NP-MRD: Showing NP-Card for Baccatin VIII (NP0139309)

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Record Information

Version

2.0

Created at

2022-06-29 19:48:34 UTC

Updated at

2022-06-29 19:48:34 UTC

NP-MRD ID

NP0139309

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Baccatin VIII

Description

Baccatin VIII 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. Baccatin VIII was first documented in 2014 (PMID: 24660136). Based on a literature review very few articles have been published on Baccatin VIII.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306292221482D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306292221482D          

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    2.6300    0.2825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0708    0.9469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2057    1.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8765    0.4182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6935    0.3034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3864   -0.2305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4250    1.5055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3386    1.1173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0537    1.5288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7675    1.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7663    0.2902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4826    1.5267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4313    2.3305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4705    1.8750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4805    1.6630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0652    2.3758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2402    2.3726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4749    3.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0595    3.8048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4692    4.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2942    4.5241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7095    3.8113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2999    3.0952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8767    1.2754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5402    0.7851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8724    1.2572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1743    2.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6603    2.6703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9901    2.1475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1077   -1.8474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5383   -1.3623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0533   -1.8396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6032   -1.5922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2218   -1.5876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6383   -2.2998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6303   -0.8708    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
  2 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 17 23  1  0  0  0  0
 13 24  1  0  0  0  0
 12 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 28 33  1  0  0  0  0
 10 34  1  0  0  0  0
 34 35  1  0  0  0  0
  9 35  1  0  0  0  0
 10 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
  7 40  1  0  0  0  0
  6 41  1  0  0  0  0
  5 42  1  0  0  0  0
  4 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 44 46  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0139309

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1C(O)C2(O)C(OC(=O)C3=CC=CC=C3)C3C4(COC4CC(O)C3(C)C(O)C(OC(C)=O)C(=C1C)C2(C)C)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C33H42O13/c1-15-22-24(44-17(3)35)26(38)31(7)20(37)13-21-32(14-42-21,46-18(4)36)25(31)28(45-29(40)19-11-9-8-10-12-19)33(41,30(22,5)6)27(39)23(15)43-16(2)34/h8-12,20-21,23-28,37-39,41H,13-14H2,1-7H3

> <INCHI_KEY>
SMMKFLQKTRZJCF-UHFFFAOYSA-N

> <FORMULA>
C33H42O13

> <MOLECULAR_WEIGHT>
646.686

> <EXACT_MASS>
646.262541412

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
88

> <JCHEM_AVERAGE_POLARIZABILITY>
64.09624249732268

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,12,15-tris(acetyloxy)-1,9,11,16-tetrahydroxy-10,14,17,17-tetramethyl-6-oxatetracyclo[11.3.1.0^{3,10}.0^{4,7}]heptadec-13-en-2-yl benzoate

> <ALOGPS_LOGP>
1.44

> <JCHEM_LOGP>
0.026194285333333123

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.349813427768165

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.261584387059925

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0088629806468816

> <JCHEM_POLAR_SURFACE_AREA>
195.34999999999997

> <JCHEM_REFRACTIVITY>
156.2888

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.67e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,12,15-tris(acetyloxy)-1,9,11,16-tetrahydroxy-10,14,17,17-tetramethyl-6-oxatetracyclo[11.3.1.0^{3,10}.0^{4,7}]heptadec-13-en-2-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      -1.868  -0.295   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.542   0.489   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.855  -0.384   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.903  -1.643   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.484  -1.934   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.736  -1.003   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.974  -1.918   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.386  -1.303   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.560   0.227   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.321   1.142   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.909   0.527   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.866   1.768   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.251   2.042   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.636   0.781   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.161   0.566   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.588  -0.430   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.793   2.810   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.632   2.086   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.967   2.854   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -3.299   2.082   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -3.297   0.542   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -4.634   2.850   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.805   4.350   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.745   3.500   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       4.630   3.104   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.855   4.435   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.315   4.429   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.620   5.772   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.844   7.102   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.609   8.439   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.149   8.445   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.924   7.114   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.160   5.778   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.236   2.381   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       8.475   1.465   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       5.362   2.347   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       5.925   3.780   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       4.966   4.985   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       7.448   4.009   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       5.801  -3.448   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       4.738  -2.543   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       3.833  -3.434   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       1.126  -2.972   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      -0.414  -2.964   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      -1.192  -4.293   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      -1.177  -1.626   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5   43                                                  
CONECT    5    4    6   42                                                  
CONECT    6    5    7   11   41                                             
CONECT    7    6    8   40                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   35                                                  
CONECT   10    9   11   34   36                                             
CONECT   11   10    6   12                                                  
CONECT   12   11   13   25                                                  
CONECT   13   12   14   17   24                                             
CONECT   14   13    3   15   16                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   13   18   23                                                  
CONECT   18   17    2   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   17                                                            
CONECT   24   13                                                            
CONECT   25   12   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   28                                                       
CONECT   34   10   35                                                       
CONECT   35   34    9                                                       
CONECT   36   10   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40    7                                                            
CONECT   41    6                                                            
CONECT   42    5                                                            
CONECT   43    4   44                                                       
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44                                                            
MASTER        0    0    0    0    0    0    0    0   46    0  100    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₄₂O₁₃

Average Mass

646.6860 Da

Monoisotopic Mass

646.26254 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=O)OC1C(O)C2(O)C(OC(=O)C3=CC=CC=C3)C3C4(COC4CC(O)C3(C)C(O)C(OC(C)=O)C(=C1C)C2(C)C)OC(C)=O

InChI Identifier

InChI=1S/C33H42O13/c1-15-22-24(44-17(3)35)26(38)31(7)20(37)13-21-32(14-42-21,46-18(4)36)25(31)28(45-29(40)19-11-9-8-10-12-19)33(41,30(22,5)6)27(39)23(15)43-16(2)34/h8-12,20-21,23-28,37-39,41H,13-14H2,1-7H3

InChI Key

SMMKFLQKTRZJCF-UHFFFAOYSA-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

Not Available

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
Tetracarboxylic acid or derivatives
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Benzenoid
Monocyclic benzene moiety
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Oxetane
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Dialkyl ether
Carboxylic acid derivative
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

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

137796403

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hai P, Wen SZ, Li Y, Gao Y, Jiang XJ, Wang F: New Taxane Diterpenoids from Taxus yunnanensis. Nat Prod Bioprospect. 2014 Feb;4(1):47-51. doi: 10.1007/s13659-014-0003-9. Epub 2014 Feb 19. [PubMed:24660136 ]

Showing NP-Card for Baccatin VIII (NP0139309)

MOL for NP0139309 (Baccatin VIII)

3D MOL for NP0139309 (Baccatin VIII)

3D SDF for NP0139309 (Baccatin VIII)

3D-SDF for NP0139309 (Baccatin VIII)

PDB for NP0139309 (Baccatin VIII)

3D PDB for NP0139309 (Baccatin VIII)

SMILES for NP0139309 (Baccatin VIII)

INCHI for NP0139309 (Baccatin VIII)

Structure for NP0139309 (Baccatin VIII)

3D Structure for NP0139309 (Baccatin VIII)