NP-MRD: Showing NP-Card for (3as,4s,5s,11ar)-6-(hydroxymethyl)-10-methyl-3-methylidene-4-[(2-methylpropanoyl)oxy]-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-5-yl 2-hydroxy-2-methylpropanoate (NP0322567)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-12 01:24:46 UTC

Updated at

2022-09-12 01:24:46 UTC

NP-MRD ID

NP0322567

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3as,4s,5s,11ar)-6-(hydroxymethyl)-10-methyl-3-methylidene-4-[(2-methylpropanoyl)oxy]-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-5-yl 2-hydroxy-2-methylpropanoate

Description

(3AS,4S,5S,11aR)-6-(hydroxymethyl)-10-methyl-3-methylidene-4-[(2-methylpropanoyl)oxy]-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-5-yl 2-hydroxy-2-methylpropanoate 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. Based on a literature review very few articles have been published on (3aS,4S,5S,11aR)-6-(hydroxymethyl)-10-methyl-3-methylidene-4-[(2-methylpropanoyl)oxy]-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-5-yl 2-hydroxy-2-methylpropanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122203242D          

 31 32  0  0  1  0            999 V2000
    2.9836   -0.4024    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
    1.9286    1.0497    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
    4.9672    0.7948    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
    6.1666   -0.6003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8810   -1.0128    0.0000 O   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
    5.1971   -0.1474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7492   -0.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5029   -1.0961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4942   -1.5451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7096   -1.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2789   -1.8001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2393   -2.3298    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
    4.7376   -0.6003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0231   -1.0128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3087   -0.6003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0231   -1.8378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7376   -2.2503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3087   -2.2503    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  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 16 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 24 31  1  0  0  0  0
 31  2  1  1  0  0  0
  6 31  1  0  0  0  0
M  END

     RDKit          3D

 63 64  0  0  0  0  0  0  0  0999 V2000
   -2.3554    1.4450    2.8329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5226    0.3208    2.2442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6870   -0.5566    2.3972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5834   -0.4760    3.3104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6708   -1.5084    1.3819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7660   -0.9398    0.3994 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7269   -1.6329   -0.8493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0528   -2.5957   -1.4322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4130   -3.0012   -2.8781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9207   -3.4159   -0.8964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8144   -3.5874    0.5426 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3239   -3.1260    1.3261 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9253   -1.9633    1.2499 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1145   -1.7195    2.1980 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3512   -2.8234    3.0028 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5514   -0.9115    0.3283 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7279   -0.2005   -0.1540 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0963   -0.0587   -1.4435 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3276   -0.5987   -2.2482 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3111    0.6728   -1.9021 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5341    0.0649   -1.2541 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1826    2.0981   -1.4160 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4257    0.6661   -3.2700 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4625    0.1097    0.8379 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5874    1.1885   -0.0753 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734    2.4588    0.1208 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5647    2.7018    1.1779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2295    3.5666   -0.8486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7438    3.7875   -0.9873 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3255    4.8602   -0.2960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7016   -0.5025    1.2645 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5259    2.1318    2.7701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1405    1.8047    3.5083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3603    0.0508    0.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5348   -1.2386   -1.5711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1261   -2.3027   -3.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4990   -2.9726   -3.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7417   -4.0376   -2.8027 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0400   -3.2863   -1.4697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1508   -4.4849   -1.3108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8106   -3.4430    1.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7829   -4.7325    0.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7786   -3.8196    2.1130 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9022   -0.8842    2.8632 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0370   -1.5898    1.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4771   -2.5812    3.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1622   -1.2247   -0.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3593    0.8179   -1.3935 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8696   -0.8633   -1.7117 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3768    0.0111   -0.1561 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1591    2.6248   -1.4050 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7437    2.0515   -0.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4446    2.5901   -2.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9504    1.4841   -3.6112 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0619    0.5162    1.7245 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1890    3.3555   -1.8408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9708    4.6647   -1.5968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1810    3.8800    0.0284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1760    2.8399   -1.4103 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1372    5.2697   -0.9280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4352    5.6634   -0.2138 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7136    4.7138    0.7544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4174   -1.3318    1.9737 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 28  1  0
 28 30  1  0
 28 26  1  0
 26 27  2  0
 26 25  1  0
 25 24  1  0
 24 31  1  0
 31  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
 16 24  1  0
  2 31  1  0
 29 57  1  0
 29 58  1  0
 29 59  1  0
 28 56  1  0
 30 60  1  0
 30 61  1  0
 30 62  1  0
 24 55  1  1
 31 63  1  1
  6 34  1  6
  1 32  1  0
  1 33  1  0
  7 35  1  0
  9 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  6
 21 48  1  0
 21 49  1  0
 21 50  1  0
 22 51  1  0
 22 52  1  0
 22 53  1  0
 23 54  1  0
M  END


  Mrv1652309122203242D          

 31 32  0  0  1  0            999 V2000
    2.9836   -0.4024    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
    1.9286    1.0497    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
    4.9672    0.7948    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
    6.1666   -0.6003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8810   -1.0128    0.0000 O   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
    5.1971   -0.1474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7492   -0.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5029   -1.0961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4942   -1.5451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7096   -1.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2789   -1.8001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2393   -2.3298    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
    4.7376   -0.6003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0231   -1.0128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3087   -0.6003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0231   -1.8378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7376   -2.2503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3087   -2.2503    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  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 16 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 24 31  1  0  0  0  0
 31  2  1  1  0  0  0
  6 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0322567

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=O)O[C@H]1[C@@H]2[C@H](OC(=O)C2=C)\C=C(C)\CC\C=C(CO)/[C@@H]1OC(=O)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C23H32O8/c1-12(2)20(25)30-19-17-14(4)21(26)29-16(17)10-13(3)8-7-9-15(11-24)18(19)31-22(27)23(5,6)28/h9-10,12,16-19,24,28H,4,7-8,11H2,1-3,5-6H3/b13-10+,15-9-/t16-,17+,18+,19+/m1/s1

> <INCHI_KEY>
BUCVLNRNADZCKH-FPPPUSSXSA-N

> <FORMULA>
C23H32O8

> <MOLECULAR_WEIGHT>
436.501

> <EXACT_MASS>
436.20971799

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
45.070871150597554

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aS,4S,5S,11aR)-6-(hydroxymethyl)-10-methyl-3-methylidene-4-[(2-methylpropanoyl)oxy]-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-5-yl 2-hydroxy-2-methylpropanoate

> <JCHEM_LOGP>
2.5812925713333326

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.086657745346297

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.842694445587856

> <JCHEM_PKA_STRONGEST_BASIC>
-2.761989342291886

> <JCHEM_POLAR_SURFACE_AREA>
119.36000000000001

> <JCHEM_REFRACTIVITY>
112.9131

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3aS,4S,5S,11aR)-6-(hydroxymethyl)-10-methyl-3-methylidene-4-[(2-methylpropanoyl)oxy]-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-5-yl 2-hydroxy-2-methylpropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       5.569  -0.751   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       3.600   1.959   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       9.272   1.484   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      11.511  -1.121   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      12.845  -1.891   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.177   1.189   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.701  -0.275   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.732  -1.420   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      12.139  -2.046   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.256  -2.884   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.791  -2.408   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.721  -3.360   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       9.780  -4.349   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.844   0.419   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.844  -1.121   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       7.510  -1.891   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.176  -1.121   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.510  -3.431   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.844  -4.201   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.176  -4.201   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   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17   24                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20                                                            
CONECT   24   16   25   31                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   24    2    6                                                  
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

View in JSmol

Synonyms

Value	Source
(3AS,4S,5S,11ar)-6-(hydroxymethyl)-10-methyl-3-methylidene-4-[(2-methylpropanoyl)oxy]-2-oxo-2H,3H,3ah,4H,5H,8H,9H,11ah-cyclodeca[b]furan-5-yl 2-hydroxy-2-methylpropanoic acid	Generator

Chemical Formula

C₂₃H₃₂O₈

Average Mass

436.5010 Da

Monoisotopic Mass

436.20972 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)C(=O)O[C@H]1[C@@H]2[C@H](OC(=O)C2=C)\C=C(C)\CC\C=C(CO)/[C@@H]1OC(=O)C(C)(C)O

InChI Identifier

InChI=1S/C23H32O8/c1-12(2)20(25)30-19-17-14(4)21(26)29-16(17)10-13(3)8-7-9-15(11-24)18(19)31-22(27)23(5,6)28/h9-10,12,16-19,24,28H,4,7-8,11H2,1-3,5-6H3/b13-10+,15-9-/t16-,17+,18+,19+/m1/s1

InChI Key

BUCVLNRNADZCKH-FPPPUSSXSA-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

Not Available

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
Tricarboxylic acid or derivatives
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Tetrahydrofuran
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Primary alcohol
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
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

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

162949885

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3as,4s,5s,11ar)-6-(hydroxymethyl)-10-methyl-3-methylidene-4-[(2-methylpropanoyl)oxy]-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-5-yl 2-hydroxy-2-methylpropanoate (NP0322567)

MOL for NP0322567 ((3as,4s,5s,11ar)-6-(hydroxymethyl)-10-methyl-3-methylidene-4-[(2-methylpropanoyl)oxy]-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-5-yl 2-hydroxy-2-methylpropanoate)

3D MOL for NP0322567 ((3as,4s,5s,11ar)-6-(hydroxymethyl)-10-methyl-3-methylidene-4-[(2-methylpropanoyl)oxy]-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-5-yl 2-hydroxy-2-methylpropanoate)

3D SDF for NP0322567 ((3as,4s,5s,11ar)-6-(hydroxymethyl)-10-methyl-3-methylidene-4-[(2-methylpropanoyl)oxy]-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-5-yl 2-hydroxy-2-methylpropanoate)

3D-SDF for NP0322567 ((3as,4s,5s,11ar)-6-(hydroxymethyl)-10-methyl-3-methylidene-4-[(2-methylpropanoyl)oxy]-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-5-yl 2-hydroxy-2-methylpropanoate)

PDB for NP0322567 ((3as,4s,5s,11ar)-6-(hydroxymethyl)-10-methyl-3-methylidene-4-[(2-methylpropanoyl)oxy]-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-5-yl 2-hydroxy-2-methylpropanoate)

3D PDB for NP0322567 ((3as,4s,5s,11ar)-6-(hydroxymethyl)-10-methyl-3-methylidene-4-[(2-methylpropanoyl)oxy]-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-5-yl 2-hydroxy-2-methylpropanoate)

SMILES for NP0322567 ((3as,4s,5s,11ar)-6-(hydroxymethyl)-10-methyl-3-methylidene-4-[(2-methylpropanoyl)oxy]-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-5-yl 2-hydroxy-2-methylpropanoate)

INCHI for NP0322567 ((3as,4s,5s,11ar)-6-(hydroxymethyl)-10-methyl-3-methylidene-4-[(2-methylpropanoyl)oxy]-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-5-yl 2-hydroxy-2-methylpropanoate)

Structure for NP0322567 ((3as,4s,5s,11ar)-6-(hydroxymethyl)-10-methyl-3-methylidene-4-[(2-methylpropanoyl)oxy]-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-5-yl 2-hydroxy-2-methylpropanoate)

3D Structure for NP0322567 ((3as,4s,5s,11ar)-6-(hydroxymethyl)-10-methyl-3-methylidene-4-[(2-methylpropanoyl)oxy]-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-5-yl 2-hydroxy-2-methylpropanoate)