NP-MRD: Showing NP-Card for (1s,2s,3r,4s,7r,9s,10s,12r,15s)-4,12-bis(acetyloxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-6-oxatetracyclo[11.3.1.0³,¹⁰.0⁴,⁷]heptadec-13-en-2-yl benzoate (NP0157277)

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Record Information

Version

1.0

Created at

2022-09-02 14:37:30 UTC

Updated at

2022-09-02 14:37:30 UTC

NP-MRD ID

NP0157277

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,3r,4s,7r,9s,10s,12r,15s)-4,12-bis(acetyloxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-6-oxatetracyclo[11.3.1.0³,¹⁰.0⁴,⁷]heptadec-13-en-2-yl benzoate

Description

7-Xylosylbaccatin III belongs to the class of organic compounds known as taxanes and derivatives. These are diterpenoids with a structure based either on the taxane skeleton, or a derivative thereof. In term of phytochemistry, several derivatives of the taxane skeleton exist: 2(3->20)-Abeotaxane, 3,11-cyclotaxane, 11(15->1),11(10->9)-abeotaxane, 3,8-seco-taxane, and 11(15->1)-abeotaxane, among others. More complex skeletons have been found recently, which include the taxane-derived [3.3.3] Propellane ring system. (1s,2s,3r,4s,7r,9s,10s,12r,15s)-4,12-bis(acetyloxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-6-oxatetracyclo[11.3.1.0³,¹⁰.0⁴,⁷]heptadec-13-en-2-yl benzoate is found in Taxus wallichiana. It was first documented in 2022 (PMID: 36055712). Based on a literature review a significant number of articles have been published on 7-Xylosylbaccatin III (PMID: 36055667) (PMID: 36055614) (PMID: 36055604) (PMID: 36055583).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309022216372D          

 51 56  0  0  1  0            999 V2000
    1.4439   -2.4359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8623   -1.7249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6873   -1.7318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4558   -1.0071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8742   -0.2961    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7160   -0.4505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9009   -1.2545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3941    0.0476    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3922   -0.7774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0567   -0.4439    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9624   -1.2635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6250   -1.7550    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3820   -1.4269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0446   -1.9184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9503   -2.7380    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6129   -3.2294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1933   -3.0661    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0990   -3.8857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5307   -2.5746    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7737   -2.9027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8137   -0.1158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9080    0.7038    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3995    1.3664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7369    1.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2454    1.1953    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7326    1.8415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0358    2.6088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5230    3.2550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8519    2.7298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4884    0.8672    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9387    1.5378    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3535    2.2509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9433    2.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1183    2.9694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3581    3.6799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9479    4.3957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3627    5.1088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1877    5.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5979    4.3904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1831    3.6772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0781    1.6850    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3416    2.4668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3100    2.0856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5622    1.6914    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1513    2.1056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5908    0.8466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1265    0.4390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3196    0.3782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7566    0.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2609    0.3453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5736    0.8839    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  6  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  1  0  0  0
 10 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 30 25  1  6  0  0  0
  8 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 35 40  1  0  0  0  0
 31 41  1  0  0  0  0
 41 42  1  6  0  0  0
 41 43  1  0  0  0  0
 43 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
 46 48  2  0  0  0  0
  5 48  1  0  0  0  0
 48 49  1  0  0  0  0
 41 49  1  0  0  0  0
 49 50  1  0  0  0  0
 49 51  1  0  0  0  0
M  END


  Mrv1652309022216372D          

 51 56  0  0  1  0            999 V2000
    1.4439   -2.4359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8623   -1.7249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6873   -1.7318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4558   -1.0071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8742   -0.2961    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7160   -0.4505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9009   -1.2545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3941    0.0476    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3922   -0.7774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0567   -0.4439    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9624   -1.2635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6250   -1.7550    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3820   -1.4269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0446   -1.9184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9503   -2.7380    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6129   -3.2294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1933   -3.0661    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0990   -3.8857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5307   -2.5746    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7737   -2.9027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8137   -0.1158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9080    0.7038    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3995    1.3664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7369    1.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2454    1.1953    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7326    1.8415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0358    2.6088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5230    3.2550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8519    2.7298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4884    0.8672    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9387    1.5378    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3535    2.2509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9433    2.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1183    2.9694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3581    3.6799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9479    4.3957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3627    5.1088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1877    5.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5979    4.3904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1831    3.6772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0781    1.6850    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3416    2.4668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3100    2.0856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5622    1.6914    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1513    2.1056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5908    0.8466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1265    0.4390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3196    0.3782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7566    0.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2609    0.3453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5736    0.8839    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  6  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  1  0  0  0
 10 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 30 25  1  6  0  0  0
  8 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 35 40  1  0  0  0  0
 31 41  1  0  0  0  0
 41 42  1  6  0  0  0
 41 43  1  0  0  0  0
 43 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
 46 48  2  0  0  0  0
  5 48  1  0  0  0  0
 48 49  1  0  0  0  0
 41 49  1  0  0  0  0
 49 50  1  0  0  0  0
 49 51  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0157277

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1C2=C(C)[C@@H](O)C[C@@](O)([C@@H](OC(=O)C3=CC=CC=C3)[C@@H]3[C@@]4(CO[C@@H]4C[C@H](O[C@@H]4OC[C@@H](O)[C@H](O)[C@H]4O)[C@@]3(C)C1=O)OC(C)=O)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C36H46O15/c1-16-20(39)13-36(45)30(50-31(44)19-10-8-7-9-11-19)28-34(6,29(43)27(48-17(2)37)24(16)33(36,4)5)22(12-23-35(28,15-47-23)51-18(3)38)49-32-26(42)25(41)21(40)14-46-32/h7-11,20-23,25-28,30,32,39-42,45H,12-15H2,1-6H3/t20-,21+,22-,23+,25-,26+,27+,28-,30-,32-,34+,35-,36+/m0/s1

> <INCHI_KEY>
CFXLQLVVACEBGI-BWGQDSEVSA-N

> <FORMULA>
C36H46O15

> <MOLECULAR_WEIGHT>
718.749

> <EXACT_MASS>
718.283670781

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
97

> <JCHEM_AVERAGE_POLARIZABILITY>
72.21241228197403

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}-6-oxatetracyclo[11.3.1.0^{3,10}.0^{4,7}]heptadec-13-en-2-yl benzoate

> <ALOGPS_LOGP>
0.66

> <JCHEM_LOGP>
-0.09777175566666807

> <ALOGPS_LOGS>
-3.11

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.216762723304493

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.479051717680345

> <JCHEM_PKA_STRONGEST_BASIC>
-3.019854631553031

> <JCHEM_POLAR_SURFACE_AREA>
224.80999999999997

> <JCHEM_REFRACTIVITY>
171.79940000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.52e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}-6-oxatetracyclo[11.3.1.0^{3,10}.0^{4,7}]heptadec-13-en-2-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       2.695  -4.547   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.476  -3.220   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.016  -3.233   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.717  -1.880   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.499  -0.553   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.070  -0.841   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.415  -2.342   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.336   0.089   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.332  -1.451   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.573  -0.829   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.396  -2.359   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.633  -3.276   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      10.046  -2.664   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      11.283  -3.581   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.107  -5.111   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      12.344  -6.028   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.694  -5.723   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.518  -7.253   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.457  -4.806   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.044  -5.418   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.986  -0.216   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.162   1.314   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.079   2.551   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.842   3.468   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.925   2.231   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.967   3.437   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.534   4.870   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.576   6.076   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       9.057   5.096   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.512   1.619   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.486   2.871   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.260   4.202   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.494   5.538   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       3.954   5.543   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       6.268   6.869   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.503   8.205   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.277   9.536   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       7.817   9.532   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       8.583   8.195   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       7.808   6.864   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       3.879   3.145   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       4.371   4.605   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       2.445   3.893   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       1.049   3.157   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      -0.282   3.930   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       1.103   1.580   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -0.236   0.819   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       2.463   0.706   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       3.279   1.863   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       4.220   0.645   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       4.804   1.650   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   48                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10   30                                             
CONECT    9    8                                                            
CONECT   10    8   11   21                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   12   20                                                  
CONECT   20   19                                                            
CONECT   21   10   22                                                       
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   22   26   30                                             
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   25    8   31                                                  
CONECT   31   30   32   41                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   40                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   35                                                       
CONECT   41   31   42   43   49                                             
CONECT   42   41                                                            
CONECT   43   41   44                                                       
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46    5   49                                                  
CONECT   49   48   41   50   51                                             
CONECT   50   49                                                            
CONECT   51   49                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  112    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₆H₄₆O₁₅

Average Mass

718.7490 Da

Monoisotopic Mass

718.28367 Da

IUPAC Name

(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}-6-oxatetracyclo[11.3.1.0^{3,10}.0^{4,7}]heptadec-13-en-2-yl benzoate

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1C2=C(C)[C@@H](O)C[C@@](O)([C@@H](OC(=O)C3=CC=CC=C3)[C@@H]3[C@@]4(CO[C@@H]4C[C@H](O[C@@H]4OC[C@@H](O)[C@H](O)[C@H]4O)[C@@]3(C)C1=O)OC(C)=O)C2(C)C

InChI Identifier

InChI=1S/C36H46O15/c1-16-20(39)13-36(45)30(50-31(44)19-10-8-7-9-11-19)28-34(6,29(43)27(48-17(2)37)24(16)33(36,4)5)22(12-23-35(28,15-47-23)51-18(3)38)49-32-26(42)25(41)21(40)14-46-32/h7-11,20-23,25-28,30,32,39-42,45H,12-15H2,1-6H3/t20-,21+,22-,23+,25-,26+,27+,28-,30-,32-,34+,35-,36+/m0/s1

InChI Key

CFXLQLVVACEBGI-BWGQDSEVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Taxus wallichiana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as taxanes and derivatives. These are diterpenoids with a structure based either on the taxane skeleton, or a derivative thereof. In term of phytochemistry, several derivatives of the taxane skeleton exist: 2(3->20)-Abeotaxane, 3,11-cyclotaxane, 11(15->1),11(10->9)-abeotaxane, 3,8-seco-taxane, and 11(15->1)-abeotaxane, among others. More complex skeletons have been found recently, which include the taxane-derived [3.3.3] Propellane ring system.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Taxanes and derivatives

Alternative Parents

Substituents

Taxane diterpenoid
O-glycosyl compound
Glycosyl compound
Benzoate ester
Tricarboxylic acid or derivatives
Benzoic acid or derivatives
Benzoyl
Alpha-acyloxy ketone
Benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Oxetane
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Dialkyl ether
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	0.66	ALOGPS
logP	-0.098	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	10.48	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	224.81 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	171.8 m³·mol⁻¹	ChemAxon
Polarizability	72.21 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

9846855

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11672124

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Pace A, Tanzilli A, Benincasa D: Prognostication in brain tumors. Handb Clin Neurol. 2022;190:149-161. doi: 10.1016/B978-0-323-85029-2.00001-4. [PubMed:36055712 ]
Demirel M, Kendirci AS, Saglam Y, Ergin ON, Sen C, Ozturk I: Comparison of High Hip Center versus Anatomical Reconstruction Technique in Crowe Types II and III Developmental Dysplasia of the Hip: a Retrospective Clinical Study. Acta Chir Orthop Traumatol Cech. 2022;89(4):272-278. [PubMed:36055667 ]
Chi N, Lozo S, Rathnayake RAC, Botros-Brey S, Ma Y, Damaser M, Wang RR: Distinctive structure, composition and biomechanics of collagen fibrils in vaginal wall connective tissues associated with pelvic organ prolapse. Acta Biomater. 2022 Oct 15;152:335-344. doi: 10.1016/j.actbio.2022.08.059. Epub 2022 Aug 31. [PubMed:36055614 ]
Prochnik A, Burgueno AL, Rubinstein MR, Marcone MP, Bianchi MS, Gonzalez Murano MR, Genaro AM, Wald MR: Sexual dimorphism modulates metabolic and cognitive alterations under HFD nutrition and chronic stress exposure in mice. Correlation between spatial memory impairment and BDNF mRNA expression in hippocampus and spleen. Neurochem Int. 2022 Nov;160:105416. doi: 10.1016/j.neuint.2022.105416. Epub 2022 Aug 30. [PubMed:36055604 ]
Wan D, Wang Y, Liu Y, Gu M, Liu Y, Xiao S, He Q: Effect of nitrate and sulfate coexistence on hydrogen autotrophic reduction of antimonate (Sb(V)) and microbial community structures. Chemosphere. 2022 Dec;308(Pt 2):136263. doi: 10.1016/j.chemosphere.2022.136263. Epub 2022 Aug 30. [PubMed:36055583 ]
LOTUS database [Link]

Showing NP-Card for (1s,2s,3r,4s,7r,9s,10s,12r,15s)-4,12-bis(acetyloxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-6-oxatetracyclo[11.3.1.0³,¹⁰.0⁴,⁷]heptadec-13-en-2-yl benzoate (NP0157277)

MOL for NP0157277 ((1s,2s,3r,4s,7r,9s,10s,12r,15s)-4,12-bis(acetyloxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-6-oxatetracyclo[11.3.1.0³,¹⁰.0⁴,⁷]heptadec-13-en-2-yl benzoate)

3D MOL for NP0157277 ((1s,2s,3r,4s,7r,9s,10s,12r,15s)-4,12-bis(acetyloxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-6-oxatetracyclo[11.3.1.0³,¹⁰.0⁴,⁷]heptadec-13-en-2-yl benzoate)

3D SDF for NP0157277 ((1s,2s,3r,4s,7r,9s,10s,12r,15s)-4,12-bis(acetyloxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-6-oxatetracyclo[11.3.1.0³,¹⁰.0⁴,⁷]heptadec-13-en-2-yl benzoate)

3D-SDF for NP0157277 ((1s,2s,3r,4s,7r,9s,10s,12r,15s)-4,12-bis(acetyloxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-6-oxatetracyclo[11.3.1.0³,¹⁰.0⁴,⁷]heptadec-13-en-2-yl benzoate)

PDB for NP0157277 ((1s,2s,3r,4s,7r,9s,10s,12r,15s)-4,12-bis(acetyloxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-6-oxatetracyclo[11.3.1.0³,¹⁰.0⁴,⁷]heptadec-13-en-2-yl benzoate)

3D PDB for NP0157277 ((1s,2s,3r,4s,7r,9s,10s,12r,15s)-4,12-bis(acetyloxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-6-oxatetracyclo[11.3.1.0³,¹⁰.0⁴,⁷]heptadec-13-en-2-yl benzoate)

SMILES for NP0157277 ((1s,2s,3r,4s,7r,9s,10s,12r,15s)-4,12-bis(acetyloxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-6-oxatetracyclo[11.3.1.0³,¹⁰.0⁴,⁷]heptadec-13-en-2-yl benzoate)

INCHI for NP0157277 ((1s,2s,3r,4s,7r,9s,10s,12r,15s)-4,12-bis(acetyloxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-6-oxatetracyclo[11.3.1.0³,¹⁰.0⁴,⁷]heptadec-13-en-2-yl benzoate)

Structure for NP0157277 ((1s,2s,3r,4s,7r,9s,10s,12r,15s)-4,12-bis(acetyloxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-6-oxatetracyclo[11.3.1.0³,¹⁰.0⁴,⁷]heptadec-13-en-2-yl benzoate)

3D Structure for NP0157277 ((1s,2s,3r,4s,7r,9s,10s,12r,15s)-4,12-bis(acetyloxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-6-oxatetracyclo[11.3.1.0³,¹⁰.0⁴,⁷]heptadec-13-en-2-yl benzoate)