NP-MRD: Showing NP-Card for (5r)-5-[(2r)-2-[(1r,3ar,5ar,7r,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-4-oxo-1h,2h,3h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]propyl]-3-methyl-5h-furan-2-one (NP0309013)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2022-09-11 03:16:03 UTC

Updated at

2022-09-11 03:16:03 UTC

NP-MRD ID

NP0309013

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5r)-5-[(2r)-2-[(1r,3ar,5ar,7r,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-4-oxo-1h,2h,3h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]propyl]-3-methyl-5h-furan-2-one

Description

(23R)-3alpha,23-Dihydroxy-7-oxo-5alpha-lanosta-8,24-dien-26-oic acid gamma-lactone belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring. (5r)-5-[(2r)-2-[(1r,3ar,5ar,7r,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-4-oxo-1h,2h,3h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]propyl]-3-methyl-5h-furan-2-one is found in Abies mariesii. It was first documented in 2022 (PMID: 36122165). Based on a literature review a significant number of articles have been published on (23R)-3alpha,23-Dihydroxy-7-oxo-5alpha-lanosta-8,24-dien-26-oic acid gamma-lactone (PMID: 36122164) (PMID: 36122163) (PMID: 36122162) (PMID: 36122161).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112205162D          

 34 38  0  0  1  0            999 V2000
    7.0978   -3.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0710   -2.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3882   -2.1239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6175   -1.3314    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1111   -0.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939   -0.7929    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9830   -1.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -0.1416    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0168    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    0.6076    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4850    1.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705    0.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -0.1684    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3228   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266    0.2673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8069   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.5577    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9098    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2793    1.6026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7182    1.9630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463    1.0432    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7781    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1220    2.1594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4420   -1.3046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7223   -2.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5148   -2.3098    0.0000 O   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
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  8  6  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  8 17  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  6  0  0  0
 14 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 13 30  1  0  0  0  0
 30 31  2  0  0  0  0
  4 32  1  0  0  0  0
 32 33  1  0  0  0  0
  2 33  1  0  0  0  0
 33 34  2  0  0  0  0
M  END

     RDKit          3D

 78 82  0  0  0  0  0  0  0  0999 V2000
    7.2819    1.6232    2.4539 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9022    0.8742    1.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3373   -0.3108    1.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1690   -0.6079   -0.3007 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8035   -1.0932   -0.6706 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6879   -0.1201   -0.5334 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8052    1.1150   -1.3718 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4044   -0.8347   -0.7804 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3255   -2.1197    0.0703 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8644   -2.3536    0.3675 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2005   -1.3559   -0.5577 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3750   -1.8718   -1.9574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1572   -1.0142   -0.1992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5379    0.2436   -0.1227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7014    1.4013   -0.4767 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6634    1.0064   -1.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1498   -0.1690   -0.3087 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2534    0.1547    1.1393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9160    0.4953    0.3587 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9724    0.1014    1.8221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3084    1.9470    0.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6630    2.1143    0.8703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6251    1.0221    0.5827 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.8511    1.6196    0.2079 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2362    0.0981   -0.5187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5689    0.8043   -1.8394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1773   -1.1075   -0.4537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8271   -0.3663   -0.4947 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6334   -1.7853   -0.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1778   -2.0414    0.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7337   -3.1575    0.5037 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6650    0.4649   -1.0101 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1306    1.4086   -0.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6496    2.5141   -0.4369 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7739    1.1951    3.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9478    2.6930    2.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3843    1.6866    2.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0616   -0.9242    1.9480 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8548   -1.4826   -0.5272 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8727   -1.4151   -1.7530 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5835   -1.9738   -0.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6790    0.2394    0.5330 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7307    1.1406   -2.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6528    2.0651   -0.8340 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9883    1.0687   -2.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3871   -1.1701   -1.8274 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8601   -2.0335    1.0178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6595   -2.9905   -0.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5992   -2.1230    1.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5625   -3.3982    0.1660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6235   -2.3161   -2.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5535   -1.0799   -2.7081 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0843   -2.7213   -2.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2227    2.0701   -1.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5619    1.9884    0.4600 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3001    1.9067   -0.7803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5992    0.9423   -2.1260 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3324   -0.0689    1.7163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4184    1.2687    1.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1011   -0.2988    1.6798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7824   -0.5857    2.0623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0673    0.9832    2.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0218   -0.4060    2.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2200    2.3547   -0.7528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5846    2.5147    0.8933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0503    3.1185    0.5264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6036    2.2301    1.9923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8893    0.4143    1.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0847    2.3527    0.8448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5271    1.9190   -1.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8687    0.5009   -2.6346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5948    0.5696   -2.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1796   -0.7237   -0.7735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2001   -1.5548    0.5485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8734   -1.8274   -1.2387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4272   -0.2833   -1.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9506   -2.4385   -0.9376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2352   -2.1060    0.7796 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4 32  1  0
 32 33  1  0
 33 34  2  0
 33  2  1  0
  2  1  1  0
  2  3  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  6
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  1
 14 19  1  0
 19 20  1  1
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
  3  4  1  0
 17  8  1  0
 28 19  1  0
 17 11  1  0
 30 13  1  0
  7 43  1  0
  7 44  1  0
  7 45  1  0
  6 42  1  1
  5 40  1  0
  5 41  1  0
  4 39  1  6
  1 35  1  0
  1 36  1  0
  1 37  1  0
  3 38  1  0
  8 46  1  6
  9 47  1  0
  9 48  1  0
 10 49  1  0
 10 50  1  0
 12 51  1  0
 12 52  1  0
 12 53  1  0
 15 54  1  0
 15 55  1  0
 16 56  1  0
 16 57  1  0
 18 58  1  0
 18 59  1  0
 18 60  1  0
 20 61  1  0
 20 62  1  0
 20 63  1  0
 21 64  1  0
 21 65  1  0
 22 66  1  0
 22 67  1  0
 23 68  1  1
 24 69  1  0
 26 70  1  0
 26 71  1  0
 26 72  1  0
 27 73  1  0
 27 74  1  0
 27 75  1  0
 28 76  1  6
 29 77  1  0
 29 78  1  0
M  END


  Mrv1652309112205162D          

 34 38  0  0  1  0            999 V2000
    7.0978   -3.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0710   -2.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3882   -2.1239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6175   -1.3314    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1111   -0.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939   -0.7929    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9830   -1.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -0.1416    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0168    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    0.6076    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4850    1.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705    0.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -0.1684    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3228   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266    0.2673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8069   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.5577    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9098    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2793    1.6026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7182    1.9630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463    1.0432    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7781    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1220    2.1594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4420   -1.3046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7223   -2.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5148   -2.3098    0.0000 O   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
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  8  6  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  8 17  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  6  0  0  0
 14 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 13 30  1  0  0  0  0
 30 31  2  0  0  0  0
  4 32  1  0  0  0  0
 32 33  1  0  0  0  0
  2 33  1  0  0  0  0
 33 34  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0309013

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](C[C@H]1OC(=O)C(C)=C1)[C@H]1CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@@H](O)C(C)(C)[C@@H]1CC3=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H44O4/c1-17(14-19-15-18(2)26(33)34-19)20-8-13-30(7)25-21(9-12-29(20,30)6)28(5)11-10-24(32)27(3,4)23(28)16-22(25)31/h15,17,19-20,23-24,32H,8-14,16H2,1-7H3/t17-,19-,20-,23+,24-,28-,29-,30+/m1/s1

> <INCHI_KEY>
ACGCEODAXBTLQJ-RIZXRZCXSA-N

> <FORMULA>
C30H44O4

> <MOLECULAR_WEIGHT>
468.678

> <EXACT_MASS>
468.323959897

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
54.06822573233086

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5R)-5-[(2R)-2-[(2S,5R,7R,11R,14R,15R)-5-hydroxy-2,6,6,11,15-pentamethyl-9-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]propyl]-3-methyl-2,5-dihydrofuran-2-one

> <JCHEM_LOGP>
5.898075149666669

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.618725644141033

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.60054597623089

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7785515983554249

> <JCHEM_POLAR_SURFACE_AREA>
63.6

> <JCHEM_REFRACTIVITY>
134.97840000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(5R)-5-[(2R)-2-[(2S,5R,7R,11R,14R,15R)-5-hydroxy-2,6,6,11,15-pentamethyl-9-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]propyl]-3-methyl-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      13.249  -6.368   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.199  -4.829   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.925  -3.965   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.353  -2.485   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.407  -1.269   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.882  -1.480   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.302  -2.907   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.937  -0.264   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.365   1.215   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.090   2.079   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.874   1.134   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.505   2.629   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.358   1.405   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.366   0.228   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.889  -1.221   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.405  -1.492   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.398  -0.314   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.069  -1.700   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.850   0.499   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.373  -0.949   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.857  -0.678   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.341  -0.407   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.182   1.041   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.698   1.312   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.810   2.218   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.521   2.992   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.341   3.664   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.326   1.947   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.319   3.125   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.835   2.854   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.828   4.031   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      13.892  -2.435   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      14.415  -3.884   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      15.894  -4.312   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   32                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   17                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   17                                             
CONECT   12   11                                                            
CONECT   13   11   14   30                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    8   11   18                                             
CONECT   18   17                                                            
CONECT   19   14   20   21   28                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25   19   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   13   31                                                  
CONECT   31   30                                                            
CONECT   32    4   33                                                       
CONECT   33   32    2   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Value	Source
(23R)-3a,23-Dihydroxy-7-oxo-5a-lanosta-8,24-dien-26-Oate g-lactone	Generator
(23R)-3a,23-Dihydroxy-7-oxo-5a-lanosta-8,24-dien-26-Oic acid g-lactone	Generator
(23R)-3alpha,23-Dihydroxy-7-oxo-5alpha-lanosta-8,24-dien-26-Oate gamma-lactone	Generator
(23R)-3Α,23-dihydroxy-7-oxo-5α-lanosta-8,24-dien-26-Oate γ-lactone	Generator
(23R)-3Α,23-dihydroxy-7-oxo-5α-lanosta-8,24-dien-26-Oic acid γ-lactone	Generator

Chemical Formula

C₃₀H₄₄O₄

Average Mass

468.6780 Da

Monoisotopic Mass

468.32396 Da

IUPAC Name

(5R)-5-[(2R)-2-[(2S,5R,7R,11R,14R,15R)-5-hydroxy-2,6,6,11,15-pentamethyl-9-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]propyl]-3-methyl-2,5-dihydrofuran-2-one

Traditional Name

(5R)-5-[(2R)-2-[(2S,5R,7R,11R,14R,15R)-5-hydroxy-2,6,6,11,15-pentamethyl-9-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]propyl]-3-methyl-5H-furan-2-one

CAS Registry Number

Not Available

SMILES

C[C@H](C[C@H]1OC(=O)C(C)=C1)[C@H]1CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@@H](O)C(C)(C)[C@@H]1CC3=O

InChI Identifier

InChI=1S/C30H44O4/c1-17(14-19-15-18(2)26(33)34-19)20-8-13-30(7)25-21(9-12-29(20,30)6)28(5)11-10-24(32)27(3,4)23(28)16-22(25)31/h15,17,19-20,23-24,32H,8-14,16H2,1-7H3/t17-,19-,20-,23+,24-,28-,29-,30+/m1/s1

InChI Key

ACGCEODAXBTLQJ-RIZXRZCXSA-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
Abies mariesii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Withanolides and derivatives

Alternative Parents

Substituents

Triterpenoid
Withanolide-skeleton
3-hydroxysteroid
14-alpha-methylsteroid
Hydroxysteroid
Oxosteroid
3-alpha-hydroxysteroid
7-oxosteroid
Cyclohexenone
2-furanone
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Ketone
Carboxylic acid ester
Secondary alcohol
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Carbonyl group
Organic oxide
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	5.9	ChemAxon
pKa (Strongest Acidic)	13.6	ChemAxon
pKa (Strongest Basic)	-0.78	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	134.98 m³·mol⁻¹	ChemAxon
Polarizability	54.07 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	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

101033265

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Orrantia-Borunda E, Acuna-Aguilar LE, Ramirez-Valdespino CA: Nanomaterials for Breast Cancer. 2022 Aug 6. [PubMed:36122165 ]
Tecalco-Cruz AC, Ramirez-Jarquin JO, Zepeda-Cervantes J, Solleiro-Villavicencio H, Abraham-Juarez MJ: Ubiquitin-Specific Peptidase 18: A Multifaceted Protein Participating in Breast Cancer. 2022 Aug 6. [PubMed:36122164 ]
Berg AL, Rowson-Hodel A, Wheeler MR, Hu M, Free SR, Carraway KL III: Engaging the Lysosome and Lysosome-Dependent Cell Death in Cancer. 2022 Aug 6. [PubMed:36122163 ]
Sridhar J, Komati R, Kumar S: Targeting RPS6K1 for Refractory Breast Cancer Therapy. 2022 Aug 6. [PubMed:36122162 ]
Arzanova E, Mayrovitz HN: The Epidemiology of Breast Cancer. 2022 Aug 6. [PubMed:36122161 ]
LOTUS database [Link]

Showing NP-Card for (5r)-5-[(2r)-2-[(1r,3ar,5ar,7r,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-4-oxo-1h,2h,3h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]propyl]-3-methyl-5h-furan-2-one (NP0309013)

MOL for NP0309013 ((5r)-5-[(2r)-2-[(1r,3ar,5ar,7r,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-4-oxo-1h,2h,3h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]propyl]-3-methyl-5h-furan-2-one)

3D MOL for NP0309013 ((5r)-5-[(2r)-2-[(1r,3ar,5ar,7r,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-4-oxo-1h,2h,3h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]propyl]-3-methyl-5h-furan-2-one)

3D SDF for NP0309013 ((5r)-5-[(2r)-2-[(1r,3ar,5ar,7r,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-4-oxo-1h,2h,3h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]propyl]-3-methyl-5h-furan-2-one)

3D-SDF for NP0309013 ((5r)-5-[(2r)-2-[(1r,3ar,5ar,7r,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-4-oxo-1h,2h,3h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]propyl]-3-methyl-5h-furan-2-one)

PDB for NP0309013 ((5r)-5-[(2r)-2-[(1r,3ar,5ar,7r,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-4-oxo-1h,2h,3h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]propyl]-3-methyl-5h-furan-2-one)

3D PDB for NP0309013 ((5r)-5-[(2r)-2-[(1r,3ar,5ar,7r,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-4-oxo-1h,2h,3h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]propyl]-3-methyl-5h-furan-2-one)

SMILES for NP0309013 ((5r)-5-[(2r)-2-[(1r,3ar,5ar,7r,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-4-oxo-1h,2h,3h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]propyl]-3-methyl-5h-furan-2-one)

INCHI for NP0309013 ((5r)-5-[(2r)-2-[(1r,3ar,5ar,7r,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-4-oxo-1h,2h,3h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]propyl]-3-methyl-5h-furan-2-one)

Structure for NP0309013 ((5r)-5-[(2r)-2-[(1r,3ar,5ar,7r,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-4-oxo-1h,2h,3h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]propyl]-3-methyl-5h-furan-2-one)

3D Structure for NP0309013 ((5r)-5-[(2r)-2-[(1r,3ar,5ar,7r,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-4-oxo-1h,2h,3h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]propyl]-3-methyl-5h-furan-2-one)