NP-MRD: Showing NP-Card for Baccatin III (NP0137197)

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Record Information

Version

2.0

Created at

2022-05-30 16:44:46 UTC

Updated at

2022-05-30 16:44:46 UTC

NP-MRD ID

NP0137197

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Baccatin III

Description

4,12-Bis(acetyloxy)-1,9,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0³,¹⁰.0⁴,⁷]Heptadec-13-en-2-yl benzoate 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 III is found in Taxus wallichiana. 4,12-Bis(acetyloxy)-1,9,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0³,¹⁰.0⁴,⁷]Heptadec-13-en-2-yl benzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241518392D          

 42 46  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004241518392D          

 42 46  0  0  0  0            999 V2000
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    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
    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  2  0  0  0  0
  5  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
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  3 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  0  0  0  0
 14 21  1  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 25 30  1  0  0  0  0
 11 31  1  0  0  0  0
 31 32  1  0  0  0  0
 10 32  1  0  0  0  0
 11 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
  8 37  1  0  0  0  0
  7 38  1  0  0  0  0
  4 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137197

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1C2=C(C)C(O)CC(O)(C(OC(=O)C3=CC=CC=C3)C3C4(COC4CC(O)C3(C)C1=O)OC(C)=O)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C31H38O11/c1-15-19(34)13-31(38)26(41-27(37)18-10-8-7-9-11-18)24-29(6,20(35)12-21-30(24,14-39-21)42-17(3)33)25(36)23(40-16(2)32)22(15)28(31,4)5/h7-11,19-21,23-24,26,34-35,38H,12-14H2,1-6H3

> <INCHI_KEY>
OVMSOCFBDVBLFW-UHFFFAOYSA-N

> <FORMULA>
C31H38O11

> <MOLECULAR_WEIGHT>
586.634

> <EXACT_MASS>
586.241412044

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
58.76977759041993

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,12-bis(acetyloxy)-1,9,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0³,¹⁰.0⁴,⁷]heptadec-13-en-2-yl benzoate

> <ALOGPS_LOGP>
1.44

> <JCHEM_LOGP>
1.0427289479999988

> <ALOGPS_LOGS>
-3.47

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.27542480660236

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.66147122764083

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0198546313290917

> <JCHEM_POLAR_SURFACE_AREA>
165.89

> <JCHEM_REFRACTIVITY>
145.3486

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.98e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,12-bis(acetyloxy)-1,9,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0³,¹⁰.0⁴,⁷]heptadec-13-en-2-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         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  O   UNK     0       3.833  -3.434   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.736  -1.003   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.974  -1.918   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.386  -1.303   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.560   0.227   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.321   1.142   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.909   0.527   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.866   1.768   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.251   2.042   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.636   0.781   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.161   0.566   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.588  -0.430   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.793   2.810   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.632   2.086   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.967   2.854   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.745   3.500   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.630   3.104   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.855   4.435   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.315   4.429   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.620   5.772   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.844   7.102   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.609   8.439   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.149   8.445   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.924   7.114   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.160   5.778   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.236   2.381   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       8.475   1.465   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       5.362   2.347   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       5.925   3.780   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       4.966   4.985   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       7.448   4.009   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       5.801  -3.448   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       4.738  -2.543   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       1.126  -2.972   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -0.414  -2.964   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -1.192  -4.293   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -1.177  -1.626   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4   15                                                  
CONECT    4    3    5   39                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   12   38                                             
CONECT    8    7    9   37                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   32                                                  
CONECT   11   10   12   31   33                                             
CONECT   12   11    7   13                                                  
CONECT   13   12   14   22                                                  
CONECT   14   13   15   18   21                                             
CONECT   15   14    3   16   17                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   14   19                                                       
CONECT   19   18    2   20                                                  
CONECT   20   19                                                            
CONECT   21   14                                                            
CONECT   22   13   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   25                                                       
CONECT   31   11   32                                                       
CONECT   32   31   10                                                       
CONECT   33   11   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37    8                                                            
CONECT   38    7                                                            
CONECT   39    4   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   92    0
END

View in JSmol

Synonyms

Value	Source
4,12-Bis(acetyloxy)-1,9,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0,.0,]heptadec-13-en-2-yl benzoic acid	Generator

Chemical Formula

C₃₁H₃₈O₁₁

Average Mass

586.6340 Da

Monoisotopic Mass

586.24141 Da

IUPAC Name

4,12-bis(acetyloxy)-1,9,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0³,¹⁰.0⁴,⁷]heptadec-13-en-2-yl benzoate

Traditional Name

4,12-bis(acetyloxy)-1,9,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0³,¹⁰.0⁴,⁷]heptadec-13-en-2-yl benzoate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1C2=C(C)C(O)CC(O)(C(OC(=O)C3=CC=CC=C3)C3C4(COC4CC(O)C3(C)C1=O)OC(C)=O)C2(C)C

InChI Identifier

InChI=1S/C31H38O11/c1-15-19(34)13-31(38)26(41-27(37)18-10-8-7-9-11-18)24-29(6,20(35)12-21-30(24,14-39-21)42-17(3)33)25(36)23(40-16(2)32)22(15)28(31,4)5/h7-11,19-21,23-24,26,34-35,38H,12-14H2,1-6H3

InChI Key

OVMSOCFBDVBLFW-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

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
Benzoate ester
Benzoic acid or derivatives
Tricarboxylic acid or derivatives
Benzoyl
Alpha-acyloxy ketone
Monocyclic benzene moiety
Benzenoid
Cyclic alcohol
Tertiary alcohol
Carboxylic acid ester
Ketone
Oxetane
Secondary alcohol
Carboxylic acid derivative
Ether
Organoheterocyclic compound
Oxacycle
Polyol
Dialkyl ether
Alcohol
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a small molecule (BACCATIN-III )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.44	ALOGPS
logP	1.04	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	9.66	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	165.89 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	145.35 m³·mol⁻¹	ChemAxon
Polarizability	58.77 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

4357887

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Baccatin III (NP0137197)

MOL for NP0137197 (Baccatin III)

3D MOL for NP0137197 (Baccatin III)

3D SDF for NP0137197 (Baccatin III)

3D-SDF for NP0137197 (Baccatin III)

PDB for NP0137197 (Baccatin III)

3D PDB for NP0137197 (Baccatin III)

SMILES for NP0137197 (Baccatin III)

INCHI for NP0137197 (Baccatin III)

Structure for NP0137197 (Baccatin III)

3D Structure for NP0137197 (Baccatin III)