NP-MRD: Showing NP-Card for Decalpenic acid (NP0009502)

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Record Information

Version

2.0

Created at

2020-12-09 06:52:19 UTC

Updated at

2021-07-15 17:03:26 UTC

NP-MRD ID

NP0009502

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Decalpenic acid

Provided By

NPAtlas

Description

Decalpenic acid is also known as decalpenate. Decalpenic acid is found in Penicillium and Talaromyces verruculosus. Decalpenic acid was first documented in 2010 (PMID: 20940725). Based on a literature review a small amount of articles have been published on Decalpenic acid (PMID: 24047272) (PMID: 23258426) (PMID: 22618236).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106363D          

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     RDKit          3D

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  Mrv1652306242106363D          

 61 62  0  0  0  0            999 V2000
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    9.4143    0.1637    1.7371 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9838    0.5801    2.8301 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3046   -0.2991    0.7947 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0395    3.9550   -1.1554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4187    3.3477   -2.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0178    4.9489   -2.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1598    3.0292   -1.7230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4918    4.4072   -0.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3001    2.6710    0.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8323    3.4599    0.7856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1134    1.6111   -0.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6407    1.7965    2.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6052   -0.3001    3.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1989   -0.5361    1.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3583   -2.8691    1.4676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6706   -2.3880    2.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2619   -3.6643    1.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1106   -4.8427    0.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9255   -4.3368    2.0663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0461   -2.8637   -1.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1978   -0.4902   -1.3171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1028   -1.7673   -2.0986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8015   -1.9465   -0.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8384   -0.4247   -2.5257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9617    0.9081   -1.9539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3285    1.2350   -2.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0117    0.7454    0.7954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0052   -1.6261   -1.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6964   -1.2143   -2.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4277   -0.1187   -2.4854 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9976   -0.6675   -1.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7723    0.5389    1.3020 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1210   -0.4784   -0.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8658    0.7493    2.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0512    0.5439    0.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0068   -1.0311    0.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9948   -1.1312    0.2800 H   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  6  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 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
 14  4  1  0  0  0  0
 13  7  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  2 31  1  0  0  0  0
  2 32  1  0  0  0  0
  3 33  1  0  0  0  0
  3 34  1  0  0  0  0
  4 35  1  6  0  0  0
  5 36  1  0  0  0  0
  6 37  1  0  0  0  0
  7 38  1  6  0  0  0
  8 39  1  0  0  0  0
  8 40  1  0  0  0  0
 10 41  1  0  0  0  0
 10 42  1  0  0  0  0
 10 43  1  0  0  0  0
 11 44  1  0  0  0  0
 12 45  1  0  0  0  0
 12 46  1  0  0  0  0
 13 47  1  1  0  0  0
 15 48  1  0  0  0  0
 15 49  1  0  0  0  0
 15 50  1  0  0  0  0
 16 51  1  0  0  0  0
 18 52  1  0  0  0  0
 18 53  1  0  0  0  0
 18 54  1  0  0  0  0
 19 55  1  0  0  0  0
 20 56  1  0  0  0  0
 21 57  1  0  0  0  0
 22 58  1  0  0  0  0
 23 59  1  0  0  0  0
 24 60  1  0  0  0  0
 27 61  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0009502

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O2/c1-5-10-22-15-14-21-17-19(2)13-16-23(21)25(22,4)18-20(3)11-8-6-7-9-12-24(26)27/h6-9,11-15,18,21-23H,5,10,16-17H2,1-4H3,(H,26,27)/b7-6+,11-8+,12-9?,20-18+/t21-,22-,23-,25-/m1/s1

> <INCHI_KEY>
LRLMBKDNFKCUAP-DPNAJYCGSA-N

> <FORMULA>
C25H34O2

> <MOLECULAR_WEIGHT>
366.545

> <EXACT_MASS>
366.255880335

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
46.38192332113946

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4E,6E)-9-[(1R,2R,4aS,8aR)-1,6-dimethyl-2-propyl-1,2,4a,5,8,8a-hexahydronaphthalen-1-yl]-8-methylnona-2,4,6,8-tetraenoic acid

> <ALOGPS_LOGP>
7.13

> <JCHEM_LOGP>
6.341329557333333

> <ALOGPS_LOGS>
-5.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.886026935947112

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
120.591

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.69e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4E,6E)-9-[(1R,2R,4aS,8aR)-1,6-dimethyl-2-propyl-4a,5,8,8a-tetrahydro-2H-naphthalen-1-yl]-8-methylnona-2,4,6,8-tetraenoic acid

> <JCHEM_VEBER_RULE>
1

$$$$

     RDKit          3D

 61 62  0  0  0  0  0  0  0  0999 V2000
   -2.1925    3.9025   -1.8539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0000    3.4120   -1.1136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2792    2.6771    0.1440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0590    1.4562    0.2378 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0661    1.1160    1.7321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5786   -0.0011    2.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1353   -0.8830    1.1506 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3122   -2.3173    1.6495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2718   -2.8819    0.6382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1792   -3.9649    1.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3234   -2.4224   -0.5824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4755   -1.3168   -1.1551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3875   -0.9820   -0.1490 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5131    0.1880   -0.4941 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9175    0.4931   -1.9199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1284    0.1323   -0.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0711   -0.0385   -0.4732 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7271   -0.9940   -1.9682 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4676   -0.2378   -0.5772 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2808    0.1397    0.4343 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6983   -0.0257    0.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4916    0.3399    1.3652 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8274    0.2724    1.4717 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0345    0.2412    1.6433 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4143    0.1637    1.7371 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9838    0.5801    2.8301 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3046   -0.2991    0.7947 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0395    3.9550   -1.1554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4187    3.3477   -2.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0178    4.9489   -2.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1598    3.0292   -1.7230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4918    4.4072   -0.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3001    2.6710    0.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8323    3.4599    0.7856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1134    1.6111   -0.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6407    1.7965    2.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6052   -0.3001    3.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1989   -0.5361    1.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3583   -2.8691    1.4676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6706   -2.3880    2.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2619   -3.6643    1.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1106   -4.8427    0.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9255   -4.3368    2.0663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0461   -2.8637   -1.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1978   -0.4902   -1.3171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1028   -1.7673   -2.0986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8015   -1.9465   -0.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8384   -0.4247   -2.5257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9617    0.9081   -1.9539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3285    1.2350   -2.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0117    0.7454    0.7954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0052   -1.6261   -1.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6964   -1.2143   -2.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4277   -0.1187   -2.4854 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9976   -0.6675   -1.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7723    0.5389    1.3020 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1210   -0.4784   -0.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8658    0.7493    2.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0512    0.5439    0.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0068   -1.0311    0.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9948   -1.1312    0.2800 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  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  6
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 14  4  1  0
 13  7  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  6
  5 36  1  0
  6 37  1  0
  7 38  1  6
  8 39  1  0
  8 40  1  0
 10 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  0
 12 45  1  0
 12 46  1  0
 13 47  1  1
 15 48  1  0
 15 49  1  0
 15 50  1  0
 16 51  1  0
 18 52  1  0
 18 53  1  0
 18 54  1  0
 19 55  1  0
 20 56  1  0
 21 57  1  0
 22 58  1  0
 23 59  1  0
 24 60  1  0
 27 61  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.192   3.902  -1.854  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.000   3.412  -1.114  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.279   2.677   0.144  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.059   1.456   0.238  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.066   1.116   1.732  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.579  -0.001   2.170  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.135  -0.883   1.151  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.312  -2.317   1.650  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.272  -2.882   0.638  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.179  -3.965   1.064  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.323  -2.422  -0.582  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.475  -1.317  -1.155  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.388  -0.982  -0.149  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.513   0.188  -0.494  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.918   0.493  -1.920  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.128   0.132  -0.385  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.071  -0.039  -0.473  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.727  -0.994  -1.968  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.468  -0.238  -0.577  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.281   0.140   0.434  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.698  -0.026   0.372  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.492   0.340   1.365  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.827   0.272   1.472  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.034   0.241   1.643  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.414   0.164   1.737  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.984   0.580   2.830  0.00  0.00           O+0
HETATM   27  O   UNK     0      10.305  -0.299   0.795  0.00  0.00           O+0
HETATM   28  H   UNK     0      -3.039   3.955  -1.155  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.419   3.348  -2.779  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.018   4.949  -2.184  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.160   3.029  -1.723  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.492   4.407  -0.763  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.300   2.671   0.700  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.832   3.460   0.786  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.113   1.611  -0.030  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.641   1.797   2.463  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.605  -0.300   3.220  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.199  -0.536   1.003  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.358  -2.869   1.468  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.671  -2.388   2.681  0.00  0.00           H+0
HETATM   41  H   UNK     0      -6.262  -3.664   1.109  0.00  0.00           H+0
HETATM   42  H   UNK     0      -5.111  -4.843   0.381  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.926  -4.337   2.066  0.00  0.00           H+0
HETATM   44  H   UNK     0      -5.046  -2.864  -1.288  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.198  -0.490  -1.317  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.103  -1.767  -2.099  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.802  -1.946  -0.194  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.838  -0.425  -2.526  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.962   0.908  -1.954  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.329   1.235  -2.445  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.012   0.745   0.795  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.005  -1.626  -1.622  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.696  -1.214  -2.296  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.428  -0.119  -2.485  0.00  0.00           H+0
HETATM   55  H   UNK     0       2.998  -0.668  -1.387  0.00  0.00           H+0
HETATM   56  H   UNK     0       2.772   0.539   1.302  0.00  0.00           H+0
HETATM   57  H   UNK     0       5.121  -0.478  -0.528  0.00  0.00           H+0
HETATM   58  H   UNK     0       4.866   0.749   2.261  0.00  0.00           H+0
HETATM   59  H   UNK     0       7.051   0.544   0.070  0.00  0.00           H+0
HETATM   60  H   UNK     0       8.007  -1.031   0.929  0.00  0.00           H+0
HETATM   61  H   UNK     0       9.995  -1.131   0.280  0.00  0.00           H+0
CONECT    1    2   28   29   30                                             
CONECT    2    1    3   31   32                                             
CONECT    3    2    4   33   34                                             
CONECT    4    3    5   14   35                                             
CONECT    5    4    6   36                                                  
CONECT    6    5    7   37                                                  
CONECT    7    6    8   13   38                                             
CONECT    8    7    9   39   40                                             
CONECT    9    8   10   11                                                  
CONECT   10    9   41   42   43                                             
CONECT   11    9   12   44                                                  
CONECT   12   11   13   45   46                                             
CONECT   13   12   14    7   47                                             
CONECT   14   13   15   16    4                                             
CONECT   15   14   48   49   50                                             
CONECT   16   14   17   51                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   52   53   54                                             
CONECT   19   17   20   55                                                  
CONECT   20   19   21   56                                                  
CONECT   21   20   22   57                                                  
CONECT   22   21   23   58                                                  
CONECT   23   22   24   59                                                  
CONECT   24   23   25   60                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   61                                                       
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    2                                                            
CONECT   32    2                                                            
CONECT   33    3                                                            
CONECT   34    3                                                            
CONECT   35    4                                                            
CONECT   36    5                                                            
CONECT   37    6                                                            
CONECT   38    7                                                            
CONECT   39    8                                                            
CONECT   40    8                                                            
CONECT   41   10                                                            
CONECT   42   10                                                            
CONECT   43   10                                                            
CONECT   44   11                                                            
CONECT   45   12                                                            
CONECT   46   12                                                            
CONECT   47   13                                                            
CONECT   48   15                                                            
CONECT   49   15                                                            
CONECT   50   15                                                            
CONECT   51   16                                                            
CONECT   52   18                                                            
CONECT   53   18                                                            
CONECT   54   18                                                            
CONECT   55   19                                                            
CONECT   56   20                                                            
CONECT   57   21                                                            
CONECT   58   22                                                            
CONECT   59   23                                                            
CONECT   60   24                                                            
CONECT   61   27                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  124    0
END

RDKit          3D

61 62  0  0  0  0  0  0  0  0999 V2000
   -2.1925    3.9025   -1.8539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0000    3.4120   -1.1136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2792    2.6771    0.1440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0590    1.4562    0.2378 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0661    1.1160    1.7321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5786   -0.0011    2.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1353   -0.8830    1.1506 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3122   -2.3173    1.6495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2718   -2.8819    0.6382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1792   -3.9649    1.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3234   -2.4224   -0.5824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4755   -1.3168   -1.1551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3875   -0.9820   -0.1490 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5131    0.1880   -0.4941 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9175    0.4931   -1.9199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1284    0.1323   -0.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0711   -0.0385   -0.4732 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7271   -0.9940   -1.9682 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4676   -0.2378   -0.5772 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2808    0.1397    0.4343 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6983   -0.0257    0.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4916    0.3399    1.3652 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8274    0.2724    1.4717 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0345    0.2412    1.6433 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4143    0.1637    1.7371 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9838    0.5801    2.8301 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3046   -0.2991    0.7947 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0395    3.9550   -1.1554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4187    3.3477   -2.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0178    4.9489   -2.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1598    3.0292   -1.7230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4918    4.4072   -0.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3001    2.6710    0.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8323    3.4599    0.7856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1134    1.6111   -0.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6407    1.7965    2.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6052   -0.3001    3.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1989   -0.5361    1.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3583   -2.8691    1.4676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6706   -2.3880    2.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2619   -3.6643    1.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1106   -4.8427    0.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9255   -4.3368    2.0663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0461   -2.8637   -1.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1978   -0.4902   -1.3171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1028   -1.7673   -2.0986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8015   -1.9465   -0.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8384   -0.4247   -2.5257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9617    0.9081   -1.9539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3285    1.2350   -2.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0117    0.7454    0.7954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0052   -1.6261   -1.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6964   -1.2143   -2.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4277   -0.1187   -2.4854 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9976   -0.6675   -1.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7723    0.5389    1.3020 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1210   -0.4784   -0.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8658    0.7493    2.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0512    0.5439    0.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0068   -1.0311    0.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9948   -1.1312    0.2800 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  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  6
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 14  4  1  0
 13  7  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  6
  5 36  1  0
  6 37  1  0
  7 38  1  6
  8 39  1  0
  8 40  1  0
 10 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  0
 12 45  1  0
 12 46  1  0
 13 47  1  1
 15 48  1  0
 15 49  1  0
 15 50  1  0
 16 51  1  0
 18 52  1  0
 18 53  1  0
 18 54  1  0
 19 55  1  0
 20 56  1  0
 21 57  1  0
 22 58  1  0
 23 59  1  0
 24 60  1  0
 27 61  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Decalpenate	Generator
(2E,4E,6E,8E)-9-[(1R,2R,4AS,8ar)-1,6-dimethyl-2-propyl-1,2,4a,5,8,8a-hexahydronaphthalen-1-yl]-8-methylnona-2,4,6,8-tetraenoate	Generator

Chemical Formula

C₂₅H₃₄O₂

Average Mass

366.5450 Da

Monoisotopic Mass

366.25588 Da

IUPAC Name

(4E,6E)-9-[(1R,2R,4aS,8aR)-1,6-dimethyl-2-propyl-1,2,4a,5,8,8a-hexahydronaphthalen-1-yl]-8-methylnona-2,4,6,8-tetraenoic acid

Traditional Name

(4E,6E)-9-[(1R,2R,4aS,8aR)-1,6-dimethyl-2-propyl-4a,5,8,8a-tetrahydro-2H-naphthalen-1-yl]-8-methylnona-2,4,6,8-tetraenoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C25H34O2/c1-5-10-22-15-14-21-17-19(2)13-16-23(21)25(22,4)18-20(3)11-8-6-7-9-12-24(26)27/h6-9,11-15,18,21-23H,5,10,16-17H2,1-4H3,(H,26,27)/b7-6+,11-8+,12-9+,20-18+/t21-,22-,23-,25-/m1/s1

InChI Key

LRLMBKDNFKCUAP-DPNAJYCGSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Penicillium	NPAtlas	20940725
Talaromyces verruculosus	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	7.13	ALOGPS
logP	6.34	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	4.89	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	120.59 m³·mol⁻¹	ChemAxon
Polarizability	46.38 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

NPAtlas ID

NPA003091

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28288359

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

50925583

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sakamoto S, Kojima F, Igarashi M, Sawa R, Umekita M, Kubota Y, Nakae K, Yamaguchi S, Adachi H, Nishimura Y, Akamatsu Y: Decalpenic acid, a novel small molecule from Penicillium verruculosum CR37010, induces early osteoblastic markers in pluripotent mesenchymal cells. J Antibiot (Tokyo). 2010 Dec;63(12):703-8. doi: 10.1038/ja.2010.114. Epub 2010 Oct 13. [PubMed:20940725 ]
Han QQ, Du Y, Yang PS: The role of small molecules in bone regeneration. Future Med Chem. 2013 Sep;5(14):1671-84. doi: 10.4155/fmc.13.133. [PubMed:24047272 ]
Wright GD, Yoshida M: First JA medal goes to a paper on decalpenic acid. J Antibiot (Tokyo). 2012 Dec;65(12):591-2. doi: 10.1038/ja.2012.100. [PubMed:23258426 ]
Sakamoto S, Kojima F, Momose I, Kawada M, Adachi H, Nishimura Y: Decalpenic acid induces early osteoblastic markers in pluripotent mesenchymal cells via activation of retinoic acid receptor gamma. Biochem Biophys Res Commun. 2012 Jun 15;422(4):751-7. doi: 10.1016/j.bbrc.2012.05.075. Epub 2012 May 19. [PubMed:22618236 ]

Showing NP-Card for Decalpenic acid (NP0009502)

MOL for NP0009502 (Decalpenic acid)

3D MOL for NP0009502 (Decalpenic acid)

3D SDF for NP0009502 (Decalpenic acid)

3D-SDF for NP0009502 (Decalpenic acid)

PDB for NP0009502 (Decalpenic acid)

3D PDB for NP0009502 (Decalpenic acid)

SMILES for NP0009502 (Decalpenic acid)

INCHI for NP0009502 (Decalpenic acid)

Structure for NP0009502 (Decalpenic acid)

3D Structure for NP0009502 (Decalpenic acid)