NP-MRD: Showing NP-Card for methyl (1r,2s,3s,6r,7s,13r)-6-ethenyl-10-methoxy-2,6-dimethyl-8,15-dioxo-9,14-dioxatetracyclo[10.3.1.0³,¹³.0⁷,¹³]hexadeca-10,12(16)-diene-2-carboxylate (NP0153909)

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Record Information

Version

2.0

Created at

2022-09-02 10:38:31 UTC

Updated at

2022-09-02 10:38:31 UTC

NP-MRD ID

NP0153909

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1r,2s,3s,6r,7s,13r)-6-ethenyl-10-methoxy-2,6-dimethyl-8,15-dioxo-9,14-dioxatetracyclo[10.3.1.0³,¹³.0⁷,¹³]hexadeca-10,12(16)-diene-2-carboxylate

Description

Basiliolide B belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. methyl (1r,2s,3s,6r,7s,13r)-6-ethenyl-10-methoxy-2,6-dimethyl-8,15-dioxo-9,14-dioxatetracyclo[10.3.1.0³,¹³.0⁷,¹³]hexadeca-10,12(16)-diene-2-carboxylate is found in Thapsia garganica. methyl (1r,2s,3s,6r,7s,13r)-6-ethenyl-10-methoxy-2,6-dimethyl-8,15-dioxo-9,14-dioxatetracyclo[10.3.1.0³,¹³.0⁷,¹³]hexadeca-10,12(16)-diene-2-carboxylate was first documented in 2006 (PMID: 16840645). Based on a literature review a small amount of articles have been published on Basiliolide B (PMID: 28252297) (PMID: 21442697) (PMID: 25159722) (PMID: 19053740).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022212382D          

 28 31  0  0  1  0            999 V2000
    4.0574   -1.6738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4936   -0.9735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1053   -0.2456    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9003   -0.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4657   -0.7953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8008   -0.2830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7820    0.5723    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9317    0.6455    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8425   -0.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1137    0.7531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7978    1.5152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6116    0.0984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9275   -0.6637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0578    1.4632    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8867    1.6110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7140    2.0024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5086    2.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2453    1.9337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8879    2.4512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6573    2.1534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4988    1.1235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9287    0.4982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2078   -0.2782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0615    0.6214    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3836    1.2511    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8960    2.1579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0296    2.2963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4837    2.9148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 24 22  1  1  0  0  0
  3 24  1  0  0  0  0
 24 25  1  0  0  0  0
 16 25  1  0  0  0  0
  7 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 14 27  1  0  0  0  0
 27 28  2  0  0  0  0
M  END

     RDKit          2D

 52 55  0  0  0  0  0  0  0  0999 V2000
   -2.4200   -5.8874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1595   -4.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500   -3.8971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4895   -5.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -3.8971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000   -2.5981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6491   -0.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6491    0.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1106    0.6268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3886    2.4414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5377    3.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500    1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6768    1.1977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2980    0.0973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7314    0.5394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9707   -0.3056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2698    0.4444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5688   -0.3056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0828   -1.8014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9832   -2.8216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3093   -3.5491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000   -2.5981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500   -1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3333   -0.5942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3479    0.5857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000    2.5981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8296   -6.4004    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2709   -6.8515    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9133   -4.1507    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2291   -6.8515    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0084   -5.2959    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8598   -5.9845    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6715   -5.3951    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1595   -4.4101    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6491   -3.5623    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9183   -2.1098    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2388   -1.4819    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7981   -1.9284    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7461    0.0588    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9916   -2.3124    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6867    4.3698    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5735    4.5546    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5018    2.2565    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1634    2.7410    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6255   -1.3311    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9549    2.0227    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8678   -1.0556    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3188    0.9935    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8188   -1.6046    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4585   -3.7519    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 10  1  0
 10 11  2  0
  8 10  1  1
  8  9  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  1  0
  3  2  1  6
  2  1  2  3
  3 24  1  0
 24 22  1  0
 22 23  2  0
 22 21  1  0
 21 18  1  0
 18 19  1  0
 19 20  1  0
 18 17  2  0
 17 16  1  0
 16 15  2  0
 15 14  1  0
 14 27  1  0
 27 28  2  0
 27 26  1  0
 25 26  1  6
 14  8  1  0
 25  7  1  0
 25 24  1  0
 25 16  1  0
 13 43  1  0
 13 44  1  0
 13 45  1  0
  9 40  1  0
  9 41  1  0
  9 42  1  0
  7 39  1  1
  6 37  1  0
  6 38  1  0
  5 35  1  0
  5 36  1  0
  4 32  1  0
  4 33  1  0
  4 34  1  0
  2 31  1  0
  1 29  1  0
  1 30  1  0
 24 52  1  1
 20 49  1  0
 20 50  1  0
 20 51  1  0
 17 48  1  0
 15 47  1  0
 14 46  1  1
M  END


  Mrv1652309022212382D          

 28 31  0  0  1  0            999 V2000
    4.0574   -1.6738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4936   -0.9735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1053   -0.2456    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9003   -0.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4657   -0.7953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8008   -0.2830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7820    0.5723    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9317    0.6455    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8425   -0.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1137    0.7531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7978    1.5152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6116    0.0984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9275   -0.6637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0578    1.4632    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8867    1.6110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7140    2.0024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5086    2.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2453    1.9337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8879    2.4512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6573    2.1534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4988    1.1235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9287    0.4982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2078   -0.2782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0615    0.6214    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3836    1.2511    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8960    2.1579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0296    2.2963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4837    2.9148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 24 22  1  1  0  0  0
  3 24  1  0  0  0  0
 24 25  1  0  0  0  0
 16 25  1  0  0  0  0
  7 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 14 27  1  0  0  0  0
 27 28  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0153909

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@]1(C)[C@@H]2CC[C@](C)(C=C)[C@@H]3C(=O)OC(OC)=CC4=C[C@H]1C(=O)O[C@]234

> <INCHI_IDENTIFIER>
InChI=1S/C21H24O7/c1-6-19(2)8-7-13-20(3,18(24)26-5)12-9-11-10-14(25-4)27-17(23)15(19)21(11,13)28-16(12)22/h6,9-10,12-13,15H,1,7-8H2,2-5H3/t12-,13-,15-,19-,20+,21+/m0/s1

> <INCHI_KEY>
UTAYDCZHINEPNU-APGXBUQOSA-N

> <FORMULA>
C21H24O7

> <MOLECULAR_WEIGHT>
388.416

> <EXACT_MASS>
388.152203113

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
46.7451073984096

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,2S,3S,6R,7S,13R)-6-ethenyl-10-methoxy-2,6-dimethyl-8,15-dioxo-9,14-dioxatetracyclo[10.3.1.0^{3,13}.0^{7,13}]hexadeca-10,12(16)-diene-2-carboxylate

> <ALOGPS_LOGP>
2.59

> <JCHEM_LOGP>
2.460371742333332

> <ALOGPS_LOGS>
-3.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-5.03140754375149

> <JCHEM_POLAR_SURFACE_AREA>
88.13

> <JCHEM_REFRACTIVITY>
108.12540000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.37e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,2S,3S,6R,7S,13R)-6-ethenyl-10-methoxy-2,6-dimethyl-8,15-dioxo-9,14-dioxatetracyclo[10.3.1.0^{3,13}.0^{7,13}]hexadeca-10,12(16)-diene-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       7.574  -3.124   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.388  -1.817   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.663  -0.459   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.147  -0.047   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.469  -1.485   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.228  -0.528   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.193   1.068   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.606   1.205   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.439  -0.326   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.079   1.406   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.489   2.828   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.142   0.184   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.731  -1.239   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.841   2.731   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.389   3.007   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.933   3.738   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.416   4.393   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.791   3.610   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.991   4.576   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      12.427   4.020   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.264   2.097   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.200   0.930   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       9.721  -0.519   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       7.582   1.160   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.316   2.335   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.406   4.028   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.789   4.286   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.770   5.441   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   24                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   25                                                  
CONECT    8    7    9   10   14                                             
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12                                                            
CONECT   14    8   15   27                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   25                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22    3   25                                                  
CONECT   25   24   16    7   26                                             
CONECT   26   25   27                                                       
CONECT   27   26   14   28                                                  
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Value	Source
(±)-epi-8-basiliolide b	MeSH

Chemical Formula

C₂₁H₂₄O₇

Average Mass

388.4160 Da

Monoisotopic Mass

388.15220 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@]1(C)[C@@H]2CC[C@](C)(C=C)[C@@H]3C(=O)OC(OC)=CC4=C[C@H]1C(=O)O[C@]234

InChI Identifier

InChI=1S/C21H24O7/c1-6-19(2)8-7-13-20(3,18(24)26-5)12-9-11-10-14(25-4)27-17(23)15(19)21(11,13)28-16(12)22/h6,9-10,12-13,15H,1,7-8H2,2-5H3/t12-,13-,15-,19-,20+,21+/m0/s1

InChI Key

UTAYDCZHINEPNU-APGXBUQOSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Thapsia garganica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Delta valerolactone
Dihydropyranone
Delta_valerolactone
Oxane
Pyran
Methyl ester
Lactone
Ketene acetal or derivatives
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	2.59	ALOGPS
logS	-4	ALOGPS

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

23326775

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21593994

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liang X, Zhou L, Min L, Ye W, Bao W, Ma W, Yang Q, Qiao F, Zhang X, Lee CS: Diastereoselective Total Synthesis of (+/-)-Basiliolide B and (+/-)-epi-8-Basiliolide B. J Org Chem. 2017 Apr 7;82(7):3463-3481. doi: 10.1021/acs.joc.6b02921. Epub 2017 Mar 15. [PubMed:28252297 ]
Nelson HM, Murakami K, Virgil SC, Stoltz BM: A general approach to the basiliolide/transtaganolide natural products: total syntheses of basiliolide B, epi-8-basiliolide B, transtaganolide C, and transtaganolide D. Angew Chem Int Ed Engl. 2011 Apr 11;50(16):3688-91. doi: 10.1002/anie.201008003. Epub 2011 Mar 25. [PubMed:21442697 ]
Navarrete C, Sancho R, Caballero FJ, Pollastro F, Fiebich BL, Sterner O, Appendino G, Munoz E: Basiliolides, a class of tetracyclic C19 dilactones from Thapsia garganica, release Ca(2+) from the endoplasmic reticulum and regulate the activity of the transcription factors nuclear factor of activated T cells, nuclear factor-kappaB, and activator protein 1 in T lymphocytes. J Pharmacol Exp Ther. 2006 Oct;319(1):422-30. doi: 10.1124/jpet.106.108209. Epub 2006 Jul 13. [PubMed:16840645 ]
Min L, Zhang Y, Liang X, Huang J, Bao W, Lee CS: A biomimetic synthesis of (+/-)-basiliolide B. Angew Chem Int Ed Engl. 2014 Oct 13;53(42):11294-7. doi: 10.1002/anie.201405770. Epub 2014 Aug 27. [PubMed:25159722 ]
Zhou X, Wu W, Liu X, Lee CS: Base-catalyzed Diels-Alder reactions of 2H-pyran-2,5-diones: a mild approach to basiliolide B. Org Lett. 2008 Dec 18;10(24):5525-8. doi: 10.1021/ol8022787. [PubMed:19053740 ]
LOTUS database [Link]

Showing NP-Card for methyl (1r,2s,3s,6r,7s,13r)-6-ethenyl-10-methoxy-2,6-dimethyl-8,15-dioxo-9,14-dioxatetracyclo[10.3.1.0³,¹³.0⁷,¹³]hexadeca-10,12(16)-diene-2-carboxylate (NP0153909)

MOL for NP0153909 (methyl (1r,2s,3s,6r,7s,13r)-6-ethenyl-10-methoxy-2,6-dimethyl-8,15-dioxo-9,14-dioxatetracyclo[10.3.1.0³,¹³.0⁷,¹³]hexadeca-10,12(16)-diene-2-carboxylate)

3D MOL for NP0153909 (methyl (1r,2s,3s,6r,7s,13r)-6-ethenyl-10-methoxy-2,6-dimethyl-8,15-dioxo-9,14-dioxatetracyclo[10.3.1.0³,¹³.0⁷,¹³]hexadeca-10,12(16)-diene-2-carboxylate)

3D SDF for NP0153909 (methyl (1r,2s,3s,6r,7s,13r)-6-ethenyl-10-methoxy-2,6-dimethyl-8,15-dioxo-9,14-dioxatetracyclo[10.3.1.0³,¹³.0⁷,¹³]hexadeca-10,12(16)-diene-2-carboxylate)

3D-SDF for NP0153909 (methyl (1r,2s,3s,6r,7s,13r)-6-ethenyl-10-methoxy-2,6-dimethyl-8,15-dioxo-9,14-dioxatetracyclo[10.3.1.0³,¹³.0⁷,¹³]hexadeca-10,12(16)-diene-2-carboxylate)

PDB for NP0153909 (methyl (1r,2s,3s,6r,7s,13r)-6-ethenyl-10-methoxy-2,6-dimethyl-8,15-dioxo-9,14-dioxatetracyclo[10.3.1.0³,¹³.0⁷,¹³]hexadeca-10,12(16)-diene-2-carboxylate)

3D PDB for NP0153909 (methyl (1r,2s,3s,6r,7s,13r)-6-ethenyl-10-methoxy-2,6-dimethyl-8,15-dioxo-9,14-dioxatetracyclo[10.3.1.0³,¹³.0⁷,¹³]hexadeca-10,12(16)-diene-2-carboxylate)

SMILES for NP0153909 (methyl (1r,2s,3s,6r,7s,13r)-6-ethenyl-10-methoxy-2,6-dimethyl-8,15-dioxo-9,14-dioxatetracyclo[10.3.1.0³,¹³.0⁷,¹³]hexadeca-10,12(16)-diene-2-carboxylate)

INCHI for NP0153909 (methyl (1r,2s,3s,6r,7s,13r)-6-ethenyl-10-methoxy-2,6-dimethyl-8,15-dioxo-9,14-dioxatetracyclo[10.3.1.0³,¹³.0⁷,¹³]hexadeca-10,12(16)-diene-2-carboxylate)

Structure for NP0153909 (methyl (1r,2s,3s,6r,7s,13r)-6-ethenyl-10-methoxy-2,6-dimethyl-8,15-dioxo-9,14-dioxatetracyclo[10.3.1.0³,¹³.0⁷,¹³]hexadeca-10,12(16)-diene-2-carboxylate)

3D Structure for NP0153909 (methyl (1r,2s,3s,6r,7s,13r)-6-ethenyl-10-methoxy-2,6-dimethyl-8,15-dioxo-9,14-dioxatetracyclo[10.3.1.0³,¹³.0⁷,¹³]hexadeca-10,12(16)-diene-2-carboxylate)