NP-MRD: Showing NP-Card for eremofarfuginoic acid (NP0039728)

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Record Information

Version

2.0

Created at

2021-06-20 22:04:32 UTC

Updated at

2021-06-30 00:13:13 UTC

NP-MRD ID

NP0039728

Secondary Accession Numbers

None

Natural Product Identification

Common Name

eremofarfuginoic acid

Provided By

JEOL Database JEOL Logo

Description

Eremofarfuginoic acid, also known as eremofarfuginoate, belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. eremofarfuginoic acid is found in Farfugium japonicum. eremofarfuginoic acid was first documented in 2010 (Tori, M., et al.). Based on a literature review very few articles have been published on Eremofarfuginoic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212100043D          

 53 54  0  0  0  0            999 V2000
   -4.8184   -2.0958    1.6232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3669   -1.8554    3.0299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2648   -1.1995    3.4440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9507   -1.0093    4.8989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2623   -0.6762    2.4749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9259   -1.2413    1.4464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7805    0.5093    2.9296 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8132    1.1578    2.0824 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8255    2.6452    2.4276 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1680    3.4176    1.5735 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5996    2.8321    1.6136 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4816    3.5819    0.6075 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1835    3.2009   -0.8279 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4862    3.9535   -1.7537 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5719    1.8601   -1.1208 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2641    1.6035   -2.5864 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8830    0.1663   -2.9447 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1286    2.5244   -3.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
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  9  8  1  0  0  0  0
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M  END

     RDKit          3D

 53 54  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306212100043D          

 53 54  0  0  0  0            999 V2000
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   -0.0584   -0.1342   -2.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6660   -0.5382   -2.6447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6304    3.3708   -4.4685 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9704    0.0126   -0.3093 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4449    1.0675    2.6258 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8020    1.0768    0.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0795   -0.3537    1.6309 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5563   -0.4978    1.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9022   -0.0894    3.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1851    1.5049    4.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2174    0.0380    4.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0  0  0  0
 24 25  1  0  0  0  0
  9 10  1  0  0  0  0
  7  5  1  0  0  0  0
  8 24  1  0  0  0  0
  5  3  1  0  0  0  0
 11 12  1  0  0  0  0
  5  6  2  0  0  0  0
 22 21  1  0  0  0  0
  3  4  1  0  0  0  0
 21 15  2  0  0  0  0
  3  2  2  0  0  0  0
 13 12  1  0  0  0  0
  2  1  1  0  0  0  0
 13 15  1  0  0  0  0
 11 38  1  1  0  0  0
 24 22  1  0  0  0  0
 13 14  2  0  0  0  0
 11 10  1  0  0  0  0
 15 16  1  0  0  0  0
 11 22  1  0  0  0  0
 16 17  1  0  0  0  0
  8  7  1  0  0  0  0
 16 18  1  0  0  0  0
 18 20  1  0  0  0  0
 22 23  1  1  0  0  0
 18 19  2  0  0  0  0
  9 34  1  0  0  0  0
  9 35  1  0  0  0  0
  8 33  1  6  0  0  0
 24 50  1  6  0  0  0
 10 36  1  0  0  0  0
 10 37  1  0  0  0  0
 21 46  1  0  0  0  0
 12 39  1  0  0  0  0
 12 40  1  0  0  0  0
 23 47  1  0  0  0  0
 23 48  1  0  0  0  0
 23 49  1  0  0  0  0
 25 51  1  0  0  0  0
 25 52  1  0  0  0  0
 25 53  1  0  0  0  0
  4 30  1  0  0  0  0
  4 31  1  0  0  0  0
  4 32  1  0  0  0  0
  2 29  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
 16 41  1  6  0  0  0
 17 42  1  0  0  0  0
 17 43  1  0  0  0  0
 17 44  1  0  0  0  0
 20 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0039728

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O5/c1-6-11(2)19(24)25-17-8-7-14-9-16(21)15(12(3)18(22)23)10-20(14,5)13(17)4/h6,10,12-14,17H,7-9H2,1-5H3,(H,22,23)/b11-6-/t12-,13+,14-,17+,20-/m1/s1

> <INCHI_KEY>
XMXSEIHUFASIQO-WEZYICSOSA-N

> <FORMULA>
C20H28O5

> <MOLECULAR_WEIGHT>
348.439

> <EXACT_MASS>
348.193674002

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
38.02963567891986

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-2-[(4aR,7S,8R,8aR)-8,8a-dimethyl-7-{[(2Z)-2-methylbut-2-enoyl]oxy}-3-oxo-3,4,4a,5,6,7,8,8a-octahydronaphthalen-2-yl]propanoic acid

> <ALOGPS_LOGP>
3.73

> <JCHEM_LOGP>
4.039569696

> <ALOGPS_LOGS>
-3.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.228090141936459

> <JCHEM_PKA_STRONGEST_BASIC>
-5.787684045662268

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
95.48169999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.40e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-[(4aR,7S,8R,8aR)-8,8a-dimethyl-7-{[(2Z)-2-methylbut-2-enoyl]oxy}-3-oxo-4,4a,5,6,7,8-hexahydronaphthalen-2-yl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 53 54  0  0  0  0  0  0  0  0999 V2000
   -4.8184   -2.0958    1.6232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3669   -1.8554    3.0299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2648   -1.1995    3.4440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9507   -1.0093    4.8989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2623   -0.6762    2.4749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9259   -1.2413    1.4464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7805    0.5093    2.9296 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8132    1.1578    2.0824 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8255    2.6452    2.4276 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1680    3.4176    1.5735 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5996    2.8321    1.6136 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4816    3.5819    0.6075 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1835    3.2009   -0.8279 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4862    3.9535   -1.7537 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5719    1.8601   -1.1208 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2641    1.6035   -2.5864 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8830    0.1663   -2.9447 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1286    2.5244   -3.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7388    3.0099   -2.3018 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1165    2.7488   -4.3433 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3700    1.0044   -0.0997 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6530    1.2939    1.3701 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0715    0.7429    1.6486 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6016    0.5554    2.2723 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9977    0.5094    3.7622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8928   -1.8963    1.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6481   -3.1407    1.3480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3265   -1.4507    0.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0433   -2.2539    3.7847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9350   -1.3537    5.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6337   -1.5748    5.5420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0317    0.0460    5.1789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1356    1.0540    1.0377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6131    2.7981    3.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8347    3.0484    2.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1927    4.4606    1.9132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2106    3.4451    0.5449 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9980    3.0425    2.6154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3291    4.6626    0.7131 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5425    3.3819    0.7929 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1558    1.8684   -3.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7422    0.0625   -4.0267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0584   -0.1342   -2.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6660   -0.5382   -2.6447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6304    3.3708   -4.4685 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9704    0.0126   -0.3093 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4449    1.0675    2.6258 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8020    1.0768    0.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0795   -0.3537    1.6309 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5563   -0.4978    1.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9022   -0.0894    3.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1851    1.5049    4.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2174    0.0380    4.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
 24 25  1  0
  9 10  1  0
  7  5  1  0
  8 24  1  0
  5  3  1  0
 11 12  1  0
  5  6  2  0
 22 21  1  0
  3  4  1  0
 21 15  2  0
  3  2  2  0
 13 12  1  0
  2  1  1  0
 13 15  1  0
 11 38  1  1
 24 22  1  0
 13 14  2  0
 11 10  1  0
 15 16  1  0
 11 22  1  0
 16 17  1  0
  8  7  1  0
 16 18  1  0
 18 20  1  0
 22 23  1  1
 18 19  2  0
  9 34  1  0
  9 35  1  0
  8 33  1  6
 24 50  1  6
 10 36  1  0
 10 37  1  0
 21 46  1  0
 12 39  1  0
 12 40  1  0
 23 47  1  0
 23 48  1  0
 23 49  1  0
 25 51  1  0
 25 52  1  0
 25 53  1  0
  4 30  1  0
  4 31  1  0
  4 32  1  0
  2 29  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 16 41  1  6
 17 42  1  0
 17 43  1  0
 17 44  1  0
 20 45  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      -4.818  -2.096   1.623  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.367  -1.855   3.030  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.265  -1.200   3.444  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.951  -1.009   4.899  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.262  -0.676   2.475  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.926  -1.241   1.446  0.00  0.00           O+0
HETATM    7  O   UNK     0      -1.781   0.509   2.930  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.813   1.158   2.082  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.826   2.645   2.428  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.168   3.418   1.573  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.600   2.832   1.614  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.482   3.582   0.608  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.184   3.201  -0.828  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.486   3.954  -1.754  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.572   1.860  -1.121  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.264   1.603  -2.586  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.883   0.166  -2.945  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.129   2.524  -3.012  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.739   3.010  -2.302  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.117   2.749  -4.343  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.370   1.004  -0.100  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.653   1.294   1.370  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.071   0.743   1.649  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.602   0.555   2.272  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.998   0.509   3.762  0.00  0.00           C+0
HETATM   26  H   UNK     0      -5.893  -1.896   1.550  0.00  0.00           H+0
HETATM   27  H   UNK     0      -4.648  -3.141   1.348  0.00  0.00           H+0
HETATM   28  H   UNK     0      -4.327  -1.451   0.892  0.00  0.00           H+0
HETATM   29  H   UNK     0      -5.043  -2.254   3.785  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.935  -1.354   5.120  0.00  0.00           H+0
HETATM   31  H   UNK     0      -3.634  -1.575   5.542  0.00  0.00           H+0
HETATM   32  H   UNK     0      -3.032   0.046   5.179  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.136   1.054   1.038  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.613   2.798   3.493  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.835   3.048   2.277  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.193   4.461   1.913  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.211   3.445   0.545  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.998   3.042   2.615  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.329   4.663   0.713  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.543   3.382   0.793  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.156   1.868  -3.170  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.742   0.063  -4.027  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.058  -0.134  -2.470  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.666  -0.538  -2.645  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.630   3.371  -4.468  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.970   0.013  -0.309  0.00  0.00           H+0
HETATM   47  H   UNK     0       3.445   1.067   2.626  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.802   1.077   0.903  0.00  0.00           H+0
HETATM   49  H   UNK     0       3.079  -0.354   1.631  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.556  -0.498   1.961  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.902  -0.089   3.909  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.185   1.505   4.174  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.217   0.038   4.368  0.00  0.00           H+0
CONECT    1    2   26   27   28                                             
CONECT    2    3    1   29                                                  
CONECT    3    5    4    2                                                  
CONECT    4    3   30   31   32                                             
CONECT    5    7    3    6                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    9   24    7   33                                             
CONECT    9    8   10   34   35                                             
CONECT   10    9   11   36   37                                             
CONECT   11   12   38   10   22                                             
CONECT   12   11   13   39   40                                             
CONECT   13   12   15   14                                                  
CONECT   14   13                                                            
CONECT   15   21   13   16                                                  
CONECT   16   15   17   18   41                                             
CONECT   17   16   42   43   44                                             
CONECT   18   16   20   19                                                  
CONECT   19   18                                                            
CONECT   20   18   45                                                       
CONECT   21   22   15   46                                                  
CONECT   22   21   24   11   23                                             
CONECT   23   22   47   48   49                                             
CONECT   24   25    8   22   50                                             
CONECT   25   24   51   52   53                                             
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    2                                                            
CONECT   30    4                                                            
CONECT   31    4                                                            
CONECT   32    4                                                            
CONECT   33    8                                                            
CONECT   34    9                                                            
CONECT   35    9                                                            
CONECT   36   10                                                            
CONECT   37   10                                                            
CONECT   38   11                                                            
CONECT   39   12                                                            
CONECT   40   12                                                            
CONECT   41   16                                                            
CONECT   42   17                                                            
CONECT   43   17                                                            
CONECT   44   17                                                            
CONECT   45   20                                                            
CONECT   46   21                                                            
CONECT   47   23                                                            
CONECT   48   23                                                            
CONECT   49   23                                                            
CONECT   50   24                                                            
CONECT   51   25                                                            
CONECT   52   25                                                            
CONECT   53   25                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  108    0
END

RDKit          3D

53 54  0  0  0  0  0  0  0  0999 V2000
   -4.8184   -2.0958    1.6232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3669   -1.8554    3.0299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2648   -1.1995    3.4440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9507   -1.0093    4.8989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2623   -0.6762    2.4749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9259   -1.2413    1.4464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7805    0.5093    2.9296 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8132    1.1578    2.0824 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8255    2.6452    2.4276 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1680    3.4176    1.5735 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5996    2.8321    1.6136 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4816    3.5819    0.6075 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1835    3.2009   -0.8279 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4862    3.9535   -1.7537 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5719    1.8601   -1.1208 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2641    1.6035   -2.5864 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8830    0.1663   -2.9447 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1286    2.5244   -3.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7388    3.0099   -2.3018 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1165    2.7488   -4.3433 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3700    1.0044   -0.0997 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6530    1.2939    1.3701 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0715    0.7429    1.6486 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6016    0.5554    2.2723 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9977    0.5094    3.7622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8928   -1.8963    1.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6481   -3.1407    1.3480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3265   -1.4507    0.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0433   -2.2539    3.7847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9350   -1.3537    5.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6337   -1.5748    5.5420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0317    0.0460    5.1789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1356    1.0540    1.0377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6131    2.7981    3.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8347    3.0484    2.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1927    4.4606    1.9132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2106    3.4451    0.5449 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9980    3.0425    2.6154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3291    4.6626    0.7131 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5425    3.3819    0.7929 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1558    1.8684   -3.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7422    0.0625   -4.0267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0584   -0.1342   -2.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6660   -0.5382   -2.6447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6304    3.3708   -4.4685 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9704    0.0126   -0.3093 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4449    1.0675    2.6258 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8020    1.0768    0.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0795   -0.3537    1.6309 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5563   -0.4978    1.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9022   -0.0894    3.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1851    1.5049    4.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2174    0.0380    4.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
 24 25  1  0
  9 10  1  0
  7  5  1  0
  8 24  1  0
  5  3  1  0
 11 12  1  0
  5  6  2  0
 22 21  1  0
  3  4  1  0
 21 15  2  0
  3  2  2  0
 13 12  1  0
  2  1  1  0
 13 15  1  0
 11 38  1  1
 24 22  1  0
 13 14  2  0
 11 10  1  0
 15 16  1  0
 11 22  1  0
 16 17  1  0
  8  7  1  0
 16 18  1  0
 18 20  1  0
 22 23  1  1
 18 19  2  0
  9 34  1  0
  9 35  1  0
  8 33  1  6
 24 50  1  6
 10 36  1  0
 10 37  1  0
 21 46  1  0
 12 39  1  0
 12 40  1  0
 23 47  1  0
 23 48  1  0
 23 49  1  0
 25 51  1  0
 25 52  1  0
 25 53  1  0
  4 30  1  0
  4 31  1  0
  4 32  1  0
  2 29  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 16 41  1  6
 17 42  1  0
 17 43  1  0
 17 44  1  0
 20 45  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
Eremofarfuginoate	Generator

Chemical Formula

C₂₀H₂₈O₅

Average Mass

348.4390 Da

Monoisotopic Mass

348.19367 Da

IUPAC Name

(2R)-2-[(4aR,7S,8R,8aR)-8,8a-dimethyl-7-{[(2Z)-2-methylbut-2-enoyl]oxy}-3-oxo-3,4,4a,5,6,7,8,8a-octahydronaphthalen-2-yl]propanoic acid

Traditional Name

(2R)-2-[(4aR,7S,8R,8aR)-8,8a-dimethyl-7-{[(2Z)-2-methylbut-2-enoyl]oxy}-3-oxo-4,4a,5,6,7,8-hexahydronaphthalen-2-yl]propanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H28O5/c1-6-11(2)19(24)25-17-8-7-14-9-16(21)15(12(3)18(22)23)10-20(14,5)13(17)4/h6,10,12-14,17H,7-9H2,1-5H3,(H,22,23)/b11-6-/t12-,13+,14-,17+,20-/m1/s1

InChI Key

XMXSEIHUFASIQO-WEZYICSOSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Farfugium japonicum	JEOL database	Tori, M., et al, Tetrahedron 66, 5235 (2010)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Eremophilane sesquiterpenoid
Fatty acid ester
Cyclohexenone
Dicarboxylic acid or derivatives
Fatty acyl
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Ketone
Cyclic ketone
Carboxylic acid
Carboxylic acid derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.73	ALOGPS
logP	4.04	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	4.23	ChemAxon
pKa (Strongest Basic)	-5.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	95.48 m³·mol⁻¹	ChemAxon
Polarizability	38.03 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

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

101517804

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tori, M., et al. (2010). Tori, M., et al, Tetrahedron 66, 5235 (2010). Tetrahedron.

Showing NP-Card for eremofarfuginoic acid (NP0039728)

MOL for NP0039728 (eremofarfuginoic acid)

3D MOL for NP0039728 (eremofarfuginoic acid)

3D SDF for NP0039728 (eremofarfuginoic acid)

3D-SDF for NP0039728 (eremofarfuginoic acid)

PDB for NP0039728 (eremofarfuginoic acid)

3D PDB for NP0039728 (eremofarfuginoic acid)

SMILES for NP0039728 (eremofarfuginoic acid)

INCHI for NP0039728 (eremofarfuginoic acid)

Structure for NP0039728 (eremofarfuginoic acid)

3D Structure for NP0039728 (eremofarfuginoic acid)