NP-MRD: Showing NP-Card for metasequoic acid C (NP0040254)

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Record Information

Version

2.0

Created at

2021-06-20 22:28:00 UTC

Updated at

2021-06-30 00:14:03 UTC

NP-MRD ID

NP0040254

Secondary Accession Numbers

None

Natural Product Identification

Common Name

metasequoic acid C

Provided By

JEOL Database JEOL Logo

Description

Metasequoic acid C, (rel)- belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. metasequoic acid C is found in Metasequoia glyptostroboides. metasequoic acid C was first documented in 2011 (Dong, L.-B., et al.). Based on a literature review very few articles have been published on Metasequoic acid C, (rel)-.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212100283D          

 55 56  0  0  0  0            999 V2000
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   -1.5610   -1.5979    1.4338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6529   -2.7690    0.4854 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4393   -2.3926   -0.7722 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8676   -1.1184   -1.4367 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8237    0.1034   -0.4347 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2192    0.5371    0.0809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1776    1.3126   -1.1651 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7896    1.6187   -2.5345 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7675    0.4185   -3.4891 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3317    0.1543   -3.9783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4463   -0.8307   -2.8573 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9761   -0.7013   -2.9269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1229   -1.9544   -3.7004 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9312   -0.3479    0.8046 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.5525    0.4628    2.7905 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8909    0.1716    2.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5353    1.3417    1.4407 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3874   -0.9349    0.8049 O   0  0  0  0  0  0  0  0  0  0  0  0
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  2  3  1  0  0  0  0
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 18 17  1  0  0  0  0
  5 30  1  6  0  0  0
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  6  7  1  1  0  0  0
 12  5  1  0  0  0  0
 18 19  1  0  0  0  0
  6  8  1  0  0  0  0
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  2  1  2  3  0  0  0
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M  END

     RDKit          3D

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   -1.7675    0.4185   -3.4891 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306212100283D          

 55 56  0  0  0  0            999 V2000
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   -2.8189    1.9725   -2.4112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3310    0.6980   -4.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1060    1.0682   -4.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3262   -0.1937   -3.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3187   -0.5969   -4.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4760   -1.5530   -2.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3604    0.2155   -2.4832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3066   -0.7111   -3.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7225   -2.6878   -3.4845 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0292   -0.6739    0.3802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4667    1.0895    2.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2745    1.6912    1.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2554   -0.3697    3.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6812    1.3168    3.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6212    1.2526    1.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1227    1.4602    0.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3473    2.2659    1.9983 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8922   -1.8441    2.7637 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8138   -2.9629    1.5720 H   0  0  0  0  0  0  0  0  0  0  0  0
 15  2  1  0  0  0  0
  2  3  1  0  0  0  0
 15 16  1  0  0  0  0
 18 17  1  0  0  0  0
  5 30  1  6  0  0  0
  9 10  1  0  0  0  0
 17 16  1  0  0  0  0
 10 11  1  0  0  0  0
  6 15  1  0  0  0  0
 12 14  1  6  0  0  0
  9  8  1  0  0  0  0
 12 13  1  0  0  0  0
 10 12  1  0  0  0  0
  6  7  1  1  0  0  0
 12  5  1  0  0  0  0
 18 19  1  0  0  0  0
  6  8  1  0  0  0  0
  6  5  1  0  0  0  0
 20 21  1  0  0  0  0
  5  4  1  0  0  0  0
 21 22  2  0  0  0  0
  4  3  1  0  0  0  0
 21 23  1  0  0  0  0
 18 20  2  0  0  0  0
  2  1  2  3  0  0  0
  9 36  1  0  0  0  0
  9 37  1  0  0  0  0
 10 38  1  6  0  0  0
  8 34  1  0  0  0  0
  8 35  1  0  0  0  0
  4 28  1  0  0  0  0
  4 29  1  0  0  0  0
 17 49  1  0  0  0  0
 17 50  1  0  0  0  0
 16 47  1  0  0  0  0
 16 48  1  0  0  0  0
 15 46  1  6  0  0  0
 20 54  1  0  0  0  0
  3 26  1  0  0  0  0
  3 27  1  0  0  0  0
 11 39  1  0  0  0  0
 11 40  1  0  0  0  0
 11 41  1  0  0  0  0
 14 45  1  0  0  0  0
 13 42  1  0  0  0  0
 13 43  1  0  0  0  0
 13 44  1  0  0  0  0
  7 31  1  0  0  0  0
  7 32  1  0  0  0  0
  7 33  1  0  0  0  0
 19 51  1  0  0  0  0
 19 52  1  0  0  0  0
 19 53  1  0  0  0  0
 23 55  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0040254

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O3/c1-13(12-18(21)22)6-8-16-14(2)7-9-17-19(16,4)11-10-15(3)20(17,5)23/h12,15-17,23H,2,6-11H2,1,3-5H3,(H,21,22)/b13-12+/t15-,16+,17-,19-,20-/m1/s1

> <INCHI_KEY>
KKSRPYFDSRXBHV-PIGWEYSDSA-N

> <FORMULA>
C20H32O3

> <MOLECULAR_WEIGHT>
320.473

> <EXACT_MASS>
320.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
36.8442115497336

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-5-[(1S,4aR,5R,6R,8aR)-5-hydroxy-5,6,8a-trimethyl-2-methylidene-decahydronaphthalen-1-yl]-3-methylpent-2-enoic acid

> <ALOGPS_LOGP>
4.30

> <JCHEM_LOGP>
4.229303465666666

> <ALOGPS_LOGS>
-4.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.75329540236933

> <JCHEM_PKA_STRONGEST_BASIC>
-0.20082202024313223

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
93.59979999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.45e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
metasequoic acid C

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 55 56  0  0  0  0  0  0  0  0999 V2000
   -2.0537   -1.7017    2.6799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5610   -1.5979    1.4338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6529   -2.7690    0.4854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4393   -2.3926   -0.7722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8676   -1.1184   -1.4367 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8237    0.1034   -0.4347 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2192    0.5371    0.0809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1776    1.3126   -1.1651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7896    1.6187   -2.5345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7675    0.4185   -3.4891 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3317    0.1543   -3.9783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4463   -0.8307   -2.8573 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9761   -0.7013   -2.9269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1229   -1.9544   -3.7004 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9312   -0.3479    0.8046 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5805    0.7949    1.7989 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5525    0.4628    2.7905 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8909    0.1716    2.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5353    1.3417    1.4407 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4218   -1.0649    2.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6798   -1.5169    1.6016 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3874   -0.9349    0.8049 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9784   -2.7527    2.0386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0519   -0.8790    3.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5005   -2.6268    3.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1302   -3.6360    0.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6386   -3.0848    0.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3896   -3.2420   -1.4622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4966   -2.2597   -0.5185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8141   -1.3810   -1.6268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8345    0.9942   -0.6928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1294    1.2977    0.8639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7930   -0.2922    0.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2712    2.2204   -0.5572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1018    1.1354   -1.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2459    2.4593   -2.9840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8189    1.9725   -2.4112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3310    0.6980   -4.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1060    1.0682   -4.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3262   -0.1937   -3.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3187   -0.5969   -4.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4760   -1.5530   -2.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3604    0.2155   -2.4832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3066   -0.7111   -3.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7225   -2.6878   -3.4845 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0292   -0.6739    0.3802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4667    1.0895    2.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2745    1.6912    1.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2554   -0.3697    3.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6812    1.3168    3.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6212    1.2526    1.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1227    1.4602    0.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3473    2.2659    1.9983 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8922   -1.8441    2.7637 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8138   -2.9629    1.5720 H   0  0  0  0  0  0  0  0  0  0  0  0
 15  2  1  0
  2  3  1  0
 15 16  1  0
 18 17  1  0
  5 30  1  6
  9 10  1  0
 17 16  1  0
 10 11  1  0
  6 15  1  0
 12 14  1  6
  9  8  1  0
 12 13  1  0
 10 12  1  0
  6  7  1  1
 12  5  1  0
 18 19  1  0
  6  8  1  0
  6  5  1  0
 20 21  1  0
  5  4  1  0
 21 22  2  0
  4  3  1  0
 21 23  1  0
 18 20  2  0
  2  1  2  3
  9 36  1  0
  9 37  1  0
 10 38  1  6
  8 34  1  0
  8 35  1  0
  4 28  1  0
  4 29  1  0
 17 49  1  0
 17 50  1  0
 16 47  1  0
 16 48  1  0
 15 46  1  6
 20 54  1  0
  3 26  1  0
  3 27  1  0
 11 39  1  0
 11 40  1  0
 11 41  1  0
 14 45  1  0
 13 42  1  0
 13 43  1  0
 13 44  1  0
  7 31  1  0
  7 32  1  0
  7 33  1  0
 19 51  1  0
 19 52  1  0
 19 53  1  0
 23 55  1  0
  1 24  1  0
  1 25  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.054  -1.702   2.680  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.561  -1.598   1.434  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.653  -2.769   0.485  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.439  -2.393  -0.772  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.868  -1.118  -1.437  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.824   0.103  -0.435  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.219   0.537   0.081  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.178   1.313  -1.165  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.790   1.619  -2.535  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.768   0.419  -3.489  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.332   0.154  -3.978  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.446  -0.831  -2.857  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.976  -0.701  -2.927  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.123  -1.954  -3.700  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.931  -0.348   0.805  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.581   0.795   1.799  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.553   0.463   2.791  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.891   0.172   2.135  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.535   1.342   1.441  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.422  -1.065   2.222  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.680  -1.517   1.602  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.387  -0.935   0.805  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.978  -2.753   2.039  0.00  0.00           O+0
HETATM   24  H   UNK     0      -2.052  -0.879   3.385  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.501  -2.627   3.034  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.130  -3.636   0.958  0.00  0.00           H+0
HETATM   27  H   UNK     0      -0.639  -3.085   0.211  0.00  0.00           H+0
HETATM   28  H   UNK     0      -2.390  -3.242  -1.462  0.00  0.00           H+0
HETATM   29  H   UNK     0      -3.497  -2.260  -0.519  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.814  -1.381  -1.627  0.00  0.00           H+0
HETATM   31  H   UNK     0      -3.834   0.994  -0.693  0.00  0.00           H+0
HETATM   32  H   UNK     0      -3.129   1.298   0.864  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.793  -0.292   0.503  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.271   2.220  -0.557  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.102   1.135  -1.287  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.246   2.459  -2.984  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.819   1.972  -2.411  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.331   0.698  -4.391  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.106   1.068  -4.395  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.326  -0.194  -3.177  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.319  -0.597  -4.775  0.00  0.00           H+0
HETATM   42  H   UNK     0      -4.476  -1.553  -2.455  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.360   0.216  -2.483  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.307  -0.711  -3.973  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.723  -2.688  -3.485  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.029  -0.674   0.380  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.467   1.089   2.373  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.275   1.691   1.251  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.255  -0.370   3.437  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.681   1.317   3.469  0.00  0.00           H+0
HETATM   51  H   UNK     0       3.621   1.253   1.367  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.123   1.460   0.434  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.347   2.266   1.998  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.892  -1.844   2.764  0.00  0.00           H+0
HETATM   55  H   UNK     0       4.814  -2.963   1.572  0.00  0.00           H+0
CONECT    1    2   24   25                                                  
CONECT    2   15    3    1                                                  
CONECT    3    2    4   26   27                                             
CONECT    4    5    3   28   29                                             
CONECT    5   30   12    6    4                                             
CONECT    6   15    7    8    5                                             
CONECT    7    6   31   32   33                                             
CONECT    8    9    6   34   35                                             
CONECT    9   10    8   36   37                                             
CONECT   10    9   11   12   38                                             
CONECT   11   10   39   40   41                                             
CONECT   12   14   13   10    5                                             
CONECT   13   12   42   43   44                                             
CONECT   14   12   45                                                       
CONECT   15    2   16    6   46                                             
CONECT   16   15   17   47   48                                             
CONECT   17   18   16   49   50                                             
CONECT   18   17   19   20                                                  
CONECT   19   18   51   52   53                                             
CONECT   20   21   18   54                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   55                                                       
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    3                                                            
CONECT   27    3                                                            
CONECT   28    4                                                            
CONECT   29    4                                                            
CONECT   30    5                                                            
CONECT   31    7                                                            
CONECT   32    7                                                            
CONECT   33    7                                                            
CONECT   34    8                                                            
CONECT   35    8                                                            
CONECT   36    9                                                            
CONECT   37    9                                                            
CONECT   38   10                                                            
CONECT   39   11                                                            
CONECT   40   11                                                            
CONECT   41   11                                                            
CONECT   42   13                                                            
CONECT   43   13                                                            
CONECT   44   13                                                            
CONECT   45   14                                                            
CONECT   46   15                                                            
CONECT   47   16                                                            
CONECT   48   16                                                            
CONECT   49   17                                                            
CONECT   50   17                                                            
CONECT   51   19                                                            
CONECT   52   19                                                            
CONECT   53   19                                                            
CONECT   54   20                                                            
CONECT   55   23                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  112    0
END

RDKit          3D

55 56  0  0  0  0  0  0  0  0999 V2000
   -2.0537   -1.7017    2.6799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5610   -1.5979    1.4338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6529   -2.7690    0.4854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4393   -2.3926   -0.7722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8676   -1.1184   -1.4367 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8237    0.1034   -0.4347 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2192    0.5371    0.0809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1776    1.3126   -1.1651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7896    1.6187   -2.5345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7675    0.4185   -3.4891 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3317    0.1543   -3.9783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4463   -0.8307   -2.8573 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9761   -0.7013   -2.9269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1229   -1.9544   -3.7004 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9312   -0.3479    0.8046 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5805    0.7949    1.7989 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5525    0.4628    2.7905 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8909    0.1716    2.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5353    1.3417    1.4407 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4218   -1.0649    2.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6798   -1.5169    1.6016 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3874   -0.9349    0.8049 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9784   -2.7527    2.0386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0519   -0.8790    3.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5005   -2.6268    3.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1302   -3.6360    0.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6386   -3.0848    0.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3896   -3.2420   -1.4622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4966   -2.2597   -0.5185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8141   -1.3810   -1.6268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8345    0.9942   -0.6928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1294    1.2977    0.8639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7930   -0.2922    0.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2712    2.2204   -0.5572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1018    1.1354   -1.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2459    2.4593   -2.9840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8189    1.9725   -2.4112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3310    0.6980   -4.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1060    1.0682   -4.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3262   -0.1937   -3.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3187   -0.5969   -4.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4760   -1.5530   -2.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3604    0.2155   -2.4832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3066   -0.7111   -3.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7225   -2.6878   -3.4845 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0292   -0.6739    0.3802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4667    1.0895    2.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2745    1.6912    1.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2554   -0.3697    3.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6812    1.3168    3.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6212    1.2526    1.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1227    1.4602    0.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3473    2.2659    1.9983 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8922   -1.8441    2.7637 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8138   -2.9629    1.5720 H   0  0  0  0  0  0  0  0  0  0  0  0
 15  2  1  0
  2  3  1  0
 15 16  1  0
 18 17  1  0
  5 30  1  6
  9 10  1  0
 17 16  1  0
 10 11  1  0
  6 15  1  0
 12 14  1  6
  9  8  1  0
 12 13  1  0
 10 12  1  0
  6  7  1  1
 12  5  1  0
 18 19  1  0
  6  8  1  0
  6  5  1  0
 20 21  1  0
  5  4  1  0
 21 22  2  0
  4  3  1  0
 21 23  1  0
 18 20  2  0
  2  1  2  3
  9 36  1  0
  9 37  1  0
 10 38  1  6
  8 34  1  0
  8 35  1  0
  4 28  1  0
  4 29  1  0
 17 49  1  0
 17 50  1  0
 16 47  1  0
 16 48  1  0
 15 46  1  6
 20 54  1  0
  3 26  1  0
  3 27  1  0
 11 39  1  0
 11 40  1  0
 11 41  1  0
 14 45  1  0
 13 42  1  0
 13 43  1  0
 13 44  1  0
  7 31  1  0
  7 32  1  0
  7 33  1  0
 19 51  1  0
 19 52  1  0
 19 53  1  0
 23 55  1  0
  1 24  1  0
  1 25  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₂O₃

Average Mass

320.4730 Da

Monoisotopic Mass

320.23514 Da

IUPAC Name

(2E)-5-[(1S,4aR,5R,6R,8aR)-5-hydroxy-5,6,8a-trimethyl-2-methylidene-decahydronaphthalen-1-yl]-3-methylpent-2-enoic acid

Traditional Name

metasequoic acid C

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H32O3/c1-13(12-18(21)22)6-8-16-14(2)7-9-17-19(16,4)11-10-15(3)20(17,5)23/h12,15-17,23H,2,6-11H2,1,3-5H3,(H,21,22)/b13-12+/t15-,16+,17-,19-,20-/m1/s1

InChI Key

KKSRPYFDSRXBHV-PIGWEYSDSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃-CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃-CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃-CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃-CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃-CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃-CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃-CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃-CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃-CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃-CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃-CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃-CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃-CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃-CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃-CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃-CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃-CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃-CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃-CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃-CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Metasequoia glyptostroboides	JEOL database	Dong, L.-B., et al, J. Nat. Prod. 74, 234 (2011)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-chain fatty acids

Alternative Parents

Substituents

Medium-chain fatty acid
Branched fatty acid
Hydroxy fatty acid
Methyl-branched fatty acid
Unsaturated fatty acid
Cyclic alcohol
Tertiary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

carbocyclic fatty acid (CHEBI:69961 )

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	4.3	ALOGPS
logP	4.23	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	4.75	ChemAxon
pKa (Strongest Basic)	-0.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	93.6 m³·mol⁻¹	ChemAxon
Polarizability	36.84 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

26392846

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

51040468

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Dong, L.-B., et al. (2011). Dong, L.-B., et al, J. Nat. Prod. 74, 234 (2011). J. Nat. Prod..

Showing NP-Card for metasequoic acid C (NP0040254)

MOL for NP0040254 (metasequoic acid C)

3D MOL for NP0040254 (metasequoic acid C)

3D SDF for NP0040254 (metasequoic acid C)

3D-SDF for NP0040254 (metasequoic acid C)

PDB for NP0040254 (metasequoic acid C)

3D PDB for NP0040254 (metasequoic acid C)

SMILES for NP0040254 (metasequoic acid C)

INCHI for NP0040254 (metasequoic acid C)

Structure for NP0040254 (metasequoic acid C)

3D Structure for NP0040254 (metasequoic acid C)