NP-MRD: Showing NP-Card for (1s,3br,4r,5as,7r,9s,9as,9br,11as)-4,9-bis(acetyloxy)-1-[(3s,6s)-6-(2-hydroxypropan-2-yl)-5-oxooxan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl benzoate (NP0217710)

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Record Information

Version

2.0

Created at

2022-09-05 18:09:01 UTC

Updated at

2022-09-05 18:09:01 UTC

NP-MRD ID

NP0217710

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3br,4r,5as,7r,9s,9as,9br,11as)-4,9-bis(acetyloxy)-1-[(3s,6s)-6-(2-hydroxypropan-2-yl)-5-oxooxan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl benzoate

Description

Melianinone belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (1s,3br,4r,5as,7r,9s,9as,9br,11as)-4,9-bis(acetyloxy)-1-[(3s,6s)-6-(2-hydroxypropan-2-yl)-5-oxooxan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl benzoate is found in Melia volkensii. Based on a literature review very few articles have been published on Melianinone.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052220092D          

 50 55  0  0  1  0            999 V2000
    2.0745   -2.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8867   -3.0076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1670   -3.7835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4185   -2.3768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1382   -1.6009    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3261   -1.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0458   -0.6798    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2336   -0.5346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7018   -1.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9821   -1.9412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1103   -1.0201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6421   -1.6508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4542   -1.5056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7345   -0.7296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2027   -0.0989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3906   -0.2441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5776   -0.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8641    0.3651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8616    0.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3897   -0.1943    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9215    0.4364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7336    0.2912    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2655    0.9219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9852    1.6978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5170    2.3285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1730    1.8430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0139   -0.4847    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5458    0.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8261   -0.6299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4774   -0.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1602   -0.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9309   -1.3791    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4373   -2.0304    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2545   -1.9175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7609   -2.5689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4500   -3.3330    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.9563   -3.9844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3050   -4.4907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6077   -3.4780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4627   -4.6357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6327   -3.4459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3219   -4.2101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1264   -2.7946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1064   -1.4059    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4662   -2.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5745   -2.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7624   -1.8914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4821   -1.1154    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6700   -0.9702    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9503   -1.7461    0.0000 C   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
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
  7 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  1  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 37 40  1  0  0  0  0
 36 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
 33 43  1  0  0  0  0
 32 44  1  0  0  0  0
 29 44  1  0  0  0  0
 44 45  1  1  0  0  0
 44 46  1  0  0  0  0
 46 47  1  0  0  0  0
 48 47  1  6  0  0  0
 27 48  1  0  0  0  0
 48 49  1  0  0  0  0
  5 49  1  0  0  0  0
 20 49  1  0  0  0  0
 49 50  1  6  0  0  0
M  END


  Mrv1652309052220092D          

 50 55  0  0  1  0            999 V2000
    2.0745   -2.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8867   -3.0076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1670   -3.7835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4185   -2.3768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1382   -1.6009    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3261   -1.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0458   -0.6798    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2336   -0.5346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7018   -1.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9821   -1.9412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1103   -1.0201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6421   -1.6508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4542   -1.5056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7345   -0.7296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2027   -0.0989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3906   -0.2441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5776   -0.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8641    0.3651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8616    0.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3897   -0.1943    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9215    0.4364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7336    0.2912    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2655    0.9219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9852    1.6978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5170    2.3285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1730    1.8430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0139   -0.4847    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5458    0.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8261   -0.6299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4774   -0.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1602   -0.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9309   -1.3791    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4373   -2.0304    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2545   -1.9175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7609   -2.5689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4500   -3.3330    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.9563   -3.9844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3050   -4.4907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6077   -3.4780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4627   -4.6357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6327   -3.4459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3219   -4.2101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1264   -2.7946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1064   -1.4059    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4662   -2.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5745   -2.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7624   -1.8914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4821   -1.1154    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6700   -0.9702    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9503   -1.7461    0.0000 C   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
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
  7 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  1  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 37 40  1  0  0  0  0
 36 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
 33 43  1  0  0  0  0
 32 44  1  0  0  0  0
 29 44  1  0  0  0  0
 44 45  1  1  0  0  0
 44 46  1  0  0  0  0
 46 47  1  0  0  0  0
 48 47  1  6  0  0  0
 27 48  1  0  0  0  0
 48 49  1  0  0  0  0
  5 49  1  0  0  0  0
 20 49  1  0  0  0  0
 49 50  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0217710

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1C[C@@H](OC(=O)C2=CC=CC=C2)C(C)(C)[C@@H]2C[C@@H](OC(C)=O)[C@]3(C)[C@H](CC[C@@]4(C)[C@@H](CC=C34)[C@H]3CO[C@H](C(=O)C3)C(C)(C)O)[C@@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C41H56O9/c1-23(42)48-33-20-31-37(3,4)32(50-36(45)25-13-11-10-12-14-25)21-34(49-24(2)43)41(31,9)30-17-18-39(7)27(15-16-29(39)40(30,33)8)26-19-28(44)35(47-22-26)38(5,6)46/h10-14,16,26-27,30-35,46H,15,17-22H2,1-9H3/t26-,27+,30+,31+,32-,33-,34+,35-,39+,40+,41-/m1/s1

> <INCHI_KEY>
XTLZDKLZZPSJNU-QMSPRJRKSA-N

> <FORMULA>
C41H56O9

> <MOLECULAR_WEIGHT>
692.89

> <EXACT_MASS>
692.392433383

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
106

> <JCHEM_AVERAGE_POLARIZABILITY>
75.80563370434841

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,3S,5R,7S,9R,10R,14S,15S)-3,9-bis(acetyloxy)-14-[(3S,6S)-6-(2-hydroxypropan-2-yl)-5-oxooxan-3-yl]-2,6,6,10,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-11-en-5-yl benzoate

> <JCHEM_LOGP>
5.592439630999998

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.96153131564605

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.143583788631027

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1727401038835543

> <JCHEM_POLAR_SURFACE_AREA>
125.43

> <JCHEM_REFRACTIVITY>
187.07700000000008

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3S,5R,7S,9R,10R,14S,15S)-3,9-bis(acetyloxy)-14-[(3S,6S)-6-(2-hydroxypropan-2-yl)-5-oxooxan-3-yl]-2,6,6,10,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-11-en-5-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       3.872  -5.343   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.388  -5.614   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.912  -7.062   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.381  -4.437   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.858  -2.988   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.342  -2.717   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.819  -1.269   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.303  -0.998   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.310  -2.175   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.833  -3.624   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.206  -1.904   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.199  -3.081   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.715  -2.810   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.238  -1.362   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.245  -0.185   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.729  -0.456   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.811  -0.092   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.480   0.682   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.342   1.354   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.327  -0.363   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.320   0.815   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.836   0.544   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       9.829   1.721   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       9.306   3.169   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.298   4.347   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.790   3.440   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       9.359  -0.905   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.352   0.273   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.875  -1.176   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.091  -0.231   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.366  -1.095   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.938  -2.574   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.883  -3.790   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      15.408  -3.579   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      16.354  -4.795   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      15.773  -6.222   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      16.719  -7.437   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      15.503  -8.383   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      17.934  -6.492   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      17.664  -8.653   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      14.248  -6.432   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      13.667  -7.859   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      13.303  -5.217   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      11.399  -2.624   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      12.070  -4.010   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      10.406  -3.802   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       8.890  -3.531   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       8.367  -2.082   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       6.851  -1.811   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       7.374  -3.259   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   49                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   17                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17    7   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17   21   49                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   22   28   29   48                                             
CONECT   28   27                                                            
CONECT   29   27   30   44                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   44                                                  
CONECT   33   32   34   43                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   41                                                  
CONECT   37   36   38   39   40                                             
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   37                                                            
CONECT   41   36   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   33                                                       
CONECT   44   32   29   45   46                                             
CONECT   45   44                                                            
CONECT   46   44   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   27   49                                                  
CONECT   49   48    5   20   50                                             
CONECT   50   49                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  110    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₁H₅₆O₉

Average Mass

692.8900 Da

Monoisotopic Mass

692.39243 Da

IUPAC Name

(1R,2S,3S,5R,7S,9R,10R,14S,15S)-3,9-bis(acetyloxy)-14-[(3S,6S)-6-(2-hydroxypropan-2-yl)-5-oxooxan-3-yl]-2,6,6,10,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-11-en-5-yl benzoate

Traditional Name

(1R,2S,3S,5R,7S,9R,10R,14S,15S)-3,9-bis(acetyloxy)-14-[(3S,6S)-6-(2-hydroxypropan-2-yl)-5-oxooxan-3-yl]-2,6,6,10,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-11-en-5-yl benzoate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1C[C@@H](OC(=O)C2=CC=CC=C2)C(C)(C)[C@@H]2C[C@@H](OC(C)=O)[C@]3(C)[C@H](CC[C@@]4(C)[C@@H](CC=C34)[C@H]3CO[C@H](C(=O)C3)C(C)(C)O)[C@@]12C

InChI Identifier

InChI=1S/C41H56O9/c1-23(42)48-33-20-31-37(3,4)32(50-36(45)25-13-11-10-12-14-25)21-34(49-24(2)43)41(31,9)30-17-18-39(7)27(15-16-29(39)40(30,33)8)26-19-28(44)35(47-22-26)38(5,6)46/h10-14,16,26-27,30-35,46H,15,17-22H2,1-9H3/t26-,27+,30+,31+,32-,33-,34+,35-,39+,40+,41-/m1/s1

InChI Key

XTLZDKLZZPSJNU-QMSPRJRKSA-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
Melia volkensii	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
Steroid ester
Steroid
Benzoate ester
Benzoic acid or derivatives
Tricarboxylic acid or derivatives
Benzoyl
Monocyclic benzene moiety
Oxane
Benzenoid
Tertiary alcohol
Carboxylic acid ester
Ketone
Cyclic ketone
Ether
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	5.59	ChemAxon
pKa (Strongest Acidic)	14.14	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	125.43 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	187.08 m³·mol⁻¹	ChemAxon
Polarizability	75.81 Å³	ChemAxon
Number of Rings	6	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

101916232

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3br,4r,5as,7r,9s,9as,9br,11as)-4,9-bis(acetyloxy)-1-[(3s,6s)-6-(2-hydroxypropan-2-yl)-5-oxooxan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl benzoate (NP0217710)

MOL for NP0217710 ((1s,3br,4r,5as,7r,9s,9as,9br,11as)-4,9-bis(acetyloxy)-1-[(3s,6s)-6-(2-hydroxypropan-2-yl)-5-oxooxan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl benzoate)

3D MOL for NP0217710 ((1s,3br,4r,5as,7r,9s,9as,9br,11as)-4,9-bis(acetyloxy)-1-[(3s,6s)-6-(2-hydroxypropan-2-yl)-5-oxooxan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl benzoate)

3D SDF for NP0217710 ((1s,3br,4r,5as,7r,9s,9as,9br,11as)-4,9-bis(acetyloxy)-1-[(3s,6s)-6-(2-hydroxypropan-2-yl)-5-oxooxan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl benzoate)

3D-SDF for NP0217710 ((1s,3br,4r,5as,7r,9s,9as,9br,11as)-4,9-bis(acetyloxy)-1-[(3s,6s)-6-(2-hydroxypropan-2-yl)-5-oxooxan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl benzoate)

PDB for NP0217710 ((1s,3br,4r,5as,7r,9s,9as,9br,11as)-4,9-bis(acetyloxy)-1-[(3s,6s)-6-(2-hydroxypropan-2-yl)-5-oxooxan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl benzoate)

3D PDB for NP0217710 ((1s,3br,4r,5as,7r,9s,9as,9br,11as)-4,9-bis(acetyloxy)-1-[(3s,6s)-6-(2-hydroxypropan-2-yl)-5-oxooxan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl benzoate)

SMILES for NP0217710 ((1s,3br,4r,5as,7r,9s,9as,9br,11as)-4,9-bis(acetyloxy)-1-[(3s,6s)-6-(2-hydroxypropan-2-yl)-5-oxooxan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl benzoate)

INCHI for NP0217710 ((1s,3br,4r,5as,7r,9s,9as,9br,11as)-4,9-bis(acetyloxy)-1-[(3s,6s)-6-(2-hydroxypropan-2-yl)-5-oxooxan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl benzoate)

Structure for NP0217710 ((1s,3br,4r,5as,7r,9s,9as,9br,11as)-4,9-bis(acetyloxy)-1-[(3s,6s)-6-(2-hydroxypropan-2-yl)-5-oxooxan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl benzoate)

3D Structure for NP0217710 ((1s,3br,4r,5as,7r,9s,9as,9br,11as)-4,9-bis(acetyloxy)-1-[(3s,6s)-6-(2-hydroxypropan-2-yl)-5-oxooxan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl benzoate)