NP-MRD: Showing NP-Card for (1s,2s,4r,5r,10s,11s,13s,16r,17r,20s)-5-chloro-16-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-4,13,17-trihydroxy-10,20-dimethyl-14-oxapentacyclo[11.6.1.0²,¹¹.0⁵,¹⁰.0¹⁷,²⁰]icos-7-en-9-one (NP0330970)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-12 16:50:20 UTC

Updated at

2022-09-12 16:50:21 UTC

NP-MRD ID

NP0330970

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Description

(1s,2s,4r,5r,10s,11s,13s,16r,17r,20s)-5-chloro-16-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-4,13,17-trihydroxy-10,20-dimethyl-14-oxapentacyclo[11.6.1.0²,¹¹.0⁵,¹⁰.0¹⁷,²⁰]icos-7-en-9-one is found in Jaborosa rotacea. Based on a literature review very few articles have been published on (1S,2S,4R,5R,10S,11S,13S,16R,17R,20S)-5-chloro-16-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-4,13,17-trihydroxy-10,20-dimethyl-14-oxapentacyclo[11.6.1.0²,¹¹.0⁵,¹⁰.0¹⁷,²⁰]Icos-7-en-9-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122218502D          

 36 41  0  0  1  0            999 V2000
   -0.9617   -1.3524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8333   -0.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4748   -0.0188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2448   -0.3150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3464    0.7962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9879    1.3149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5764    1.0924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0651    0.5737    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8351    0.8699    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9636    1.6849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7335    1.9811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3751    1.4624    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6163    2.2514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3565    1.5476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8761    0.9068    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5811    0.1364    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1007   -0.5044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9155   -0.3747    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4352   -1.0154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2106    0.3957    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7302   -0.2450    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.0253    0.5254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3204    1.2959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8007    1.9366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9859    1.8069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4663    2.4477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6909    1.0365    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1712    1.6773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7663    0.0067    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3175   -0.6855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5205   -0.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4767    0.3512    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7419   -0.0239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2466    0.6475    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0434    0.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0633   -0.2412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 15 27  1  0  0  0  0
 20 27  1  0  0  0  0
 27 28  1  6  0  0  0
 16 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
  9 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  0  0  0  0
 29 34  1  0  0  0  0
 12 34  1  0  0  0  0
 34 35  1  6  0  0  0
  8 36  1  0  0  0  0
  2 36  1  0  0  0  0
M  END

     RDKit          3D

 73 78  0  0  0  0  0  0  0  0999 V2000
    7.1499   -0.6462    0.1495 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8573   -0.2595   -0.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8225    0.2615   -1.6373 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0899    0.4531   -2.4039 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5695    0.6993   -2.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5344    1.1948   -3.4340 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4055    0.5216   -1.5035 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6035    0.5409   -0.1141 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3248    0.5532    0.6749 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5701    1.7863    0.2661 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2204    1.6177    0.1308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2468    0.9810    1.2801 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3072    1.4753    2.4372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7283    1.1680    1.3366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4707    0.5884    0.1574 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0683   -0.8669    0.0202 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8925   -1.6313   -0.9509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3538   -1.5110   -0.5407 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5057   -1.9923    0.7497 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7216   -0.0631   -0.6812 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2809    0.4166   -2.3588 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -6.1912    0.1907   -0.5345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4720    1.6212   -0.7423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5588    2.5703   -0.6074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1910    2.2310   -0.2353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3221    3.1302   -0.3310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9167    0.8429    0.2325 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4447    0.7721    1.6628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6184   -0.8320   -0.2510 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0787   -2.0699   -0.6303 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5360   -1.5631   -0.5018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5417   -0.6929    0.7070 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0467   -1.5073    1.7584 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0825   -0.4852    1.0679 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3859   -1.3112    2.2106 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5984   -0.4694    0.3102 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7647    0.2803    0.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0277   -1.1250    1.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7393   -1.3362   -0.4695 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9705    0.2289   -1.8012 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1345    1.5524   -2.6380 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0631   -0.0507   -3.3896 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0580    1.5533    0.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6711    0.7610    1.7379 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9445    2.1980   -0.7179 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7218    2.6503    0.9774 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5957    0.7370    3.0291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1751    0.8235    2.3033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9167    2.2742    1.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0574    1.1009   -0.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2288   -1.3181    1.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6359   -2.7052   -0.8448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7520   -1.3225   -1.9916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9981   -2.0923   -1.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0087   -2.8471    0.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6356   -0.2272    0.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6977   -0.3562   -1.3813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4782    1.9687   -1.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8139    3.5993   -0.7701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5514    0.9687    1.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0236    1.6764    2.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1844   -0.1587    2.1673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3461   -0.0281   -0.9625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0876   -2.3937   -1.6822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0711   -2.9238    0.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1182   -2.5198   -0.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7328   -1.0823   -1.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4732   -0.9507    2.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4976   -1.4658    2.8978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1660   -0.8673    2.8269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7029   -2.3352    1.9286 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2703   -1.5162    0.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7787   -0.4653    1.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8 36  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  1
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  6
 20 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  1
 16 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  1
 32 34  1  0
 34 35  1  1
 36  2  1  0
 32  9  1  0
 34 12  1  0
 27 15  1  0
 34 29  1  0
 27 20  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  4 40  1  0
  4 41  1  0
  4 42  1  0
  8 43  1  6
 36 72  1  0
 36 73  1  0
  9 44  1  1
 10 45  1  0
 10 46  1  0
 13 47  1  0
 14 48  1  0
 14 49  1  0
 15 50  1  6
 16 51  1  1
 17 52  1  0
 17 53  1  0
 18 54  1  6
 19 55  1  0
 22 56  1  0
 22 57  1  0
 23 58  1  0
 24 59  1  0
 28 60  1  0
 28 61  1  0
 28 62  1  0
 29 63  1  6
 30 64  1  0
 30 65  1  0
 31 66  1  0
 31 67  1  0
 33 68  1  0
 35 69  1  0
 35 70  1  0
 35 71  1  0
M  END


  Mrv1652309122218502D          

 36 41  0  0  1  0            999 V2000
   -0.9617   -1.3524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8333   -0.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4748   -0.0188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2448   -0.3150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3464    0.7962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9879    1.3149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5764    1.0924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0651    0.5737    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8351    0.8699    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9636    1.6849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7335    1.9811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3751    1.4624    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6163    2.2514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3565    1.5476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8761    0.9068    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5811    0.1364    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1007   -0.5044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9155   -0.3747    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4352   -1.0154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2106    0.3957    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7302   -0.2450    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.0253    0.5254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3204    1.2959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8007    1.9366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9859    1.8069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4663    2.4477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6909    1.0365    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1712    1.6773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7663    0.0067    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3175   -0.6855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5205   -0.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4767    0.3512    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7419   -0.0239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2466    0.6475    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0434    0.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0633   -0.2412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 15 27  1  0  0  0  0
 20 27  1  0  0  0  0
 27 28  1  6  0  0  0
 16 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
  9 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  0  0  0  0
 29 34  1  0  0  0  0
 12 34  1  0  0  0  0
 34 35  1  6  0  0  0
  8 36  1  0  0  0  0
  2 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0330970

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(C)C(=O)O[C@H](C1)[C@H]1CO[C@@]2(O)C[C@H]3[C@@H](C[C@@H](O)[C@@]4(Cl)CC=CC(=O)[C@]34C)[C@@H]3CC[C@]1(O)[C@@]23C

> <INCHI_IDENTIFIER>
InChI=1S/C28H37ClO7/c1-14-10-20(36-23(32)15(14)2)19-13-35-28(34)12-18-16(17-7-9-27(19,33)25(17,28)4)11-22(31)26(29)8-5-6-21(30)24(18,26)3/h5-6,16-20,22,31,33-34H,7-13H2,1-4H3/t16-,17-,18-,19+,20+,22+,24-,25-,26-,27+,28-/m0/s1

> <INCHI_KEY>
GLSQHTYIOIWXHF-ULOYMMBOSA-N

> <FORMULA>
C28H37ClO7

> <MOLECULAR_WEIGHT>
521.05

> <EXACT_MASS>
520.2227812

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
54.19503136273509

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,4R,5R,10S,11S,13S,16R,17R,20S)-5-chloro-16-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-4,13,17-trihydroxy-10,20-dimethyl-14-oxapentacyclo[11.6.1.0^{2,11}.0^{5,10}.0^{17,20}]icos-7-en-9-one

> <JCHEM_LOGP>
3.1937941956666647

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.612758413349482

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.57460874523179

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2906048675825756

> <JCHEM_POLAR_SURFACE_AREA>
113.29

> <JCHEM_REFRACTIVITY>
133.35389999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,4R,5R,10S,11S,13S,16R,17R,20S)-5-chloro-16-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-4,13,17-trihydroxy-10,20-dimethyl-14-oxapentacyclo[11.6.1.0^{2,11}.0^{5,10}.0^{17,20}]icos-7-en-9-one

> <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      -1.795  -2.525   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.555  -1.003   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.753  -0.035   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.190  -0.588   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.513   1.486   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -3.711   2.454   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -1.076   2.039   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.122   1.071   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.559   1.624   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.799   3.145   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.236   3.698   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.433   2.730   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.884   4.203   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.265   2.889   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.235   1.693   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.685   0.255   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.655  -0.941   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.176  -0.699   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.146  -1.895   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.726   0.739   0.000  0.00  0.00           C+0
HETATM   21 Cl   UNK     0      10.696  -0.457   0.000  0.00  0.00          Cl+0
HETATM   22  C   UNK     0      11.247   0.981   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.798   2.419   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.828   3.615   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.307   3.373   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.337   4.569   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       8.756   1.935   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.786   3.131   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.164   0.013   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.326  -1.280   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.838  -0.882   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.756   0.656   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       1.385  -0.045   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       4.194   1.209   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.681   1.608   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.118  -0.450   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   36                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   36                                                  
CONECT    9    8   10   32                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   34                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   27                                                  
CONECT   16   15   17   29                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22   27                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   15   20   28                                             
CONECT   28   27                                                            
CONECT   29   16   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31    9   33   34                                             
CONECT   33   32                                                            
CONECT   34   32   29   12   35                                             
CONECT   35   34                                                            
CONECT   36    8    2                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₇ClO₇

Average Mass

521.0500 Da

Monoisotopic Mass

520.22278 Da

IUPAC Name

(1S,2S,4R,5R,10S,11S,13S,16R,17R,20S)-5-chloro-16-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-4,13,17-trihydroxy-10,20-dimethyl-14-oxapentacyclo[11.6.1.0^{2,11}.0^{5,10}.0^{17,20}]icos-7-en-9-one

Traditional Name

(1S,2S,4R,5R,10S,11S,13S,16R,17R,20S)-5-chloro-16-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-4,13,17-trihydroxy-10,20-dimethyl-14-oxapentacyclo[11.6.1.0^{2,11}.0^{5,10}.0^{17,20}]icos-7-en-9-one

CAS Registry Number

Not Available

SMILES

CC1=C(C)C(=O)O[C@H](C1)[C@H]1CO[C@@]2(O)C[C@H]3[C@@H](C[C@@H](O)[C@@]4(Cl)CC=CC(=O)[C@]34C)[C@@H]3CC[C@]1(O)[C@@]23C

InChI Identifier

InChI=1S/C28H37ClO7/c1-14-10-20(36-23(32)15(14)2)19-13-35-28(34)12-18-16(17-7-9-27(19,33)25(17,28)4)11-22(31)26(29)8-5-6-21(30)24(18,26)3/h5-6,16-20,22,31,33-34H,7-13H2,1-4H3/t16-,17-,18-,19+,20+,22+,24-,25-,26-,27+,28-/m0/s1

InChI Key

GLSQHTYIOIWXHF-ULOYMMBOSA-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
Jaborosa rotacea	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	3.19	ChemAxon
pKa (Strongest Acidic)	11.57	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	133.35 m³·mol⁻¹	ChemAxon
Polarizability	54.2 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

162970133

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2s,4r,5r,10s,11s,13s,16r,17r,20s)-5-chloro-16-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-4,13,17-trihydroxy-10,20-dimethyl-14-oxapentacyclo[11.6.1.0²,¹¹.0⁵,¹⁰.0¹⁷,²⁰]icos-7-en-9-one (NP0330970)

MOL for NP0330970 ((1s,2s,4r,5r,10s,11s,13s,16r,17r,20s)-5-chloro-16-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-4,13,17-trihydroxy-10,20-dimethyl-14-oxapentacyclo[11.6.1.0²,¹¹.0⁵,¹⁰.0¹⁷,²⁰]icos-7-en-9-one)

3D MOL for NP0330970 ((1s,2s,4r,5r,10s,11s,13s,16r,17r,20s)-5-chloro-16-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-4,13,17-trihydroxy-10,20-dimethyl-14-oxapentacyclo[11.6.1.0²,¹¹.0⁵,¹⁰.0¹⁷,²⁰]icos-7-en-9-one)

3D SDF for NP0330970 ((1s,2s,4r,5r,10s,11s,13s,16r,17r,20s)-5-chloro-16-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-4,13,17-trihydroxy-10,20-dimethyl-14-oxapentacyclo[11.6.1.0²,¹¹.0⁵,¹⁰.0¹⁷,²⁰]icos-7-en-9-one)

3D-SDF for NP0330970 ((1s,2s,4r,5r,10s,11s,13s,16r,17r,20s)-5-chloro-16-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-4,13,17-trihydroxy-10,20-dimethyl-14-oxapentacyclo[11.6.1.0²,¹¹.0⁵,¹⁰.0¹⁷,²⁰]icos-7-en-9-one)

PDB for NP0330970 ((1s,2s,4r,5r,10s,11s,13s,16r,17r,20s)-5-chloro-16-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-4,13,17-trihydroxy-10,20-dimethyl-14-oxapentacyclo[11.6.1.0²,¹¹.0⁵,¹⁰.0¹⁷,²⁰]icos-7-en-9-one)

3D PDB for NP0330970 ((1s,2s,4r,5r,10s,11s,13s,16r,17r,20s)-5-chloro-16-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-4,13,17-trihydroxy-10,20-dimethyl-14-oxapentacyclo[11.6.1.0²,¹¹.0⁵,¹⁰.0¹⁷,²⁰]icos-7-en-9-one)

SMILES for NP0330970 ((1s,2s,4r,5r,10s,11s,13s,16r,17r,20s)-5-chloro-16-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-4,13,17-trihydroxy-10,20-dimethyl-14-oxapentacyclo[11.6.1.0²,¹¹.0⁵,¹⁰.0¹⁷,²⁰]icos-7-en-9-one)

INCHI for NP0330970 ((1s,2s,4r,5r,10s,11s,13s,16r,17r,20s)-5-chloro-16-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-4,13,17-trihydroxy-10,20-dimethyl-14-oxapentacyclo[11.6.1.0²,¹¹.0⁵,¹⁰.0¹⁷,²⁰]icos-7-en-9-one)

Structure for NP0330970 ((1s,2s,4r,5r,10s,11s,13s,16r,17r,20s)-5-chloro-16-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-4,13,17-trihydroxy-10,20-dimethyl-14-oxapentacyclo[11.6.1.0²,¹¹.0⁵,¹⁰.0¹⁷,²⁰]icos-7-en-9-one)

3D Structure for NP0330970 ((1s,2s,4r,5r,10s,11s,13s,16r,17r,20s)-5-chloro-16-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-4,13,17-trihydroxy-10,20-dimethyl-14-oxapentacyclo[11.6.1.0²,¹¹.0⁵,¹⁰.0¹⁷,²⁰]icos-7-en-9-one)