NP-MRD: Showing NP-Card for 8beta-Acetoxy-3beta-angeloyloxy-5alpha-hydroperoxycostic acid methyl ester (NP0065526)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 09:44:32 UTC

Updated at

2022-04-28 09:44:32 UTC

NP-MRD ID

NP0065526

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8beta-Acetoxy-3beta-angeloyloxy-5alpha-hydroperoxycostic acid methyl ester

Description

(2S,4aR,6R,7R,8aS)-6-(acetyloxy)-8a-hydroperoxy-7-(3-methoxy-3-oxoprop-1-en-2-yl)-4a-methyl-1-methylidene-decahydronaphthalen-2-yl (2Z)-2-methylbut-2-enoate belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. 8beta-Acetoxy-3beta-angeloyloxy-5alpha-hydroperoxycostic acid methyl ester is found in Eriocephalus pauperrimus. Based on a literature review very few articles have been published on (2S,4aR,6R,7R,8aS)-6-(acetyloxy)-8a-hydroperoxy-7-(3-methoxy-3-oxoprop-1-en-2-yl)-4a-methyl-1-methylidene-decahydronaphthalen-2-yl (2Z)-2-methylbut-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282211442D          

 31 32  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 10 12  1  1  0  0  0
 12 13  2  0  0  0  0
 12 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
  9 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  6 22  1  1  0  0  0
  5 23  1  6  0  0  0
 23 24  1  0  0  0  0
  2 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  2  0  0  0  0
 29 30  1  0  0  0  0
 28 31  1  0  0  0  0
M  END

     RDKit          3D

 63 64  0  0  0  0  0  0  0  0999 V2000
    3.5428   -0.5621    3.0684 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1607    0.0260    1.9547 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7904    1.2811    1.5859 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4267    1.8443    0.5280 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7754    1.8945    2.3411 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3690    3.1362    1.9361 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1051   -0.5893    1.1077 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8397    0.2796    1.1195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1058   -0.4443    0.2492 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1069   -1.8082    0.5345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4691   -2.0328    1.7970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5106    0.0057    0.3078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8997    1.0265    1.0551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4597   -0.7783   -0.5397 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6909   -0.1255   -0.6375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8328   -0.7111   -0.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7164   -1.8507    0.4633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1506   -0.1188   -0.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2987   -0.8350    0.4422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3171    1.0538   -0.7355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2077    1.8203   -1.3535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9126   -1.0708   -1.9082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4488   -1.3462   -1.9472 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3262   -0.2862   -1.1928 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2062    1.0612   -1.6981 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7852   -0.3261   -1.3873 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5772   -0.9215   -0.2671 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9315   -0.5439   -0.4239 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9327   -1.4522   -0.7328 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3588   -1.0328   -0.8945 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6463   -2.6682   -0.8842 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1347   -1.4970    3.4277 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3052   -0.0957    3.6657 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6841    3.6031    1.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5379    3.7108    2.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3635    2.8750    1.4878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7891   -1.5373    1.5947 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4809    0.2441    2.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0712    1.3029    0.8188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0912   -1.3297    2.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1399    1.5404    1.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9035    1.3801    1.1232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003   -1.7427   -0.0097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0737   -1.1935    1.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5204   -1.7541   -0.1604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1942   -0.1841    0.5428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3161    1.5260   -0.7850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7111    1.2717   -2.1819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5901    2.7729   -1.8213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4074    2.0821   -0.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1554   -0.2778   -2.6546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4365   -1.9928   -2.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2127   -2.3182   -1.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1268   -1.4031   -2.9895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2223    1.2622   -1.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2964    1.0144   -2.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4777    1.8872   -1.4448 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9889   -0.9344   -2.3184 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1900    0.6786   -1.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5537   -2.0395   -0.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4375    0.0669   -1.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9771   -1.2974   -0.0197 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7725   -1.5464   -1.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  2  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  1
 10 11  1  0
  9 12  1  0
 12 13  2  3
 12 14  1  0
 14 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  6
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 27  7  1  0
 24  9  1  0
  6 34  1  0
  6 35  1  0
  6 36  1  0
  1 32  1  0
  1 33  1  0
  7 37  1  1
  8 38  1  0
  8 39  1  0
 11 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  1
 22 51  1  0
 22 52  1  0
 23 53  1  0
 23 54  1  0
 25 55  1  0
 25 56  1  0
 25 57  1  0
 26 58  1  0
 26 59  1  0
 27 60  1  6
 30 61  1  0
 30 62  1  0
 30 63  1  0
 19 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  0
 21 48  1  0
 21 49  1  0
 21 50  1  0
M  END


  Mrv1652304282211442D          

 31 32  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 10 12  1  1  0  0  0
 12 13  2  0  0  0  0
 12 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
  9 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  6 22  1  1  0  0  0
  5 23  1  6  0  0  0
 23 24  1  0  0  0  0
  2 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  2  0  0  0  0
 29 30  1  0  0  0  0
 28 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0065526

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C23H32O8/c1-8-13(2)20(25)30-18-9-10-22(6)12-19(29-16(5)24)17(14(3)21(26)28-7)11-23(22,31-27)15(18)4/h8,17-19,27H,3-4,9-12H2,1-2,5-7H3/b13-8-/t17-,18+,19-,22-,23-/m1/s1

> <INCHI_KEY>
RQMMHQBGBXTVEG-XOMHRJEHSA-N

> <FORMULA>
C23H32O8

> <MOLECULAR_WEIGHT>
436.501

> <EXACT_MASS>
436.20971799

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
46.06991858281962

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,4aR,6R,7R,8aS)-6-(acetyloxy)-8a-hydroperoxy-7-(3-methoxy-3-oxoprop-1-en-2-yl)-4a-methyl-1-methylidene-decahydronaphthalen-2-yl (2Z)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
3.13

> <JCHEM_LOGP>
3.708592903666665

> <ALOGPS_LOGS>
-4.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.693827162958293

> <JCHEM_PKA_STRONGEST_BASIC>
-4.244919998922058

> <JCHEM_POLAR_SURFACE_AREA>
108.36000000000001

> <JCHEM_REFRACTIVITY>
111.67979999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.27e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4aR,6R,7R,8aS)-6-(acetyloxy)-8a-hydroperoxy-7-(3-methoxy-3-oxoprop-1-en-2-yl)-4a-methyl-1-methylidene-hexahydro-2H-naphthalen-2-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.334  -3.850   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    3   25                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   11   23                                             
CONECT    6    5    7    8   22                                             
CONECT    7    6    1                                                       
CONECT    8    6    9                                                       
CONECT    9    8   10   18                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10    5                                                       
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16                                                            
CONECT   18    9   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22    6                                                            
CONECT   23    5   24                                                       
CONECT   24   23                                                            
CONECT   25    2   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

View in JSmol

Synonyms

Value	Source
(2S,4AR,6R,7R,8as)-6-(acetyloxy)-8a-hydroperoxy-7-(3-methoxy-3-oxoprop-1-en-2-yl)-4a-methyl-1-methylidene-decahydronaphthalen-2-yl (2Z)-2-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₃H₃₂O₈

Average Mass

436.5010 Da

Monoisotopic Mass

436.20972 Da

IUPAC Name

(2S,4aR,6R,7R,8aS)-6-(acetyloxy)-8a-hydroperoxy-7-(3-methoxy-3-oxoprop-1-en-2-yl)-4a-methyl-1-methylidene-decahydronaphthalen-2-yl (2Z)-2-methylbut-2-enoate

Traditional Name

(2S,4aR,6R,7R,8aS)-6-(acetyloxy)-8a-hydroperoxy-7-(3-methoxy-3-oxoprop-1-en-2-yl)-4a-methyl-1-methylidene-hexahydro-2H-naphthalen-2-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C23H32O8/c1-8-13(2)20(25)30-18-9-10-22(6)12-19(29-16(5)24)17(14(3)21(26)28-7)11-23(22,31-27)15(18)4/h8,17-19,27H,3-4,9-12H2,1-2,5-7H3/b13-8-/t17-,18+,19-,22-,23-/m1/s1

InChI Key

RQMMHQBGBXTVEG-XOMHRJEHSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Eriocephalus pauperrimus	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids

Alternative Parents

Substituents

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid
Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Hydroperoxide
Carboxylic acid ester
Alkyl hydroperoxide
Peroxol
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	3.13	ALOGPS
logP	3.71	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	11.69	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	108.36 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	111.68 m³·mol⁻¹	ChemAxon
Polarizability	46.07 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

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

13895657

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 8beta-Acetoxy-3beta-angeloyloxy-5alpha-hydroperoxycostic acid methyl ester (NP0065526)

MOL for NP0065526 (8beta-Acetoxy-3beta-angeloyloxy-5alpha-hydroperoxycostic acid methyl ester)

3D MOL for NP0065526 (8beta-Acetoxy-3beta-angeloyloxy-5alpha-hydroperoxycostic acid methyl ester)

3D SDF for NP0065526 (8beta-Acetoxy-3beta-angeloyloxy-5alpha-hydroperoxycostic acid methyl ester)

3D-SDF for NP0065526 (8beta-Acetoxy-3beta-angeloyloxy-5alpha-hydroperoxycostic acid methyl ester)

PDB for NP0065526 (8beta-Acetoxy-3beta-angeloyloxy-5alpha-hydroperoxycostic acid methyl ester)

3D PDB for NP0065526 (8beta-Acetoxy-3beta-angeloyloxy-5alpha-hydroperoxycostic acid methyl ester)

SMILES for NP0065526 (8beta-Acetoxy-3beta-angeloyloxy-5alpha-hydroperoxycostic acid methyl ester)

INCHI for NP0065526 (8beta-Acetoxy-3beta-angeloyloxy-5alpha-hydroperoxycostic acid methyl ester)

Structure for NP0065526 (8beta-Acetoxy-3beta-angeloyloxy-5alpha-hydroperoxycostic acid methyl ester)

3D Structure for NP0065526 (8beta-Acetoxy-3beta-angeloyloxy-5alpha-hydroperoxycostic acid methyl ester)