NP-MRD: Showing NP-Card for methyl (3as,4s,5s,11ar)-5-(acetyloxy)-10-methyl-4-{[(2z)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate (NP0317652)

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Record Information

Version

2.0

Created at

2022-09-11 17:39:34 UTC

Updated at

2022-09-11 17:39:34 UTC

NP-MRD ID

NP0317652

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (3as,4s,5s,11ar)-5-(acetyloxy)-10-methyl-4-{[(2z)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate

Description

Polymatin B belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. methyl (3as,4s,5s,11ar)-5-(acetyloxy)-10-methyl-4-{[(2z)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate is found in Espeletia killipii, Smallanthus fruticosus and Smallanthus sonchifolius. methyl (3as,4s,5s,11ar)-5-(acetyloxy)-10-methyl-4-{[(2z)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate was first documented in 2010 (PMID: 21375130). Based on a literature review a small amount of articles have been published on Polymatin B (PMID: 29132413) (PMID: 26125943) (PMID: 24522008) (PMID: 23840260).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112219392D          

 31 32  0  0  1  0            999 V2000
    2.7118   -0.3271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2385    0.3823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7536    1.0497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9175    1.2493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2385    1.7171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0231    1.4622    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7376    1.8747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4521    1.4622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7418    0.9123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1666    1.8747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8810    1.4622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8810    0.6372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1666    0.2247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7335   -0.7336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5381   -1.6059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4809   -1.3067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7094   -2.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4521    0.6372    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5054   -0.2243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2002   -0.6919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0326   -0.2478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9173   -1.5487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7376    0.2247    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2864   -0.6493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7349   -1.3699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9239   -1.0636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6480   -2.2738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1042   -3.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9721   -2.8288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1999   -2.5384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0231    0.6372    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 29 30  1  0  0  0  0
 23 31  1  0  0  0  0
 31  2  1  1  0  0  0
  6 31  1  0  0  0  0
M  END

     RDKit          3D

 59 60  0  0  0  0  0  0  0  0999 V2000
    2.4315    2.3061   -1.7446 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1866    1.9188   -1.7752 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4233    1.7061   -2.9934 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9661    1.5332   -4.1463 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9433    1.7148   -2.7475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1036    1.8481   -1.3492 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6832    3.1932   -0.9978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7242    3.2794   -0.1486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2194    4.6513    0.1302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3322    2.0607    0.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4053    1.4795    1.5350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3227    0.0208    1.5459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6520   -0.8710    0.8906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9173   -2.3004    1.2727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3006   -3.2059    0.6768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8167   -2.6499    2.2573 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9950   -4.0232    2.5426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6551   -0.7158   -0.2044 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0041   -1.9858   -0.4638 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0287   -2.6305   -1.6688 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6292   -3.9179   -1.9621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6724   -2.0877   -2.6154 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3853    0.3494    0.0292 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7004   -0.1642    0.0836 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5014   -0.2298    1.1623 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0323    0.2146    2.2226 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8235   -0.7739    1.1250 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6564   -0.7954    2.3826 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3704   -1.2661    0.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6708   -1.3086   -1.2478 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2432    1.6159   -0.7047 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0028    2.5025   -2.6401 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9877    2.4601   -0.8066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8914    1.1525   -1.0819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2055    4.0338   -1.4697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7276    5.0042   -0.8090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9074    4.6335    0.9927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3364    5.3291    0.3186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2716    2.4276    0.9817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7049    1.3231   -0.2437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8233    1.8531    2.5480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4917    2.0611    1.4821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0257   -0.4099    2.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9708   -4.2176    3.6331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2237   -4.6414    2.0467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0166   -4.2840    2.1605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1033   -0.5279   -1.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1860   -4.6563   -2.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2879   -4.2505   -1.1543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1711   -3.7958   -2.9342 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2463    0.6344    1.0962 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2889    0.1180    2.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0321   -0.7669    3.2792 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3459   -1.6564    2.3494 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3898   -1.6631    0.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5778   -0.3079   -1.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2673   -1.9443   -1.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6844   -1.8462   -1.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3512    2.4697    0.0357 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 14  1  0
 14 15  2  0
 14 13  1  0
 13 12  2  0
 12 11  1  0
 11 10  1  0
 10  8  1  0
  8  9  1  0
  8  7  2  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  2 31  1  0
 31 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 27 29  2  0
 29 30  1  0
 23 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 18 13  1  0
 31  6  1  0
 17 44  1  0
 17 45  1  0
 17 46  1  0
 12 43  1  0
 11 41  1  0
 11 42  1  0
 10 39  1  0
 10 40  1  0
  9 36  1  0
  9 37  1  0
  9 38  1  0
  7 35  1  0
  6 34  1  1
  1 32  1  0
  1 33  1  0
 31 59  1  1
 23 51  1  1
 28 52  1  0
 28 53  1  0
 28 54  1  0
 29 55  1  0
 30 56  1  0
 30 57  1  0
 30 58  1  0
 18 47  1  6
 21 48  1  0
 21 49  1  0
 21 50  1  0
M  END


  Mrv1652309112219392D          

 31 32  0  0  1  0            999 V2000
    2.7118   -0.3271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2385    0.3823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7536    1.0497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9175    1.2493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2385    1.7171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0231    1.4622    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7376    1.8747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4521    1.4622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7418    0.9123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1666    1.8747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8810    1.4622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8810    0.6372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1666    0.2247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7335   -0.7336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5381   -1.6059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4809   -1.3067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7094   -2.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4521    0.6372    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5054   -0.2243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2002   -0.6919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0326   -0.2478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9173   -1.5487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7376    0.2247    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2864   -0.6493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7349   -1.3699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9239   -1.0636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6480   -2.2738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1042   -3.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9721   -2.8288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1999   -2.5384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0231    0.6372    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 29 30  1  0  0  0  0
 23 31  1  0  0  0  0
 31  2  1  1  0  0  0
  6 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0317652

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=C/CC\C(C)=C\[C@H]2OC(=O)C(=C)[C@@H]2[C@H](OC(=O)C(\C)=C/C)[C@H]\1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H28O8/c1-7-13(3)21(25)31-20-18-14(4)22(26)30-17(18)11-12(2)9-8-10-16(23(27)28-6)19(20)29-15(5)24/h7,10-11,17-20H,4,8-9H2,1-3,5-6H3/b12-11+,13-7-,16-10+/t17-,18+,19+,20+/m1/s1

> <INCHI_KEY>
UHWAWGCDKJMSNN-OTZUQKQKSA-N

> <FORMULA>
C23H28O8

> <MOLECULAR_WEIGHT>
432.469

> <EXACT_MASS>
432.178417862

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
43.789312744064524

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (3aS,4S,5S,11aR)-5-(acetyloxy)-10-methyl-4-{[(2Z)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate

> <JCHEM_LOGP>
3.7769913329999993

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.316943847748434

> <JCHEM_POLAR_SURFACE_AREA>
105.20000000000002

> <JCHEM_REFRACTIVITY>
112.1922

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (3aS,4S,5S,11aR)-5-(acetyloxy)-10-methyl-4-{[(2Z)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       5.062  -0.611   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.045   0.714   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.140   1.959   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.579   2.332   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       6.045   3.205   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       7.510   2.729   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.844   3.499   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.177   2.729   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.851   1.703   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.511   3.499   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.845   2.729   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.845   1.189   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.511   0.419   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.569  -1.369   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      12.205  -2.998   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      13.964  -2.439   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      14.391  -4.006   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.177   1.189   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.277  -0.419   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      11.574  -1.292   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.128  -0.463   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      11.046  -2.891   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.844   0.419   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.001  -1.212   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.972  -2.557   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.458  -1.985   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.810  -4.244   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.661  -5.685   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.548  -5.280   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.106  -4.738   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.510   1.189   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   31                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16                                                            
CONECT   18   13   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   18   24   31                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29                                                            
CONECT   31   23    2    6                                                  
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₈O₈

Average Mass

432.4690 Da

Monoisotopic Mass

432.17842 Da

IUPAC Name

methyl (3aS,4S,5S,11aR)-5-(acetyloxy)-10-methyl-4-{[(2Z)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate

Traditional Name

methyl (3aS,4S,5S,11aR)-5-(acetyloxy)-10-methyl-4-{[(2Z)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=C/CC\C(C)=C\[C@H]2OC(=O)C(=C)[C@@H]2[C@H](OC(=O)C(\C)=C/C)[C@H]\1OC(C)=O

InChI Identifier

InChI=1S/C23H28O8/c1-7-13(3)21(25)31-20-18-14(4)22(26)30-17(18)11-12(2)9-8-10-16(23(27)28-6)19(20)29-15(5)24/h7,10-11,17-20H,4,8-9H2,1-3,5-6H3/b12-11+,13-7-,16-10+/t17-,18+,19+,20+/m1/s1

InChI Key

UHWAWGCDKJMSNN-OTZUQKQKSA-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
Espeletia killipii	LOTUS Database	35616633
Smallanthus fruticosus	LOTUS Database	35616633
Smallanthus sonchifolius	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Germacrane sesquiterpenoid
Sesquiterpenoid
Tetracarboxylic acid or derivatives
Fatty acid ester
Gamma butyrolactone
Fatty acyl
Enoate ester
Methyl ester
Tetrahydrofuran
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
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	3.78	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	105.2 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	112.19 m³·mol⁻¹	ChemAxon
Polarizability	43.79 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00011831

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

101324862

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ulloa JL, Spina R, Casasco A, Petray PB, Martino V, Sosa MA, Frank FM, Muschietti LV: Germacranolide-type sesquiterpene lactones from Smallanthus sonchifolius with promising activity against Leishmania mexicana and Trypanosoma cruzi. Parasit Vectors. 2017 Nov 13;10(1):567. doi: 10.1186/s13071-017-2509-6. [PubMed:29132413 ]
De Ford C, Ulloa JL, Catalan CAN, Grau A, Martino VS, Muschietti LV, Merfort I: The sesquiterpene lactone polymatin B from Smallanthus sonchifolius induces different cell death mechanisms in three cancer cell lines. Phytochemistry. 2015 Sep;117:332-339. doi: 10.1016/j.phytochem.2015.06.020. Epub 2015 Jun 27. [PubMed:26125943 ]
Sanchez-Toranzo G, Zapata-Martinez J, Catalan C, Buhler MI: Effect of different types of sesquiterpene lactones on the maturation of Rhinella arenarum oocytes. Zygote. 2015 Jun;23(3):406-11. doi: 10.1017/S0967199413000695. Epub 2014 Feb 13. [PubMed:24522008 ]
Frank FM, Ulloa J, Cazorla SI, Maravilla G, Malchiodi EL, Grau A, Martino V, Catalan C, Muschietti LV: Trypanocidal Activity of Smallanthus sonchifolius: Identification of Active Sesquiterpene Lactones by Bioassay-Guided Fractionation. Evid Based Complement Alternat Med. 2013;2013:627898. doi: 10.1155/2013/627898. Epub 2013 Jun 6. [PubMed:23840260 ]
Choi JG, Kang OH, Lee YS, Oh YC, Chae HS, Obiang-Obounou B, Park SC, Shin DW, Hwang BY, Kwon DY: Antimicrobial activity of the constituents of Smallanthus sonchifolius leaves against methicillin-resistant Staphylococcus aureus. Eur Rev Med Pharmacol Sci. 2010 Dec;14(12):1005-9. [PubMed:21375130 ]
LOTUS database [Link]

Showing NP-Card for methyl (3as,4s,5s,11ar)-5-(acetyloxy)-10-methyl-4-{[(2z)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate (NP0317652)

MOL for NP0317652 (methyl (3as,4s,5s,11ar)-5-(acetyloxy)-10-methyl-4-{[(2z)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

3D MOL for NP0317652 (methyl (3as,4s,5s,11ar)-5-(acetyloxy)-10-methyl-4-{[(2z)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

3D SDF for NP0317652 (methyl (3as,4s,5s,11ar)-5-(acetyloxy)-10-methyl-4-{[(2z)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

3D-SDF for NP0317652 (methyl (3as,4s,5s,11ar)-5-(acetyloxy)-10-methyl-4-{[(2z)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

PDB for NP0317652 (methyl (3as,4s,5s,11ar)-5-(acetyloxy)-10-methyl-4-{[(2z)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

3D PDB for NP0317652 (methyl (3as,4s,5s,11ar)-5-(acetyloxy)-10-methyl-4-{[(2z)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

SMILES for NP0317652 (methyl (3as,4s,5s,11ar)-5-(acetyloxy)-10-methyl-4-{[(2z)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

INCHI for NP0317652 (methyl (3as,4s,5s,11ar)-5-(acetyloxy)-10-methyl-4-{[(2z)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

Structure for NP0317652 (methyl (3as,4s,5s,11ar)-5-(acetyloxy)-10-methyl-4-{[(2z)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

3D Structure for NP0317652 (methyl (3as,4s,5s,11ar)-5-(acetyloxy)-10-methyl-4-{[(2z)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)