0091   -1.3397   -2.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7302   -1.3038   -1.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6377   -2.0212   -0.5340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4086    1.7933   -0.0099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5964    0.7575    1.7881 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5843   -0.6950    1.7481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3288    1.7994    2.9005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9026    2.0040    3.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4930    3.1789    1.7155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6767    1.9190    1.3904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7604    0.7381   -0.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5881   -1.4588    1.4927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5693   -1.7436    0.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7974   -1.8884    2.2041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4393   -0.2074    2.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7828   -0.4345    2.9287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8596   -1.0845    1.7036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4686    0.6594    1.7387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1011   -0.7983   -0.9819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0380    0.6845   -0.4871 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  6
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  6
 12 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 27  1  0
 25 26  2  0
 19 17  1  0
 17 18  1  0
 17 16  2  0
 16 15  1  0
 15 14  1  0
 14  7  1  0
 14 12  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  0
  6 38  1  0
  8 39  1  0
  8 40  1  0
  8 41  1  0
  9 42  1  0
  9 43  1  0
 10 44  1  0
 10 45  1  0
 11 46  1  0
 11 47  1  0
 13 48  1  0
 13 49  1  0
 13 50  1  0
 19 58  1  6
 20 59  1  0
 20 60  1  0
 21 61  1  0
 21 62  1  0
 23 63  1  0
 23 64  1  0
 23 65  1  0
 24 66  1  0
 27 67  1  0
 18 55  1  0
 18 56  1  0
 18 57  1  0
 16 54  1  0
 15 52  1  0
 15 53  1  0
 14 51  1  1
M  END


  Mrv1652309082222222D          

 27 28  0  0  1  0            999 V2000
   -1.0266    3.4465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4963    2.8145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3162    2.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7784    2.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2481    1.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5303    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5303    0.6320    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  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  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
    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  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
    1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  1  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  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0273361

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC[C@@]1(C)CCC[C@]2(C)[C@@H](CC\C(C)=C\C(O)=O)C(C)=CC[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C25H40O2/c1-18(2)9-7-14-24(5)15-8-16-25(6)21(20(4)11-13-22(24)25)12-10-19(3)17-23(26)27/h9,11,17,21-22H,7-8,10,12-16H2,1-6H3,(H,26,27)/b19-17+/t21-,22-,24-,25+/m0/s1

> <INCHI_KEY>
WZOUGXJIBZOMTP-CTXZGABSSA-N

> <FORMULA>
C25H40O2

> <MOLECULAR_WEIGHT>
372.593

> <EXACT_MASS>
372.302830528

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
46.706316700596545

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-5-[(1S,4aS,5R,8aS)-2,5,8a-trimethyl-5-(4-methylpent-3-en-1-yl)-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-methylpent-2-enoic acid

> <JCHEM_LOGP>
7.081365589

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.816420390382797

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
116.79629999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-5-[(1S,4aS,5R,8aS)-2,5,8a-trimethyl-5-(4-methylpent-3-en-1-yl)-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-2-enoic acid

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.916   6.433   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.926   5.254   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.590   5.521   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.453   3.807   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.463   2.627   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.990   1.180   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.990   1.180   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   14                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   19                                             
CONECT   13   12                                                            
CONECT   14   12    7   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   12   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

View in JSmol

Synonyms

Value	Source
Kohamaate a	Generator

Chemical Formula

C₂₅H₄₀O₂

Average Mass

372.5930 Da

Monoisotopic Mass

372.30283 Da

IUPAC Name

(2E)-5-[(1S,4aS,5R,8aS)-2,5,8a-trimethyl-5-(4-methylpent-3-en-1-yl)-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-methylpent-2-enoic acid

Traditional Name

(2E)-5-[(1S,4aS,5R,8aS)-2,5,8a-trimethyl-5-(4-methylpent-3-en-1-yl)-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-2-enoic acid

CAS Registry Number

Not Available

SMILES

CC(C)=CCC[C@@]1(C)CCC[C@]2(C)[C@@H](CC\C(C)=C\C(O)=O)C(C)=CC[C@@H]12

InChI Identifier

InChI=1S/C25H40O2/c1-18(2)9-7-14-24(5)15-8-16-25(6)21(20(4)11-13-22(24)25)12-10-19(3)17-23(26)27/h9,11,17,21-22H,7-8,10,12-16H2,1-6H3,(H,26,27)/b19-17+/t21-,22-,24-,25+/m0/s1

InChI Key

WZOUGXJIBZOMTP-CTXZGABSSA-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 sesterterpenoids. These are terpenes composed of five consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Sesterterpenoids

Alternative Parents

Substituents

Sesterterpenoid
Medium-chain fatty acid
Branched fatty acid
Methyl-branched fatty acid
Unsaturated fatty acid
Fatty acyl
Fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
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	7.08	ChemAxon
pKa (Strongest Acidic)	4.82	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	116.8 m³·mol⁻¹	ChemAxon
Polarizability	46.71 Å³	ChemAxon
Number of Rings	2	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8266239

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10090702

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Mizushina Y, Manita D, Takeuchi T, Sugawara F, Kumamoto-Yonezawa Y, Matsui Y, Takemura M, Sasaki M, Yoshida H, Takikawa H: The inhibitory action of kohamaic acid A derivatives on mammalian DNA polymerase beta. Molecules. 2008 Dec 29;14(1):102-21. doi: 10.3390/molecules14010102. [PubMed:19127241 ]
Takikawa H, Kamatani N, Nakanishi K, Tashiro T, Sasaki M, Yoshida H, Mizushina Y: Synthetic studies on kohamaic acids: synthesis of structurally simplified analogs of kohamaic acid A. Biosci Biotechnol Biochem. 2008 Nov;72(11):3071-4. doi: 10.1271/bbb.80629. Epub 2008 Nov 7. [PubMed:18997393 ]
Mizushina Y, Murakami C, Yogi K, Ueda K, Ishidoh T, Takemura M, Perpelescu M, Suzuki M, Oshige M, Yamaguchi T, Saneyoshi M, Yoshida H, Sakaguchi K: Kohamaic acid A, a novel sesterterpenic acid, inhibits activities of DNA polymerases from deuterostomes. Biochim Biophys Acta. 2003 May 30;1648(1-2):55-61. doi: 10.1016/s1570-9639(03)00108-0. [PubMed:12758147 ]
LOTUS database [Link]

Showing NP-Card for (2e)-5-[(1s,4as,5r,8as)-2,5,8a-trimethyl-5-(4-methylpent-3-en-1-yl)-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-2-enoic acid (NP0273361)

MOL for NP0273361 ((2e)-5-[(1s,4as,5r,8as)-2,5,8a-trimethyl-5-(4-methylpent-3-en-1-yl)-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-2-enoic acid)

3D MOL for NP0273361 ((2e)-5-[(1s,4as,5r,8as)-2,5,8a-trimethyl-5-(4-methylpent-3-en-1-yl)-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-2-enoic acid)

3D SDF for NP0273361 ((2e)-5-[(1s,4as,5r,8as)-2,5,8a-trimethyl-5-(4-methylpent-3-en-1-yl)-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-2-enoic acid)

3D-SDF for NP0273361 ((2e)-5-[(1s,4as,5r,8as)-2,5,8a-trimethyl-5-(4-methylpent-3-en-1-yl)-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-2-enoic acid)

PDB for NP0273361 ((2e)-5-[(1s,4as,5r,8as)-2,5,8a-trimethyl-5-(4-methylpent-3-en-1-yl)-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-2-enoic acid)

3D PDB for NP0273361 ((2e)-5-[(1s,4as,5r,8as)-2,5,8a-trimethyl-5-(4-methylpent-3-en-1-yl)-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-2-enoic acid)

SMILES for NP0273361 ((2e)-5-[(1s,4as,5r,8as)-2,5,8a-trimethyl-5-(4-methylpent-3-en-1-yl)-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-2-enoic acid)

INCHI for NP0273361 ((2e)-5-[(1s,4as,5r,8as)-2,5,8a-trimethyl-5-(4-methylpent-3-en-1-yl)-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-2-enoic acid)

Structure for NP0273361 ((2e)-5-[(1s,4as,5r,8as)-2,5,8a-trimethyl-5-(4-methylpent-3-en-1-yl)-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-2-enoic acid)

3D Structure for NP0273361 ((2e)-5-[(1s,4as,5r,8as)-2,5,8a-trimethyl-5-(4-methylpent-3-en-1-yl)-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-2-enoic acid)