NP-MRD: Showing NP-Card for 19-Hydroxy-10-deacetylbaccatin III (NP0078177)

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Record Information

Version

2.0

Created at

2022-04-28 23:18:05 UTC

Updated at

2022-04-28 23:18:05 UTC

NP-MRD ID

NP0078177

Secondary Accession Numbers

None

Natural Product Identification

Common Name

19-Hydroxy-10-deacetylbaccatin III

Description

CHEMBL501666 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. 19-Hydroxy-10-deacetylbaccatin III is found in Taxus sumatrana . Based on a literature review very few articles have been published on CHEMBL501666.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292201182D          

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M  END

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M  END


  Mrv1652304292201182D          

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    4.5604   -2.3753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1439   -1.6631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5525   -0.9463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3757    0.2739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1574    1.8462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4662    2.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8528    2.2994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  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
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  4  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  2  0  0  0  0
 11 13  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  6  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  9 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 17 20  1  6  0  0  0
 18 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 15 25  1  6  0  0  0
 10 26  1  6  0  0  0
 26 27  1  0  0  0  0
  8 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 31 36  1  0  0  0  0
  4 37  1  6  0  0  0
  3 38  1  0  0  0  0
  3 39  1  0  0  0  0
  1 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0078177

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@]12CO[C@@H]1C[C@H](O)[C@]1(CO)[C@@H]2[C@H](OC(=O)C2=CC=CC=C2)[C@]2(O)C[C@H](O)C(C)=C([C@@H](O)C1=O)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C29H36O11/c1-14-17(32)11-29(37)24(39-25(36)16-8-6-5-7-9-16)22-27(12-30,23(35)21(34)20(14)26(29,3)4)18(33)10-19-28(22,13-38-19)40-15(2)31/h5-9,17-19,21-22,24,30,32-34,37H,10-13H2,1-4H3/t17-,18-,19+,21+,22-,24-,27+,28-,29+/m0/s1

> <INCHI_KEY>
LCBRTOBUIDCSID-ZHPRIASZSA-N

> <FORMULA>
C29H36O11

> <MOLECULAR_WEIGHT>
560.596

> <EXACT_MASS>
560.225761979

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
55.40179631894526

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.17

> <JCHEM_LOGP>
-0.679167619

> <ALOGPS_LOGS>
-2.82

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.516747399220861

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.22131433779745

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8635117049438836

> <JCHEM_POLAR_SURFACE_AREA>
180.04999999999998

> <JCHEM_REFRACTIVITY>
137.9718

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.41e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      15.197   3.512   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.803   4.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.018   3.227   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.400   1.968   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.855   1.195   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.282   1.915   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      16.615   1.143   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      10.786   2.247   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.744   3.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.922   5.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.179   5.948   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      10.827   7.447   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      12.758   5.652   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      13.540   6.979   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.686   5.919   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.272   5.308   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.094   3.779   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.330   2.860   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.411   1.624   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.175   2.543   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       9.286   1.652   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.718   0.221   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       9.673  -0.987   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       7.194  -0.003   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.864   7.449   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       9.917   6.540   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      10.539   7.949   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      10.023   0.909   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      10.801  -0.420   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      12.341  -0.412   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      10.038  -1.758   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.815  -3.087   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.053  -4.425   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.513  -4.434   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.735  -3.104   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.498  -1.766   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      11.901   0.511   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      11.494   3.446   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      12.070   4.441   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      16.525   4.292   0.000  0.00  0.00           C+0
CONECT    1    2    6   40                                                  
CONECT    2    1    3   13                                                  
CONECT    3    2    4   38   39                                             
CONECT    4    3    5    8   37                                             
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    4    9   28                                                  
CONECT    9    8   10   18                                                  
CONECT   10    9   11   15   26                                             
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    2   14                                                  
CONECT   14   13                                                            
CONECT   15   10   16   25                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17    9   19   21                                             
CONECT   19   18   20                                                       
CONECT   20   19   17                                                       
CONECT   21   18   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   15                                                            
CONECT   26   10   27                                                       
CONECT   27   26                                                            
CONECT   28    8   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   31                                                       
CONECT   37    4                                                            
CONECT   38    3                                                            
CONECT   39    3                                                            
CONECT   40    1                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₆O₁₁

Average Mass

560.5960 Da

Monoisotopic Mass

560.22576 Da

IUPAC Name

(1S,2S,3R,4S,7R,9S,10R,12R,15S)-4-(acetyloxy)-1,9,12,15-tetrahydroxy-10-(hydroxymethyl)-14,17,17-trimethyl-11-oxo-6-oxatetracyclo[11.3.1.0^{3,10}.0^{4,7}]heptadec-13-en-2-yl benzoate

Traditional Name

(1S,2S,3R,4S,7R,9S,10R,12R,15S)-4-(acetyloxy)-1,9,12,15-tetrahydroxy-10-(hydroxymethyl)-14,17,17-trimethyl-11-oxo-6-oxatetracyclo[11.3.1.0^{3,10}.0^{4,7}]heptadec-13-en-2-yl benzoate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@]12CO[C@@H]1C[C@H](O)[C@]1(CO)[C@@H]2[C@H](OC(=O)C2=CC=CC=C2)[C@]2(O)C[C@H](O)C(C)=C([C@@H](O)C1=O)C2(C)C

InChI Identifier

InChI=1S/C29H36O11/c1-14-17(32)11-29(37)24(39-25(36)16-8-6-5-7-9-16)22-27(12-30,23(35)21(34)20(14)26(29,3)4)18(33)10-19-28(22,13-38-19)40-15(2)31/h5-9,17-19,21-22,24,30,32-34,37H,10-13H2,1-4H3/t17-,18-,19+,21+,22-,24-,27+,28-,29+/m0/s1

InChI Key

LCBRTOBUIDCSID-ZHPRIASZSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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 sumatrana	Plant	KNApSAcK

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
Benzoyl
Monocyclic benzene moiety
Benzenoid
Dicarboxylic acid or derivatives
Cyclic alcohol
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Ketone
Oxetane
Ether
Dialkyl ether
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Polyol
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Primary 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	0.17	ALOGPS
logP	-0.68	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	9.22	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	180.05 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	137.97 m³·mol⁻¹	ChemAxon
Polarizability	55.4 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

8546011

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10370566

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 19-Hydroxy-10-deacetylbaccatin III (NP0078177)

MOL for NP0078177 (19-Hydroxy-10-deacetylbaccatin III)

3D MOL for NP0078177 (19-Hydroxy-10-deacetylbaccatin III)

3D SDF for NP0078177 (19-Hydroxy-10-deacetylbaccatin III)

3D-SDF for NP0078177 (19-Hydroxy-10-deacetylbaccatin III)

PDB for NP0078177 (19-Hydroxy-10-deacetylbaccatin III)

3D PDB for NP0078177 (19-Hydroxy-10-deacetylbaccatin III)

SMILES for NP0078177 (19-Hydroxy-10-deacetylbaccatin III)

INCHI for NP0078177 (19-Hydroxy-10-deacetylbaccatin III)

Structure for NP0078177 (19-Hydroxy-10-deacetylbaccatin III)

3D Structure for NP0078177 (19-Hydroxy-10-deacetylbaccatin III)