NP-MRD: Showing NP-Card for Cyasterone (NP0052164)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-27 23:19:15 UTC

Updated at

2022-04-27 23:19:15 UTC

NP-MRD ID

NP0052164

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cyasterone

Description

Cyasterone belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Thus, cyasterone is considered to be a sterol. Cyasterone is found in Ajuga chamaepitys , Ajuga decumbens , Ajuga iva, Ajuga nipponensis, Ajuga reptans , Ajuga taiwanensis, Ajuga turkestanica, Cyathula capitata, Cyathula capitata Monquim-Tandon and Cyathula officinalis. Cyasterone was first documented in 2016 (PMID: 27677846). Based on a literature review a significant number of articles have been published on cyasterone (PMID: 33717979) (PMID: 33342285) (PMID: 32387464) (PMID: 29945384) (PMID: 29659734) (PMID: 29200735).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282201192D          

 37 41  0  0  1  0            999 V2000
    4.2475    2.1537    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5278    1.3777    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9960    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1838    0.8922    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9035    1.6682    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4354    2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914    1.8134    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5596    1.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8399    0.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520    0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9323   -0.5144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475    1.3279    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4672    2.1038    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9990    2.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8111    2.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574    2.0770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5867    1.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0962    0.8215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8637    2.7283    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3701    3.3797    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1873    3.2668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6937    3.9181    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5182    3.8913    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7985    4.6673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5910    4.8966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1472    5.1736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4644    4.7106    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6884    4.9909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9812    3.2085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0592    4.1438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5151    2.2220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2124    3.2347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1073    2.8462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9451    0.5269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6232    2.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399    1.2325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7793    2.7844    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
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 12 18  1  0  0  0  0
 16 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  6  0  0  0
 23 29  1  6  0  0  0
 20 30  1  1  0  0  0
 19 31  1  6  0  0  0
 19 32  1  6  0  0  0
 13 33  1  6  0  0  0
 12 34  1  1  0  0  0
  5 35  1  6  0  0  0
  2 36  1  6  0  0  0
  1 37  1  6  0  0  0
M  END

     RDKit          3D

 81 85  0  0  0  0  0  0  0  0999 V2000
    6.4998    1.6890   -0.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7435    1.1222    0.9774 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7828    1.2149    2.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2370    2.3379    2.4374 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0848   -0.0148    2.5645 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2042   -0.9535    2.0819 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8606   -2.2441    1.6699 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4567   -0.3062    0.8616 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1160   -0.8656    0.8613 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0197   -0.6559   -0.0852 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9864   -1.5441    0.5100 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3166    0.6162   -0.2559 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2093    1.7245   -0.8598 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9689    1.0845    1.0125 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0881    0.6556   -1.0578 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0870    0.2690   -2.4767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3951    0.2878   -2.9009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0727    0.8241   -1.6709 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9708    2.2089   -1.5402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4445    0.3390   -1.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1325   -0.2332   -2.4606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4697   -0.6808   -2.2024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1922   -1.0992   -3.1564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0540   -0.6801   -0.8747 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.1369    0.3933   -0.8137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0418   -0.0816    0.3320 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.4027   -1.3996   -0.0286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2414   -0.1342    1.5657 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4319   -1.3630    2.2033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7869    0.1817    1.4563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1098   -0.4343    0.2456 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5304   -1.7759    0.6370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0454    0.5646   -0.1691 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1064    0.8876    0.9360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6739    0.7163    0.7216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2263    0.1254   -0.5740 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4560   -1.3328   -0.7459 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5930    1.7204   -0.0731 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3632    0.9523   -1.0734 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1833    2.7074   -0.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9556    1.7889    1.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4128   -1.1927    2.8138 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3548   -2.6427    2.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6874   -2.0370    0.9483 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1432   -2.9739    1.2897 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0818   -0.7027   -0.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2926   -2.0205    0.9939 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7224   -0.6878    1.9575 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2428   -1.2246   -1.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4251   -2.3901    0.7360 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5919    2.2586   -1.6663 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4194    2.5334   -0.1541 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0303    1.2982   -1.4234 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7203    1.0232    1.6222 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8464    1.8004   -1.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4729   -0.6884   -2.7735 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6248    1.0510   -3.0822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5223    0.9385   -3.7771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7472   -0.7537   -3.0597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8877    2.5641   -1.6582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6530   -0.3406   -3.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5550   -1.6629   -0.7246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7600    0.3853   -1.7219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7095    1.3842   -0.5820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9593    0.5038    0.3898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3392   -1.5860    0.1909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6720    0.6276    2.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3906   -1.4789    2.4233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3011   -0.2632    2.3519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6177    1.2749    1.5217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4031   -2.4469   -0.2289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6192   -1.6445    1.2499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2677   -2.2454    1.3579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6875    1.5074   -0.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4116    0.2655    1.8207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3311    1.9310    1.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1865    1.7456    0.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1674    0.1555    1.5333 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2782   -1.7339   -1.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5520   -1.9333    0.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4414   -1.4763   -1.3056 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  1  0
  2  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  1
 12 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 31 32  1  1
 31 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  1
  8  6  1  0
 36 15  1  0
 36 18  1  0
 33 20  1  0
 31 24  1  0
  7 43  1  0
  7 44  1  0
  7 45  1  0
  6 42  1  1
  2 41  1  1
  1 38  1  0
  1 39  1  0
  1 40  1  0
  8 46  1  6
  9 47  1  0
  9 48  1  0
 10 49  1  6
 11 50  1  0
 13 51  1  0
 13 52  1  0
 13 53  1  0
 14 54  1  0
 15 55  1  6
 16 56  1  0
 16 57  1  0
 17 58  1  0
 17 59  1  0
 19 60  1  0
 21 61  1  0
 24 62  1  1
 25 63  1  0
 25 64  1  0
 26 65  1  1
 27 66  1  0
 28 67  1  1
 29 68  1  0
 30 69  1  0
 30 70  1  0
 32 71  1  0
 32 72  1  0
 32 73  1  0
 33 74  1  6
 34 75  1  0
 34 76  1  0
 35 77  1  0
 35 78  1  0
 37 79  1  0
 37 80  1  0
 37 81  1  0
M  END


  Mrv1652304282201192D          

 37 41  0  0  1  0            999 V2000
    4.2475    2.1537    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5278    1.3777    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9960    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1838    0.8922    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9035    1.6682    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4354    2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914    1.8134    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5596    1.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8399    0.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520    0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9323   -0.5144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475    1.3279    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4672    2.1038    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9990    2.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8111    2.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574    2.0770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5867    1.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0962    0.8215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8637    2.7283    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3701    3.3797    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1873    3.2668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6937    3.9181    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5182    3.8913    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7985    4.6673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5910    4.8966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1472    5.1736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4644    4.7106    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6884    4.9909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9812    3.2085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0592    4.1438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5151    2.2220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2124    3.2347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1073    2.8462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9451    0.5269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6232    2.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399    1.2325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7793    2.7844    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
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 12 18  1  0  0  0  0
 16 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  6  0  0  0
 23 29  1  6  0  0  0
 20 30  1  1  0  0  0
 19 31  1  6  0  0  0
 19 32  1  6  0  0  0
 13 33  1  6  0  0  0
 12 34  1  1  0  0  0
  5 35  1  6  0  0  0
  2 36  1  6  0  0  0
  1 37  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0052164

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1OC(=O)[C@@H](C)[C@@H]1C[C@@H](O)[C@](C)(O)[C@H]1CC[C@@]2(O)C3=CC(=O)[C@@H]4C[C@@H](O)[C@@H](O)C[C@]4(C)[C@H]3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C29H44O8/c1-14-16(15(2)37-25(14)34)10-24(33)28(5,35)23-7-9-29(36)18-11-20(30)19-12-21(31)22(32)13-26(19,3)17(18)6-8-27(23,29)4/h11,14-17,19,21-24,31-33,35-36H,6-10,12-13H2,1-5H3/t14-,15+,16-,17-,19-,21+,22-,23-,24+,26+,27+,28+,29+/m0/s1

> <INCHI_KEY>
NEFYSBQJYCICOG-YSEUJXISSA-N

> <FORMULA>
C29H44O8

> <MOLECULAR_WEIGHT>
520.663

> <EXACT_MASS>
520.303618377

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
56.75809382262486

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,4S,5R)-4-[(2R,3R)-2,3-dihydroxy-3-[(1R,2R,4S,5R,7R,11S,14S,15R)-4,5,11-trihydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-14-yl]butyl]-3,5-dimethyloxolan-2-one

> <ALOGPS_LOGP>
1.66

> <JCHEM_LOGP>
1.0260426656666661

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.741081308558048

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.25869951698553

> <JCHEM_PKA_STRONGEST_BASIC>
-3.153288443303487

> <JCHEM_POLAR_SURFACE_AREA>
144.52

> <JCHEM_REFRACTIVITY>
136.05790000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.92e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4S,5R)-4-[(2R,3R)-2,3-dihydroxy-3-[(1R,2R,4S,5R,7R,11S,14S,15R)-4,5,11-trihydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-14-yl]butyl]-3,5-dimethyloxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       7.929   4.020   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.452   2.572   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.459   1.394   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.943   1.666   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.420   3.114   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.413   4.291   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.904   3.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.911   2.208   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.434   0.759   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.950   0.488   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.474  -0.960   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.395   2.479   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.872   3.927   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.865   5.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.381   4.833   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.667   3.877   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.095   2.398   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.179   1.534   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.612   5.093   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.557   6.309   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.083   6.098   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.028   7.314   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -6.567   7.264   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -7.091   8.712   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -8.570   9.140   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -5.875   9.657   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -4.600   8.793   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.152   9.316   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -7.432   5.989   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.977   7.735   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -2.828   4.148   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -0.396   6.038   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.200   5.313   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.764   0.984   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       4.897   4.562   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       9.968   2.301   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       8.921   5.197   0.000  0.00  0.00           O+0
CONECT    1    2    6   37                                                  
CONECT    2    1    3   36                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   35                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   15                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    8   13   18   34                                             
CONECT   13   12   14   16   33                                             
CONECT   14   13   15                                                       
CONECT   15   14    7                                                       
CONECT   16   13   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17   12                                                       
CONECT   19   16   20   31   32                                             
CONECT   20   19   21   30                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24   29                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   22   28                                                  
CONECT   28   27                                                            
CONECT   29   23                                                            
CONECT   30   20                                                            
CONECT   31   19                                                            
CONECT   32   19                                                            
CONECT   33   13                                                            
CONECT   34   12                                                            
CONECT   35    5                                                            
CONECT   36    2                                                            
CONECT   37    1                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Value	Source
Cyasteron	ChEBI

Chemical Formula

C₂₉H₄₄O₈

Average Mass

520.6630 Da

Monoisotopic Mass

520.30362 Da

IUPAC Name

(3S,4S,5R)-4-[(2R,3R)-2,3-dihydroxy-3-[(1R,2R,4S,5R,7R,11S,14S,15R)-4,5,11-trihydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-14-yl]butyl]-3,5-dimethyloxolan-2-one

Traditional Name

(3S,4S,5R)-4-[(2R,3R)-2,3-dihydroxy-3-[(1R,2R,4S,5R,7R,11S,14S,15R)-4,5,11-trihydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-14-yl]butyl]-3,5-dimethyloxolan-2-one

CAS Registry Number

Not Available

SMILES

C[C@H]1OC(=O)[C@@H](C)[C@@H]1C[C@@H](O)[C@](C)(O)[C@H]1CC[C@@]2(O)C3=CC(=O)[C@@H]4C[C@@H](O)[C@@H](O)C[C@]4(C)[C@H]3CC[C@]12C

InChI Identifier

InChI=1S/C29H44O8/c1-14-16(15(2)37-25(14)34)10-24(33)28(5,35)23-7-9-29(36)18-11-20(30)19-12-21(31)22(32)13-26(19,3)17(18)6-8-27(23,29)4/h11,14-17,19,21-24,31-33,35-36H,6-10,12-13H2,1-5H3/t14-,15+,16-,17-,19-,21+,22-,23-,24+,26+,27+,28+,29+/m0/s1

InChI Key

NEFYSBQJYCICOG-YSEUJXISSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Ajuga chamaepitys	Plant	KNApSAcK
Ajuga decumbens	Plant	KNApSAcK
Ajuga iva	LOTUS Database	35616633
Ajuga nipponensis	LOTUS Database	35616633
Ajuga reptans	Plant	KNApSAcK
Ajuga taiwanensis	Plant	KNApSAcK
Ajuga turkestanica	Plant	KNApSAcK
Cyathula capitata	LOTUS Database	35616633
Cyathula capitata Monquim-Tandon	Plant	KNApSAcK
Cyathula officinalis	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
Pentahydroxy bile acid, alcohol, or derivatives
Cholesterol-skeleton
Cholestane-skeleton
Ecdysteroid
Hydroxy bile acid, alcohol, or derivatives
Steroid lactone
Bile acid, alcohol, or derivatives
22-hydroxysteroid
20-hydroxysteroid
3-beta-hydroxysteroid
6-oxosteroid
2-hydroxysteroid
14-hydroxysteroid
3-hydroxysteroid
Hydroxysteroid
Oxosteroid
3-hydroxy-delta-7-steroid
Delta-7-steroid
Steroid
Cyclohexenone
Gamma butyrolactone
Tertiary alcohol
Tetrahydrofuran
Cyclic alcohol
Lactone
Ketone
Secondary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Polyol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Alcohol
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

3beta-hydroxy steroid (CHEBI:29012 )
steroid lactone (CHEBI:29012 )
21-hydroxy steroid (CHEBI:29012 )
20-hydroxy steroid (CHEBI:29012 )
6-oxo steroid (CHEBI:29012 )
2beta-hydroxy steroid (CHEBI:29012 )
14alpha-hydroxy steroid (CHEBI:29012 )
phytoecdysteroid (CHEBI:29012 )
stigmastane (C08816 )
Stigmasterols and C24-ethyl derivatives (C08816 )
Stigmasterols and C24-ethyl derivatives (LMST01040153 )

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	1.66	ALOGPS
logP	1.03	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	13.26	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	144.52 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	136.06 m³·mol⁻¹	ChemAxon
Polarizability	56.76 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

C00003649

Chemspider ID

106675

KEGG Compound ID

C08816

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

119444

PDB ID

Not Available

ChEBI ID

29012

Good Scents ID

Not Available

References

General References

Zhu J, Liu Y, Chen C, Chen H, Huang J, Luo Y, Zhao K, Chen D, Xu Z, Li W, Zhang X, Xiong Y, Xu L, Wang B: Cyasterone accelerates fracture healing by promoting MSCs migration and osteogenesis. J Orthop Translat. 2021 Feb 19;28:28-38. doi: 10.1016/j.jot.2020.11.004. eCollection 2021 May. [PubMed:33717979 ]
Yusupova U, Usmanov D, Azamatov A, Ramazonov N, Rejepov J: Phytochemical constituents and biological activities of Dianthus helenae Vved., growing in Uzbekistan. Nat Prod Res. 2020 Dec 21:1-5. doi: 10.1080/14786419.2020.1862834. [PubMed:33342285 ]
Bouyahya A, El Omari N, Elmenyiy N, Guaouguaou FE, Balahbib A, El-Shazly M, Chamkhi I: Ethnomedicinal use, phytochemistry, pharmacology, and toxicology of Ajuga iva (L.,) schreb. J Ethnopharmacol. 2020 Aug 10;258:112875. doi: 10.1016/j.jep.2020.112875. Epub 2020 May 6. [PubMed:32387464 ]
Shi CJ, Wang SS, Cheng ZQ, Liu XM, Yuan QH, Liu L, Hu M, Song Y: [Comparison of chemical constituents between Cyathula offinalis and adulterant and their admixture by HPLC characteristic chromatogram fingerprint combined with chemometrics]. Zhongguo Zhong Yao Za Zhi. 2018 Jun;43(11):2313-2320. doi: 10.19540/j.cnki.cjcmm.2018.0071. [PubMed:29945384 ]
Li F, Wu H, Sun LL, Wu H, Wang R, Li SP, Wang WY, Dai L, Zhang ZR, Fu J, Deng R: Quantitative Analysis of Multi-components by Single Marker and Fingerprint Analysis of Achyranthes bidentata Blume. J Chromatogr Sci. 2018 Aug 1;56(7):595-603. doi: 10.1093/chromsci/bmy031. [PubMed:29659734 ]
Cao Y, Gu C, Zhao F, Tang Y, Cui X, Shi L, Xu L, Yin L: Therapeutic Effects of Cyathula officinalis Kuan and Its Active Fraction on Acute Blood Stasis Rat Model and Identification Constituents by HPLC-QTOF/MS/MS. Pharmacogn Mag. 2017 Oct-Dec;13(52):693-701. doi: 10.4103/pm.pm_560_16. Epub 2017 Nov 13. [PubMed:29200735 ]
Kayani WK, Dilshad E, Ahmed T, Ismail H, Mirza B: Evaluation of Ajuga bracteosa for antioxidant, anti-inflammatory, analgesic, antidepressant and anticoagulant activities. BMC Complement Altern Med. 2016 Sep 27;16(1):375. doi: 10.1186/s12906-016-1363-y. [PubMed:27677846 ]
Lu X, Qiu H, Yang L, Zhang J, Ma S, Zhen L: Anti-proliferation effects, efficacy of cyasterone in vitro and in vivo and its mechanism. Biomed Pharmacother. 2016 Dec;84:330-339. doi: 10.1016/j.biopha.2016.09.041. Epub 2016 Sep 23. [PubMed:27668532 ]
Fang B, Bao S, Wang S, Chen M, Chen B, Su K, Wen C, Zhou Y, Wang X, Jin Y: Pharmacokinetic study of ardisiacrispin A in rat plasma after intravenous administration by UPLC-MS/MS. Biomed Chromatogr. 2017 Mar;31(3). doi: 10.1002/bmc.3826. Epub 2016 Sep 16. [PubMed:27565758 ]
Li F, Li G, Zhao J, Xiao J, Liu Z, Su G: A simple LC-MS method for determination of cyasterone in rat plasma: application to a pilot pharmacokinetic study. Biomed Chromatogr. 2016 Jun;30(6):867-71. doi: 10.1002/bmc.3621. Epub 2015 Nov 17. [PubMed:26390114 ]

Showing NP-Card for Cyasterone (NP0052164)

MOL for NP0052164 (Cyasterone)

3D MOL for NP0052164 (Cyasterone)

3D SDF for NP0052164 (Cyasterone)

3D-SDF for NP0052164 (Cyasterone)

PDB for NP0052164 (Cyasterone)

3D PDB for NP0052164 (Cyasterone)

SMILES for NP0052164 (Cyasterone)

INCHI for NP0052164 (Cyasterone)

Structure for NP0052164 (Cyasterone)

3D Structure for NP0052164 (Cyasterone)