NP-MRD: Showing NP-Card for spicatolide C (NP0030037)

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Record Information

Version

2.0

Created at

2021-06-19 21:30:18 UTC

Updated at

2021-06-29 23:57:46 UTC

NP-MRD ID

NP0030037

Secondary Accession Numbers

None

Natural Product Identification

Common Name

spicatolide C

Provided By

JEOL Database JEOL Logo

Description

Spicatolide C belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. spicatolide C is found in Pseudoelephantopus spicatus. spicatolide C was first documented in 2006 (PMID: 17077561). Based on a literature review very few articles have been published on Spicatolide C.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192123303D          

 42 44  0  0  0  0            999 V2000
    3.1709   -0.1828    0.5672 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8075   -0.6218    0.0079 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8016   -2.0512    0.1000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6740   -0.0970    0.9179 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3876    1.4035    0.8620 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0494    1.9758   -0.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3493    3.0929   -0.8297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0602    1.1858   -1.3478 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4162    1.2813   -0.6317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2112    1.8072   -2.7587 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0285    1.4810   -3.6773 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1475    2.1866   -3.3118 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2656    0.0294   -3.5653 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3130   -0.9267   -4.4959 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1623   -0.9737   -5.9681 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3676    0.2449   -6.4697 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4621   -2.1862   -3.7594 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5774   -3.2849   -4.2722 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4135   -1.9482   -2.4234 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4060   -0.5339   -2.2018 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7276   -0.1984   -1.4760 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7657   -0.2042   -1.4620 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9893   -0.6449    0.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2943   -0.5126    1.6054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3008    0.9031    0.5303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0449   -2.3982   -0.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9263   -0.3490    1.9583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2452   -0.6692    0.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4020    1.6439    1.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2800    1.9543    1.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7243    2.3222   -0.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3822    0.7962    0.3505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1972    0.7619   -1.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3516    2.8929   -2.6908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1142    1.3949   -3.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2772    1.7933   -4.6925 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8954    3.0150   -2.8568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5227   -1.7754   -6.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1344   -1.1510   -6.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3744    0.1650   -7.4394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9535    0.8687   -1.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5431   -0.7021   -2.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  6  1  0  0  0  0
 20 19  1  6  0  0  0
 19 17  1  0  0  0  0
 17 14  1  0  0  0  0
 14 13  2  0  0  0  0
  8 10  1  0  0  0  0
 14 15  1  0  0  0  0
  5  4  1  0  0  0  0
 15 16  1  0  0  0  0
 10 11  1  0  0  0  0
  6  7  2  0  0  0  0
 21 20  1  0  0  0  0
  2  1  1  0  0  0  0
 13 11  1  0  0  0  0
  2  3  1  6  0  0  0
 13 20  1  0  0  0  0
  8  9  1  1  0  0  0
  5  6  1  0  0  0  0
 20 22  1  0  0  0  0
  4  2  1  0  0  0  0
 11 12  1  0  0  0  0
  8 22  1  0  0  0  0
  2 21  1  0  0  0  0
 17 18  2  0  0  0  0
  5 29  1  0  0  0  0
  5 30  1  0  0  0  0
  4 27  1  0  0  0  0
  4 28  1  0  0  0  0
 21 41  1  0  0  0  0
 21 42  1  0  0  0  0
 10 34  1  0  0  0  0
 10 35  1  0  0  0  0
 11 36  1  6  0  0  0
 15 38  1  0  0  0  0
 15 39  1  0  0  0  0
 16 40  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  3 26  1  0  0  0  0
  9 31  1  0  0  0  0
  9 32  1  0  0  0  0
  9 33  1  0  0  0  0
 12 37  1  0  0  0  0
M  END

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
    3.1709   -0.1828    0.5672 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8075   -0.6218    0.0079 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8016   -2.0512    0.1000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6740   -0.0970    0.9179 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3876    1.4035    0.8620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0494    1.9758   -0.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3493    3.0929   -0.8297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0602    1.1858   -1.3478 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4162    1.2813   -0.6317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2112    1.8072   -2.7587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0285    1.4810   -3.6773 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1475    2.1866   -3.3118 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2656    0.0294   -3.5653 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3130   -0.9267   -4.4959 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1623   -0.9737   -5.9681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3676    0.2449   -6.4697 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4621   -2.1862   -3.7594 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5774   -3.2849   -4.2722 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4135   -1.9482   -2.4234 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4060   -0.5339   -2.2018 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7276   -0.1984   -1.4760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7657   -0.2042   -1.4620 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9893   -0.6449    0.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2943   -0.5126    1.6054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3008    0.9031    0.5303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0449   -2.3982   -0.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9263   -0.3490    1.9583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2452   -0.6692    0.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4020    1.6439    1.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2800    1.9543    1.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7243    2.3222   -0.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3822    0.7962    0.3505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1972    0.7619   -1.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3516    2.8929   -2.6908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1142    1.3949   -3.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2772    1.7933   -4.6925 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8954    3.0150   -2.8568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5227   -1.7754   -6.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1344   -1.1510   -6.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3744    0.1650   -7.4394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9535    0.8687   -1.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5431   -0.7021   -2.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  6  1  0
 20 19  1  6
 19 17  1  0
 17 14  1  0
 14 13  2  0
  8 10  1  0
 14 15  1  0
  5  4  1  0
 15 16  1  0
 10 11  1  0
  6  7  2  0
 21 20  1  0
  2  1  1  0
 13 11  1  0
  2  3  1  6
 13 20  1  0
  8  9  1  1
  5  6  1  0
 20 22  1  0
  4  2  1  0
 11 12  1  0
  8 22  1  0
  2 21  1  0
 17 18  2  0
  5 29  1  0
  5 30  1  0
  4 27  1  0
  4 28  1  0
 21 41  1  0
 21 42  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  6
 15 38  1  0
 15 39  1  0
 16 40  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 12 37  1  0
M  END


  Mrv1652306192123303D          

 42 44  0  0  0  0            999 V2000
    3.1709   -0.1828    0.5672 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8075   -0.6218    0.0079 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8016   -2.0512    0.1000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6740   -0.0970    0.9179 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3876    1.4035    0.8620 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0494    1.9758   -0.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3493    3.0929   -0.8297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0602    1.1858   -1.3478 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4162    1.2813   -0.6317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2112    1.8072   -2.7587 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0285    1.4810   -3.6773 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1475    2.1866   -3.3118 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2656    0.0294   -3.5653 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3130   -0.9267   -4.4959 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1623   -0.9737   -5.9681 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3676    0.2449   -6.4697 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4621   -2.1862   -3.7594 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5774   -3.2849   -4.2722 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4135   -1.9482   -2.4234 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4060   -0.5339   -2.2018 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7276   -0.1984   -1.4760 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7657   -0.2042   -1.4620 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9893   -0.6449    0.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2943   -0.5126    1.6054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3008    0.9031    0.5303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0449   -2.3982   -0.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9263   -0.3490    1.9583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2452   -0.6692    0.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4020    1.6439    1.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2800    1.9543    1.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7243    2.3222   -0.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3822    0.7962    0.3505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1972    0.7619   -1.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3516    2.8929   -2.6908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1142    1.3949   -3.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2772    1.7933   -4.6925 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8954    3.0150   -2.8568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5227   -1.7754   -6.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1344   -1.1510   -6.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3744    0.1650   -7.4394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9535    0.8687   -1.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5431   -0.7021   -2.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  6  1  0  0  0  0
 20 19  1  6  0  0  0
 19 17  1  0  0  0  0
 17 14  1  0  0  0  0
 14 13  2  0  0  0  0
  8 10  1  0  0  0  0
 14 15  1  0  0  0  0
  5  4  1  0  0  0  0
 15 16  1  0  0  0  0
 10 11  1  0  0  0  0
  6  7  2  0  0  0  0
 21 20  1  0  0  0  0
  2  1  1  0  0  0  0
 13 11  1  0  0  0  0
  2  3  1  6  0  0  0
 13 20  1  0  0  0  0
  8  9  1  1  0  0  0
  5  6  1  0  0  0  0
 20 22  1  0  0  0  0
  4  2  1  0  0  0  0
 11 12  1  0  0  0  0
  8 22  1  0  0  0  0
  2 21  1  0  0  0  0
 17 18  2  0  0  0  0
  5 29  1  0  0  0  0
  5 30  1  0  0  0  0
  4 27  1  0  0  0  0
  4 28  1  0  0  0  0
 21 41  1  0  0  0  0
 21 42  1  0  0  0  0
 10 34  1  0  0  0  0
 10 35  1  0  0  0  0
 11 36  1  6  0  0  0
 15 38  1  0  0  0  0
 15 39  1  0  0  0  0
 16 40  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  3 26  1  0  0  0  0
  9 31  1  0  0  0  0
  9 32  1  0  0  0  0
  9 33  1  0  0  0  0
 12 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0030037

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])C1=C2[C@]([H])(O[H])C([H])([H])[C@]3(O[C@]2(OC1=O)C([H])([H])[C@@](O[H])(C([H])([H])[H])C([H])([H])C([H])([H])C3=O)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O7/c1-13(20)4-3-10(18)14(2)5-9(17)11-8(6-16)12(19)21-15(11,7-13)22-14/h9,16-17,20H,3-7H2,1-2H3/t9-,13-,14-,15-/m1/s1

> <INCHI_KEY>
UTMMQAKYUSCCMW-SEWBAHNZSA-N

> <FORMULA>
C15H20O7

> <MOLECULAR_WEIGHT>
312.318

> <EXACT_MASS>
312.120902984

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
30.261511571509416

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,6R,8R,12R)-6,12-dihydroxy-4-(hydroxymethyl)-8,12-dimethyl-2,14-dioxatricyclo[6.5.1.0^{1,5}]tetradec-4-ene-3,9-dione

> <ALOGPS_LOGP>
-0.34

> <JCHEM_LOGP>
-0.32472474999999973

> <ALOGPS_LOGS>
-1.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.652980002361598

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.06909727545203

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8619425544302137

> <JCHEM_POLAR_SURFACE_AREA>
113.29000000000002

> <JCHEM_REFRACTIVITY>
73.93330000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.61e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,6R,8R,12R)-6,12-dihydroxy-4-(hydroxymethyl)-8,12-dimethyl-2,14-dioxatricyclo[6.5.1.0^{1,5}]tetradec-4-ene-3,9-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
    3.1709   -0.1828    0.5672 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8075   -0.6218    0.0079 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8016   -2.0512    0.1000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6740   -0.0970    0.9179 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3876    1.4035    0.8620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0494    1.9758   -0.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3493    3.0929   -0.8297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0602    1.1858   -1.3478 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4162    1.2813   -0.6317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2112    1.8072   -2.7587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0285    1.4810   -3.6773 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1475    2.1866   -3.3118 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2656    0.0294   -3.5653 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3130   -0.9267   -4.4959 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1623   -0.9737   -5.9681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3676    0.2449   -6.4697 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4621   -2.1862   -3.7594 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5774   -3.2849   -4.2722 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4135   -1.9482   -2.4234 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4060   -0.5339   -2.2018 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7276   -0.1984   -1.4760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7657   -0.2042   -1.4620 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9893   -0.6449    0.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2943   -0.5126    1.6054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3008    0.9031    0.5303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0449   -2.3982   -0.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9263   -0.3490    1.9583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2452   -0.6692    0.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4020    1.6439    1.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2800    1.9543    1.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7243    2.3222   -0.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3822    0.7962    0.3505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1972    0.7619   -1.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3516    2.8929   -2.6908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1142    1.3949   -3.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2772    1.7933   -4.6925 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8954    3.0150   -2.8568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5227   -1.7754   -6.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1344   -1.1510   -6.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3744    0.1650   -7.4394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9535    0.8687   -1.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5431   -0.7021   -2.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  6  1  0
 20 19  1  6
 19 17  1  0
 17 14  1  0
 14 13  2  0
  8 10  1  0
 14 15  1  0
  5  4  1  0
 15 16  1  0
 10 11  1  0
  6  7  2  0
 21 20  1  0
  2  1  1  0
 13 11  1  0
  2  3  1  6
 13 20  1  0
  8  9  1  1
  5  6  1  0
 20 22  1  0
  4  2  1  0
 11 12  1  0
  8 22  1  0
  2 21  1  0
 17 18  2  0
  5 29  1  0
  5 30  1  0
  4 27  1  0
  4 28  1  0
 21 41  1  0
 21 42  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  6
 15 38  1  0
 15 39  1  0
 16 40  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 12 37  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       3.171  -0.183   0.567  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.808  -0.622   0.008  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.802  -2.051   0.100  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.674  -0.097   0.918  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.388   1.403   0.862  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.049   1.976  -0.481  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.349   3.093  -0.830  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.060   1.186  -1.348  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.416   1.281  -0.632  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.211   1.807  -2.759  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.029   1.481  -3.677  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.147   2.187  -3.312  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.266   0.029  -3.565  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.313  -0.927  -4.496  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.162  -0.974  -5.968  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.368   0.245  -6.470  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.462  -2.186  -3.759  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.577  -3.285  -4.272  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.414  -1.948  -2.423  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.406  -0.534  -2.202  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.728  -0.198  -1.476  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.766  -0.204  -1.462  0.00  0.00           O+0
HETATM   23  H   UNK     0       3.989  -0.645   0.002  0.00  0.00           H+0
HETATM   24  H   UNK     0       3.294  -0.513   1.605  0.00  0.00           H+0
HETATM   25  H   UNK     0       3.301   0.903   0.530  0.00  0.00           H+0
HETATM   26  H   UNK     0       1.045  -2.398  -0.410  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.926  -0.349   1.958  0.00  0.00           H+0
HETATM   28  H   UNK     0      -0.245  -0.669   0.748  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.402   1.644   1.583  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.280   1.954   1.181  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.724   2.322  -0.485  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.382   0.796   0.351  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.197   0.762  -1.199  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.352   2.893  -2.691  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.114   1.395  -3.231  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.277   1.793  -4.692  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.895   3.015  -2.857  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.523  -1.775  -6.262  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.134  -1.151  -6.439  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.374   0.165  -7.439  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.954   0.869  -1.531  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.543  -0.702  -2.016  0.00  0.00           H+0
CONECT    1    2   23   24   25                                             
CONECT    2    1    3    4   21                                             
CONECT    3    2   26                                                       
CONECT    4    5    2   27   28                                             
CONECT    5    4    6   29   30                                             
CONECT    6    8    7    5                                                  
CONECT    7    6                                                            
CONECT    8    6   10    9   22                                             
CONECT    9    8   31   32   33                                             
CONECT   10    8   11   34   35                                             
CONECT   11   10   13   12   36                                             
CONECT   12   11   37                                                       
CONECT   13   14   11   20                                                  
CONECT   14   17   13   15                                                  
CONECT   15   14   16   38   39                                             
CONECT   16   15   40                                                       
CONECT   17   19   14   18                                                  
CONECT   18   17                                                            
CONECT   19   20   17                                                       
CONECT   20   19   21   13   22                                             
CONECT   21   20    2   41   42                                             
CONECT   22   20    8                                                       
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    3                                                            
CONECT   27    4                                                            
CONECT   28    4                                                            
CONECT   29    5                                                            
CONECT   30    5                                                            
CONECT   31    9                                                            
CONECT   32    9                                                            
CONECT   33    9                                                            
CONECT   34   10                                                            
CONECT   35   10                                                            
CONECT   36   11                                                            
CONECT   37   12                                                            
CONECT   38   15                                                            
CONECT   39   15                                                            
CONECT   40   16                                                            
CONECT   41   21                                                            
CONECT   42   21                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   88    0
END

RDKit          3D

42 44  0  0  0  0  0  0  0  0999 V2000
    3.1709   -0.1828    0.5672 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8075   -0.6218    0.0079 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8016   -2.0512    0.1000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6740   -0.0970    0.9179 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3876    1.4035    0.8620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0494    1.9758   -0.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3493    3.0929   -0.8297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0602    1.1858   -1.3478 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4162    1.2813   -0.6317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2112    1.8072   -2.7587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0285    1.4810   -3.6773 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1475    2.1866   -3.3118 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2656    0.0294   -3.5653 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3130   -0.9267   -4.4959 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1623   -0.9737   -5.9681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3676    0.2449   -6.4697 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4621   -2.1862   -3.7594 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5774   -3.2849   -4.2722 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4135   -1.9482   -2.4234 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4060   -0.5339   -2.2018 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7276   -0.1984   -1.4760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7657   -0.2042   -1.4620 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9893   -0.6449    0.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2943   -0.5126    1.6054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3008    0.9031    0.5303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0449   -2.3982   -0.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9263   -0.3490    1.9583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2452   -0.6692    0.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4020    1.6439    1.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2800    1.9543    1.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7243    2.3222   -0.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3822    0.7962    0.3505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1972    0.7619   -1.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3516    2.8929   -2.6908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1142    1.3949   -3.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2772    1.7933   -4.6925 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8954    3.0150   -2.8568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5227   -1.7754   -6.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1344   -1.1510   -6.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3744    0.1650   -7.4394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9535    0.8687   -1.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5431   -0.7021   -2.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  6  1  0
 20 19  1  6
 19 17  1  0
 17 14  1  0
 14 13  2  0
  8 10  1  0
 14 15  1  0
  5  4  1  0
 15 16  1  0
 10 11  1  0
  6  7  2  0
 21 20  1  0
  2  1  1  0
 13 11  1  0
  2  3  1  6
 13 20  1  0
  8  9  1  1
  5  6  1  0
 20 22  1  0
  4  2  1  0
 11 12  1  0
  8 22  1  0
  2 21  1  0
 17 18  2  0
  5 29  1  0
  5 30  1  0
  4 27  1  0
  4 28  1  0
 21 41  1  0
 21 42  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  6
 15 38  1  0
 15 39  1  0
 16 40  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 12 37  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₇

Average Mass

312.3180 Da

Monoisotopic Mass

312.12090 Da

IUPAC Name

(1S,6R,8R,12R)-6,12-dihydroxy-4-(hydroxymethyl)-8,12-dimethyl-2,14-dioxatricyclo[6.5.1.0^{1,5}]tetradec-4-ene-3,9-dione

Traditional Name

(1S,6R,8R,12R)-6,12-dihydroxy-4-(hydroxymethyl)-8,12-dimethyl-2,14-dioxatricyclo[6.5.1.0^{1,5}]tetradec-4-ene-3,9-dione

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])C1=C2[C@]([H])(O[H])C([H])([H])[C@]3(O[C@]2(OC1=O)C([H])([H])[C@@](O[H])(C([H])([H])[H])C([H])([H])C([H])([H])C3=O)C([H])([H])[H]

InChI Identifier

InChI=1S/C15H20O7/c1-13(20)4-3-10(18)14(2)5-9(17)11-8(6-16)12(19)21-15(11,7-13)22-14/h9,16-17,20H,3-7H2,1-2H3/t9-,13-,14-,15-/m1/s1

InChI Key

UTMMQAKYUSCCMW-SEWBAHNZSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₅D₅N, 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
Pseudoelephantopus spicatus	JEOL database	Issa, H. H., et al, Chem. Pharm. Bull. 54, 1599 (2006)

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
Germacrane sesquiterpenoid
Sesquiterpenoid
Furopyran
Ketal
2-furanone
Oxane
Pyran
Dihydrofuran
Furan
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Carboxylic acid ester
Ketone
Lactone
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Aldehyde
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
Primary alcohol
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	-0.34	ALOGPS
logP	-0.32	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	14.07	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	73.93 m³·mol⁻¹	ChemAxon
Polarizability	30.26 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

101418621

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Issa HH, Chang SM, Yang YL, Chang FR, Wu YC: New sesquiterpene lactones from the aerial parts of Pseudoelephantopus spicatus. Chem Pharm Bull (Tokyo). 2006 Nov;54(11):1599-601. doi: 10.1248/cpb.54.1599. [PubMed:17077561 ]
Issa, H. H., et al. (2006). Issa, H. H., et al, Chem. Pharm. Bull. 54, 1599 (2006). Chem. Pharm. Bull..

Showing NP-Card for spicatolide C (NP0030037)

MOL for NP0030037 (spicatolide C)

3D MOL for NP0030037 (spicatolide C)

3D SDF for NP0030037 (spicatolide C)

3D-SDF for NP0030037 (spicatolide C)

PDB for NP0030037 (spicatolide C)

3D PDB for NP0030037 (spicatolide C)

SMILES for NP0030037 (spicatolide C)

INCHI for NP0030037 (spicatolide C)

Structure for NP0030037 (spicatolide C)

3D Structure for NP0030037 (spicatolide C)