NP-MRD: Showing NP-Card for methyl 15,16-epoxy-12(R)-acetoxy-8(17),13(16),14-ent-labdatrien-19-oate (NP0030969)

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Record Information

Version

2.0

Created at

2021-06-19 22:11:12 UTC

Updated at

2021-06-29 23:59:16 UTC

NP-MRD ID

NP0030969

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 15,16-epoxy-12(R)-acetoxy-8(17),13(16),14-ent-labdatrien-19-oate

Provided By

JEOL Database JEOL Logo

Description

Methyl 15,16-epoxy-12(R)-acetoxy-8(20),13(16),14-ent-labdatrien-19-oate belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations. methyl 15,16-epoxy-12(R)-acetoxy-8(17),13(16),14-ent-labdatrien-19-oate is found in Potamogeton pectinatus. methyl 15,16-epoxy-12(R)-acetoxy-8(17),13(16),14-ent-labdatrien-19-oate was first documented in 2003 (Waridel, P., et al.). Based on a literature review very few articles have been published on Methyl 15,16-epoxy-12(R)-acetoxy-8(20),13(16),14-ent-labdatrien-19-oate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100113D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306202100113D          

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   -0.7987    2.1403   -3.8663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3605   -0.0844   -3.1328 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0867   -0.0134   -0.8864 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0893   -0.9862   -1.1701 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2589   -0.5175   -0.6211 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0530    0.6833   -0.0251 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7421    0.9875   -0.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5713   -3.2157    0.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4215   -4.3487   -0.3908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0371   -2.0063   -1.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8623   -3.7256   -0.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7945   -2.7550    0.3909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6714   -3.5505    1.4819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0322   -0.5537    1.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0474    0.6407    2.8679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5478    0.4752    3.7410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5749    1.1198    2.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7456   -3.0865    2.8405 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1736   -1.8289    3.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7379   -1.2237    5.0331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4801   -2.9473    5.1119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3026   -3.4325    3.6518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8814   -2.3445    4.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1337   -3.0096    2.2020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8833   -1.8178    3.2584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5123   -1.3896    1.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8154    2.5826    3.5386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5547    2.1240    3.6516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8946    2.7926    2.1454 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7888   -1.1351    1.3718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3450    0.1241   -0.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1054    0.9609    0.4537 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4690   -0.9856   -1.8455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6042    1.9929   -4.5914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0523    2.9925   -3.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1291    2.3291   -4.4120 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9686   -1.9164   -1.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2704   -0.8960   -0.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4270    1.9336    0.2234 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0  0  0  0
 18 19  1  0  0  0  0
 10 11  1  0  0  0  0
 19 24  1  0  0  0  0
 11  5  1  0  0  0  0
 11 12  1  0  0  0  0
  6  8  1  0  0  0  0
 19 20  1  0  0  0  0
 24 25  1  0  0  0  0
  6 17  1  0  0  0  0
  5  4  1  0  0  0  0
  4  3  1  0  0  0  0
  3  2  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 24  2  0  0  0  0
  2 17  1  0  0  0  0
  2  1  2  3  0  0  0
  6  5  1  0  0  0  0
 13 15  1  0  0  0  0
  6  7  1  1  0  0  0
 15 16  1  0  0  0  0
 13 14  2  0  0  0  0
 17 18  1  0  0  0  0
 20 21  1  0  0  0  0
  9 10  1  0  0  0  0
 21 22  1  0  0  0  0
 11 13  1  1  0  0  0
 21 23  2  0  0  0  0
  9 41  1  0  0  0  0
  9 42  1  0  0  0  0
 10 43  1  0  0  0  0
 10 44  1  0  0  0  0
  8 39  1  0  0  0  0
  8 40  1  0  0  0  0
  5 35  1  6  0  0  0
  4 33  1  0  0  0  0
  4 34  1  0  0  0  0
  3 31  1  0  0  0  0
  3 32  1  0  0  0  0
 17 51  1  1  0  0  0
  7 36  1  0  0  0  0
  7 37  1  0  0  0  0
  7 38  1  0  0  0  0
 18 52  1  0  0  0  0
 18 53  1  0  0  0  0
 19 54  1  6  0  0  0
 12 45  1  0  0  0  0
 12 46  1  0  0  0  0
 12 47  1  0  0  0  0
 25 58  1  0  0  0  0
 26 59  1  0  0  0  0
 28 60  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
 16 48  1  0  0  0  0
 16 49  1  0  0  0  0
 16 50  1  0  0  0  0
 22 55  1  0  0  0  0
 22 56  1  0  0  0  0
 22 57  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0030969

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C([H])=C1C([H])([H])C([H])([H])[C@@]2([H])[C@@](C(=O)OC([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@@]2(C([H])([H])[H])[C@]1([H])C([H])([H])[C@@]([H])(OC(=O)C([H])([H])[H])C1=C([H])OC([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H32O5/c1-15-7-8-20-22(3,10-6-11-23(20,4)21(25)26-5)18(15)13-19(28-16(2)24)17-9-12-27-14-17/h9,12,14,18-20H,1,6-8,10-11,13H2,2-5H3/t18-,19-,20-,22+,23-/m1/s1

> <INCHI_KEY>
XYXTXIACRWPXFQ-VOUHSTLWSA-N

> <FORMULA>
C23H32O5

> <MOLECULAR_WEIGHT>
388.504

> <EXACT_MASS>
388.22497413

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
42.51052486494274

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,4aS,5R,8aR)-5-[(2R)-2-(acetyloxy)-2-(furan-3-yl)ethyl]-1,4a-dimethyl-6-methylidene-decahydronaphthalene-1-carboxylate

> <ALOGPS_LOGP>
4.82

> <JCHEM_LOGP>
4.4914551493333335

> <ALOGPS_LOGS>
-4.57

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8885758354709954

> <JCHEM_POLAR_SURFACE_AREA>
65.74000000000001

> <JCHEM_REFRACTIVITY>
105.44019999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.06e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,4aS,5R,8aR)-5-[(2R)-2-(acetyloxy)-2-(furan-3-yl)ethyl]-1,4a-dimethyl-6-methylidene-hexahydro-2H-naphthalene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 60 62  0  0  0  0  0  0  0  0999 V2000
    0.5808   -3.3974    0.1083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4053   -2.4941    0.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1035    0.3692    2.7509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8263   -2.0766    3.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7489   -1.4356    2.9005 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1438   -1.9448    2.4578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0437   -0.0483    3.4985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0403    0.2142    4.6946 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3143    0.0168   -0.0643 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6373   -0.0608   -1.2799 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3633    1.0680   -2.1418 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6536    0.9074   -3.0279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7987    2.1403   -3.8663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3605   -0.0844   -3.1328 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0867   -0.0134   -0.8864 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0893   -0.9862   -1.1701 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2589   -0.5175   -0.6211 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0530    0.6833   -0.0251 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7421    0.9875   -0.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5713   -3.2157    0.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4215   -4.3487   -0.3908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0371   -2.0063   -1.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8623   -3.7256   -0.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6714   -3.5505    1.4819 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0474    0.6407    2.8679 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1736   -1.8289    3.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7379   -1.2237    5.0331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4801   -2.9473    5.1119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3026   -3.4325    3.6518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8814   -2.3445    4.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1337   -3.0096    2.2020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8833   -1.8178    3.2584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5123   -1.3896    1.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8154    2.5826    3.5386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5547    2.1240    3.6516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8946    2.7926    2.1454 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7888   -1.1351    1.3718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3450    0.1241   -0.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1054    0.9609    0.4537 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4690   -0.9856   -1.8455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6042    1.9929   -4.5914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0523    2.9925   -3.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1291    2.3291   -4.4120 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9686   -1.9164   -1.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2704   -0.8960   -0.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4270    1.9336    0.2234 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
 18 19  1  0
 10 11  1  0
 19 24  1  0
 11  5  1  0
 11 12  1  0
  6  8  1  0
 19 20  1  0
 24 25  1  0
  6 17  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 28 24  2  0
  2 17  1  0
  2  1  2  3
  6  5  1  0
 13 15  1  0
  6  7  1  1
 15 16  1  0
 13 14  2  0
 17 18  1  0
 20 21  1  0
  9 10  1  0
 21 22  1  0
 11 13  1  1
 21 23  2  0
  9 41  1  0
  9 42  1  0
 10 43  1  0
 10 44  1  0
  8 39  1  0
  8 40  1  0
  5 35  1  6
  4 33  1  0
  4 34  1  0
  3 31  1  0
  3 32  1  0
 17 51  1  1
  7 36  1  0
  7 37  1  0
  7 38  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  6
 12 45  1  0
 12 46  1  0
 12 47  1  0
 25 58  1  0
 26 59  1  0
 28 60  1  0
  1 29  1  0
  1 30  1  0
 16 48  1  0
 16 49  1  0
 16 50  1  0
 22 55  1  0
 22 56  1  0
 22 57  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       0.581  -3.397   0.108  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.405  -2.494   0.230  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.789  -2.743  -0.293  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.800  -2.668   0.844  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.723  -1.367   1.700  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.240  -1.057   2.156  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.103   0.369   2.751  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.826  -2.077   3.259  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.795  -2.141   4.438  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.235  -2.395   4.004  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.749  -1.436   2.901  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.144  -1.945   2.458  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.044  -0.048   3.498  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.040   0.214   4.695  0.00  0.00           O+0
HETATM   15  O   UNK     0      -4.359   0.850   2.521  0.00  0.00           O+0
HETATM   16  C   UNK     0      -4.671   2.156   3.006  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.222  -1.167   0.941  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.314   0.017  -0.064  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.637  -0.061  -1.280  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.363   1.068  -2.142  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.654   0.907  -3.028  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.799   2.140  -3.866  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.361  -0.084  -3.133  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.087  -0.013  -0.886  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.089  -0.986  -1.170  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.259  -0.518  -0.621  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.053   0.683  -0.025  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.742   0.988  -0.195  0.00  0.00           C+0
HETATM   29  H   UNK     0       1.571  -3.216   0.515  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.422  -4.349  -0.391  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.037  -2.006  -1.065  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.862  -3.726  -0.774  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.795  -2.755   0.391  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.671  -3.551   1.482  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.032  -0.554   1.030  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.047   0.641   2.868  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.548   0.475   3.741  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.575   1.120   2.108  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.746  -3.087   2.841  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.174  -1.829   3.639  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.738  -1.224   5.033  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.480  -2.947   5.112  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.303  -3.433   3.652  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.881  -2.345   4.890  0.00  0.00           H+0
HETATM   45  H   UNK     0      -5.134  -3.010   2.202  0.00  0.00           H+0
HETATM   46  H   UNK     0      -5.883  -1.818   3.258  0.00  0.00           H+0
HETATM   47  H   UNK     0      -5.512  -1.390   1.587  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.815   2.583   3.539  0.00  0.00           H+0
HETATM   49  H   UNK     0      -5.555   2.124   3.652  0.00  0.00           H+0
HETATM   50  H   UNK     0      -4.895   2.793   2.145  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.789  -1.135   1.372  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.345   0.124  -0.423  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.105   0.961   0.454  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.469  -0.986  -1.845  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.604   1.993  -4.591  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.052   2.993  -3.231  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.129   2.329  -4.412  0.00  0.00           H+0
HETATM   58  H   UNK     0       2.969  -1.916  -1.708  0.00  0.00           H+0
HETATM   59  H   UNK     0       5.270  -0.896  -0.574  0.00  0.00           H+0
HETATM   60  H   UNK     0       2.427   1.934   0.223  0.00  0.00           H+0
CONECT    1    2   29   30                                                  
CONECT    2    3   17    1                                                  
CONECT    3    4    2   31   32                                             
CONECT    4    5    3   33   34                                             
CONECT    5   11    4    6   35                                             
CONECT    6    8   17    5    7                                             
CONECT    7    6   36   37   38                                             
CONECT    8    9    6   39   40                                             
CONECT    9    8   10   41   42                                             
CONECT   10   11    9   43   44                                             
CONECT   11   10    5   12   13                                             
CONECT   12   11   45   46   47                                             
CONECT   13   15   14   11                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   48   49   50                                             
CONECT   17    6    2   18   51                                             
CONECT   18   19   17   52   53                                             
CONECT   19   18   24   20   54                                             
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21   55   56   57                                             
CONECT   23   21                                                            
CONECT   24   19   25   28                                                  
CONECT   25   24   26   58                                                  
CONECT   26   25   27   59                                                  
CONECT   27   26   28                                                       
CONECT   28   27   24   60                                                  
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    3                                                            
CONECT   32    3                                                            
CONECT   33    4                                                            
CONECT   34    4                                                            
CONECT   35    5                                                            
CONECT   36    7                                                            
CONECT   37    7                                                            
CONECT   38    7                                                            
CONECT   39    8                                                            
CONECT   40    8                                                            
CONECT   41    9                                                            
CONECT   42    9                                                            
CONECT   43   10                                                            
CONECT   44   10                                                            
CONECT   45   12                                                            
CONECT   46   12                                                            
CONECT   47   12                                                            
CONECT   48   16                                                            
CONECT   49   16                                                            
CONECT   50   16                                                            
CONECT   51   17                                                            
CONECT   52   18                                                            
CONECT   53   18                                                            
CONECT   54   19                                                            
CONECT   55   22                                                            
CONECT   56   22                                                            
CONECT   57   22                                                            
CONECT   58   25                                                            
CONECT   59   26                                                            
CONECT   60   28                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  124    0
END

RDKit          3D

60 62  0  0  0  0  0  0  0  0999 V2000
    0.5808   -3.3974    0.1083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4053   -2.4941    0.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7887   -2.7425   -0.2930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8002   -2.6683    0.8440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7234   -1.3672    1.7002 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2395   -1.0574    2.1562 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1035    0.3692    2.7509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8263   -2.0766    3.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7949   -2.1408    4.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2349   -2.3950    4.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7489   -1.4356    2.9005 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1438   -1.9448    2.4578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0437   -0.0483    3.4985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0403    0.2142    4.6946 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3591    0.8502    2.5208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6714    2.1564    3.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2223   -1.1674    0.9406 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3143    0.0168   -0.0643 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6373   -0.0608   -1.2799 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3633    1.0680   -2.1418 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6536    0.9074   -3.0279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7987    2.1403   -3.8663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3605   -0.0844   -3.1328 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0867   -0.0134   -0.8864 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0893   -0.9862   -1.1701 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2589   -0.5175   -0.6211 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0530    0.6833   -0.0251 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7421    0.9875   -0.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5713   -3.2157    0.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4215   -4.3487   -0.3908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0371   -2.0063   -1.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8623   -3.7256   -0.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7945   -2.7550    0.3909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6714   -3.5505    1.4819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0322   -0.5537    1.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0474    0.6407    2.8679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5478    0.4752    3.7410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5749    1.1198    2.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7456   -3.0865    2.8405 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1736   -1.8289    3.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7379   -1.2237    5.0331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4801   -2.9473    5.1119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3026   -3.4325    3.6518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8814   -2.3445    4.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1337   -3.0096    2.2020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8833   -1.8178    3.2584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5123   -1.3896    1.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8154    2.5826    3.5386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5547    2.1240    3.6516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8946    2.7926    2.1454 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7888   -1.1351    1.3718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3450    0.1241   -0.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1054    0.9609    0.4537 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4690   -0.9856   -1.8455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6042    1.9929   -4.5914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0523    2.9925   -3.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1291    2.3291   -4.4120 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9686   -1.9164   -1.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2704   -0.8960   -0.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4270    1.9336    0.2234 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
 18 19  1  0
 10 11  1  0
 19 24  1  0
 11  5  1  0
 11 12  1  0
  6  8  1  0
 19 20  1  0
 24 25  1  0
  6 17  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 28 24  2  0
  2 17  1  0
  2  1  2  3
  6  5  1  0
 13 15  1  0
  6  7  1  1
 15 16  1  0
 13 14  2  0
 17 18  1  0
 20 21  1  0
  9 10  1  0
 21 22  1  0
 11 13  1  1
 21 23  2  0
  9 41  1  0
  9 42  1  0
 10 43  1  0
 10 44  1  0
  8 39  1  0
  8 40  1  0
  5 35  1  6
  4 33  1  0
  4 34  1  0
  3 31  1  0
  3 32  1  0
 17 51  1  1
  7 36  1  0
  7 37  1  0
  7 38  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  6
 12 45  1  0
 12 46  1  0
 12 47  1  0
 25 58  1  0
 26 59  1  0
 28 60  1  0
  1 29  1  0
  1 30  1  0
 16 48  1  0
 16 49  1  0
 16 50  1  0
 22 55  1  0
 22 56  1  0
 22 57  1  0
M  END

View in JSmol

Synonyms

Value	Source
Methyl 15,16-epoxy-12(R)-acetoxy-8(20),13(16),14-ent-labdatrien-19-Oic acid	Generator

Chemical Formula

C₂₃H₃₂O₅

Average Mass

388.5040 Da

Monoisotopic Mass

388.22497 Da

IUPAC Name

methyl (1R,4aS,5R,8aR)-5-[(2R)-2-(acetyloxy)-2-(furan-3-yl)ethyl]-1,4a-dimethyl-6-methylidene-decahydronaphthalene-1-carboxylate

Traditional Name

methyl (1R,4aS,5R,8aR)-5-[(2R)-2-(acetyloxy)-2-(furan-3-yl)ethyl]-1,4a-dimethyl-6-methylidene-hexahydro-2H-naphthalene-1-carboxylate

CAS Registry Number

Not Available

SMILES

[H]C([H])=C1C([H])([H])C([H])([H])[C@@]2([H])[C@@](C(=O)OC([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@@]2(C([H])([H])[H])[C@]1([H])C([H])([H])[C@@]([H])(OC(=O)C([H])([H])[H])C1=C([H])OC([H])=C1[H]

InChI Identifier

InChI=1S/C23H32O5/c1-15-7-8-20-22(3,10-6-11-23(20,4)21(25)26-5)18(15)13-19(28-16(2)24)17-9-12-27-14-17/h9,12,14,18-20H,1,6-8,10-11,13H2,2-5H3/t18-,19-,20-,22+,23-/m1/s1

InChI Key

XYXTXIACRWPXFQ-VOUHSTLWSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, 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
Stuckenia pectinata	JEOL database	Waridel, P., et al, Phytochemistry 64, 1309 (2003)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Colensane and clerodane diterpenoids

Alternative Parents

Substituents

Clerodane diterpenoid
Dicarboxylic acid or derivatives
Heteroaromatic compound
Methyl ester
Furan
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	4.82	ALOGPS
logP	4.49	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	65.74 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	105.44 m³·mol⁻¹	ChemAxon
Polarizability	42.51 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12082402

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Waridel, P., et al. (2003). Waridel, P., et al, Phytochemistry 64, 1309 (2003) . Phytochem..

Showing NP-Card for methyl 15,16-epoxy-12(R)-acetoxy-8(17),13(16),14-ent-labdatrien-19-oate (NP0030969)

MOL for NP0030969 (methyl 15,16-epoxy-12(R)-acetoxy-8(17),13(16),14-ent-labdatrien-19-oate)

3D MOL for NP0030969 (methyl 15,16-epoxy-12(R)-acetoxy-8(17),13(16),14-ent-labdatrien-19-oate)

3D SDF for NP0030969 (methyl 15,16-epoxy-12(R)-acetoxy-8(17),13(16),14-ent-labdatrien-19-oate)

3D-SDF for NP0030969 (methyl 15,16-epoxy-12(R)-acetoxy-8(17),13(16),14-ent-labdatrien-19-oate)

PDB for NP0030969 (methyl 15,16-epoxy-12(R)-acetoxy-8(17),13(16),14-ent-labdatrien-19-oate)

3D PDB for NP0030969 (methyl 15,16-epoxy-12(R)-acetoxy-8(17),13(16),14-ent-labdatrien-19-oate)

SMILES for NP0030969 (methyl 15,16-epoxy-12(R)-acetoxy-8(17),13(16),14-ent-labdatrien-19-oate)

INCHI for NP0030969 (methyl 15,16-epoxy-12(R)-acetoxy-8(17),13(16),14-ent-labdatrien-19-oate)

Structure for NP0030969 (methyl 15,16-epoxy-12(R)-acetoxy-8(17),13(16),14-ent-labdatrien-19-oate)

3D Structure for NP0030969 (methyl 15,16-epoxy-12(R)-acetoxy-8(17),13(16),14-ent-labdatrien-19-oate)