NP-MRD: Showing NP-Card for subspicatin G (NP0040220)

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Record Information

Version

2.0

Created at

2021-06-20 22:26:36 UTC

Updated at

2021-06-30 00:14:00 UTC

NP-MRD ID

NP0040220

Secondary Accession Numbers

None

Natural Product Identification

Common Name

subspicatin G

Provided By

JEOL Database JEOL Logo

Description

Subspicatin G 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. subspicatin G is found in Ligularia lamarum and Ligularia subspicata. subspicatin G was first documented in 2011 (Saito, Y., et al.). Based on a literature review very few articles have been published on Subspicatin G.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212100263D          

 53 55  0  0  0  0            999 V2000
    1.0471   -4.0871    3.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3922   -3.8233    3.7100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3192   -3.2536    2.9148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7583   -3.1296    3.3193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0282   -2.7070    1.5623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7686   -2.8591    0.6033 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1043   -1.9610    1.5926 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4634   -1.2942    0.3644 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2375   -2.2834   -0.5100 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7941   -1.6336   -1.7684 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6613   -0.3962   -1.4682 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0173   -0.8545   -0.9008 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9070    0.6505   -0.5626 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9073    1.7606   -0.1301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7357    1.3208   -1.4024 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2941    2.1861   -2.3873 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2514    2.0272   -0.5233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3038    2.9559   -0.8005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7364    3.5564   -2.0907 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0987    2.9617   -3.2194 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8878    3.2137    0.4300 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5505    0.9144    1.6523 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3317   -0.0634    0.7267 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -3.3983   -3.7168    2.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1688   -0.4337    1.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  9  8  1  0  0  0  0
  8  7  1  0  0  0  0
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 13 14  1  1  0  0  0
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  3  2  2  0  0  0  0
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  2 29  1  0  0  0  0
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M  END

     RDKit          3D

 53 55  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306212100263D          

 53 55  0  0  0  0            999 V2000
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    3.4821    2.1330   -0.9857 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4040    2.6235    0.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6202    1.3891    0.6141 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1748    0.5515   -1.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5198    2.5346   -2.8782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8181    3.4329   -2.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5052    4.6267   -2.0983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5383    3.3372   -4.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7082    3.8436    0.7456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0440    0.3796    2.3999 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2628    1.5384    2.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1688   -0.4337    1.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  9  8  1  0  0  0  0
  8  7  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 25 24  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 25 53  1  1  0  0  0
 15 17  1  0  0  0  0
 15 16  1  0  0  0  0
 23 24  1  0  0  0  0
 18 19  1  0  0  0  0
 23 17  2  0  0  0  0
  7  5  1  0  0  0  0
 11 13  1  0  0  0  0
  5  3  1  0  0  0  0
 25  8  1  0  0  0  0
  3  2  2  0  0  0  0
 25 13  1  0  0  0  0
  5  6  2  0  0  0  0
  2  1  1  0  0  0  0
  9 10  1  0  0  0  0
  3  4  1  0  0  0  0
 17 18  1  0  0  0  0
 19 20  1  0  0  0  0
  9 34  1  0  0  0  0
  9 35  1  0  0  0  0
 10 36  1  0  0  0  0
 10 37  1  0  0  0  0
 11 38  1  6  0  0  0
  8 33  1  6  0  0  0
 15 45  1  6  0  0  0
 24 51  1  0  0  0  0
 24 52  1  0  0  0  0
 21 50  1  0  0  0  0
 12 39  1  0  0  0  0
 12 40  1  0  0  0  0
 12 41  1  0  0  0  0
 14 42  1  0  0  0  0
 14 43  1  0  0  0  0
 14 44  1  0  0  0  0
 16 46  1  0  0  0  0
 19 47  1  0  0  0  0
 19 48  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
  4 30  1  0  0  0  0
  4 31  1  0  0  0  0
  4 32  1  0  0  0  0
 20 49  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0040220

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])C1=C([H])OC2=C1[C@@]([H])(O[H])[C@]1(C([H])([H])[H])[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]([H])(OC(=O)C(=C(\[H])C([H])([H])[H])\C([H])([H])[H])[C@]1([H])C2([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O5/c1-5-11(2)19(23)25-15-7-6-12(3)20(4)14(15)8-16-17(18(20)22)13(9-21)10-24-16/h5,10,12,14-15,18,21-22H,6-9H2,1-4H3/b11-5-/t12-,14-,15+,18+,20+/m0/s1

> <INCHI_KEY>
HJKOGLIIZSEPBC-SZZDAHFOSA-N

> <FORMULA>
C20H28O5

> <MOLECULAR_WEIGHT>
348.439

> <EXACT_MASS>
348.193674002

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
38.44049572030815

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S,4aR,5S,8R,8aR)-4-hydroxy-3-(hydroxymethyl)-4a,5-dimethyl-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-8-yl (2Z)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
2.93

> <JCHEM_LOGP>
2.9782741056666655

> <ALOGPS_LOGS>
-3.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.41043786953366

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.425589592962499

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9332351371878103

> <JCHEM_POLAR_SURFACE_AREA>
79.9

> <JCHEM_REFRACTIVITY>
95.20549999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.27e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S,4aR,5S,8R,8aR)-4-hydroxy-3-(hydroxymethyl)-4a,5-dimethyl-4H,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-8-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 53 55  0  0  0  0  0  0  0  0999 V2000
    1.0471   -4.0871    3.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3922   -3.8233    3.7100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3192   -3.2536    2.9148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7583   -3.1296    3.3193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0282   -2.7070    1.5623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7686   -2.8591    0.6033 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1043   -1.9610    1.5926 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4634   -1.2942    0.3644 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2375   -2.2834   -0.5100 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7941   -1.6336   -1.7684 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6613   -0.3962   -1.4682 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0173   -0.8545   -0.9008 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9070    0.6505   -0.5626 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9073    1.7606   -0.1301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7357    1.3208   -1.4024 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2941    2.1861   -2.3873 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2514    2.0272   -0.5233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3038    2.9559   -0.8005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7364    3.5564   -2.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0987    2.9617   -3.2194 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8878    3.2137    0.4300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2885    2.5094    1.4236 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3095    1.7930    0.8322 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5505    0.9144    1.6523 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3317   -0.0634    0.7267 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2685   -4.0536    2.3282 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6838   -3.3659    3.9183 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3153   -5.0904    3.7452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7046   -4.1752    4.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0780   -2.0830    3.2767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9296   -3.4852    4.3410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3983   -3.7168    2.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4441   -0.9650   -0.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5868   -3.1197   -0.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0477   -2.7380    0.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9639   -1.3606   -2.4290 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3782   -2.3749   -2.3279 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8853    0.0798   -2.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4582   -1.6323   -1.5343 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9297   -1.2600    0.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7365   -0.0300   -0.8755 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4821    2.1330   -0.9857 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4040    2.6235    0.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6202    1.3891    0.6141 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1748    0.5515   -1.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5198    2.5346   -2.8782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8181    3.4329   -2.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5052    4.6267   -2.0983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5383    3.3372   -4.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7082    3.8436    0.7456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0440    0.3796    2.3999 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2628    1.5384    2.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1688   -0.4337    1.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 21  2  0
 21 22  1  0
 22 23  1  0
  9  8  1  0
  8  7  1  0
 10 11  1  0
 11 12  1  0
 25 24  1  0
 13 14  1  1
 13 15  1  0
 25 53  1  1
 15 17  1  0
 15 16  1  0
 23 24  1  0
 18 19  1  0
 23 17  2  0
  7  5  1  0
 11 13  1  0
  5  3  1  0
 25  8  1  0
  3  2  2  0
 25 13  1  0
  5  6  2  0
  2  1  1  0
  9 10  1  0
  3  4  1  0
 17 18  1  0
 19 20  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  6
  8 33  1  6
 15 45  1  6
 24 51  1  0
 24 52  1  0
 21 50  1  0
 12 39  1  0
 12 40  1  0
 12 41  1  0
 14 42  1  0
 14 43  1  0
 14 44  1  0
 16 46  1  0
 19 47  1  0
 19 48  1  0
  2 29  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 30  1  0
  4 31  1  0
  4 32  1  0
 20 49  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       1.047  -4.087   3.398  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.392  -3.823   3.710  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.319  -3.254   2.915  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.758  -3.130   3.319  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.028  -2.707   1.562  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.769  -2.859   0.603  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.104  -1.961   1.593  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.463  -1.294   0.364  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.238  -2.283  -0.510  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.794  -1.634  -1.768  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.661  -0.396  -1.468  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.017  -0.855  -0.901  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.907   0.651  -0.563  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.907   1.761  -0.130  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.736   1.321  -1.402  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.294   2.186  -2.387  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.251   2.027  -0.523  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.304   2.956  -0.801  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.736   3.556  -2.091  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.099   2.962  -3.219  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.888   3.214   0.430  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.289   2.509   1.424  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.310   1.793   0.832  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.551   0.914   1.652  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.332  -0.063   0.727  0.00  0.00           C+0
HETATM   26  H   UNK     0       1.268  -4.054   2.328  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.684  -3.366   3.918  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.315  -5.090   3.745  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.705  -4.175   4.692  0.00  0.00           H+0
HETATM   30  H   UNK     0      -3.078  -2.083   3.277  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.930  -3.485   4.341  0.00  0.00           H+0
HETATM   32  H   UNK     0      -3.398  -3.717   2.653  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.444  -0.965  -0.157  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.587  -3.120  -0.792  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.048  -2.738   0.074  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.964  -1.361  -2.429  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.378  -2.375  -2.328  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.885   0.080  -2.433  0.00  0.00           H+0
HETATM   39  H   UNK     0       4.458  -1.632  -1.534  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.930  -1.260   0.111  0.00  0.00           H+0
HETATM   41  H   UNK     0       4.737  -0.030  -0.876  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.482   2.133  -0.986  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.404   2.624   0.317  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.620   1.389   0.614  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.175   0.552  -1.943  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.520   2.535  -2.878  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.818   3.433  -2.212  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.505   4.627  -2.098  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.538   3.337  -4.003  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.708   3.844   0.746  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.044   0.380   2.400  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.263   1.538   2.205  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.169  -0.434   1.336  0.00  0.00           H+0
CONECT    1    2   26   27   28                                             
CONECT    2    3    1   29                                                  
CONECT    3    5    2    4                                                  
CONECT    4    3   30   31   32                                             
CONECT    5    7    3    6                                                  
CONECT    6    5                                                            
CONECT    7    8    5                                                       
CONECT    8    9    7   25   33                                             
CONECT    9    8   10   34   35                                             
CONECT   10   11    9   36   37                                             
CONECT   11   10   12   13   38                                             
CONECT   12   11   39   40   41                                             
CONECT   13   14   15   11   25                                             
CONECT   14   13   42   43   44                                             
CONECT   15   13   17   16   45                                             
CONECT   16   15   46                                                       
CONECT   17   15   23   18                                                  
CONECT   18   21   19   17                                                  
CONECT   19   18   20   47   48                                             
CONECT   20   19   49                                                       
CONECT   21   18   22   50                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   17                                                  
CONECT   24   25   23   51   52                                             
CONECT   25   24   53    8   13                                             
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   12                                                            
CONECT   42   14                                                            
CONECT   43   14                                                            
CONECT   44   14                                                            
CONECT   45   15                                                            
CONECT   46   16                                                            
CONECT   47   19                                                            
CONECT   48   19                                                            
CONECT   49   20                                                            
CONECT   50   21                                                            
CONECT   51   24                                                            
CONECT   52   24                                                            
CONECT   53   25                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  110    0
END

RDKit          3D

53 55  0  0  0  0  0  0  0  0999 V2000
    1.0471   -4.0871    3.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3922   -3.8233    3.7100 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7686   -2.8591    0.6033 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4634   -1.2942    0.3644 C   0  0  2  0  0  0  0  0  0  0  0  0
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    4.0173   -0.8545   -0.9008 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9070    0.6505   -0.5626 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9073    1.7606   -0.1301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7357    1.3208   -1.4024 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2941    2.1861   -2.3873 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2514    2.0272   -0.5233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3038    2.9559   -0.8005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7364    3.5564   -2.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0987    2.9617   -3.2194 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8878    3.2137    0.4300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2885    2.5094    1.4236 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3095    1.7930    0.8322 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5505    0.9144    1.6523 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3317   -0.0634    0.7267 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2685   -4.0536    2.3282 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6838   -3.3659    3.9183 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3153   -5.0904    3.7452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7046   -4.1752    4.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0780   -2.0830    3.2767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9296   -3.4852    4.3410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3983   -3.7168    2.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4441   -0.9650   -0.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5868   -3.1197   -0.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0477   -2.7380    0.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9639   -1.3606   -2.4290 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3782   -2.3749   -2.3279 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8853    0.0798   -2.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4582   -1.6323   -1.5343 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9297   -1.2600    0.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7365   -0.0300   -0.8755 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4821    2.1330   -0.9857 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4040    2.6235    0.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6202    1.3891    0.6141 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1748    0.5515   -1.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5198    2.5346   -2.8782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8181    3.4329   -2.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5052    4.6267   -2.0983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5383    3.3372   -4.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7082    3.8436    0.7456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0440    0.3796    2.3999 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2628    1.5384    2.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1688   -0.4337    1.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 21  2  0
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  9  8  1  0
  8  7  1  0
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 15 16  1  0
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 18 19  1  0
 23 17  2  0
  7  5  1  0
 11 13  1  0
  5  3  1  0
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  3  2  2  0
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  5  6  2  0
  2  1  1  0
  9 10  1  0
  3  4  1  0
 17 18  1  0
 19 20  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  6
  8 33  1  6
 15 45  1  6
 24 51  1  0
 24 52  1  0
 21 50  1  0
 12 39  1  0
 12 40  1  0
 12 41  1  0
 14 42  1  0
 14 43  1  0
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 19 47  1  0
 19 48  1  0
  2 29  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 30  1  0
  4 31  1  0
  4 32  1  0
 20 49  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₈O₅

Average Mass

348.4390 Da

Monoisotopic Mass

348.19367 Da

IUPAC Name

(4S,4aR,5S,8R,8aR)-4-hydroxy-3-(hydroxymethyl)-4a,5-dimethyl-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-8-yl (2Z)-2-methylbut-2-enoate

Traditional Name

(4S,4aR,5S,8R,8aR)-4-hydroxy-3-(hydroxymethyl)-4a,5-dimethyl-4H,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-8-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])C1=C([H])OC2=C1[C@@]([H])(O[H])[C@]1(C([H])([H])[H])[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]([H])(OC(=O)C(=C(\[H])C([H])([H])[H])\C([H])([H])[H])[C@]1([H])C2([H])[H]

InChI Identifier

InChI=1S/C20H28O5/c1-5-11(2)19(23)25-15-7-6-12(3)20(4)14(15)8-16-17(18(20)22)13(9-21)10-24-16/h5,10,12,14-15,18,21-22H,6-9H2,1-4H3/b11-5-/t12-,14-,15+,18+,20+/m0/s1

InChI Key

HJKOGLIIZSEPBC-SZZDAHFOSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₆D₆, 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
Ligularia lamarum	JEOL database	Saito, Y., et al, Tetrahedron 67, 2220 (2011).
Ligularia subspicata	JEOL database	Saito, Y., et al, Tetrahedron 67, 2220 (2011).

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

Furoeremophilane sesquiterpenoid
Naphthofuran
Benzofuran
Fatty acid ester
Fatty acyl
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Furan
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Primary alcohol
Aromatic alcohol
Carbonyl group
Organic oxygen compound
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	2.93	ALOGPS
logP	2.98	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	13.43	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.9 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	95.21 m³·mol⁻¹	ChemAxon
Polarizability	38.44 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	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

101780477

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Saito, Y., et al. (2011). Saito, Y., et al, Tetrahedron 67, 2220 (2011).. Tetrahedron.

Showing NP-Card for subspicatin G (NP0040220)

MOL for NP0040220 (subspicatin G)

3D MOL for NP0040220 (subspicatin G)

3D SDF for NP0040220 (subspicatin G)

3D-SDF for NP0040220 (subspicatin G)

PDB for NP0040220 (subspicatin G)

3D PDB for NP0040220 (subspicatin G)

SMILES for NP0040220 (subspicatin G)

INCHI for NP0040220 (subspicatin G)

Structure for NP0040220 (subspicatin G)

3D Structure for NP0040220 (subspicatin G)