NP-MRD: Showing NP-Card for (2r,3e)-5-(3-formyl-2,6-dihydroxy-4-methylphenyl)-3-methyl-1-[(1s,2r,6r)-1,2,6-trimethyl-3-oxocyclohexyl]pent-3-en-2-yl propanoate (NP0328741)

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Record Information

Version

2.0

Created at

2022-09-12 12:29:58 UTC

Updated at

2022-09-12 12:29:58 UTC

NP-MRD ID

NP0328741

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3e)-5-(3-formyl-2,6-dihydroxy-4-methylphenyl)-3-methyl-1-[(1s,2r,6r)-1,2,6-trimethyl-3-oxocyclohexyl]pent-3-en-2-yl propanoate

Description

CYLINDROL A belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group. (2r,3e)-5-(3-formyl-2,6-dihydroxy-4-methylphenyl)-3-methyl-1-[(1s,2r,6r)-1,2,6-trimethyl-3-oxocyclohexyl]pent-3-en-2-yl propanoate is found in Thelonectria lucida. (2r,3e)-5-(3-formyl-2,6-dihydroxy-4-methylphenyl)-3-methyl-1-[(1s,2r,6r)-1,2,6-trimethyl-3-oxocyclohexyl]pent-3-en-2-yl propanoate was first documented in 2013 (PMID: 23168404). Based on a literature review very few articles have been published on CYLINDROL A (PMID: 24059235).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122214292D          

 32 33  0  0  1  0            999 V2000
    3.8743   -1.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243   -1.7605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243   -3.1895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3493   -3.1895    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7618   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3493   -1.7605    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7173   -2.2908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1246   -1.4784    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7566   -2.0087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2678   -0.6659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6358   -0.1356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8606   -0.4178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2286    0.1125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7173   -1.2302    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9421   -1.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7618   -3.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5868   -3.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3493   -4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7618   -5.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3493   -6.0474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7618   -6.7618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5868   -6.7618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3493   -7.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243   -7.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118   -8.1908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118   -6.7618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.7618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8743   -6.0474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243   -6.0474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118   -5.3329    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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  1  0  0  0
  6 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 28 31  2  0  0  0  0
 22 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  END

     RDKit          3D

 68 69  0  0  0  0  0  0  0  0999 V2000
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   -1.6050   -3.1474   -3.0668 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6120    1.4474    2.8146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9639    2.3261    1.8018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2357    3.2598    2.0763 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2786    1.9719    0.3720 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6964    2.2796    0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8329   -0.2855   -0.4235 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5235    0.0798    0.8494 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5019   -0.2581   -1.5462 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8751    0.0348   -1.8683 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9000    0.2534   -0.8854 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5271   -0.8283   -0.2733 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1187   -2.0917   -0.6192 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5046   -0.6004    0.6293 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9255    0.6734    0.9861 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0145    0.8543    1.9943 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3200    1.7522    0.3945 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7144    3.1181    0.7258 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1474    4.0945    0.1737 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2993    1.5381   -0.5483 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7301    2.6655   -1.1047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9651   -4.8260   -2.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0542    1.3928   -0.7163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6036   -0.8888   -1.3867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6127    0.4443   -2.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2582    0.8257   -1.5328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7014   -1.3493    1.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4188   -0.4055    1.7304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1389   -0.8293   -0.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8524   -1.9985    1.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8129   -0.6230    3.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1453   -0.0696    2.9530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6997    1.5846    2.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2232    1.7599    3.8063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6564    2.6125   -0.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8710    2.6965   -0.9527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4358    1.5138    0.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9783    3.1565    0.7437 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2542   -0.6448    1.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7339    0.1191    1.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8378   -0.5233   -2.4360 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2136   -0.8135   -2.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  8  7  1  6
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 14 16  1  0
 16 17  1  0
  6 18  1  0
 18 19  1  0
 18 20  2  0
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 29 30  2  0
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 31 32  1  0
 16  8  1  0
 31 22  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  2 37  1  0
  6 38  1  1
  7 39  1  0
  7 40  1  0
  9 41  1  0
  9 42  1  0
  9 43  1  0
 10 44  1  1
 11 45  1  0
 11 46  1  0
 11 47  1  0
 12 48  1  0
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 13 50  1  0
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 16 52  1  6
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 24 62  1  0
 25 63  1  0
 27 64  1  0
 27 65  1  0
 27 66  1  0
 29 67  1  0
 32 68  1  0
M  END


  Mrv1652309122214292D          

 32 33  0  0  1  0            999 V2000
    3.8743   -1.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243   -1.7605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243   -3.1895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3493   -3.1895    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7618   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3493   -1.7605    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    6.6358   -0.1356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8606   -0.4178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2286    0.1125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7173   -1.2302    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9421   -1.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.5868   -3.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3493   -4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7618   -5.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3493   -6.0474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7618   -6.7618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5868   -6.7618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3493   -7.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243   -7.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118   -8.1908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118   -6.7618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.7618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8743   -6.0474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243   -6.0474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118   -5.3329    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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
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 29 30  2  0  0  0  0
 28 31  2  0  0  0  0
 22 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0328741

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(=O)O[C@H](C[C@@]1(C)[C@H](C)CCC(=O)[C@@H]1C)C(\C)=C\CC1=C(O)C=C(C)C(C=O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H36O6/c1-7-24(30)32-23(13-26(6)17(4)9-11-21(28)18(26)5)15(2)8-10-19-22(29)12-16(3)20(14-27)25(19)31/h8,12,14,17-18,23,29,31H,7,9-11,13H2,1-6H3/b15-8+/t17-,18+,23-,26+/m1/s1

> <INCHI_KEY>
VLFRJRBSRCFKPU-AXNCTASFSA-N

> <FORMULA>
C26H36O6

> <MOLECULAR_WEIGHT>
444.568

> <EXACT_MASS>
444.251188879

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
49.30391555825865

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3E)-5-(3-formyl-2,6-dihydroxy-4-methylphenyl)-3-methyl-1-[(1S,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]pent-3-en-2-yl propanoate

> <JCHEM_LOGP>
6.322996049333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.07461836415362

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.325905799039513

> <JCHEM_PKA_STRONGEST_BASIC>
-5.749655812942868

> <JCHEM_POLAR_SURFACE_AREA>
100.9

> <JCHEM_REFRACTIVITY>
125.77369999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3E)-5-(3-formyl-2,6-dihydroxy-4-methylphenyl)-3-methyl-1-[(1S,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]pent-3-en-2-yl propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       7.232  -3.286   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.542  -4.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      10.312  -3.286   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      10.312  -5.954   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      11.852  -5.954   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.622  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.852  -3.286   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.672  -4.276   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.299  -2.760   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.479  -3.750   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.567  -1.243   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.387  -0.253   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.940  -0.780   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.760   0.210   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.672  -2.296   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.225  -2.823   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.622  -7.287   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.162  -7.287   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.852  -8.621   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.622  -9.955   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.852 -11.288   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.622 -12.622   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      14.162 -12.622   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      11.852 -13.956   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.312 -13.956   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.542 -15.289   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.542 -12.622   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.002 -12.622   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       7.232 -11.288   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      10.312 -11.288   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       9.542  -9.955   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   18                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10   16                                             
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    8   17                                                  
CONECT   17   16                                                            
CONECT   18    6   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   31                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28   22   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₆O₆

Average Mass

444.5680 Da

Monoisotopic Mass

444.25119 Da

IUPAC Name

(2R,3E)-5-(3-formyl-2,6-dihydroxy-4-methylphenyl)-3-methyl-1-[(1S,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]pent-3-en-2-yl propanoate

Traditional Name

(2R,3E)-5-(3-formyl-2,6-dihydroxy-4-methylphenyl)-3-methyl-1-[(1S,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]pent-3-en-2-yl propanoate

CAS Registry Number

Not Available

SMILES

CCC(=O)O[C@H](C[C@@]1(C)[C@H](C)CCC(=O)[C@@H]1C)C(\C)=C\CC1=C(O)C=C(C)C(C=O)=C1O

InChI Identifier

InChI=1S/C26H36O6/c1-7-24(30)32-23(13-26(6)17(4)9-11-21(28)18(26)5)15(2)8-10-19-22(29)12-16(3)20(14-27)25(19)31/h8,12,14,17-18,23,29,31H,7,9-11,13H2,1-6H3/b15-8+/t17-,18+,23-,26+/m1/s1

InChI Key

VLFRJRBSRCFKPU-AXNCTASFSA-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
Thelonectria lucida	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Hydroxybenzaldehydes

Alternative Parents

Substituents

Hydroxybenzaldehyde
Benzoyl
M-cresol
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Toluene
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Carboxylic acid ester
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	6.32	ChemAxon
pKa (Strongest Acidic)	7.33	ChemAxon
pKa (Strongest Basic)	-5.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	125.77 m³·mol⁻¹	ChemAxon
Polarizability	49.3 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8631549

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10456134

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kawaguchi M, Fukuda T, Uchida R, Nonaka K, Masuma R, Tomoda H: A new ascochlorin derivative from Cylindrocarpon sp. FKI-4602. J Antibiot (Tokyo). 2013 Jan;66(1):23-9. doi: 10.1038/ja.2012.75. Epub 2012 Nov 21. [PubMed:23168404 ]
Moorthy NS, Sousa SF, Ramos MJ, Fernandes PA: Farnesyltransferase inhibitors: a comprehensive review based on quantitative structural analysis. Curr Med Chem. 2013;20(38):4888-923. doi: 10.2174/09298673113206660262. [PubMed:24059235 ]
LOTUS database [Link]

Showing NP-Card for (2r,3e)-5-(3-formyl-2,6-dihydroxy-4-methylphenyl)-3-methyl-1-[(1s,2r,6r)-1,2,6-trimethyl-3-oxocyclohexyl]pent-3-en-2-yl propanoate (NP0328741)

MOL for NP0328741 ((2r,3e)-5-(3-formyl-2,6-dihydroxy-4-methylphenyl)-3-methyl-1-[(1s,2r,6r)-1,2,6-trimethyl-3-oxocyclohexyl]pent-3-en-2-yl propanoate)

3D MOL for NP0328741 ((2r,3e)-5-(3-formyl-2,6-dihydroxy-4-methylphenyl)-3-methyl-1-[(1s,2r,6r)-1,2,6-trimethyl-3-oxocyclohexyl]pent-3-en-2-yl propanoate)

3D SDF for NP0328741 ((2r,3e)-5-(3-formyl-2,6-dihydroxy-4-methylphenyl)-3-methyl-1-[(1s,2r,6r)-1,2,6-trimethyl-3-oxocyclohexyl]pent-3-en-2-yl propanoate)

3D-SDF for NP0328741 ((2r,3e)-5-(3-formyl-2,6-dihydroxy-4-methylphenyl)-3-methyl-1-[(1s,2r,6r)-1,2,6-trimethyl-3-oxocyclohexyl]pent-3-en-2-yl propanoate)

PDB for NP0328741 ((2r,3e)-5-(3-formyl-2,6-dihydroxy-4-methylphenyl)-3-methyl-1-[(1s,2r,6r)-1,2,6-trimethyl-3-oxocyclohexyl]pent-3-en-2-yl propanoate)

3D PDB for NP0328741 ((2r,3e)-5-(3-formyl-2,6-dihydroxy-4-methylphenyl)-3-methyl-1-[(1s,2r,6r)-1,2,6-trimethyl-3-oxocyclohexyl]pent-3-en-2-yl propanoate)

SMILES for NP0328741 ((2r,3e)-5-(3-formyl-2,6-dihydroxy-4-methylphenyl)-3-methyl-1-[(1s,2r,6r)-1,2,6-trimethyl-3-oxocyclohexyl]pent-3-en-2-yl propanoate)

INCHI for NP0328741 ((2r,3e)-5-(3-formyl-2,6-dihydroxy-4-methylphenyl)-3-methyl-1-[(1s,2r,6r)-1,2,6-trimethyl-3-oxocyclohexyl]pent-3-en-2-yl propanoate)

Structure for NP0328741 ((2r,3e)-5-(3-formyl-2,6-dihydroxy-4-methylphenyl)-3-methyl-1-[(1s,2r,6r)-1,2,6-trimethyl-3-oxocyclohexyl]pent-3-en-2-yl propanoate)

3D Structure for NP0328741 ((2r,3e)-5-(3-formyl-2,6-dihydroxy-4-methylphenyl)-3-methyl-1-[(1s,2r,6r)-1,2,6-trimethyl-3-oxocyclohexyl]pent-3-en-2-yl propanoate)