NP-MRD: Showing NP-Card for 7-{[3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-10-yl acetate (NP0149773)

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Record Information

Version

1.0

Created at

2022-09-02 05:42:40 UTC

Updated at

2022-09-02 05:42:41 UTC

NP-MRD ID

NP0149773

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-{[3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-10-yl acetate

Description

5-{[3-(Acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-14-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-17-yl acetate belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton. 7-{[3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-10-yl acetate is found in Betula ermanii. 5-{[3-(Acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-14-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-17-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161523252D          

 51 56  0  0  0  0            999 V2000
    4.6762   -4.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4883   -4.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0201   -5.0391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7686   -3.6325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3708   -0.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6744   -0.8310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1376   -0.3850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1351   -0.7453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2974   -2.2757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1095   -2.1305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6413   -2.7612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4534   -2.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9852   -3.2467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3610   -3.5371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8928   -4.1678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5489   -3.6824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2686   -4.4583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0171   -3.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2049   -3.1969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9246   -3.9728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4565   -4.6035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1125   -4.1180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2626   -3.5763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9671   -2.5692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2396   -2.9582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3848   -3.7703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2020   -3.8832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8131   -4.3652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2415   -4.9600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4080   -4.9368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2183   -3.7935    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
  5 26  1  0  0  0  0
 13 26  1  0  0  0  0
 21 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 28 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
  8 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 42 47  1  0  0  0  0
 46 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  1  0  0  0  0
 48 51  1  0  0  0  0
M  END

     RDKit          3D

117122  0  0  0  0  0  0  0  0999 V2000
    2.6054    2.0532    5.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8405    2.0609    3.7618 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0574    2.9740    3.4547 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9992    1.0266    2.8852 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3147    0.9253    1.6230 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3794    1.1735    0.5748 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3060    0.0404    0.3413 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6177    0.2718    1.0073 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7779    0.4337    0.0281 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0850    0.6199    0.8170 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6382    1.6754   -0.8115 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5085    1.1932   -2.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9245   -0.2436   -2.1137 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2322   -0.4462   -2.8550 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6151   -1.8967   -2.9592 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0288    0.0795   -4.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2782    0.2682   -2.2830 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9427   -0.6292   -0.8069 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8033   -0.8564    1.9518 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4919   -1.6258    2.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7999   -1.3025    0.7963 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3444   -2.3274   -0.2187 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3052   -1.4502    0.7541 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0180   -2.8059    1.4239 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9712   -1.5772   -0.7069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3328   -0.9984   -1.1347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3233   -1.1643    0.0142 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7223   -1.0532   -0.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7561   -1.6123   -1.8948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6265   -2.0028    0.3097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3541    0.2754   -0.4456 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -5.6554    0.6625   -0.4243 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.1499    1.9165   -0.0308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0824    2.3971   -0.9111 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.5325    3.5574   -1.7126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1541    4.6015   -0.8707 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.9491    1.3493   -3.0935 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8247    0.0139   -1.2946 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.1163   -0.1170   -0.7885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7820   -0.2959   -0.2444 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.4284   -0.0734    1.0219 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5732   -1.1254    1.8966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2406   -0.8866    3.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1319   -2.2474    1.5481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4949    1.4292   -0.0614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2374    1.1773    0.6604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8979   -0.2171    1.0778 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.7126    3.1221    5.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6445    1.2077    1.6124 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.3769    1.1229   -4.3822 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6572   -0.5319   -4.9483 H   0  0  0  0  0  0  0  0  0  0  0  0
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    8.3570    1.1769   -2.6707 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1678   -0.5478    2.9554 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.3931    0.7414   -1.4751 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.9718    5.1730   -0.7479 H   0  0  0  0  0  0  0  0  0  0  0  0
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 40104  1  6
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 16 72  1  0
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 17 74  1  0
M  END


  Mrv1533004161523252D          

 51 56  0  0  0  0            999 V2000
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    2.2020   -3.8832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8131   -4.3652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2415   -4.9600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4080   -4.9368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2183   -3.7935    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
  5 26  1  0  0  0  0
 13 26  1  0  0  0  0
 21 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 28 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
  8 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 42 47  1  0  0  0  0
 46 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  1  0  0  0  0
 48 51  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0149773

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1CC2C(CCC2(C)C2(C)CCC3C(C)(C)C(CCC3(C)C12)OC1OC(CO)C(O)C(O)C1OC(C)=O)C1(C)CCC(O1)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C40H66O11/c1-21(42)47-25-19-24-23(40(10)18-14-29(51-40)36(5,6)46)11-16-38(24,8)39(9)17-12-27-35(3,4)28(13-15-37(27,7)33(25)39)50-34-32(48-22(2)43)31(45)30(44)26(20-41)49-34/h23-34,41,44-46H,11-20H2,1-10H3

> <INCHI_KEY>
VARDBQBWTSGXRK-UHFFFAOYSA-N

> <FORMULA>
C40H66O11

> <MOLECULAR_WEIGHT>
722.957

> <EXACT_MASS>
722.460512945

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
117

> <JCHEM_AVERAGE_POLARIZABILITY>
80.1636614367313

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-{[3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-14-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-17-yl acetate

> <ALOGPS_LOGP>
4.45

> <JCHEM_LOGP>
3.664617741666663

> <ALOGPS_LOGS>
-5.22

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.85376316266311

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.685592410760666

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810841892493256

> <JCHEM_POLAR_SURFACE_AREA>
161.21

> <JCHEM_REFRACTIVITY>
186.7897

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.36e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-{[3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-14-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-17-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       8.729  -8.500   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.245  -8.229   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      11.238  -9.406   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      10.768  -6.781   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.159  -1.754   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.725  -1.551   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.323  -0.719   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.185  -1.391   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      17.355  -4.248   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      18.871  -3.977   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      19.864  -5.154   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      21.380  -4.883   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      22.372  -6.061   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      19.341  -6.603   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      20.333  -7.780   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      17.825  -6.874   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      17.301  -8.322   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      16.832  -5.696   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      15.316  -5.967   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      14.793  -7.416   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      15.785  -8.593   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      13.277  -7.687   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       6.090  -6.676   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       3.672  -4.796   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       2.314  -5.522   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       2.585  -7.038   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       4.110  -7.249   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0       1.518  -8.148   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       0.451  -9.259   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       2.628  -9.215   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       0.407  -7.081   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   26                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9   42                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    7   12   13                                             
CONECT   12   11                                                            
CONECT   13   11   14   15   26                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   22   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   17   25   26                                             
CONECT   25   24                                                            
CONECT   26   24    5   13                                                  
CONECT   27   21   28                                                       
CONECT   28   27   29   37                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   30   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   28   38                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39                                                            
CONECT   42    8   43   44   47                                             
CONECT   43   42                                                            
CONECT   44   42   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47   48                                                  
CONECT   47   46   42                                                       
CONECT   48   46   49   50   51                                             
CONECT   49   48                                                            
CONECT   50   48                                                            
CONECT   51   48                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  112    0
END

View in JSmol

Synonyms

Value	Source
5-{[3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-14-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0,.0,]heptadecan-17-yl acetic acid	Generator
5-{[3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-14-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-17-yl acetic acid	Generator

Chemical Formula

C₄₀H₆₆O₁₁

Average Mass

722.9570 Da

Monoisotopic Mass

722.46051 Da

IUPAC Name

5-{[3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-14-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-17-yl acetate

Traditional Name

5-{[3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-14-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-17-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1CC2C(CCC2(C)C2(C)CCC3C(C)(C)C(CCC3(C)C12)OC1OC(CO)C(O)C(O)C1OC(C)=O)C1(C)CCC(O1)C(C)(C)O

InChI Identifier

InChI=1S/C40H66O11/c1-21(42)47-25-19-24-23(40(10)18-14-29(51-40)36(5,6)46)11-16-38(24,8)39(9)17-12-27-35(3,4)28(13-15-37(27,7)33(25)39)50-34-32(48-22(2)43)31(45)30(44)26(20-41)49-34/h23-34,41,44-46H,11-20H2,1-10H3

InChI Key

VARDBQBWTSGXRK-UHFFFAOYSA-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
Betula ermanii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Triterpene saponins

Alternative Parents

Substituents

Triterpene saponin
Triterpenoid
Steroidal glycoside
Steroid ester
Steroid
Glycosyl compound
O-glycosyl compound
Dicarboxylic acid or derivatives
Monosaccharide
Oxane
Tetrahydrofuran
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Dialkyl ether
Acetal
Ether
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organic oxide
Organooxygen compound
Carbonyl group
Primary alcohol
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	4.45	ALOGPS
logP	3.66	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	12.69	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	161.21 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	186.79 m³·mol⁻¹	ChemAxon
Polarizability	80.16 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

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

73022739

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7-{[3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-10-yl acetate (NP0149773)

MOL for NP0149773 (7-{[3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-10-yl acetate)

3D MOL for NP0149773 (7-{[3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-10-yl acetate)

3D SDF for NP0149773 (7-{[3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-10-yl acetate)

3D-SDF for NP0149773 (7-{[3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-10-yl acetate)

PDB for NP0149773 (7-{[3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-10-yl acetate)

3D PDB for NP0149773 (7-{[3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-10-yl acetate)

SMILES for NP0149773 (7-{[3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-10-yl acetate)

INCHI for NP0149773 (7-{[3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-10-yl acetate)

Structure for NP0149773 (7-{[3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-10-yl acetate)

3D Structure for NP0149773 (7-{[3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-10-yl acetate)