NP-MRD: Showing NP-Card for Taxumairol B (NP0139333)

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Record Information

Version

2.0

Created at

2022-06-29 19:49:41 UTC

Updated at

2022-06-29 19:49:41 UTC

NP-MRD ID

NP0139333

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Taxumairol B

Description

Taxumairol B 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. Taxumairol B is found in Taxus mairei and Taxus wallichiana. Based on a literature review very few articles have been published on Taxumairol B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306292221492D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306292221492D          

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    3.9215    0.8323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7400   -0.1025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3366   -0.6723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1284   -0.4406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414   -1.4739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7660   -2.1690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2621   -1.6162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7209   -2.0287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3134   -1.6009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6285   -2.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4464   -2.4717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1258   -3.0175    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
 11 10  1  6  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  1  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 13 23  1  6  0  0  0
 12 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 10 28  1  0  0  0  0
 28 29  1  0  0  0  0
 10 29  1  6  0  0  0
  9 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
  7 34  1  6  0  0  0
  6 35  1  6  0  0  0
  5 36  1  1  0  0  0
  4 37  1  6  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0139333

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1C[C@@]2(O)[C@@H](OC(C)=O)[C@@H]3[C@@]4(CO4)[C@H](C[C@H](O)[C@@]3(C)[C@@H](O)[C@H](OC(C)=O)C(=C1C)C2(C)C)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H40O12/c1-12-17(37-13(2)29)10-28(35)24(40-16(5)32)22-26(8,18(33)9-19(38-14(3)30)27(22)11-36-27)23(34)21(39-15(4)31)20(12)25(28,6)7/h17-19,21-24,33-35H,9-11H2,1-8H3/t17-,18-,19-,21+,22-,23-,24-,26+,27+,28+/m0/s1

> <INCHI_KEY>
WJMBBODKITXTJA-HIRGMTDPSA-N

> <FORMULA>
C28H40O12

> <MOLECULAR_WEIGHT>
568.616

> <EXACT_MASS>
568.251976728

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
57.061597707861594

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1'S,2R,2'S,3'R,5'S,7'S,8'S,9'R,10'R,13'S)-2',5',10'-tris(acetyloxy)-1',7',9'-trihydroxy-8',12',15',15'-tetramethylspiro[oxirane-2,4'-tricyclo[9.3.1.0^{3,8}]pentadecan]-11'-en-13'-yl acetate

> <ALOGPS_LOGP>
0.77

> <JCHEM_LOGP>
-1.337685472

> <ALOGPS_LOGS>
-2.82

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.698660253794916

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.078868731625754

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0093324112093836

> <JCHEM_POLAR_SURFACE_AREA>
178.42

> <JCHEM_REFRACTIVITY>
134.52119999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.71e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,2R,2'S,3'R,5'S,7'S,8'S,9'R,10'R,13'S)-2',5',10'-tris(acetyloxy)-1',7',9'-trihydroxy-8',12',15',15'-tetramethylspiro[oxirane-2,4'-tricyclo[9.3.1.0^{3,8}]pentadecan]-11'-en-13'-yl acetate

> <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      -2.048   0.044   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.635   0.655   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.642  -0.387   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.523  -1.767   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.055  -2.255   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.414  -1.489   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.528  -2.553   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.006  -2.120   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.370  -0.624   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.256   0.440   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.778   0.007   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.899   1.369   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.331   1.844   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.563   0.670   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.049   0.266   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.355  -0.650   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.982   2.790   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.523   2.250   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.751   3.180   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -3.170   2.582   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.397   3.512   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -3.361   1.054   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.005   3.229   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.826   2.599   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.224   4.017   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.695   4.204   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.151   5.247   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.824   1.918   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       7.320   1.554   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       8.848  -0.191   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       9.962  -1.255   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      11.440  -0.822   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       9.597  -2.751   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.163  -4.049   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       4.223  -3.017   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       3.212  -3.787   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       0.585  -2.988   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       1.173  -4.412   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       2.700  -4.614   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       0.235  -5.633   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   37                                                  
CONECT    5    4    6   36                                                  
CONECT    6    5    7   11   35                                             
CONECT    7    6    8   34                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   30                                                  
CONECT   10    9   11   28   29                                             
CONECT   11   10    6   12                                                  
CONECT   12   11   13   24                                                  
CONECT   13   12   14   17   23                                             
CONECT   14   13    3   15   16                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   13   18                                                       
CONECT   18   17    2   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   13                                                            
CONECT   24   12   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   10   29                                                       
CONECT   29   28   10                                                       
CONECT   30    9   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34    7                                                            
CONECT   35    6                                                            
CONECT   36    5                                                            
CONECT   37    4   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

View in JSmol

Synonyms

Value	Source
2,5,10,13-Tetraacetoxy-1,7,9-trihydroxy-4,20-epoxytax-11-ene	MeSH

Chemical Formula

C₂₈H₄₀O₁₂

Average Mass

568.6160 Da

Monoisotopic Mass

568.25198 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1C[C@@]2(O)[C@@H](OC(C)=O)[C@@H]3[C@@]4(CO4)[C@H](C[C@H](O)[C@@]3(C)[C@@H](O)[C@H](OC(C)=O)C(=C1C)C2(C)C)OC(C)=O

InChI Identifier

InChI=1S/C28H40O12/c1-12-17(37-13(2)29)10-28(35)24(40-16(5)32)22-26(8,18(33)9-19(38-14(3)30)27(22)11-36-27)23(34)21(39-15(4)31)20(12)25(28,6)7/h17-19,21-24,33-35H,9-11H2,1-8H3/t17-,18-,19-,21+,22-,23-,24-,26+,27+,28+/m0/s1

InChI Key

WJMBBODKITXTJA-HIRGMTDPSA-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 mairei	LOTUS Database	35616633
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
Tetracarboxylic acid or derivatives
Cyclic alcohol
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Polyol
Oxacycle
Organoheterocyclic compound
Carbonyl group
Alcohol
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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

8229269

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10053709

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Taxumairol B (NP0139333)

MOL for NP0139333 (Taxumairol B)

3D MOL for NP0139333 (Taxumairol B)

3D SDF for NP0139333 (Taxumairol B)

3D-SDF for NP0139333 (Taxumairol B)

PDB for NP0139333 (Taxumairol B)

3D PDB for NP0139333 (Taxumairol B)

SMILES for NP0139333 (Taxumairol B)

INCHI for NP0139333 (Taxumairol B)

Structure for NP0139333 (Taxumairol B)

3D Structure for NP0139333 (Taxumairol B)