NP-MRD: Showing NP-Card for methyl (2e)-5-[(1s,2s,3ar,4r,5s,6r,7ar)-2-acetyl-6-(acetyloxy)-1-hydroxy-1,4,5,7a-tetramethyl-hexahydroinden-4-yl]-3-methylpent-2-enoate (NP0324421)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-12 04:29:25 UTC

Updated at

2022-09-12 04:29:25 UTC

NP-MRD ID

NP0324421

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2e)-5-[(1s,2s,3ar,4r,5s,6r,7ar)-2-acetyl-6-(acetyloxy)-1-hydroxy-1,4,5,7a-tetramethyl-hexahydroinden-4-yl]-3-methylpent-2-enoate

Description

(2S,4S,5alpha,8alpha,9R,10beta)-7alpha-Acetoxy-2-acetyl-4-hydroxy-2-demethyl-3,4-seco-2,4-cyclocleroda-13-ene-15-oic acid methyl ester belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open. Based on a literature review very few articles have been published on (2S,4S,5alpha,8alpha,9R,10beta)-7alpha-Acetoxy-2-acetyl-4-hydroxy-2-demethyl-3,4-seco-2,4-cyclocleroda-13-ene-15-oic acid methyl ester.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122206292D          

 30 31  0  0  1  0            999 V2000
    7.8375    3.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3072    2.7037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4948    2.8469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2126    3.6222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9645    2.2150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1520    2.3582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8698    3.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6217    1.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8092    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7486    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7079    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4782   -0.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1726   -0.8134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9429   -1.0637    0.0000 O   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  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 10 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 24 28  1  0  0  0  0
 20 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  1  0  0  0
M  END

     RDKit          3D

 68 69  0  0  0  0  0  0  0  0999 V2000
    8.2075    0.0684   -1.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9973   -0.3680   -0.5963 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7440   -0.0503   -1.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6659    0.6943   -2.0681 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5548   -0.5700   -0.4089 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3447   -0.3050   -0.8083 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1299    0.5688   -1.9915 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1477   -0.8804   -0.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3590    0.2650    0.4034 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1015   -0.0599    1.1855 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5403   -0.8550    2.3911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4050    1.3101    1.6612 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8516    1.3431    3.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3878    1.8884    0.6467 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5568    3.2599    0.8505 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0964    4.2651    0.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2957    5.7116    0.3125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4515    3.9324   -0.9544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5921    1.0951    0.3967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3141   -0.3649    0.4809 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0114   -1.0001    1.6345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8592   -0.7379    0.3164 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9506   -2.2214    0.3394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2667   -2.4867   -0.3960 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0910   -3.3593   -1.5534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2266   -3.7546   -2.4225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9856   -3.7824   -1.8247 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8388   -1.1276   -0.7540 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3344   -1.1111   -0.8001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2401   -0.6712   -1.9091 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0234   -0.3508   -0.4863 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4094   -0.3603   -2.1604 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3315    1.1586   -1.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6377   -1.2237    0.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0393    0.6977   -2.2132 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5767    0.1452   -2.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5227    1.5905   -1.8469 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5278   -1.5684    0.6621 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5976   -1.3915   -0.9314 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0083    0.9720    0.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9847    0.8394   -0.4936 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2910   -0.2328    2.9361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0725   -1.7703    2.0712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2531   -1.1278    3.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4372    2.0747    1.6179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3826    2.3072    3.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0712    1.4385    3.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3964    0.5052    3.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7843    1.8359   -0.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3260    5.9510   -0.0753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3361    5.8975    1.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5380    6.3372   -0.1903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9480    1.3085   -0.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4662    1.3011    1.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9793   -1.4970    1.3284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3771   -0.1574    2.2976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4354   -1.6783    2.2529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6234   -0.4595   -0.7568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9358   -2.6813    1.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1871   -2.7686   -0.2363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9839   -2.9540    0.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6360   -2.8501   -2.9177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9461   -4.5458   -3.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0602   -4.1698   -1.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6884   -0.2836   -0.1468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8102   -2.0543   -0.4782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6348   -0.8242   -1.8433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8401   -0.1070   -2.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
 10  9  1  6
 10 11  1  0
 10 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 24 28  1  0
 28 29  1  0
 28 30  1  6
 28 20  1  0
 20 21  1  1
 20 19  1  0
 19 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 14 12  1  0
 12 13  1  0
 12 10  1  0
 20 22  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  5 34  1  0
  7 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
  9 41  1  0
 11 42  1  0
 11 43  1  0
 11 44  1  0
 22 58  1  6
 23 59  1  0
 23 60  1  0
 24 61  1  1
 26 62  1  0
 26 63  1  0
 26 64  1  0
 29 65  1  0
 29 66  1  0
 29 67  1  0
 30 68  1  0
 21 55  1  0
 21 56  1  0
 21 57  1  0
 19 53  1  0
 19 54  1  0
 14 49  1  6
 17 50  1  0
 17 51  1  0
 17 52  1  0
 12 45  1  1
 13 46  1  0
 13 47  1  0
 13 48  1  0
M  END


  Mrv1652309122206292D          

 30 31  0  0  1  0            999 V2000
    7.8375    3.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3072    2.7037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4948    2.8469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2126    3.6222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9645    2.2150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1520    2.3582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8698    3.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6217    1.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8092    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7486    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7079    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4782   -0.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1726   -0.8134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9429   -1.0637    0.0000 O   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  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 10 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 24 28  1  0  0  0  0
 20 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0324421

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C24H38O6/c1-14(11-21(27)29-8)9-10-22(5)15(2)19(30-17(4)26)13-23(6)20(22)12-18(16(3)25)24(23,7)28/h11,15,18-20,28H,9-10,12-13H2,1-8H3/b14-11+/t15-,18-,19-,20-,22+,23-,24+/m1/s1

> <INCHI_KEY>
JFXHBZJISWEQOJ-BQLPAVKISA-N

> <FORMULA>
C24H38O6

> <MOLECULAR_WEIGHT>
422.562

> <EXACT_MASS>
422.266838944

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
47.73000523793181

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2E)-5-[(1S,2S,3aR,4R,5S,6R,7aR)-2-acetyl-6-(acetyloxy)-1-hydroxy-1,4,5,7a-tetramethyl-octahydro-1H-inden-4-yl]-3-methylpent-2-enoate

> <JCHEM_LOGP>
3.3652741340000003

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.630834981398998

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.17944523502701

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1576622995603216

> <JCHEM_POLAR_SURFACE_AREA>
89.9

> <JCHEM_REFRACTIVITY>
114.29789999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2E)-5-[(1S,2S,3aR,4R,5S,6R,7aR)-2-acetyl-6-(acetyloxy)-1-hydroxy-1,4,5,7a-tetramethyl-hexahydroinden-4-yl]-3-methylpent-2-enoate

> <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      14.630   6.227   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      13.640   5.047   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      12.124   5.314   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      11.597   6.761   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      11.134   4.135   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.617   4.402   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.090   5.849   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.627   3.222   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.111   3.490   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.131   3.490   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.788   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.788  -0.770   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.788  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.122  -3.080   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       7.454  -3.080   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.626  -1.532   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.877   0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.107  -0.564   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.107   2.104   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.189  -1.518   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.627  -1.986   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   22                                             
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   14   20                                                       
CONECT   20   19   21   22   28                                             
CONECT   21   20                                                            
CONECT   22   20   10   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   28                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   24   20   29   30                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

View in JSmol

Synonyms

Value	Source
(2S,4S,5a,8a,9R,10b)-7a-Acetoxy-2-acetyl-4-hydroxy-2-demethyl-3,4-seco-2,4-cyclocleroda-13-ene-15-Oate methyl ester	Generator
(2S,4S,5a,8a,9R,10b)-7a-Acetoxy-2-acetyl-4-hydroxy-2-demethyl-3,4-seco-2,4-cyclocleroda-13-ene-15-Oic acid methyl ester	Generator
(2S,4S,5alpha,8alpha,9R,10beta)-7alpha-Acetoxy-2-acetyl-4-hydroxy-2-demethyl-3,4-seco-2,4-cyclocleroda-13-ene-15-Oate methyl ester	Generator
(2S,4S,5Α,8α,9R,10β)-7α-acetoxy-2-acetyl-4-hydroxy-2-demethyl-3,4-seco-2,4-cyclocleroda-13-ene-15-Oate methyl ester	Generator
(2S,4S,5Α,8α,9R,10β)-7α-acetoxy-2-acetyl-4-hydroxy-2-demethyl-3,4-seco-2,4-cyclocleroda-13-ene-15-Oic acid methyl ester	Generator

Chemical Formula

C₂₄H₃₈O₆

Average Mass

422.5620 Da

Monoisotopic Mass

422.26684 Da

IUPAC Name

methyl (2E)-5-[(1S,2S,3aR,4R,5S,6R,7aR)-2-acetyl-6-(acetyloxy)-1-hydroxy-1,4,5,7a-tetramethyl-octahydro-1H-inden-4-yl]-3-methylpent-2-enoate

Traditional Name

methyl (2E)-5-[(1S,2S,3aR,4R,5S,6R,7aR)-2-acetyl-6-(acetyloxy)-1-hydroxy-1,4,5,7a-tetramethyl-hexahydroinden-4-yl]-3-methylpent-2-enoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C24H38O6/c1-14(11-21(27)29-8)9-10-22(5)15(2)19(30-17(4)26)13-23(6)20(22)12-18(16(3)25)24(23,7)28/h11,15,18-20,28H,9-10,12-13H2,1-8H3/b14-11+/t15-,18-,19-,20-,22+,23-,24+/m1/s1

InChI Key

JFXHBZJISWEQOJ-BQLPAVKISA-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 iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Iridoids and derivatives

Alternative Parents

Substituents

Bicyclic monoterpenoid
11-noriridane monoterpenoid
Fatty acid ester
Dicarboxylic acid or derivatives
Fatty acyl
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tertiary alcohol
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
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	3.37	ChemAxon
pKa (Strongest Acidic)	14.18	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	114.3 m³·mol⁻¹	ChemAxon
Polarizability	47.73 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

101036867

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (2e)-5-[(1s,2s,3ar,4r,5s,6r,7ar)-2-acetyl-6-(acetyloxy)-1-hydroxy-1,4,5,7a-tetramethyl-hexahydroinden-4-yl]-3-methylpent-2-enoate (NP0324421)

MOL for NP0324421 (methyl (2e)-5-[(1s,2s,3ar,4r,5s,6r,7ar)-2-acetyl-6-(acetyloxy)-1-hydroxy-1,4,5,7a-tetramethyl-hexahydroinden-4-yl]-3-methylpent-2-enoate)

3D MOL for NP0324421 (methyl (2e)-5-[(1s,2s,3ar,4r,5s,6r,7ar)-2-acetyl-6-(acetyloxy)-1-hydroxy-1,4,5,7a-tetramethyl-hexahydroinden-4-yl]-3-methylpent-2-enoate)

3D SDF for NP0324421 (methyl (2e)-5-[(1s,2s,3ar,4r,5s,6r,7ar)-2-acetyl-6-(acetyloxy)-1-hydroxy-1,4,5,7a-tetramethyl-hexahydroinden-4-yl]-3-methylpent-2-enoate)

3D-SDF for NP0324421 (methyl (2e)-5-[(1s,2s,3ar,4r,5s,6r,7ar)-2-acetyl-6-(acetyloxy)-1-hydroxy-1,4,5,7a-tetramethyl-hexahydroinden-4-yl]-3-methylpent-2-enoate)

PDB for NP0324421 (methyl (2e)-5-[(1s,2s,3ar,4r,5s,6r,7ar)-2-acetyl-6-(acetyloxy)-1-hydroxy-1,4,5,7a-tetramethyl-hexahydroinden-4-yl]-3-methylpent-2-enoate)

3D PDB for NP0324421 (methyl (2e)-5-[(1s,2s,3ar,4r,5s,6r,7ar)-2-acetyl-6-(acetyloxy)-1-hydroxy-1,4,5,7a-tetramethyl-hexahydroinden-4-yl]-3-methylpent-2-enoate)

SMILES for NP0324421 (methyl (2e)-5-[(1s,2s,3ar,4r,5s,6r,7ar)-2-acetyl-6-(acetyloxy)-1-hydroxy-1,4,5,7a-tetramethyl-hexahydroinden-4-yl]-3-methylpent-2-enoate)

INCHI for NP0324421 (methyl (2e)-5-[(1s,2s,3ar,4r,5s,6r,7ar)-2-acetyl-6-(acetyloxy)-1-hydroxy-1,4,5,7a-tetramethyl-hexahydroinden-4-yl]-3-methylpent-2-enoate)

Structure for NP0324421 (methyl (2e)-5-[(1s,2s,3ar,4r,5s,6r,7ar)-2-acetyl-6-(acetyloxy)-1-hydroxy-1,4,5,7a-tetramethyl-hexahydroinden-4-yl]-3-methylpent-2-enoate)

3D Structure for NP0324421 (methyl (2e)-5-[(1s,2s,3ar,4r,5s,6r,7ar)-2-acetyl-6-(acetyloxy)-1-hydroxy-1,4,5,7a-tetramethyl-hexahydroinden-4-yl]-3-methylpent-2-enoate)