NP-MRD: Showing NP-Card for Secomahoganin (NP0066528)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 10:47:04 UTC

Updated at

2022-04-28 10:47:04 UTC

NP-MRD ID

NP0066528

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Secomahoganin

Description

Methyl (1R,3S,6R,7S,10R,11R)-10-[(1R,6S)-6-[(acetyloxy)methyl]-1,5,5-trimethyl-4-oxocyclohex-2-en-1-yl]-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0¹,³]Undecane-11-carboxylate belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. Secomahoganin is found in Swietenia macrophylla , Swietenia mahagoni and Swietenia mahagoni JACQ. . Based on a literature review very few articles have been published on methyl (1R,3S,6R,7S,10R,11R)-10-[(1R,6S)-6-[(acetyloxy)methyl]-1,5,5-trimethyl-4-oxocyclohex-2-en-1-yl]-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0¹,³]Undecane-11-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282212472D          

 38 42  0  0  1  0            999 V2000
   -3.0779    0.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9024    0.0864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6906   -0.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8661   -0.6996    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8163    0.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6408    0.7572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  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
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3873    0.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2118    0.7572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0499    1.4281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8744    1.3993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3873    0.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  1  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 O   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
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0964   -2.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -3.7445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -3.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7615   -2.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6874    0.3617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4788   -1.4281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9160   -2.1277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5287   -2.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9659   -3.5558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7042   -2.8849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4051   -1.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7482   -1.4938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  1  7  1  0  0  0  0
  5  8  1  6  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  1  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  6  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 11 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 24 28  1  0  0  0  0
 19 29  1  6  0  0  0
 12 29  1  6  0  0  0
 11 30  1  1  0  0  0
  5 31  1  1  0  0  0
  4 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
  3 37  1  0  0  0  0
  3 38  1  0  0  0  0
M  END

     RDKit          3D

 74 78  0  0  0  0  0  0  0  0999 V2000
   -2.9228   -1.3941   -3.8141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3484   -0.4687   -2.9434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2221   -0.7901   -2.2349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7370   -1.9169   -2.3917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5669    0.2034   -1.2733 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1281    1.2430   -2.2283 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3792   -0.4960   -0.3722 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8042   -0.6513   -0.5550 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2232   -1.8931    0.3310 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2399   -1.1686   -1.8810 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9767   -0.5115   -2.7525 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4238    0.8303   -2.4415 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9332    1.5944   -3.3034 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3015    1.3801   -1.0680 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7764    1.6998   -0.6825 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6115    2.6763   -0.9663 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8577    0.3053   -0.1456 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0858    0.6044    1.3029 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4476   -0.5432    2.0620 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7041   -0.5121    3.4053 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0840   -1.7099    4.2091 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6090    0.6150    3.9929 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0577   -0.0519    1.0903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3284   -0.5176    1.4558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3747    0.0510    0.5065 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1340   -1.1736   -0.0077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3913    0.7707    1.3418 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5115   -0.1005    1.7927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6001   -0.8114    2.9641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8328   -1.4743    2.9419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4278   -1.1645    1.8174 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6791   -0.3531    1.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9889    1.9012    0.8180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7132    2.2680   -0.4711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6515    2.8325   -1.1343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3713    1.9961   -1.0135 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3473    2.1629   -0.1202 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7483    0.8375   -0.5552 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4207   -0.8009   -4.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7612   -1.9414   -3.3214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1968   -2.0659   -4.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0571    2.2606   -1.8118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0154    1.3630   -2.9526 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6228    0.9712   -2.9857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0649   -1.5212   -0.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8143   -2.7901   -0.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7625   -1.9240    1.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3131   -2.0186    0.2646 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9624   -2.1809   -2.2217 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2723   -0.9270   -3.7071 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8007    2.5607    0.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3109    0.8129   -0.3598 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2356    2.0861   -1.6144 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2253    3.0475   -1.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2606    3.4528   -0.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7494    2.5644   -0.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8041   -0.3786   -0.2761 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0473    1.2135    1.3154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3892    1.2270    1.8269 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1914   -1.8385    4.1846 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6570   -2.6262    3.7735 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8135   -1.5755    5.2748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1006    1.0178    1.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7612   -0.5248    1.7515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3373   -1.6227    1.5139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5247   -0.1449    2.4772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4374   -1.9918   -0.3150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9282   -0.9430   -0.7072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6469   -1.6687    0.8754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8545    1.0609    2.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8723   -0.8679    3.7693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2619   -2.1303    3.6863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0011    0.0179    0.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2040    2.5568   -1.9368 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
  5  3  1  0
  5  6  1  6
  5  7  1  0
  7 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  6
 25 27  1  0
 27 33  1  0
 33 34  1  0
 34 35  2  0
 34 36  1  0
 36 37  1  0
 38 37  1  1
 27 28  1  0
 28 32  2  0
 32 31  1  0
 31 30  1  0
 30 29  2  0
  7  8  1  0
  8  9  1  1
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  1
 14 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 38  5  1  0
 29 28  1  0
 17  8  1  0
 38 25  1  0
 38 36  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  6 42  1  0
  6 43  1  0
  6 44  1  0
  7 45  1  1
 23 63  1  0
 23 64  1  0
 24 65  1  0
 24 66  1  0
 26 67  1  0
 26 68  1  0
 26 69  1  0
 27 70  1  1
 36 74  1  6
 32 73  1  0
 30 72  1  0
 29 71  1  0
  9 46  1  0
  9 47  1  0
  9 48  1  0
 10 49  1  0
 11 50  1  0
 15 51  1  0
 15 52  1  0
 15 53  1  0
 16 54  1  0
 16 55  1  0
 16 56  1  0
 17 57  1  6
 18 58  1  0
 18 59  1  0
 21 60  1  0
 21 61  1  0
 21 62  1  0
M  END


  Mrv1652304282212472D          

 38 42  0  0  1  0            999 V2000
   -3.0779    0.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9024    0.0864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6906   -0.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8661   -0.6996    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8163    0.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6408    0.7572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  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
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3873    0.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2118    0.7572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0499    1.4281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8744    1.3993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3873    0.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  1  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 O   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
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0964   -2.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -3.7445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -3.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7615   -2.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6874    0.3617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4788   -1.4281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9160   -2.1277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5287   -2.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9659   -3.5558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7042   -2.8849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4051   -1.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7482   -1.4938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  1  7  1  0  0  0  0
  5  8  1  6  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  1  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  6  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 11 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 24 28  1  0  0  0  0
 19 29  1  6  0  0  0
 12 29  1  6  0  0  0
 11 30  1  1  0  0  0
  5 31  1  1  0  0  0
  4 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
  3 37  1  0  0  0  0
  3 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0066528

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@]1(C)[C@H](CC[C@@]2(C)[C@@H](OC(=O)[C@H]3O[C@@]123)C1=COC=C1)[C@@]1(C)C=CC(=O)C(C)(C)[C@H]1COC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H36O9/c1-16(30)36-15-19-25(2,3)20(31)9-11-26(19,4)18-8-12-27(5)21(17-10-13-35-14-17)37-23(32)22-29(27,38-22)28(18,6)24(33)34-7/h9-11,13-14,18-19,21-22H,8,12,15H2,1-7H3/t18-,19-,21+,22-,26-,27+,28+,29-/m1/s1

> <INCHI_KEY>
PTLZHOLOQAFTMS-XCSDLGRBSA-N

> <FORMULA>
C29H36O9

> <MOLECULAR_WEIGHT>
528.598

> <EXACT_MASS>
528.235932739

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
54.364706749753864

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1R,3S,6R,7S,10R,11R)-10-[(1R,6S)-6-[(acetyloxy)methyl]-1,5,5-trimethyl-4-oxocyclohex-2-en-1-yl]-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0^{1,3}]undecane-11-carboxylate

> <ALOGPS_LOGP>
4.02

> <JCHEM_LOGP>
3.973383051

> <ALOGPS_LOGS>
-4.49

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.870044629673985

> <JCHEM_POLAR_SURFACE_AREA>
121.64000000000001

> <JCHEM_REFRACTIVITY>
133.61769999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.69e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,3S,6R,7S,10R,11R)-10-[(1R,6S)-6-[(acetyloxy)methyl]-1,5,5-trimethyl-4-oxocyclohex-2-en-1-yl]-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0^{1,3}]undecane-11-carboxylate

> <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      -5.745   0.107   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -7.285   0.161   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -5.022  -1.252   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.483  -1.306   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.390   1.360   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.929   1.413   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.723   1.360   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.262   1.413   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -0.093   2.666   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.632   2.612   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.723   1.360   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.913  -5.525   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.437  -6.990   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.897  -6.990   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.421  -5.525   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.334   0.770   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.283   0.675   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.760  -2.666   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -3.577  -3.972   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -2.854  -5.331   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -3.670  -6.637   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -1.314  -5.385   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -6.356  -2.022   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -5.130  -2.788   0.000  0.00  0.00           C+0
CONECT    1    2    3    7                                                  
CONECT    2    1                                                            
CONECT    3    1    4   37   38                                             
CONECT    4    3    5   32                                                  
CONECT    5    4    6    8   31                                             
CONECT    6    5    7                                                       
CONECT    7    6    1                                                       
CONECT    8    5    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   23   30                                             
CONECT   12   11   13   19   29                                             
CONECT   13   12    8   14   18                                             
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16                                                            
CONECT   18   13                                                            
CONECT   19   12   20   29                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   11   24                                                  
CONECT   24   23   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   24                                                       
CONECT   29   19   12                                                       
CONECT   30   11                                                            
CONECT   31    5                                                            
CONECT   32    4   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37    3                                                            
CONECT   38    3                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1R,3S,6R,7S,10R,11R)-10-[(1R,6S)-6-[(acetyloxy)methyl]-1,5,5-trimethyl-4-oxocyclohex-2-en-1-yl]-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0,]undecane-11-carboxylic acid	Generator

Chemical Formula

C₂₉H₃₆O₉

Average Mass

528.5980 Da

Monoisotopic Mass

528.23593 Da

IUPAC Name

methyl (1R,3S,6R,7S,10R,11R)-10-[(1R,6S)-6-[(acetyloxy)methyl]-1,5,5-trimethyl-4-oxocyclohex-2-en-1-yl]-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0^{1,3}]undecane-11-carboxylate

Traditional Name

methyl (1R,3S,6R,7S,10R,11R)-10-[(1R,6S)-6-[(acetyloxy)methyl]-1,5,5-trimethyl-4-oxocyclohex-2-en-1-yl]-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0^{1,3}]undecane-11-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@]1(C)[C@H](CC[C@@]2(C)[C@@H](OC(=O)[C@H]3O[C@@]123)C1=COC=C1)[C@@]1(C)C=CC(=O)C(C)(C)[C@H]1COC(C)=O

InChI Identifier

InChI=1S/C29H36O9/c1-16(30)36-15-19-25(2,3)20(31)9-11-26(19,4)18-8-12-27(5)21(17-10-13-35-14-17)37-23(32)22-29(27,38-22)28(18,6)24(33)34-7/h9-11,13-14,18-19,21-22H,8,12,15H2,1-7H3/t18-,19-,21+,22-,26-,27+,28+,29-/m1/s1

InChI Key

PTLZHOLOQAFTMS-XCSDLGRBSA-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
Swietenia macrophylla	Plant	KNApSAcK
Swietenia mahagoni	LOTUS Database	35616633
Swietenia mahagoni JACQ.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Cyclohexenone
Delta_valerolactone
Dioxepane
Delta valerolactone
1,4-dioxepane
Oxane
Heteroaromatic compound
Methyl ester
Furan
Cyclic ketone
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	4.02	ALOGPS
logP	3.97	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	121.64 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	133.62 m³·mol⁻¹	ChemAxon
Polarizability	54.36 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

162875676

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Secomahoganin (NP0066528)

MOL for NP0066528 (Secomahoganin)

3D MOL for NP0066528 (Secomahoganin)

3D SDF for NP0066528 (Secomahoganin)

3D-SDF for NP0066528 (Secomahoganin)

PDB for NP0066528 (Secomahoganin)

3D PDB for NP0066528 (Secomahoganin)

SMILES for NP0066528 (Secomahoganin)

INCHI for NP0066528 (Secomahoganin)

Structure for NP0066528 (Secomahoganin)

3D Structure for NP0066528 (Secomahoganin)