NP-MRD: Showing NP-Card for (1s,3r,4s,5r,8s,9r,10r,11r,14r,16s,17s,18s,19s)-4-(acetyloxy)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl (2r)-2-methylbutanoate (NP0230069)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 10:24:03 UTC

Updated at

2022-09-06 10:24:03 UTC

NP-MRD ID

NP0230069

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3r,4s,5r,8s,9r,10r,11r,14r,16s,17s,18s,19s)-4-(acetyloxy)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl (2r)-2-methylbutanoate

Description

(1S,3R,4S,5R,8S,9R,10R,11R,14R,16S,17S,18S,19S)-4-(acetyloxy)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]Nonadecan-3-yl (2R)-2-methylbutanoate belongs to the class of organic compounds known as atisane diterpenoids. These are diterpenoids with a structure based on the atisane skeleton, which is a tetracyclic compound containing the [2,2,2]bicyc1ic ring system with the C15-C16 bridge attached at C12. (1s,3r,4s,5r,8s,9r,10r,11r,14r,16s,17s,18s,19s)-4-(acetyloxy)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl (2r)-2-methylbutanoate is found in Consolida glandulosa. Based on a literature review very few articles have been published on (1S,3R,4S,5R,8S,9R,10R,11R,14R,16S,17S,18S,19S)-4-(acetyloxy)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]Nonadecan-3-yl (2R)-2-methylbutanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062212242D          

 35 41  0  0  1  0            999 V2000
   -1.2458    0.4698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3903    0.2968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1988    0.9528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1128    0.6351    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9516    1.0290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7866    0.6292    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4136   -0.0353    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5683    0.1536    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4731    0.5965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3497    0.4169    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8097    1.1659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6412    1.3223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8694    0.5295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2194    1.9223    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9828    2.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0629    1.7223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6291    2.3224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8199   -0.3124    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6887   -0.5983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0790   -1.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9031   -1.3923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6336   -2.0482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0427   -0.6656    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2995   -1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3020   -1.0703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8522   -0.3416    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0880   -0.6035    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2808   -0.3359    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4211   -0.5339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6444   -0.9375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6581   -1.8123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0319   -0.4575    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7302   -0.0373    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6984    0.9056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6760    0.1684    0.0000 C   0  0  2  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  1  0  0  0  0
  4  5  1  6  0  0  0
  6  5  1  1  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 18 23  1  0  0  0  0
  7 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
  6 26  1  0  0  0  0
 27 26  1  6  0  0  0
  8 27  1  0  0  0  0
 27 28  1  0  0  0  0
  4 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32  2  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
 35  8  1  6  0  0  0
  4 35  1  0  0  0  0
M  END

     RDKit          3D

 72 78  0  0  0  0  0  0  0  0999 V2000
   -5.5591   -2.2721    2.3084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5885   -1.7547    1.6016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6400   -0.3154    1.1619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3433   -0.0231    0.5039 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4262    1.3260   -0.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2065    1.6817   -0.8730 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0775    1.5859    0.1661 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0156    0.0937    0.3432 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3268   -0.3887    0.7055 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4906    0.5353    0.6605 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5951   -0.0731    0.0056 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8106   -0.2917    0.6353 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8890    0.0819    1.8376 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9771   -0.9122    0.0086 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4639   -0.1150   -1.1973 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7251   -2.3217   -0.4775 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2363   -3.2378    0.6037 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2642    1.8676   -0.0065 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4471    2.3498   -0.6053 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1651    3.4491   -0.2195 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4085    3.9015   -0.9000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7012    4.0565    0.7556 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0431    1.9967   -0.8031 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1310    3.4741   -1.1620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2516    1.0867   -1.9060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6722    0.6789   -1.7670 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5930   -0.5317   -0.9248 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0095   -0.9372   -0.6714 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8096   -0.5403   -1.7491 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2617   -2.3520   -0.3637 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5576   -2.6791   -0.8316 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3823   -2.4746    1.1670 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1119   -1.7617    1.6699 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1079   -2.4832    1.0169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1211   -0.2900    1.3370 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4928   -3.3123    2.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4084   -1.6801    2.5873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7115    0.2780    2.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4471   -0.1461    0.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6758    2.1247    0.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2771    1.2700   -0.8649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2540    2.6562   -1.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1919    2.1926    1.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2658   -0.7851    1.7654 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5659   -1.2407   -0.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8699    0.7454    1.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8013   -0.9703    0.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1483   -0.7325   -1.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6094    0.1706   -1.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0611    0.7313   -0.8157 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1032   -2.3421   -1.3927 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7336   -2.7172   -0.7965 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2030   -3.5787    0.3032 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1969   -2.7963    1.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8268   -4.1853    0.6780 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1040    2.6066    0.8201 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1025    4.6798   -1.6251 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1151    4.3573   -0.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9093    3.0402   -1.3904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6316    3.5974   -2.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6214    4.0388   -0.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8760    3.9659   -1.2975 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3445    0.1818   -2.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2507    1.6729   -2.8722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9521   -1.2959   -1.3531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7431   -0.6486   -1.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5656   -3.0792   -0.7803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5940   -2.7137   -1.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3134   -3.5109    1.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9800   -1.9306    2.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3318   -3.4014    0.8161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0720    0.3478    2.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 14  1  0
 14 15  1  0
 14 12  1  0
 12 13  2  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  8  9  1  1
  8  7  1  0
  7  6  1  0
  6  5  1  0
  4  5  1  6
  4  3  1  0
  3  2  1  0
  2  1  2  3
  2 32  1  0
 32 33  1  0
 33 34  1  0
 33 35  1  0
 32 30  1  0
 30 31  1  0
 30 28  1  0
 28 29  1  6
 28 27  1  0
 27 26  1  0
 26 25  1  0
 25 23  1  0
 23 24  1  6
 23 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 18 10  1  0
 35  8  1  0
 27  8  1  0
 23  7  1  0
 26  6  1  0
 35  4  1  0
 28  4  1  0
 17 53  1  0
 17 54  1  0
 17 55  1  0
 16 51  1  0
 16 52  1  0
 14 47  1  1
 15 48  1  0
 15 49  1  0
 15 50  1  0
 10 46  1  1
  9 44  1  0
  9 45  1  0
  7 43  1  1
  6 42  1  6
  5 40  1  0
  5 41  1  0
  3 38  1  0
  3 39  1  0
  1 36  1  0
  1 37  1  0
 32 69  1  6
 33 70  1  1
 34 71  1  0
 35 72  1  1
 30 67  1  6
 31 68  1  0
 29 66  1  0
 27 65  1  6
 25 63  1  0
 25 64  1  0
 24 60  1  0
 24 61  1  0
 24 62  1  0
 18 56  1  1
 21 57  1  0
 21 58  1  0
 21 59  1  0
M  END


  Mrv1652309062212242D          

 35 41  0  0  1  0            999 V2000
   -1.2458    0.4698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3903    0.2968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1988    0.9528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1128    0.6351    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9516    1.0290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7866    0.6292    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4136   -0.0353    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5683    0.1536    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4731    0.5965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3497    0.4169    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8097    1.1659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6412    1.3223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8694    0.5295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2194    1.9223    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9828    2.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0629    1.7223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6291    2.3224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8199   -0.3124    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6887   -0.5983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0790   -1.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9031   -1.3923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6336   -2.0482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0427   -0.6656    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2995   -1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3020   -1.0703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8522   -0.3416    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0880   -0.6035    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2808   -0.3359    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4211   -0.5339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6444   -0.9375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6581   -1.8123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0319   -0.4575    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7302   -0.0373    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6984    0.9056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6760    0.1684    0.0000 C   0  0  2  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  1  0  0  0  0
  4  5  1  6  0  0  0
  6  5  1  1  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 18 23  1  0  0  0  0
  7 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
  6 26  1  0  0  0  0
 27 26  1  6  0  0  0
  8 27  1  0  0  0  0
 27 28  1  0  0  0  0
  4 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32  2  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
 35  8  1  6  0  0  0
  4 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0230069

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H](C)C(=O)O[C@@H]1C[C@]23[C@@H]4[C@@H]5C[C@]67CC(=C)[C@H]([C@@H](O)[C@@H]26)[C@@H](O)[C@]7(O)[C@H]3N5C[C@]4(C)[C@@H]1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H37NO7/c1-6-11(2)22(32)35-15-9-26-18-14-8-25-7-12(3)16(17(30)19(25)26)20(31)27(25,33)23(26)28(14)10-24(18,5)21(15)34-13(4)29/h11,14-21,23,30-31,33H,3,6-10H2,1-2,4-5H3/t11-,14+,15-,16-,17-,18-,19-,20-,21-,23+,24+,25-,26+,27+/m1/s1

> <INCHI_KEY>
AFNCJAGURSSCGO-SKQVHSELSA-N

> <FORMULA>
C27H37NO7

> <MOLECULAR_WEIGHT>
487.593

> <EXACT_MASS>
487.257002535

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
33.31839556341557

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R,4S,5R,8S,9R,10R,11R,14R,16S,17S,18S,19S)-4-(acetyloxy)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{7,16}.0^{9,14}.0^{14,18}]nonadecan-3-yl (2R)-2-methylbutanoate

> <JCHEM_LOGP>
0.07340048999999987

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.184844549143037

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.81344761431846

> <JCHEM_PKA_STRONGEST_BASIC>
8.574804260912405

> <JCHEM_POLAR_SURFACE_AREA>
116.53000000000002

> <JCHEM_REFRACTIVITY>
122.85940000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,4S,5R,8S,9R,10R,11R,14R,16S,17S,18S,19S)-4-(acetyloxy)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{7,16}.0^{9,14}.0^{14,18}]nonadecan-3-yl (2R)-2-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.326   0.877   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.728   0.554   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.371   1.778   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.077   1.185   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.643   1.921   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.202   1.174   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.372  -0.066   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.794   0.287   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.483   1.113   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.119   0.778   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.978   2.176   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.530   2.468   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      10.956   0.988   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      11.610   3.588   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.168   5.064   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.184   3.215   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.241   4.335   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.997  -0.583   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.619  -1.117   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      11.347  -2.527   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.886  -2.599   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.516  -3.823   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.546  -1.242   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.026  -2.786   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.164  -1.998   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0       5.324  -0.638   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0       3.898  -1.127   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.391  -0.627   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.786  -0.997   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.203  -1.750   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.229  -3.383   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -0.060  -0.854   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.363  -0.070   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.304   1.691   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       3.129   0.314   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   32                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   28   35                                             
CONECT    5    4    6                                                       
CONECT    6    5    7   26                                                  
CONECT    7    6    8   23                                                  
CONECT    8    7    9   27   35                                             
CONECT    9    8   10                                                       
CONECT   10    9   11   18                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16                                                            
CONECT   18   10   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   18    7   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25    6   27                                                  
CONECT   27   26    8   28                                                  
CONECT   28   27    4   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30    2   33                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33    8    4                                                  
MASTER        0    0    0    0    0    0    0    0   35    0   82    0
END

View in JSmol

Synonyms

Value	Source
(1S,3R,4S,5R,8S,9R,10R,11R,14R,16S,17S,18S,19S)-4-(Acetyloxy)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0,.0,.0,.0,.0,]nonadecan-3-yl (2R)-2-methylbutanoic acid	Generator

Chemical Formula

C₂₇H₃₇NO₇

Average Mass

487.5930 Da

Monoisotopic Mass

487.25700 Da

IUPAC Name

(1S,3R,4S,5R,8S,9R,10R,11R,14R,16S,17S,18S,19S)-4-(acetyloxy)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{7,16}.0^{9,14}.0^{14,18}]nonadecan-3-yl (2R)-2-methylbutanoate

Traditional Name

CAS Registry Number

Not Available

SMILES

CC[C@@H](C)C(=O)O[C@@H]1C[C@]23[C@@H]4[C@@H]5C[C@]67CC(=C)[C@H]([C@@H](O)[C@@H]26)[C@@H](O)[C@]7(O)[C@H]3N5C[C@]4(C)[C@@H]1OC(C)=O

InChI Identifier

InChI=1S/C27H37NO7/c1-6-11(2)22(32)35-15-9-26-18-14-8-25-7-12(3)16(17(30)19(25)26)20(31)27(25,33)23(26)28(14)10-24(18,5)21(15)34-13(4)29/h11,14-21,23,30-31,33H,3,6-10H2,1-2,4-5H3/t11-,14+,15-,16-,17-,18-,19-,20-,21-,23+,24+,25-,26+,27+/m1/s1

InChI Key

AFNCJAGURSSCGO-SKQVHSELSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Consolida glandulosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as atisane diterpenoids. These are diterpenoids with a structure based on the atisane skeleton, which is a tetracyclic compound containing the [2,2,2]bicyc1ic ring system with the C15-C16 bridge attached at C12.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Atisane diterpenoids

Alternative Parents

Substituents

Atisane diterpenoid
Azaspirodecane
Quinolizidine
Indolizidine
Isoindoline
Isoindole or derivatives
Alkaloid or derivatives
Indole or derivatives
Azepane
Fatty acid ester
Fatty acyl
Piperidine
Dicarboxylic acid or derivatives
N-alkylpyrrolidine
Pyrrolidine
Cyclic alcohol
Tertiary alcohol
1,2-aminoalcohol
Carboxylic acid ester
Amino acid or derivatives
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Polyol
Alcohol
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
Organooxygen compound
Organonitrogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.073	ChemAxon
pKa (Strongest Acidic)	12.81	ChemAxon
pKa (Strongest Basic)	8.57	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	116.53 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	122.86 m³·mol⁻¹	ChemAxon
Polarizability	33.32 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

162900551

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3r,4s,5r,8s,9r,10r,11r,14r,16s,17s,18s,19s)-4-(acetyloxy)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl (2r)-2-methylbutanoate (NP0230069)

MOL for NP0230069 ((1s,3r,4s,5r,8s,9r,10r,11r,14r,16s,17s,18s,19s)-4-(acetyloxy)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl (2r)-2-methylbutanoate)

3D MOL for NP0230069 ((1s,3r,4s,5r,8s,9r,10r,11r,14r,16s,17s,18s,19s)-4-(acetyloxy)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl (2r)-2-methylbutanoate)

3D SDF for NP0230069 ((1s,3r,4s,5r,8s,9r,10r,11r,14r,16s,17s,18s,19s)-4-(acetyloxy)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl (2r)-2-methylbutanoate)

3D-SDF for NP0230069 ((1s,3r,4s,5r,8s,9r,10r,11r,14r,16s,17s,18s,19s)-4-(acetyloxy)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl (2r)-2-methylbutanoate)

PDB for NP0230069 ((1s,3r,4s,5r,8s,9r,10r,11r,14r,16s,17s,18s,19s)-4-(acetyloxy)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl (2r)-2-methylbutanoate)

3D PDB for NP0230069 ((1s,3r,4s,5r,8s,9r,10r,11r,14r,16s,17s,18s,19s)-4-(acetyloxy)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl (2r)-2-methylbutanoate)

SMILES for NP0230069 ((1s,3r,4s,5r,8s,9r,10r,11r,14r,16s,17s,18s,19s)-4-(acetyloxy)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl (2r)-2-methylbutanoate)

INCHI for NP0230069 ((1s,3r,4s,5r,8s,9r,10r,11r,14r,16s,17s,18s,19s)-4-(acetyloxy)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl (2r)-2-methylbutanoate)

Structure for NP0230069 ((1s,3r,4s,5r,8s,9r,10r,11r,14r,16s,17s,18s,19s)-4-(acetyloxy)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl (2r)-2-methylbutanoate)

3D Structure for NP0230069 ((1s,3r,4s,5r,8s,9r,10r,11r,14r,16s,17s,18s,19s)-4-(acetyloxy)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl (2r)-2-methylbutanoate)