NP-MRD: Showing NP-Card for (1r,3s,3ar,4s,5ar,7s,9as,11ar)-3,4,7-trihydroxy-1-[(2r)-6-hydroxy-4-oxoheptan-2-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-10-one (NP0287431)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-09 16:30:35 UTC

Updated at

2022-09-09 16:30:35 UTC

NP-MRD ID

NP0287431

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

26-Nor-11,23-dioxo-5alpha-lanost-8-en-3beta,7beta,15alpha,25-tetrol belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (1r,3s,3ar,4s,5ar,7s,9as,11ar)-3,4,7-trihydroxy-1-[(2r)-6-hydroxy-4-oxoheptan-2-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-10-one is found in Ganoderma tropicum. (1r,3s,3ar,4s,5ar,7s,9as,11ar)-3,4,7-trihydroxy-1-[(2r)-6-hydroxy-4-oxoheptan-2-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-10-one was first documented in 2016 (PMID: 27213329). Based on a literature review very few articles have been published on 26-nor-11,23-dioxo-5alpha-lanost-8-en-3beta,7beta,15alpha,25-tetrol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309092218302D          

 35 38  0  0  1  0            999 V2000
   -0.9747   -7.5155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2602   -7.1030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2602   -6.2780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4542   -7.5155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1687   -7.1030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1687   -6.2780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8832   -7.5155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5977   -7.1030    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5977   -6.2780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3121   -7.5155    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3984   -8.3360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2053   -8.5075    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5409   -9.2612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6178   -7.7930    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1028   -8.4605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4248   -7.6215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6798   -6.8369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1277   -6.2238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3827   -5.4392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3207   -6.3953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0658   -7.1799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4527   -6.6279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4867   -6.6654    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9347   -6.0523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7417   -5.8807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5486   -5.7092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1007   -6.3223    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.9076   -6.1508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8457   -7.1069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6627   -7.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8745   -7.9314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0388   -7.2785    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7838   -8.0631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9768   -8.2346    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7219   -9.0192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  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
 10  8  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 10 21  1  0  0  0  0
 14 21  1  0  0  0  0
 21 22  1  6  0  0  0
 17 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
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 29 32  1  0  0  0  0
 23 32  1  0  0  0  0
 32 33  1  6  0  0  0
 33 34  1  0  0  0  0
 16 34  1  0  0  0  0
 34 35  1  6  0  0  0
M  END

     RDKit          3D

 81 84  0  0  0  0  0  0  0  0999 V2000
    7.5050   -0.4561    0.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6267    0.7164   -0.8156 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.0107    0.9150   -1.0420 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0117    0.5108   -2.1515 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5748    0.2428   -2.1846 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0960    0.0502   -3.3091 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6620    0.1816   -1.0453 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2261   -0.1576   -1.4816 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2970   -1.5323   -2.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3363   -0.2552   -0.2470 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3738    1.0834    0.5086 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9613    1.3831    0.9528 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0295    1.6777    2.3169 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2797    0.0563    0.7519 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7604   -0.8509    1.8622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1831    0.1181    0.7750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8125   -0.6426   -0.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1092   -1.6196   -0.9259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7694   -2.4771   -1.5386 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3618   -1.6241   -1.0399 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8714   -0.3174   -0.5858 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6028    0.7862   -1.5938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2957   -0.4288   -0.2358 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4301    0.9077   -0.9715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9859   -1.4413   -1.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4692   -1.0361   -1.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0327   -1.1572    0.2750 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.3251   -0.5825    0.2516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2591   -0.5464    1.3729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4414   -1.4666    2.5970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9312    0.7604    1.8244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8172   -0.3399    1.1660 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3446    1.0358    1.6655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8391    0.9938    1.7669 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4203    2.3245    1.6447 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1358   -1.3734   -0.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5014   -0.7323    0.5643 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8782   -0.1719    1.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2999    1.6536   -0.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4542    0.7893   -0.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6037   -0.3139   -2.6523 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2881    1.4175   -2.7685 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6031    1.1810   -0.5704 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9041   -0.5529   -0.2631 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8628    0.5438   -2.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8972   -2.3236   -1.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8054   -1.5828   -3.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3520   -1.8495   -2.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7121   -1.0925    0.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0705    0.9787    1.3771 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7622    1.8885   -0.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5302    2.1896    0.3624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2657    2.5992    2.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7817   -0.5586    2.2131 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0916   -0.6472    2.7335 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6690   -1.9135    1.6368 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7549   -2.4268   -0.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6869   -1.8853   -2.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3088    1.6309   -1.4819 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7429    0.2943   -2.6004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4051    1.1931   -1.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4143    1.3612   -0.8568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5987    1.5874   -0.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3020    0.6895   -2.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6729   -1.3127   -2.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9200   -2.4781   -0.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9665   -1.8188   -1.7342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6162   -0.0921   -1.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2344   -2.2550    0.4576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9661   -1.1216   -0.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8865   -1.0699    3.4495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0000   -2.4490    2.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5069   -1.6295    2.8017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7409    0.9482    2.9083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0286    0.5628    1.7627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7077    1.5968    1.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2089   -1.0686    1.7795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6928    1.8438    0.9844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7478    1.2745    2.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6178    0.6427    2.8227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8495    2.8357    2.3499 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  1
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  6
 17 23  1  0
 23 24  1  6
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  1  0
 29 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 21 10  1  0
 32 23  1  0
 21 14  1  0
 34 16  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  1
  3 40  1  0
  4 41  1  0
  4 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  6
  9 46  1  0
  9 47  1  0
  9 48  1  0
 10 49  1  1
 11 50  1  0
 11 51  1  0
 12 52  1  6
 13 53  1  0
 15 54  1  0
 15 55  1  0
 15 56  1  0
 20 57  1  0
 20 58  1  0
 22 59  1  0
 22 60  1  0
 22 61  1  0
 24 62  1  0
 24 63  1  0
 24 64  1  0
 25 65  1  0
 25 66  1  0
 26 67  1  0
 26 68  1  0
 27 69  1  1
 28 70  1  0
 30 71  1  0
 30 72  1  0
 30 73  1  0
 31 74  1  0
 31 75  1  0
 31 76  1  0
 32 77  1  1
 33 78  1  0
 33 79  1  0
 34 80  1  1
 35 81  1  0
M  END

  Mrv1652309092218302D          

 35 38  0  0  1  0            999 V2000
   -0.9747   -7.5155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2602   -7.1030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2602   -6.2780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4542   -7.5155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1687   -7.1030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1687   -6.2780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8832   -7.5155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5977   -7.1030    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5977   -6.2780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3121   -7.5155    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3984   -8.3360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2053   -8.5075    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5409   -9.2612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6178   -7.7930    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1028   -8.4605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4248   -7.6215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6798   -6.8369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1277   -6.2238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3827   -5.4392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3207   -6.3953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0658   -7.1799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4527   -6.6279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4867   -6.6654    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9347   -6.0523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7417   -5.8807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5486   -5.7092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1007   -6.3223    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.9076   -6.1508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8457   -7.1069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6627   -7.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8745   -7.9314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0388   -7.2785    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7838   -8.0631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9768   -8.2346    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7219   -9.0192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  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
 10  8  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 10 21  1  0  0  0  0
 14 21  1  0  0  0  0
 21 22  1  6  0  0  0
 17 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
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 29 32  1  0  0  0  0
 23 32  1  0  0  0  0
 32 33  1  6  0  0  0
 33 34  1  0  0  0  0
 16 34  1  0  0  0  0
 34 35  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0287431

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)CC(=O)C[C@@H](C)[C@H]1C[C@H](O)[C@@]2(C)C3=C(C(=O)C[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@@H]1C[C@@H]3O

> <INCHI_IDENTIFIER>
InChI=1S/C29H46O6/c1-15(10-17(31)11-16(2)30)18-12-23(35)29(7)25-19(32)13-21-26(3,4)22(34)8-9-27(21,5)24(25)20(33)14-28(18,29)6/h15-16,18-19,21-23,30,32,34-35H,8-14H2,1-7H3/t15-,16?,18-,19+,21+,22+,23+,27+,28-,29+/m1/s1

> <INCHI_KEY>
BYRGJKZMDMBDDL-POESAPRRSA-N

> <FORMULA>
C29H46O6

> <MOLECULAR_WEIGHT>
490.681

> <EXACT_MASS>
490.329439201

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
56.139911024534925

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,5S,7R,9S,11R,12S,14R,15R)-5,9,12-trihydroxy-14-[(2R)-6-hydroxy-4-oxoheptan-2-yl]-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-17-one

> <JCHEM_LOGP>
2.2083448883333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.809200287649801

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.241474143835923

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8070039932709377

> <JCHEM_POLAR_SURFACE_AREA>
115.06

> <JCHEM_REFRACTIVITY>
135.10420000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,5S,7R,9S,11R,12S,14R,15R)-5,9,12-trihydroxy-14-[(2R)-6-hydroxy-4-oxoheptan-2-yl]-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-17-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.819 -14.029   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.486 -13.259   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.486 -11.719   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.848 -14.029   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.182 -13.259   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.182 -11.719   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.515 -14.029   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.849 -13.259   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.849 -11.719   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.183 -14.029   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.344 -15.560   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.850 -15.881   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.476 -17.288   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.620 -14.547   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.525 -15.793   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.126 -14.227   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.602 -12.762   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.572 -11.618   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.048 -10.153   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.065 -11.938   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.590 -13.403   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.445 -12.372   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.109 -12.442   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.078 -11.298   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.584 -10.977   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.091 -10.657   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.121 -11.802   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      16.628 -11.481   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      14.645 -13.266   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      16.170 -13.481   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      14.699 -14.805   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      13.139 -13.586   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.663 -15.051   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      11.157 -15.371   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      10.681 -16.836   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   21                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16   21                                             
CONECT   15   14                                                            
CONECT   16   14   17   34                                                  
CONECT   17   16   18   23                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   10   14   22                                             
CONECT   22   21                                                            
CONECT   23   17   24   25   32                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31   32                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   29   23   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33   16   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
26-Nor-11,23-dioxo-5a-lanost-8-en-3b,7b,15a,25-tetrol	Generator
26-Nor-11,23-dioxo-5α-lanost-8-en-3β,7β,15α,25-tetrol	Generator

Chemical Formula

C₂₉H₄₆O₆

Average Mass

490.6810 Da

Monoisotopic Mass

490.32944 Da

IUPAC Name

(2S,5S,7R,9S,11R,12S,14R,15R)-5,9,12-trihydroxy-14-[(2R)-6-hydroxy-4-oxoheptan-2-yl]-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-17-one

Traditional Name

(2S,5S,7R,9S,11R,12S,14R,15R)-5,9,12-trihydroxy-14-[(2R)-6-hydroxy-4-oxoheptan-2-yl]-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-17-one

CAS Registry Number

Not Available

SMILES

CC(O)CC(=O)C[C@@H](C)[C@H]1C[C@H](O)[C@@]2(C)C3=C(C(=O)C[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@@H]1C[C@@H]3O

InChI Identifier

InChI=1S/C29H46O6/c1-15(10-17(31)11-16(2)30)18-12-23(35)29(7)25-19(32)13-21-26(3,4)22(34)8-9-27(21,5)24(25)20(33)14-28(18,29)6/h15-16,18-19,21-23,30,32,34-35H,8-14H2,1-7H3/t15-,16?,18-,19+,21+,22+,23+,27+,28-,29+/m1/s1

InChI Key

BYRGJKZMDMBDDL-POESAPRRSA-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
Ganoderma tropicum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Cholesterol-skeleton
Cholestane-skeleton
Tetrahydroxy bile acid, alcohol, or derivatives
25-hydroxysteroid
23-oxosteroid
Hydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
14-alpha-methylsteroid
7-hydroxysteroid
7-alpha-hydroxysteroid
3-beta-hydroxysteroid
Oxosteroid
11-oxosteroid
Hydroxysteroid
15-hydroxysteroid
3-hydroxysteroid
Steroid
Fatty alcohol
Cyclohexenone
Fatty acyl
Beta-hydroxy ketone
Cyclic alcohol
Secondary alcohol
Ketone
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	2.21	ChemAxon
pKa (Strongest Acidic)	14.24	ChemAxon
pKa (Strongest Basic)	-0.81	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	115.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	135.1 m³·mol⁻¹	ChemAxon
Polarizability	56.14 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

78441090

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102217928

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Shao Y, Qiao L, Wu L, Sun X, Zhu D, Yang G, Zhang X, Mao X, Chen W, Liang W, Zhang Y, Zhang L: Structure Identification and Anti-Cancer Pharmacological Prediction of Triterpenes from Ganoderma lucidum. Molecules. 2016 May 21;21(5). pii: molecules21050678. doi: 10.3390/molecules21050678. [PubMed:27213329 ]
LOTUS database [Link]

Showing NP-Card for (1r,3s,3ar,4s,5ar,7s,9as,11ar)-3,4,7-trihydroxy-1-[(2r)-6-hydroxy-4-oxoheptan-2-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-10-one (NP0287431)

MOL for NP0287431 ((1r,3s,3ar,4s,5ar,7s,9as,11ar)-3,4,7-trihydroxy-1-[(2r)-6-hydroxy-4-oxoheptan-2-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-10-one)

3D MOL for NP0287431 ((1r,3s,3ar,4s,5ar,7s,9as,11ar)-3,4,7-trihydroxy-1-[(2r)-6-hydroxy-4-oxoheptan-2-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-10-one)

3D SDF for NP0287431 ((1r,3s,3ar,4s,5ar,7s,9as,11ar)-3,4,7-trihydroxy-1-[(2r)-6-hydroxy-4-oxoheptan-2-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-10-one)

3D-SDF for NP0287431 ((1r,3s,3ar,4s,5ar,7s,9as,11ar)-3,4,7-trihydroxy-1-[(2r)-6-hydroxy-4-oxoheptan-2-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-10-one)

PDB for NP0287431 ((1r,3s,3ar,4s,5ar,7s,9as,11ar)-3,4,7-trihydroxy-1-[(2r)-6-hydroxy-4-oxoheptan-2-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-10-one)

3D PDB for NP0287431 ((1r,3s,3ar,4s,5ar,7s,9as,11ar)-3,4,7-trihydroxy-1-[(2r)-6-hydroxy-4-oxoheptan-2-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-10-one)

SMILES for NP0287431 ((1r,3s,3ar,4s,5ar,7s,9as,11ar)-3,4,7-trihydroxy-1-[(2r)-6-hydroxy-4-oxoheptan-2-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-10-one)

INCHI for NP0287431 ((1r,3s,3ar,4s,5ar,7s,9as,11ar)-3,4,7-trihydroxy-1-[(2r)-6-hydroxy-4-oxoheptan-2-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-10-one)

Structure for NP0287431 ((1r,3s,3ar,4s,5ar,7s,9as,11ar)-3,4,7-trihydroxy-1-[(2r)-6-hydroxy-4-oxoheptan-2-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-10-one)

3D Structure for NP0287431 ((1r,3s,3ar,4s,5ar,7s,9as,11ar)-3,4,7-trihydroxy-1-[(2r)-6-hydroxy-4-oxoheptan-2-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-10-one)