NP-MRD: Showing NP-Card for toluccanolide A (NP0030598)

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Record Information

Version

2.0

Created at

2021-06-19 21:54:46 UTC

Updated at

2021-06-29 23:58:40 UTC

NP-MRD ID

NP0030598

Secondary Accession Numbers

None

Natural Product Identification

Common Name

toluccanolide A

Provided By

JEOL Database JEOL Logo

Description

Toluccanolide A belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. toluccanolide A is found in Senecio toluccanus. toluccanolide A was first documented in 2004 (Burgueno-Tapia, E., et al.). Based on a literature review very few articles have been published on Toluccanolide A.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192123543D          

 38 40  0  0  0  0            999 V2000
    1.5252   -3.8276    1.3858 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1068   -3.5509    1.7116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5922   -2.4296    1.9080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0290   -2.7406    2.1174 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8846   -2.0670    1.0440 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5879   -0.5791    0.9457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5949    0.3119    0.9900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4215    1.7917    0.8716 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0401    2.1912    0.3699 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9290    1.3832    1.0658 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4247    1.9866    0.6666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0934   -0.1713    0.8149 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6228   -0.5486   -0.6124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2524   -0.9678    1.8922 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1429   -0.8008    1.7008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1077   -4.1581    2.0128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8614   -4.6582    1.7943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5905   -5.8398    1.6808 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0657   -2.9388    1.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0418   -4.2373    2.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5976   -4.5582    0.5730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3544   -2.4454    3.1222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9424   -2.2554    1.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7139   -2.5382    0.0671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6219   -0.0310    1.1045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6056    2.2416    1.8545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1790    2.1939    0.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9864    2.0516   -0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9016    3.2649    0.5485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0403    1.5590    2.1461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4545    3.0513    0.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2589    1.5177    1.1909 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6032    1.9151   -0.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1869   -0.0063   -1.3788 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4391   -0.3309   -0.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7515   -1.6166   -0.8200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4862   -0.5615    2.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5836   -1.1261    2.5042 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0  0  0  0
 10 12  1  0  0  0  0
  6  7  2  0  0  0  0
  6 12  1  0  0  0  0
  8  9  1  0  0  0  0
  3  2  2  0  0  0  0
 17 16  1  0  0  0  0
 16  4  1  0  0  0  0
  8  7  1  0  0  0  0
 10 11  1  0  0  0  0
  9 10  1  0  0  0  0
 12 13  1  6  0  0  0
  6  5  1  0  0  0  0
 14 15  1  0  0  0  0
 12 14  1  0  0  0  0
  2  1  1  0  0  0  0
  4  3  1  0  0  0  0
 17  2  1  0  0  0  0
 14  3  1  0  0  0  0
 17 18  2  0  0  0  0
  8 26  1  0  0  0  0
  8 27  1  0  0  0  0
  9 28  1  0  0  0  0
  9 29  1  0  0  0  0
 10 30  1  1  0  0  0
  7 25  1  0  0  0  0
 14 37  1  1  0  0  0
  5 23  1  0  0  0  0
  5 24  1  0  0  0  0
  4 22  1  1  0  0  0
 11 31  1  0  0  0  0
 11 32  1  0  0  0  0
 11 33  1  0  0  0  0
 13 34  1  0  0  0  0
 13 35  1  0  0  0  0
 13 36  1  0  0  0  0
 15 38  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
M  END

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
    1.5252   -3.8276    1.3858 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1068   -3.5509    1.7116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5922   -2.4296    1.9080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0290   -2.7406    2.1174 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8846   -2.0670    1.0440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5879   -0.5791    0.9457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5949    0.3119    0.9900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4215    1.7917    0.8716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0401    2.1912    0.3699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9290    1.3832    1.0658 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4247    1.9866    0.6666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0934   -0.1713    0.8149 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6228   -0.5486   -0.6124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2524   -0.9678    1.8922 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1429   -0.8008    1.7008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1077   -4.1581    2.0128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8614   -4.6582    1.7943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5905   -5.8398    1.6808 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0657   -2.9388    1.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0418   -4.2373    2.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5976   -4.5582    0.5730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3544   -2.4454    3.1222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9424   -2.2554    1.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7139   -2.5382    0.0671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6219   -0.0310    1.1045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6056    2.2416    1.8545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1790    2.1939    0.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9864    2.0516   -0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9016    3.2649    0.5485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0403    1.5590    2.1461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4545    3.0513    0.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2589    1.5177    1.1909 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6032    1.9151   -0.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1869   -0.0063   -1.3788 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4391   -0.3309   -0.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7515   -1.6166   -0.8200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4862   -0.5615    2.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5836   -1.1261    2.5042 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
 10 12  1  0
  6  7  2  0
  6 12  1  0
  8  9  1  0
  3  2  2  0
 17 16  1  0
 16  4  1  0
  8  7  1  0
 10 11  1  0
  9 10  1  0
 12 13  1  6
  6  5  1  0
 14 15  1  0
 12 14  1  0
  2  1  1  0
  4  3  1  0
 17  2  1  0
 14  3  1  0
 17 18  2  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  1
  7 25  1  0
 14 37  1  1
  5 23  1  0
  5 24  1  0
  4 22  1  1
 11 31  1  0
 11 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 15 38  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
M  END


  Mrv1652306192123543D          

 38 40  0  0  0  0            999 V2000
    1.5252   -3.8276    1.3858 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1068   -3.5509    1.7116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5922   -2.4296    1.9080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0290   -2.7406    2.1174 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8846   -2.0670    1.0440 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5879   -0.5791    0.9457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5949    0.3119    0.9900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4215    1.7917    0.8716 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0401    2.1912    0.3699 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9290    1.3832    1.0658 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4247    1.9866    0.6666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0934   -0.1713    0.8149 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6228   -0.5486   -0.6124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2524   -0.9678    1.8922 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1429   -0.8008    1.7008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1077   -4.1581    2.0128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8614   -4.6582    1.7943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5905   -5.8398    1.6808 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0657   -2.9388    1.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0418   -4.2373    2.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5976   -4.5582    0.5730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3544   -2.4454    3.1222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9424   -2.2554    1.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7139   -2.5382    0.0671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6219   -0.0310    1.1045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6056    2.2416    1.8545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1790    2.1939    0.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9864    2.0516   -0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9016    3.2649    0.5485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0403    1.5590    2.1461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4545    3.0513    0.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2589    1.5177    1.1909 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6032    1.9151   -0.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1869   -0.0063   -1.3788 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4391   -0.3309   -0.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7515   -1.6166   -0.8200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4862   -0.5615    2.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5836   -1.1261    2.5042 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0  0  0  0
 10 12  1  0  0  0  0
  6  7  2  0  0  0  0
  6 12  1  0  0  0  0
  8  9  1  0  0  0  0
  3  2  2  0  0  0  0
 17 16  1  0  0  0  0
 16  4  1  0  0  0  0
  8  7  1  0  0  0  0
 10 11  1  0  0  0  0
  9 10  1  0  0  0  0
 12 13  1  6  0  0  0
  6  5  1  0  0  0  0
 14 15  1  0  0  0  0
 12 14  1  0  0  0  0
  2  1  1  0  0  0  0
  4  3  1  0  0  0  0
 17  2  1  0  0  0  0
 14  3  1  0  0  0  0
 17 18  2  0  0  0  0
  8 26  1  0  0  0  0
  8 27  1  0  0  0  0
  9 28  1  0  0  0  0
  9 29  1  0  0  0  0
 10 30  1  1  0  0  0
  7 25  1  0  0  0  0
 14 37  1  1  0  0  0
  5 23  1  0  0  0  0
  5 24  1  0  0  0  0
  4 22  1  1  0  0  0
 11 31  1  0  0  0  0
 11 32  1  0  0  0  0
 11 33  1  0  0  0  0
 13 34  1  0  0  0  0
 13 35  1  0  0  0  0
 13 36  1  0  0  0  0
 15 38  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0030598

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])C2=C(C(=O)O[C@]2([H])C([H])([H])C2=C([H])C([H])([H])C([H])([H])[C@]([H])(C([H])([H])[H])[C@@]12C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-8-5-4-6-10-7-11-12(9(2)14(17)18-11)13(16)15(8,10)3/h6,8,11,13,16H,4-5,7H2,1-3H3/t8-,11+,13+,15+/m0/s1

> <INCHI_KEY>
OGIYZEJLIRMHKE-DGFVYPATSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.322

> <EXACT_MASS>
248.141244504

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
27.27270064742851

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S,4aR,5S,9aR)-4-hydroxy-3,4a,5-trimethyl-2H,4H,4aH,5H,6H,7H,9H,9aH-naphtho[2,3-b]furan-2-one

> <ALOGPS_LOGP>
2.72

> <JCHEM_LOGP>
2.2015002796666665

> <ALOGPS_LOGS>
-2.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.519744933208194

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.543894573664538

> <JCHEM_PKA_STRONGEST_BASIC>
-3.266901723884944

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
69.36029999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.28e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S,4aR,5S,9aR)-4-hydroxy-3,4a,5-trimethyl-4H,5H,6H,7H,9H,9aH-naphtho[2,3-b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
    1.5252   -3.8276    1.3858 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1068   -3.5509    1.7116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5922   -2.4296    1.9080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0290   -2.7406    2.1174 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8846   -2.0670    1.0440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5879   -0.5791    0.9457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5949    0.3119    0.9900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4215    1.7917    0.8716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0401    2.1912    0.3699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9290    1.3832    1.0658 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4247    1.9866    0.6666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0934   -0.1713    0.8149 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6228   -0.5486   -0.6124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2524   -0.9678    1.8922 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1429   -0.8008    1.7008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1077   -4.1581    2.0128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8614   -4.6582    1.7943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5905   -5.8398    1.6808 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0657   -2.9388    1.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0418   -4.2373    2.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5976   -4.5582    0.5730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3544   -2.4454    3.1222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9424   -2.2554    1.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7139   -2.5382    0.0671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6219   -0.0310    1.1045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6056    2.2416    1.8545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1790    2.1939    0.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9864    2.0516   -0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9016    3.2649    0.5485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0403    1.5590    2.1461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4545    3.0513    0.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2589    1.5177    1.1909 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6032    1.9151   -0.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1869   -0.0063   -1.3788 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4391   -0.3309   -0.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7515   -1.6166   -0.8200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4862   -0.5615    2.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5836   -1.1261    2.5042 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
 10 12  1  0
  6  7  2  0
  6 12  1  0
  8  9  1  0
  3  2  2  0
 17 16  1  0
 16  4  1  0
  8  7  1  0
 10 11  1  0
  9 10  1  0
 12 13  1  6
  6  5  1  0
 14 15  1  0
 12 14  1  0
  2  1  1  0
  4  3  1  0
 17  2  1  0
 14  3  1  0
 17 18  2  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  1
  7 25  1  0
 14 37  1  1
  5 23  1  0
  5 24  1  0
  4 22  1  1
 11 31  1  0
 11 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 15 38  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       1.525  -3.828   1.386  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.107  -3.551   1.712  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.592  -2.430   1.908  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.029  -2.741   2.117  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.885  -2.067   1.044  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.588  -0.579   0.946  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.595   0.312   0.990  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.422   1.792   0.872  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.040   2.191   0.370  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.929   1.383   1.066  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.425   1.987   0.667  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.093  -0.171   0.815  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.623  -0.549  -0.612  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.252  -0.968   1.892  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.143  -0.801   1.701  0.00  0.00           O+0
HETATM   16  O   UNK     0      -2.108  -4.158   2.013  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.861  -4.658   1.794  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.591  -5.840   1.681  0.00  0.00           O+0
HETATM   19  H   UNK     0       2.066  -2.939   1.055  0.00  0.00           H+0
HETATM   20  H   UNK     0       2.042  -4.237   2.259  0.00  0.00           H+0
HETATM   21  H   UNK     0       1.598  -4.558   0.573  0.00  0.00           H+0
HETATM   22  H   UNK     0      -2.354  -2.445   3.122  0.00  0.00           H+0
HETATM   23  H   UNK     0      -3.942  -2.255   1.268  0.00  0.00           H+0
HETATM   24  H   UNK     0      -2.714  -2.538   0.067  0.00  0.00           H+0
HETATM   25  H   UNK     0      -4.622  -0.031   1.105  0.00  0.00           H+0
HETATM   26  H   UNK     0      -3.606   2.242   1.855  0.00  0.00           H+0
HETATM   27  H   UNK     0      -4.179   2.194   0.189  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.986   2.052  -0.717  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.902   3.265   0.549  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.040   1.559   2.146  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.455   3.051   0.927  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.259   1.518   1.191  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.603   1.915  -0.411  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.187  -0.006  -1.379  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.439  -0.331  -0.765  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.752  -1.617  -0.820  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.486  -0.562   2.886  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.584  -1.126   2.504  0.00  0.00           H+0
CONECT    1    2   19   20   21                                             
CONECT    2    3    1   17                                                  
CONECT    3    2    4   14                                                  
CONECT    4    5   16    3   22                                             
CONECT    5    4    6   23   24                                             
CONECT    6    7   12    5                                                  
CONECT    7    6    8   25                                                  
CONECT    8    9    7   26   27                                             
CONECT    9    8   10   28   29                                             
CONECT   10   12   11    9   30                                             
CONECT   11   10   31   32   33                                             
CONECT   12   10    6   13   14                                             
CONECT   13   12   34   35   36                                             
CONECT   14   15   12    3   37                                             
CONECT   15   14   38                                                       
CONECT   16   17    4                                                       
CONECT   17   16    2   18                                                  
CONECT   18   17                                                            
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    4                                                            
CONECT   23    5                                                            
CONECT   24    5                                                            
CONECT   25    7                                                            
CONECT   26    8                                                            
CONECT   27    8                                                            
CONECT   28    9                                                            
CONECT   29    9                                                            
CONECT   30   10                                                            
CONECT   31   11                                                            
CONECT   32   11                                                            
CONECT   33   11                                                            
CONECT   34   13                                                            
CONECT   35   13                                                            
CONECT   36   13                                                            
CONECT   37   14                                                            
CONECT   38   15                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   80    0
END

RDKit          3D

38 40  0  0  0  0  0  0  0  0999 V2000
    1.5252   -3.8276    1.3858 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1068   -3.5509    1.7116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5922   -2.4296    1.9080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0290   -2.7406    2.1174 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8846   -2.0670    1.0440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5879   -0.5791    0.9457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5949    0.3119    0.9900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4215    1.7917    0.8716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0401    2.1912    0.3699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9290    1.3832    1.0658 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4247    1.9866    0.6666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0934   -0.1713    0.8149 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6228   -0.5486   -0.6124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2524   -0.9678    1.8922 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1429   -0.8008    1.7008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1077   -4.1581    2.0128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8614   -4.6582    1.7943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5905   -5.8398    1.6808 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0657   -2.9388    1.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0418   -4.2373    2.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5976   -4.5582    0.5730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3544   -2.4454    3.1222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9424   -2.2554    1.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7139   -2.5382    0.0671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6219   -0.0310    1.1045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6056    2.2416    1.8545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1790    2.1939    0.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9864    2.0516   -0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9016    3.2649    0.5485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0403    1.5590    2.1461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4545    3.0513    0.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2589    1.5177    1.1909 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6032    1.9151   -0.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1869   -0.0063   -1.3788 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4391   -0.3309   -0.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7515   -1.6166   -0.8200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4862   -0.5615    2.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5836   -1.1261    2.5042 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
 10 12  1  0
  6  7  2  0
  6 12  1  0
  8  9  1  0
  3  2  2  0
 17 16  1  0
 16  4  1  0
  8  7  1  0
 10 11  1  0
  9 10  1  0
 12 13  1  6
  6  5  1  0
 14 15  1  0
 12 14  1  0
  2  1  1  0
  4  3  1  0
 17  2  1  0
 14  3  1  0
 17 18  2  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  1
  7 25  1  0
 14 37  1  1
  5 23  1  0
  5 24  1  0
  4 22  1  1
 11 31  1  0
 11 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 15 38  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₃

Average Mass

248.3220 Da

Monoisotopic Mass

248.14124 Da

IUPAC Name

(4S,4aR,5S,9aR)-4-hydroxy-3,4a,5-trimethyl-2H,4H,4aH,5H,6H,7H,9H,9aH-naphtho[2,3-b]furan-2-one

Traditional Name

(4S,4aR,5S,9aR)-4-hydroxy-3,4a,5-trimethyl-4H,5H,6H,7H,9H,9aH-naphtho[2,3-b]furan-2-one

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])C2=C(C(=O)O[C@]2([H])C([H])([H])C2=C([H])C([H])([H])C([H])([H])[C@]([H])(C([H])([H])[H])[C@@]12C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C15H20O3/c1-8-5-4-6-10-7-11-12(9(2)14(17)18-11)13(16)15(8,10)3/h6,8,11,13,16H,4-5,7H2,1-3H3/t8-,11+,13+,15+/m0/s1

InChI Key

OGIYZEJLIRMHKE-DGFVYPATSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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
Senecio toluccanus	JEOL database	Burgueno-Tapia, E., et al, Magn. Reson. Chem. 42, 887 (2004)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Eremophilanolide or secoeremophilanolide
Sesquiterpenoid
Naphthofuran
2-furanone
Cyclic alcohol
Dihydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
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	2.72	ALOGPS
logP	2.2	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	12.54	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.36 m³·mol⁻¹	ChemAxon
Polarizability	27.27 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

9812128

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11637386

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Burgueno-Tapia, E., et al. (2004). Burgueno-Tapia, E., et al, Magn. Reson. Chem. 42, 887 (2004). Mag. Reson. Chem..

Showing NP-Card for toluccanolide A (NP0030598)

MOL for NP0030598 (toluccanolide A)

3D MOL for NP0030598 (toluccanolide A)

3D SDF for NP0030598 (toluccanolide A)

3D-SDF for NP0030598 (toluccanolide A)

PDB for NP0030598 (toluccanolide A)

3D PDB for NP0030598 (toluccanolide A)

SMILES for NP0030598 (toluccanolide A)

INCHI for NP0030598 (toluccanolide A)

Structure for NP0030598 (toluccanolide A)

3D Structure for NP0030598 (toluccanolide A)