NP-MRD: Showing NP-Card for (1s)-2-methoxy-2-methyl-1-[(1s,4r,5r,6r,8r,10s,11r,12s,13r,16s,18s,20s,21s)-10,11,20-trihydroxy-4,6,12,17,17-pentamethyl-18-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-9-oxahexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]docosan-8-yl]propyl acetate (NP0223398)

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Record Information

Version

2.0

Created at

2022-09-06 01:28:40 UTC

Updated at

2022-09-06 01:28:40 UTC

NP-MRD ID

NP0223398

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s)-2-methoxy-2-methyl-1-[(1s,4r,5r,6r,8r,10s,11r,12s,13r,16s,18s,20s,21s)-10,11,20-trihydroxy-4,6,12,17,17-pentamethyl-18-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-9-oxahexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]docosan-8-yl]propyl acetate

Description

(1S)-2-methoxy-2-methyl-1-[(1S,4R,5R,6R,8R,10S,11R,12S,13R,16S,18S,20S,21S)-10,11,20-trihydroxy-4,6,12,17,17-pentamethyl-18-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}-9-oxahexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]Docosan-8-yl]propyl acetate belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus. (1s)-2-methoxy-2-methyl-1-[(1s,4r,5r,6r,8r,10s,11r,12s,13r,16s,18s,20s,21s)-10,11,20-trihydroxy-4,6,12,17,17-pentamethyl-18-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-9-oxahexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]docosan-8-yl]propyl acetate is found in Actaea simplex. Based on a literature review very few articles have been published on (1S)-2-methoxy-2-methyl-1-[(1S,4R,5R,6R,8R,10S,11R,12S,13R,16S,18S,20S,21S)-10,11,20-trihydroxy-4,6,12,17,17-pentamethyl-18-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}-9-oxahexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]Docosan-8-yl]propyl acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062203282D          

 50 56  0  0  1  0            999 V2000
    9.8963    1.9865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1119    2.2420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4983    1.6905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9468    2.3040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0499    1.0770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8848    1.1389    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0557    0.3318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8401    0.0763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4537    0.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0111   -0.7308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1004    1.3945    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9295    2.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1451    2.4571    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9742    3.2642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5315    1.9055    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7024    1.0984    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7881    0.2779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4869    0.8429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9877    0.6865    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9008   -0.1339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3750    1.2390    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1194    0.4546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5544    1.1534    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2183    0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3978    0.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9133    0.9822    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0928    0.8966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3196    0.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3510    0.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6084    1.5644    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2122    1.4788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6966    2.1466    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5171    2.0610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0015    2.7288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6654    3.4822    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1498    4.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8448    3.5678    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5087    4.3213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3604    2.9000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4601    2.9856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9445    2.3178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7651    2.4034    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1012    3.1568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2495    1.7356    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5856    2.4890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0700    1.8212    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4062    2.5746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2267    2.6602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7111    1.9924    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1242    2.7066    0.0000 C   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
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 11  6  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 11 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 26 25  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 30 31  1  1  0  0  0
 32 31  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
 32 39  1  0  0  0  0
 39 40  1  1  0  0  0
 30 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  6  0  0  0
 42 44  1  0  0  0  0
 26 44  1  0  0  0  0
 44 45  1  1  0  0  0
 46 45  1  1  0  0  0
 23 46  1  0  0  0  0
 44 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 15 49  1  0  0  0  0
 21 49  1  0  0  0  0
 49 50  1  1  0  0  0
M  END


  Mrv1652309062203282D          

 50 56  0  0  1  0            999 V2000
    9.8963    1.9865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1119    2.2420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4983    1.6905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9468    2.3040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0499    1.0770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8848    1.1389    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0557    0.3318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8401    0.0763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4537    0.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0111   -0.7308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1004    1.3945    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9295    2.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1451    2.4571    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9742    3.2642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5315    1.9055    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7024    1.0984    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7881    0.2779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4869    0.8429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9877    0.6865    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9008   -0.1339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3750    1.2390    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1194    0.4546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5544    1.1534    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2183    0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3978    0.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9133    0.9822    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0928    0.8966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3196    0.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3510    0.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6084    1.5644    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2122    1.4788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6966    2.1466    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5171    2.0610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0015    2.7288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6654    3.4822    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1498    4.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8448    3.5678    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5087    4.3213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3604    2.9000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4601    2.9856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9445    2.3178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7651    2.4034    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1012    3.1568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2495    1.7356    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5856    2.4890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0700    1.8212    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4062    2.5746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2267    2.6602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7111    1.9924    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1242    2.7066    0.0000 C   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
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 11  6  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 11 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 26 25  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 30 31  1  1  0  0  0
 32 31  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
 32 39  1  0  0  0  0
 39 40  1  1  0  0  0
 30 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  6  0  0  0
 42 44  1  0  0  0  0
 26 44  1  0  0  0  0
 44 45  1  1  0  0  0
 46 45  1  1  0  0  0
 23 46  1  0  0  0  0
 44 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 15 49  1  0  0  0  0
 21 49  1  0  0  0  0
 49 50  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0223398

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(C)(C)[C@@H](OC(C)=O)[C@H]1C[C@@H](C)[C@@H]2[C@@]3(C)CC[C@@]45C[C@@]44[C@@H](O)C[C@H](O[C@@H]6OC[C@@H](O)[C@H](O)[C@H]6O)C(C)(C)[C@@H]4CC[C@H]5[C@]3(C)[C@@H](O)[C@@]2(O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C38H62O12/c1-18-14-21(29(48-19(2)39)33(5,6)46-9)50-38(45)28(18)34(7)12-13-36-17-37(36)22(10-11-23(36)35(34,8)31(38)44)32(3,4)25(15-24(37)41)49-30-27(43)26(42)20(40)16-47-30/h18,20-31,40-45H,10-17H2,1-9H3/t18-,20-,21-,22+,23+,24+,25+,26+,27-,28-,29+,30+,31-,34-,35-,36+,37-,38+/m1/s1

> <INCHI_KEY>
CDVLNJHGGOFODI-GINPRTKDSA-N

> <FORMULA>
C38H62O12

> <MOLECULAR_WEIGHT>
710.902

> <EXACT_MASS>
710.424127436

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
112

> <JCHEM_AVERAGE_POLARIZABILITY>
79.12237935981894

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S)-2-methoxy-2-methyl-1-[(1S,4R,5R,6R,8R,10S,11R,12S,13R,16S,18S,20S,21S)-10,11,20-trihydroxy-4,6,12,17,17-pentamethyl-18-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}-9-oxahexacyclo[11.9.0.0^{1,21}.0^{4,12}.0^{5,10}.0^{16,21}]docosan-8-yl]propyl acetate

> <JCHEM_LOGP>
1.602373952666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.246287900041345

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.882180423902028

> <JCHEM_PKA_STRONGEST_BASIC>
-2.978112911995079

> <JCHEM_POLAR_SURFACE_AREA>
184.6

> <JCHEM_REFRACTIVITY>
178.3801

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S)-2-methoxy-2-methyl-1-[(1S,4R,5R,6R,8R,10S,11R,12S,13R,16S,18S,20S,21S)-10,11,20-trihydroxy-4,6,12,17,17-pentamethyl-18-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}-9-oxahexacyclo[11.9.0.0^{1,21}.0^{4,12}.0^{5,10}.0^{16,21}]docosan-8-yl]propyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      18.473   3.708   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      17.009   4.185   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      15.864   3.156   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.834   4.301   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.893   2.010   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.718   2.126   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      15.037   0.619   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      16.502   0.142   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.647   1.172   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      16.821  -1.364   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      13.254   2.603   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.935   4.110   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.471   4.587   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.152   6.093   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.326   3.557   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.645   2.050   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.804   0.519   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      12.109   1.573   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.310   1.281   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.148  -0.250   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.167   2.313   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.690   0.849   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.635   2.153   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.008   0.747   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.476   0.587   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.572   1.833   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.040   1.674   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.463   0.193   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.655   1.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.136   2.920   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -0.396   2.760   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -1.300   4.007   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -2.832   3.847   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -3.736   5.094   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -3.109   6.500   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -4.013   7.747   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -1.577   6.660   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -0.950   8.066   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -0.673   5.413   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       0.859   5.573   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       1.763   4.327   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       3.295   4.486   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       3.922   5.893   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       4.199   3.240   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       4.827   4.646   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       5.731   3.400   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       6.358   4.806   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       7.890   4.966   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       8.794   3.719   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       9.565   5.052   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    6   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   49                                                  
CONECT   16   15   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16   11                                                       
CONECT   19   16   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23   49                                             
CONECT   22   21                                                            
CONECT   23   21   24   46                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   44                                                  
CONECT   27   26   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27   31   41                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   39                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   32   40                                                  
CONECT   40   39                                                            
CONECT   41   30   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   26   45   46                                             
CONECT   45   44   46                                                       
CONECT   46   45   23   44   47                                             
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   15   21   50                                             
CONECT   50   49                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  112    0
END

View in JSmol

Synonyms

Value	Source
(1S)-2-Methoxy-2-methyl-1-[(1S,4R,5R,6R,8R,10S,11R,12S,13R,16S,18S,20S,21S)-10,11,20-trihydroxy-4,6,12,17,17-pentamethyl-18-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}-9-oxahexacyclo[11.9.0.0,.0,.0,.0,]docosan-8-yl]propyl acetic acid	Generator

Chemical Formula

C₃₈H₆₂O₁₂

Average Mass

710.9020 Da

Monoisotopic Mass

710.42413 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(C)(C)[C@@H](OC(C)=O)[C@H]1C[C@@H](C)[C@@H]2[C@@]3(C)CC[C@@]45C[C@@]44[C@@H](O)C[C@H](O[C@@H]6OC[C@@H](O)[C@H](O)[C@H]6O)C(C)(C)[C@@H]4CC[C@H]5[C@]3(C)[C@@H](O)[C@@]2(O)O1

InChI Identifier

InChI=1S/C38H62O12/c1-18-14-21(29(48-19(2)39)33(5,6)46-9)50-38(45)28(18)34(7)12-13-36-17-37(36)22(10-11-23(36)35(34,8)31(38)44)32(3,4)25(15-24(37)41)49-30-27(43)26(42)20(40)16-47-30/h18,20-31,40-45H,10-17H2,1-9H3/t18-,20-,21-,22+,23+,24+,25+,26+,27-,28-,29+,30+,31-,34-,35-,36+,37-,38+/m1/s1

InChI Key

CDVLNJHGGOFODI-GINPRTKDSA-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
Actaea simplex	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Cucurbitacin glycosides

Alternative Parents

Substituents

Cucurbitacin glycoside skeleton
Cycloartanol-skeleton
9b,19-cyclo-lanostane-skeleton
Cycloartane-skeleton
Triterpenoid
1-hydroxysteroid
16-hydroxysteroid
16-beta-hydroxysteroid
15-hydroxysteroid
Hydroxysteroid
Glycosyl compound
O-glycosyl compound
Oxane
Monosaccharide
Cyclic alcohol
Carboxylic acid ester
Hemiacetal
Secondary alcohol
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Acetal
Dialkyl ether
Ether
Polyol
Organic oxide
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxygen compound
Carbonyl group
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	1.6	ChemAxon
pKa (Strongest Acidic)	10.88	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	184.6 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	178.38 m³·mol⁻¹	ChemAxon
Polarizability	79.12 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	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

162942837

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s)-2-methoxy-2-methyl-1-[(1s,4r,5r,6r,8r,10s,11r,12s,13r,16s,18s,20s,21s)-10,11,20-trihydroxy-4,6,12,17,17-pentamethyl-18-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-9-oxahexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]docosan-8-yl]propyl acetate (NP0223398)

MOL for NP0223398 ((1s)-2-methoxy-2-methyl-1-[(1s,4r,5r,6r,8r,10s,11r,12s,13r,16s,18s,20s,21s)-10,11,20-trihydroxy-4,6,12,17,17-pentamethyl-18-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-9-oxahexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]docosan-8-yl]propyl acetate)

3D MOL for NP0223398 ((1s)-2-methoxy-2-methyl-1-[(1s,4r,5r,6r,8r,10s,11r,12s,13r,16s,18s,20s,21s)-10,11,20-trihydroxy-4,6,12,17,17-pentamethyl-18-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-9-oxahexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]docosan-8-yl]propyl acetate)

3D SDF for NP0223398 ((1s)-2-methoxy-2-methyl-1-[(1s,4r,5r,6r,8r,10s,11r,12s,13r,16s,18s,20s,21s)-10,11,20-trihydroxy-4,6,12,17,17-pentamethyl-18-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-9-oxahexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]docosan-8-yl]propyl acetate)

3D-SDF for NP0223398 ((1s)-2-methoxy-2-methyl-1-[(1s,4r,5r,6r,8r,10s,11r,12s,13r,16s,18s,20s,21s)-10,11,20-trihydroxy-4,6,12,17,17-pentamethyl-18-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-9-oxahexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]docosan-8-yl]propyl acetate)

PDB for NP0223398 ((1s)-2-methoxy-2-methyl-1-[(1s,4r,5r,6r,8r,10s,11r,12s,13r,16s,18s,20s,21s)-10,11,20-trihydroxy-4,6,12,17,17-pentamethyl-18-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-9-oxahexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]docosan-8-yl]propyl acetate)

3D PDB for NP0223398 ((1s)-2-methoxy-2-methyl-1-[(1s,4r,5r,6r,8r,10s,11r,12s,13r,16s,18s,20s,21s)-10,11,20-trihydroxy-4,6,12,17,17-pentamethyl-18-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-9-oxahexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]docosan-8-yl]propyl acetate)

SMILES for NP0223398 ((1s)-2-methoxy-2-methyl-1-[(1s,4r,5r,6r,8r,10s,11r,12s,13r,16s,18s,20s,21s)-10,11,20-trihydroxy-4,6,12,17,17-pentamethyl-18-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-9-oxahexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]docosan-8-yl]propyl acetate)

INCHI for NP0223398 ((1s)-2-methoxy-2-methyl-1-[(1s,4r,5r,6r,8r,10s,11r,12s,13r,16s,18s,20s,21s)-10,11,20-trihydroxy-4,6,12,17,17-pentamethyl-18-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-9-oxahexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]docosan-8-yl]propyl acetate)

Structure for NP0223398 ((1s)-2-methoxy-2-methyl-1-[(1s,4r,5r,6r,8r,10s,11r,12s,13r,16s,18s,20s,21s)-10,11,20-trihydroxy-4,6,12,17,17-pentamethyl-18-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-9-oxahexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]docosan-8-yl]propyl acetate)

3D Structure for NP0223398 ((1s)-2-methoxy-2-methyl-1-[(1s,4r,5r,6r,8r,10s,11r,12s,13r,16s,18s,20s,21s)-10,11,20-trihydroxy-4,6,12,17,17-pentamethyl-18-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-9-oxahexacyclo[11.9.0.0¹,²¹.0⁴,¹².0⁵,¹⁰.0¹⁶,²¹]docosan-8-yl]propyl acetate)