NP-MRD: Showing NP-Card for (1s,3ar,3br,5as,7s,9as,9br,10r,11ar)-7-{[(2r,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-[(2s,5r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-10-yl acetate (NP0306077)

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Record Information

Version

2.0

Created at

2022-09-10 22:19:56 UTC

Updated at

2022-09-10 22:19:57 UTC

NP-MRD ID

NP0306077

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3ar,3br,5as,7s,9as,9br,10r,11ar)-7-{[(2r,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-[(2s,5r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-10-yl acetate

Description

(1R,2S,5S,7S,10R,11R,14S,15R,17R)-5-{[(2R,3R,4S,5S,6R)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-14-[(2S,5R)-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. (1s,3ar,3br,5as,7s,9as,9br,10r,11ar)-7-{[(2r,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-[(2s,5r)-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. Based on a literature review very few articles have been published on (1R,2S,5S,7S,10R,11R,14S,15R,17R)-5-{[(2R,3R,4S,5S,6R)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-14-[(2S,5R)-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.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309112200192D          

 51 56  0  0  1  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  2  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  2  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  2  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  2  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
    0.2183   -3.7935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4080   -4.9368    0.0000 O   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
    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  2  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  2  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  2  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  1  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  2  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  2  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
   11.7337   -1.8401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3610   -3.5371    0.0000 C   0  0  1  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  2  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  1  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1125   -4.1180    0.0000 O   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  1  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  1  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
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 13 18  1  0  0  0  0
  9 18  1  1  0  0  0
  8 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  7 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 27 26  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  1  0  0  0
 33 32  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  6  0  0  0
 36 37  1  0  0  0  0
 35 38  1  0  0  0  0
 38 39  1  1  0  0  0
 38 40  1  0  0  0  0
 40 41  1  6  0  0  0
 40 42  1  0  0  0  0
 33 42  1  0  0  0  0
 42 43  1  1  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 44 46  2  0  0  0  0
 31 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 27 49  1  0  0  0  0
 49 50  1  1  0  0  0
 51 49  1  1  0  0  0
  5 51  1  0  0  0  0
 23 51  1  0  0  0  0
M  END


  Mrv1652309112200192D          

 51 56  0  0  1  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  2  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  2  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  2  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  2  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
    0.2183   -3.7935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4080   -4.9368    0.0000 O   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
    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  2  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  2  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  2  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  1  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  2  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  2  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
   11.7337   -1.8401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3610   -3.5371    0.0000 C   0  0  1  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  2  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  1  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1125   -4.1180    0.0000 O   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  1  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  1  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
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 13 18  1  0  0  0  0
  9 18  1  1  0  0  0
  8 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  7 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 27 26  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  1  0  0  0
 33 32  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  6  0  0  0
 36 37  1  0  0  0  0
 35 38  1  0  0  0  0
 38 39  1  1  0  0  0
 38 40  1  0  0  0  0
 40 41  1  6  0  0  0
 40 42  1  0  0  0  0
 33 42  1  0  0  0  0
 42 43  1  1  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 44 46  2  0  0  0  0
 31 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 27 49  1  0  0  0  0
 49 50  1  1  0  0  0
 51 49  1  1  0  0  0
  5 51  1  0  0  0  0
 23 51  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0306077

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1C[C@@H]2[C@H](CC[C@@]2(C)[C@]2(C)CC[C@@H]3C(C)(C)[C@H](CC[C@]3(C)[C@@H]12)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1OC(C)=O)[C@]1(C)CC[C@@H](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/t23-,24+,25+,26+,27+,28-,29+,30+,31-,32+,33+,34-,37-,38+,39+,40-/m0/s1

> <INCHI_KEY>
VARDBQBWTSGXRK-OAXIWDCRSA-N

> <FORMULA>
C40H66O11

> <MOLECULAR_WEIGHT>
722.957

> <EXACT_MASS>
722.460512945

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
117

> <JCHEM_AVERAGE_POLARIZABILITY>
80.41165485865596

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,5S,7S,10R,11R,14S,15R,17R)-5-{[(2R,3R,4S,5S,6R)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-14-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-17-yl acetate

> <JCHEM_LOGP>
3.664617741666663

> <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>
186.78970000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,5S,7S,10R,11R,14S,15R,17R)-5-{[(2R,3R,4S,5S,6R)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-14-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-17-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       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       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.090  -6.676   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.672  -4.796   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.314  -5.522   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.585  -7.038   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.518  -8.148   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.451  -9.259   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.407  -7.081   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.628  -9.215   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.110  -7.249   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.159  -1.754   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.725  -1.551   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.323  -0.719   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      15.185  -1.391   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      17.355  -4.248   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      18.871  -3.977   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      19.864  -5.154   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      21.380  -4.883   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      21.903  -3.435   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      19.341  -6.603   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      20.333  -7.780   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      17.825  -6.874   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      17.301  -8.322   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      16.832  -5.696   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      15.316  -5.967   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      14.793  -7.416   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      15.785  -8.593   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      13.277  -7.687   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   51                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   21                                                  
CONECT    8    7    9   19                                                  
CONECT    9    8   10   11   18                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14                                                            
CONECT   18   13    9                                                       
CONECT   19    8   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20    7   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   24   25   51                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   49                                                  
CONECT   28   27   29   30   31                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28   32   47                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   42                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   38                                                  
CONECT   36   35   37                                                       
CONECT   37   36                                                            
CONECT   38   35   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   33   43                                                  
CONECT   43   42   44                                                       
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44                                                            
CONECT   47   31   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   27   50   51                                             
CONECT   50   49                                                            
CONECT   51   49    5   23                                                  
MASTER        0    0    0    0    0    0    0    0   51    0  112    0
END

View in JSmol

Synonyms

Value	Source
(1R,2S,5S,7S,10R,11R,14S,15R,17R)-5-{[(2R,3R,4S,5S,6R)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-14-[(2S,5R)-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

Chemical Formula

C₄₀H₆₆O₁₁

Average Mass

722.9570 Da

Monoisotopic Mass

722.46051 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1C[C@@H]2[C@H](CC[C@@]2(C)[C@]2(C)CC[C@@H]3C(C)(C)[C@H](CC[C@]3(C)[C@@H]12)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1OC(C)=O)[C@]1(C)CC[C@@H](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/t23-,24+,25+,26+,27+,28-,29+,30+,31-,32+,33+,34-,37-,38+,39+,40-/m0/s1

InChI Key

VARDBQBWTSGXRK-OAXIWDCRSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

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
14-alpha-methylsteroid
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

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

162905243

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3ar,3br,5as,7s,9as,9br,10r,11ar)-7-{[(2r,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-[(2s,5r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-10-yl acetate (NP0306077)

MOL for NP0306077 ((1s,3ar,3br,5as,7s,9as,9br,10r,11ar)-7-{[(2r,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-[(2s,5r)-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 NP0306077 ((1s,3ar,3br,5as,7s,9as,9br,10r,11ar)-7-{[(2r,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-[(2s,5r)-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 NP0306077 ((1s,3ar,3br,5as,7s,9as,9br,10r,11ar)-7-{[(2r,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-[(2s,5r)-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 NP0306077 ((1s,3ar,3br,5as,7s,9as,9br,10r,11ar)-7-{[(2r,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-[(2s,5r)-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 NP0306077 ((1s,3ar,3br,5as,7s,9as,9br,10r,11ar)-7-{[(2r,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-[(2s,5r)-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 NP0306077 ((1s,3ar,3br,5as,7s,9as,9br,10r,11ar)-7-{[(2r,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-[(2s,5r)-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 NP0306077 ((1s,3ar,3br,5as,7s,9as,9br,10r,11ar)-7-{[(2r,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-[(2s,5r)-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 NP0306077 ((1s,3ar,3br,5as,7s,9as,9br,10r,11ar)-7-{[(2r,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-[(2s,5r)-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 NP0306077 ((1s,3ar,3br,5as,7s,9as,9br,10r,11ar)-7-{[(2r,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-[(2s,5r)-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 NP0306077 ((1s,3ar,3br,5as,7s,9as,9br,10r,11ar)-7-{[(2r,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-[(2s,5r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-10-yl acetate)