NP-MRD: Showing NP-Card for (2r,3r)-3-[(1s,3as,5ar,7r,8s,9ar,9br,11ar)-7,8-bis(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-1-[(2s,3r,4s)-2,4-dimethyl-5-oxooxolan-3-yl]-3-hydroxybutan-2-yl acetate (NP0327406)

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Record Information

Version

2.0

Created at

2022-09-12 09:57:30 UTC

Updated at

2022-09-12 09:57:30 UTC

NP-MRD ID

NP0327406

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r)-3-[(1s,3as,5ar,7r,8s,9ar,9br,11ar)-7,8-bis(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-1-[(2s,3r,4s)-2,4-dimethyl-5-oxooxolan-3-yl]-3-hydroxybutan-2-yl acetate

Description

(2R,3R)-3-[(1R,2R,4S,5R,7R,11S,14S,15R)-4,5-bis(acetyloxy)-11-hydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-9-en-14-yl]-1-[(2S,3R,4S)-2,4-dimethyl-5-oxooxolan-3-yl]-3-hydroxybutan-2-yl acetate belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (2r,3r)-3-[(1s,3as,5ar,7r,8s,9ar,9br,11ar)-7,8-bis(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-1-[(2s,3r,4s)-2,4-dimethyl-5-oxooxolan-3-yl]-3-hydroxybutan-2-yl acetate is found in Cyathula capitata. Based on a literature review very few articles have been published on (2R,3R)-3-[(1R,2R,4S,5R,7R,11S,14S,15R)-4,5-bis(acetyloxy)-11-hydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-9-en-14-yl]-1-[(2S,3R,4S)-2,4-dimethyl-5-oxooxolan-3-yl]-3-hydroxybutan-2-yl acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309122211572D          

 46 50  0  0  1  0            999 V2000
    8.0466   -1.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5148   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7951    0.0722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7026   -0.8489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1708   -0.2182    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3587   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8269    0.2673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5466   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1072    1.0432    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9193    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4511    0.5577    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2632    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5435    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0117    2.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3557    1.6241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8557    2.4498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4830    0.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0148    0.1221    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7345   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3905   -0.1684    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0307   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5660   -0.1416    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0596   -0.7929    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4083   -0.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7109   -1.2992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5533   -1.4442    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2640   -1.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5749   -0.5672    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3758   -0.3695    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0066   -0.9013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4354    0.4533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6712    0.7642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4735    1.5652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1394    0.1335    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6835    0.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8642   -2.2084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3578   -2.8597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4594   -2.7469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6687   -3.6239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6708    0.6076    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8685    1.4085    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
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
  9 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 20 19  1  1  0  0  0
  7 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  6  0  0  0
 26 28  1  6  0  0  0
 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
 31 30  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 31 37  1  0  0  0  0
 37 38  1  1  0  0  0
 29 39  1  6  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  2  0  0  0  0
 25 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 19 45  1  0  0  0  0
 23 45  1  0  0  0  0
 45 46  1  6  0  0  0
M  END


  Mrv1652309122211572D          

 46 50  0  0  1  0            999 V2000
    8.0466   -1.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5148   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7951    0.0722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7026   -0.8489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1708   -0.2182    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3587   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8269    0.2673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5466   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1072    1.0432    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9193    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4511    0.5577    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2632    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5435    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0117    2.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3557    1.6241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8557    2.4498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4830    0.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0148    0.1221    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7345   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3905   -0.1684    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0307   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5660   -0.1416    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0596   -0.7929    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4083   -0.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7109   -1.2992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5533   -1.4442    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2640   -1.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5749   -0.5672    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3758   -0.3695    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0066   -0.9013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4354    0.4533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6712    0.7642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4735    1.5652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1394    0.1335    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6835    0.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8642   -2.2084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3578   -2.8597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4594   -2.7469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6687   -3.6239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6708    0.6076    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8685    1.4085    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
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
  9 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 20 19  1  1  0  0  0
  7 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  6  0  0  0
 26 28  1  6  0  0  0
 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
 31 30  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 31 37  1  0  0  0  0
 37 38  1  1  0  0  0
 29 39  1  6  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  2  0  0  0  0
 25 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 19 45  1  0  0  0  0
 23 45  1  0  0  0  0
 45 46  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0327406

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C35H50O11/c1-17-22(18(2)43-31(17)40)13-30(46-21(5)38)34(8,41)29-10-12-35(42)24-14-26(39)25-15-27(44-19(3)36)28(45-20(4)37)16-32(25,6)23(24)9-11-33(29,35)7/h14,17-18,22-23,25,27-30,41-42H,9-13,15-16H2,1-8H3/t17-,18-,22+,23-,25-,27+,28-,29-,30+,32+,33+,34+,35+/m0/s1

> <INCHI_KEY>
KELLSCRUBKTFHD-NZQXLUJASA-N

> <FORMULA>
C35H50O11

> <MOLECULAR_WEIGHT>
646.774

> <EXACT_MASS>
646.33531243

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
96

> <JCHEM_AVERAGE_POLARIZABILITY>
69.58424807703985

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R)-3-[(1R,2R,4S,5R,7R,11S,14S,15R)-4,5-bis(acetyloxy)-11-hydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-14-yl]-1-[(2S,3R,4S)-2,4-dimethyl-5-oxooxolan-3-yl]-3-hydroxybutan-2-yl acetate

> <JCHEM_LOGP>
2.3494188966666654

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.089771594412845

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.48131016788166

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3290466455750876

> <JCHEM_POLAR_SURFACE_AREA>
162.73000000000002

> <JCHEM_REFRACTIVITY>
163.5124

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R)-3-[(1R,2R,4S,5R,7R,11S,14S,15R)-4,5-bis(acetyloxy)-11-hydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-14-yl]-1-[(2S,3R,4S)-2,4-dimethyl-5-oxooxolan-3-yl]-3-hydroxybutan-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      15.020  -2.491   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.028  -1.314   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      14.551   0.135   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      12.512  -1.585   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      11.519  -0.407   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.003  -0.678   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.010   0.499   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.487  -0.949   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.533   1.947   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.049   2.218   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.042   1.041   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      13.558   1.312   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      14.081   2.761   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.089   3.938   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      15.597   3.032   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.541   3.125   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.064   4.573   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.025   2.854   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.502   1.405   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.494   0.228   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.971  -1.221   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.455  -1.492   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.462  -0.314   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.791  -1.700   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.923  -0.264   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.978  -1.480   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.762  -0.535   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.194  -2.425   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.033  -2.696   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.493  -2.485   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.073  -1.059   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.568  -0.690   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -3.746  -1.683   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -2.679   0.846   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -1.253   1.427   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -0.884   2.922   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -0.260   0.249   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       1.276   0.360   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       1.613  -4.122   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       0.668  -5.338   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -0.858  -5.127   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       1.248  -6.765   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       2.495   1.215   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       3.770   2.079   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       4.986   1.134   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       5.355   2.629   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   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9   20                                             
CONECT    8    7                                                            
CONECT    9    7   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10    5   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    9   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   45                                                  
CONECT   20   19    7   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25   45                                             
CONECT   24   23                                                            
CONECT   25   23   26   43                                                  
CONECT   26   25   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   26   30   39                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   37                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   31   38                                                  
CONECT   38   37                                                            
CONECT   39   29   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40                                                            
CONECT   43   25   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   19   23   46                                             
CONECT   46   45                                                            
MASTER        0    0    0    0    0    0    0    0   46    0  100    0
END

View in JSmol

Synonyms

Value	Source
(2R,3R)-3-[(1R,2R,4S,5R,7R,11S,14S,15R)-4,5-Bis(acetyloxy)-11-hydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0,.0,]heptadec-9-en-14-yl]-1-[(2S,3R,4S)-2,4-dimethyl-5-oxooxolan-3-yl]-3-hydroxybutan-2-yl acetic acid	Generator

Chemical Formula

C₃₅H₅₀O₁₁

Average Mass

646.7740 Da

Monoisotopic Mass

646.33531 Da

IUPAC Name

(2R,3R)-3-[(1R,2R,4S,5R,7R,11S,14S,15R)-4,5-bis(acetyloxy)-11-hydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-14-yl]-1-[(2S,3R,4S)-2,4-dimethyl-5-oxooxolan-3-yl]-3-hydroxybutan-2-yl acetate

Traditional Name

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C35H50O11/c1-17-22(18(2)43-31(17)40)13-30(46-21(5)38)34(8,41)29-10-12-35(42)24-14-26(39)25-15-27(44-19(3)36)28(45-20(4)37)16-32(25,6)23(24)9-11-33(29,35)7/h14,17-18,22-23,25,27-30,41-42H,9-13,15-16H2,1-8H3/t17-,18-,22+,23-,25-,27+,28-,29-,30+,32+,33+,34+,35+/m0/s1

InChI Key

KELLSCRUBKTFHD-NZQXLUJASA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cyathula capitata	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
Cholestane-skeleton
Ecdysteroid
Dihydroxy bile acid, alcohol, or derivatives
Hydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
Steroid lactone
20-hydroxysteroid
Steroid ester
14-hydroxysteroid
Hydroxysteroid
Oxosteroid
6-oxosteroid
Steroid
Delta-7-steroid
Tetracarboxylic acid or derivatives
Cyclohexenone
Gamma butyrolactone
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Carboxylic acid ester
Lactone
Ketone
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxide
Organooxygen compound
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
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	2.35	ChemAxon
pKa (Strongest Acidic)	13.48	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	162.73 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	163.51 m³·mol⁻¹	ChemAxon
Polarizability	69.58 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	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

162964746

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3r)-3-[(1s,3as,5ar,7r,8s,9ar,9br,11ar)-7,8-bis(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-1-[(2s,3r,4s)-2,4-dimethyl-5-oxooxolan-3-yl]-3-hydroxybutan-2-yl acetate (NP0327406)

MOL for NP0327406 ((2r,3r)-3-[(1s,3as,5ar,7r,8s,9ar,9br,11ar)-7,8-bis(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-1-[(2s,3r,4s)-2,4-dimethyl-5-oxooxolan-3-yl]-3-hydroxybutan-2-yl acetate)

3D MOL for NP0327406 ((2r,3r)-3-[(1s,3as,5ar,7r,8s,9ar,9br,11ar)-7,8-bis(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-1-[(2s,3r,4s)-2,4-dimethyl-5-oxooxolan-3-yl]-3-hydroxybutan-2-yl acetate)

3D SDF for NP0327406 ((2r,3r)-3-[(1s,3as,5ar,7r,8s,9ar,9br,11ar)-7,8-bis(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-1-[(2s,3r,4s)-2,4-dimethyl-5-oxooxolan-3-yl]-3-hydroxybutan-2-yl acetate)

3D-SDF for NP0327406 ((2r,3r)-3-[(1s,3as,5ar,7r,8s,9ar,9br,11ar)-7,8-bis(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-1-[(2s,3r,4s)-2,4-dimethyl-5-oxooxolan-3-yl]-3-hydroxybutan-2-yl acetate)

PDB for NP0327406 ((2r,3r)-3-[(1s,3as,5ar,7r,8s,9ar,9br,11ar)-7,8-bis(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-1-[(2s,3r,4s)-2,4-dimethyl-5-oxooxolan-3-yl]-3-hydroxybutan-2-yl acetate)

3D PDB for NP0327406 ((2r,3r)-3-[(1s,3as,5ar,7r,8s,9ar,9br,11ar)-7,8-bis(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-1-[(2s,3r,4s)-2,4-dimethyl-5-oxooxolan-3-yl]-3-hydroxybutan-2-yl acetate)

SMILES for NP0327406 ((2r,3r)-3-[(1s,3as,5ar,7r,8s,9ar,9br,11ar)-7,8-bis(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-1-[(2s,3r,4s)-2,4-dimethyl-5-oxooxolan-3-yl]-3-hydroxybutan-2-yl acetate)

INCHI for NP0327406 ((2r,3r)-3-[(1s,3as,5ar,7r,8s,9ar,9br,11ar)-7,8-bis(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-1-[(2s,3r,4s)-2,4-dimethyl-5-oxooxolan-3-yl]-3-hydroxybutan-2-yl acetate)

Structure for NP0327406 ((2r,3r)-3-[(1s,3as,5ar,7r,8s,9ar,9br,11ar)-7,8-bis(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-1-[(2s,3r,4s)-2,4-dimethyl-5-oxooxolan-3-yl]-3-hydroxybutan-2-yl acetate)

3D Structure for NP0327406 ((2r,3r)-3-[(1s,3as,5ar,7r,8s,9ar,9br,11ar)-7,8-bis(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-1-[(2s,3r,4s)-2,4-dimethyl-5-oxooxolan-3-yl]-3-hydroxybutan-2-yl acetate)