NP-MRD: Showing NP-Card for (1s,2r,3r,4r,7r,8s,10s,11e,13s,17s)-2,17-bis(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-11,14-dien-10-yl acetate (NP0161801)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 20:03:52 UTC

Updated at

2022-09-02 20:03:52 UTC

NP-MRD ID

NP0161801

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,3r,4r,7r,8s,10s,11e,13s,17s)-2,17-bis(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-11,14-dien-10-yl acetate

Description

(1S,2R,3R,4R,7R,8S,10S,11E,13S,17S)-2,17-bis(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0³,⁷]Heptadeca-11,14-dien-10-yl acetate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (1s,2r,3r,4r,7r,8s,10s,11e,13s,17s)-2,17-bis(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-11,14-dien-10-yl acetate is found in Briareum asbestinum. Based on a literature review very few articles have been published on (1S,2R,3R,4R,7R,8S,10S,11E,13S,17S)-2,17-bis(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0³,⁷]Heptadeca-11,14-dien-10-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022222032D          

 37 39  0  0  1  0            999 V2000
    2.8939    2.1648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3972    1.5112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1744    1.7879    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4074    2.5793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8385    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0715    3.9682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0366    2.9828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6778    1.1342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4692    0.9013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4922    0.0766    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0897    0.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3148    0.0133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6712   -0.7308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2051   -1.4115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5616   -2.1555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3825   -1.3481    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5879   -1.5700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4630   -2.1692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2143   -2.5100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0007   -2.2606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2948   -3.3311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0261   -0.6041    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2489   -0.8808    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2719   -1.7055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9976   -2.0979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6258   -2.6327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0206   -2.9226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4575   -0.6479    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7342   -1.4251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9913   -1.3286    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2681   -2.1058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1999   -1.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5463   -1.5990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1769   -0.2709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9541    0.0058    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9311    0.8305    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1397    1.0634    0.0000 Cl  0  0  0  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  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 22 16  1  6  0  0  0
 10 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 35 34  1  1  0  0  0
 28 35  1  0  0  0  0
 35 36  1  0  0  0  0
  2 36  1  0  0  0  0
 36 37  1  1  0  0  0
M  END

     RDKit          3D

 68 70  0  0  0  0  0  0  0  0999 V2000
    2.2077    1.1807    1.8276 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4469    1.1092    0.5076 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0114   -0.1566    0.0411 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8872   -1.1845    1.0412 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9366   -1.6889    1.7529 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7704   -2.7654    2.7931 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0820   -1.2188    1.5121 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6071   -0.6650   -1.2799 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5432   -1.2573   -1.7180 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2892   -1.6696   -1.0671 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6074   -2.3585   -2.0850 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6940   -2.8338   -0.1801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1666   -3.3627    0.6809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4880   -2.7364    0.6859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4764   -3.4427    0.9956 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6823   -1.3328    0.3429 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8738   -1.1579   -0.5467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9656   -0.6335    1.5407 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0251   -0.8248    2.3736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1800   -0.0042    3.6236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8766   -1.6813    2.1092 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3928   -0.6854   -0.2132 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6677    0.6688   -0.5657 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7574    1.4246    0.6712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8495    2.0880    1.1227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7213    2.8081    2.4409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8934    2.0854    0.4585 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0046    1.5665   -1.4788 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7158    2.8054   -1.2388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2741    1.4283   -2.9678 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7095    1.6961   -3.3310 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5180    2.6377   -3.4282 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4706    3.0574   -4.6370 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2468    3.1609   -2.3664 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3833    1.9774   -1.4998 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1332    2.3042   -0.2894 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4367    3.6159    0.6753 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.8051    2.0966    2.2225 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3885    0.3868    2.5284 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1351    0.0449    0.0639 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7311   -3.3413    2.7612 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7019   -2.2800    3.7651 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9363   -3.4248    2.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4180   -0.4877   -2.0357 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5663   -1.5142   -2.8134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8655   -1.6795   -2.9240 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0883   -3.1099   -2.5797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4156   -2.9465   -1.6980 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6772   -3.2806   -0.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0209   -4.1718    1.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6387   -0.4496   -0.1648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4222   -2.1524   -0.5553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6938   -0.9259   -1.5821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8207    0.8651    3.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2137    0.3797    3.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7267   -0.5712    4.4009 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2322   -0.6975    0.7450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7432    0.7411   -0.9335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6851    2.9337    2.9321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9275    2.3633    3.0586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3589    3.8499    2.1968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5975    3.4372   -1.9509 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0565    0.5135   -3.4250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8012    1.4390   -4.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4365    1.0919   -2.8030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0082    2.7515   -3.2483 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1115    1.4751   -2.2001 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1403    2.7093   -0.6251 H   0  0  0  0  0  0  0  0  0  0  0  0
 31 30  1  0
 30 32  1  0
 32 33  2  0
 32 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 36  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  3  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  6
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 16 18  1  1
 18 19  1  0
 19 20  1  0
 19 21  2  0
 16 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 23 28  1  0
 28 29  1  1
 28 30  1  0
 28 35  1  0
 22 10  1  0
 31 64  1  0
 31 65  1  0
 31 66  1  0
 30 63  1  6
 35 67  1  6
 36 68  1  6
  1 38  1  0
  1 39  1  0
  3 40  1  6
  6 41  1  0
  6 42  1  0
  6 43  1  0
  8 44  1  0
  9 45  1  0
 11 46  1  0
 11 47  1  0
 11 48  1  0
 12 49  1  0
 13 50  1  0
 17 51  1  0
 17 52  1  0
 17 53  1  0
 20 54  1  0
 20 55  1  0
 20 56  1  0
 22 57  1  1
 23 58  1  6
 26 59  1  0
 26 60  1  0
 26 61  1  0
 29 62  1  0
M  END


  Mrv1652309022222032D          

 37 39  0  0  1  0            999 V2000
    2.8939    2.1648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3972    1.5112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1744    1.7879    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4074    2.5793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8385    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0715    3.9682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0366    2.9828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6778    1.1342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4692    0.9013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4922    0.0766    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0897    0.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3148    0.0133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6712   -0.7308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2051   -1.4115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5616   -2.1555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3825   -1.3481    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5879   -1.5700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4630   -2.1692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2143   -2.5100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0007   -2.2606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2948   -3.3311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0261   -0.6041    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2489   -0.8808    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2719   -1.7055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9976   -2.0979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6258   -2.6327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0206   -2.9226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4575   -0.6479    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7342   -1.4251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9913   -1.3286    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2681   -2.1058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1999   -1.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5463   -1.5990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1769   -0.2709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9541    0.0058    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9311    0.8305    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1397    1.0634    0.0000 Cl  0  0  0  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  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 22 16  1  6  0  0  0
 10 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 35 34  1  1  0  0  0
 28 35  1  0  0  0  0
 35 36  1  0  0  0  0
  2 36  1  0  0  0  0
 36 37  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0161801

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C(=O)O[C@H]2[C@@H](Cl)C(=C)[C@@H](OC(C)=O)\C=C\[C@@]3(C)C=CC(=O)[C@@](C)(OC(C)=O)[C@@H]3[C@@H](OC(C)=O)[C@]12O

> <INCHI_IDENTIFIER>
InChI=1S/C26H31ClO10/c1-12-17(34-14(3)28)8-10-24(6)11-9-18(31)25(7,37-16(5)30)20(24)22(35-15(4)29)26(33)13(2)23(32)36-21(26)19(12)27/h8-11,13,17,19-22,33H,1H2,2-7H3/b10-8+/t13-,17-,19-,20+,21-,22+,24-,25+,26-/m0/s1

> <INCHI_KEY>
ZMERMQBCOJBQPB-NBKSOLDASA-N

> <FORMULA>
C26H31ClO10

> <MOLECULAR_WEIGHT>
538.97

> <EXACT_MASS>
538.1605749

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
53.12820435064491

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,3R,4R,7R,8S,10S,11E,13S,17S)-2,17-bis(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0^{3,7}]heptadeca-11,14-dien-10-yl acetate

> <ALOGPS_LOGP>
2.13

> <JCHEM_LOGP>
1.816215958666667

> <ALOGPS_LOGS>
-4.60

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.36656459952414

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9506646441681417

> <JCHEM_POLAR_SURFACE_AREA>
142.50000000000003

> <JCHEM_REFRACTIVITY>
129.41209999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.36e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3R,4R,7R,8S,10S,11E,13S,17S)-2,17-bis(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0^{3,7}]heptadeca-11,14-dien-10-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       5.402   4.041   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.342   2.821   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.792   3.337   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.227   4.815   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.165   5.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.600   7.407   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.668   5.568   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.732   2.117   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.209   1.682   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.252   0.143   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.367   1.205   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.788   0.025   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.453  -1.364   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.583  -2.635   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      12.248  -4.024   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.047  -2.517   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.564  -2.931   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.198  -4.049   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      11.600  -4.685   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.068  -4.220   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      11.750  -6.218   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.382  -1.128   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.931  -1.644   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.974  -3.184   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.329  -3.916   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.502  -4.914   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       9.372  -5.456   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.454  -1.209   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.970  -2.660   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       5.584  -2.480   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.100  -3.931   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.107  -2.045   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.886  -2.985   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       4.064  -0.506   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       5.514   0.011   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.471   1.550   0.000  0.00  0.00           C+0
HETATM   37 Cl   UNK     0       3.994   1.985   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3   36                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    3    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   22                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18   22                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   16   10   23                                                  
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   23   29   30   35                                             
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   28   36                                                  
CONECT   36   35    2   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

View in JSmol

Synonyms

Value	Source
(1S,2R,3R,4R,7R,8S,10S,11E,13S,17S)-2,17-Bis(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0,]heptadeca-11,14-dien-10-yl acetic acid	Generator

Chemical Formula

C₂₆H₃₁ClO₁₀

Average Mass

538.9700 Da

Monoisotopic Mass

538.16057 Da

IUPAC Name

(1S,2R,3R,4R,7R,8S,10S,11E,13S,17S)-2,17-bis(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0^{3,7}]heptadeca-11,14-dien-10-yl acetate

Traditional Name

(1S,2R,3R,4R,7R,8S,10S,11E,13S,17S)-2,17-bis(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0^{3,7}]heptadeca-11,14-dien-10-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@H]1C(=O)O[C@H]2[C@@H](Cl)C(=C)[C@@H](OC(C)=O)\C=C\[C@@]3(C)C=CC(=O)[C@@](C)(OC(C)=O)[C@@H]3[C@@H](OC(C)=O)[C@]12O

InChI Identifier

InChI=1S/C26H31ClO10/c1-12-17(34-14(3)28)8-10-24(6)11-9-18(31)25(7,37-16(5)30)20(24)22(35-15(4)29)26(33)13(2)23(32)36-21(26)19(12)27/h8-11,13,17,19-22,33H,1H2,2-7H3/b10-8+/t13-,17-,19-,20+,21-,22+,24-,25+,26-/m0/s1

InChI Key

ZMERMQBCOJBQPB-NBKSOLDASA-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
Briareum asbestinum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Briarane diterpenoid
Tetracarboxylic acid or derivatives
Cyclohexenone
Alpha-acyloxy ketone
Gamma butyrolactone
Tertiary alcohol
Tetrahydrofuran
Carboxylic acid ester
Ketone
Lactone
Cyclic ketone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organochloride
Organohalogen compound
Alkyl chloride
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen compound
Alkyl halide
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	2.13	ALOGPS
logP	1.82	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	12.37	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	142.5 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	129.41 m³·mol⁻¹	ChemAxon
Polarizability	53.13 Å³	ChemAxon
Number of Rings	3	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

27022566

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162892244

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2r,3r,4r,7r,8s,10s,11e,13s,17s)-2,17-bis(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-11,14-dien-10-yl acetate (NP0161801)

MOL for NP0161801 ((1s,2r,3r,4r,7r,8s,10s,11e,13s,17s)-2,17-bis(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-11,14-dien-10-yl acetate)

3D MOL for NP0161801 ((1s,2r,3r,4r,7r,8s,10s,11e,13s,17s)-2,17-bis(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-11,14-dien-10-yl acetate)

3D SDF for NP0161801 ((1s,2r,3r,4r,7r,8s,10s,11e,13s,17s)-2,17-bis(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-11,14-dien-10-yl acetate)

3D-SDF for NP0161801 ((1s,2r,3r,4r,7r,8s,10s,11e,13s,17s)-2,17-bis(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-11,14-dien-10-yl acetate)

PDB for NP0161801 ((1s,2r,3r,4r,7r,8s,10s,11e,13s,17s)-2,17-bis(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-11,14-dien-10-yl acetate)

3D PDB for NP0161801 ((1s,2r,3r,4r,7r,8s,10s,11e,13s,17s)-2,17-bis(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-11,14-dien-10-yl acetate)

SMILES for NP0161801 ((1s,2r,3r,4r,7r,8s,10s,11e,13s,17s)-2,17-bis(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-11,14-dien-10-yl acetate)

INCHI for NP0161801 ((1s,2r,3r,4r,7r,8s,10s,11e,13s,17s)-2,17-bis(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-11,14-dien-10-yl acetate)

Structure for NP0161801 ((1s,2r,3r,4r,7r,8s,10s,11e,13s,17s)-2,17-bis(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-11,14-dien-10-yl acetate)

3D Structure for NP0161801 ((1s,2r,3r,4r,7r,8s,10s,11e,13s,17s)-2,17-bis(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-11,14-dien-10-yl acetate)