NP-MRD: Showing NP-Card for 5-Deacetyltaxachitriene B (NP0077485)

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Record Information

Version

2.0

Created at

2022-04-28 22:37:47 UTC

Updated at

2022-04-28 22:37:47 UTC

NP-MRD ID

NP0077485

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-Deacetyltaxachitriene B

Description

5-Deacetyltaxachitriene 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. 5-Deacetyltaxachitriene B is found in Taxus chinensis and Taxus mairei. 5-Deacetyltaxachitriene B was first documented in 1996 (PMID: 17252502). Based on a literature review very few articles have been published on 5-Deacetyltaxachitriene B (PMID: 9834176).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292200372D          

 39 40  0  0  1  0            999 V2000
    2.3778   -0.2156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
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  1 39  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304292200372D          

 39 40  0  0  1  0            999 V2000
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    4.0443    2.0770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0886    2.1600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1975    3.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5330    1.4726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6950    2.4696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1942    3.2167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6558    2.5549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7355    0.3742    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  2  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  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
  1 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 12 19  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 11 22  1  6  0  0  0
  9 23  1  0  0  0  0
 23 24  1  0  0  0  0
  8 25  1  6  0  0  0
  6 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
  5 30  1  0  0  0  0
  4 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
  3 35  1  1  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
  1 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0077485

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1C[C@H]2[C@@H](O)\C=C(CO)\[C@@H](O)C[C@H](OC(C)=O)\C(C)=C(OC(C)=O)\[C@H](OC(C)=O)C(=C1C)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C28H40O11/c1-13-23(36-15(3)30)10-20-22(35)9-19(12-29)21(34)11-24(37-16(4)31)14(2)26(38-17(5)32)27(39-18(6)33)25(13)28(20,7)8/h9,20-24,27,29,34-35H,10-12H2,1-8H3/b19-9+,26-14-/t20-,21-,22-,23-,24-,27+/m0/s1

> <INCHI_KEY>
DEWSERBDPFVHMP-CCFPQACYSA-N

> <FORMULA>
C28H40O11

> <MOLECULAR_WEIGHT>
552.617

> <EXACT_MASS>
552.257062108

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
56.96917497449242

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,3E,5S,7S,8Z,10R,13S)-7,9,10-tris(acetyloxy)-2,5-dihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethylbicyclo[9.3.1]pentadeca-3,8,11-trien-13-yl acetate

> <ALOGPS_LOGP>
1.15

> <JCHEM_LOGP>
-0.6329715079999996

> <ALOGPS_LOGS>
-3.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.683678518958367

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.126208165411793

> <JCHEM_PKA_STRONGEST_BASIC>
-2.765836686313408

> <JCHEM_POLAR_SURFACE_AREA>
165.89000000000001

> <JCHEM_REFRACTIVITY>
139.6368

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.27e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3E,5S,7S,8Z,10R,13S)-7,9,10-tris(acetyloxy)-2,5-dihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethylbicyclo[9.3.1]pentadeca-3,8,11-trien-13-yl acetate

> <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       4.439  -0.402   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.978  -0.376   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.725   0.971   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.265   0.997   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.058  -0.323   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.598  -0.297   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.390  -1.617   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.643  -2.964   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.104  -2.990   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.357  -4.337   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.817  -4.363   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.024  -3.043   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.484  -3.069   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.692  -1.749   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.063  -2.060   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.004  -3.295   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.582  -3.228   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.263  -4.865   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.929  -1.062   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.128  -2.627   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.121  -0.134   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.231  -5.900   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.704  -1.670   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.930  -2.096   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      11.710  -4.245   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      12.031   0.594   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      13.611   1.020   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      14.273   2.475   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      14.907   0.111   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.825  -1.447   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       8.542   2.583   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       7.549   3.877   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       5.765   4.032   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       7.835   5.635   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       6.595   2.749   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       6.897   4.610   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       5.962   6.004   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       8.691   4.769   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       3.240   0.698   0.000  0.00  0.00           C+0
CONECT    1    2   14   39                                                  
CONECT    2    1    3   19                                                  
CONECT    3    2    4   35                                                  
CONECT    4    3    5   31                                                  
CONECT    5    4    6   30                                                  
CONECT    6    5    7   26                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   25                                                  
CONECT    9    8   10   23                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   22                                                  
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13    1   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   12    2   20   21                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   11                                                            
CONECT   23    9   24                                                       
CONECT   24   23                                                            
CONECT   25    8                                                            
CONECT   26    6   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30    5                                                            
CONECT   31    4   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35    3   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39    1                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₀O₁₁

Average Mass

552.6170 Da

Monoisotopic Mass

552.25706 Da

IUPAC Name

(1R,2S,3E,5S,7S,8Z,10R,13S)-7,9,10-tris(acetyloxy)-2,5-dihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethylbicyclo[9.3.1]pentadeca-3,8,11-trien-13-yl acetate

Traditional Name

(1R,2S,3E,5S,7S,8Z,10R,13S)-7,9,10-tris(acetyloxy)-2,5-dihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethylbicyclo[9.3.1]pentadeca-3,8,11-trien-13-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1C[C@H]2[C@@H](O)\C=C(CO)\[C@@H](O)C[C@H](OC(C)=O)\C(C)=C(OC(C)=O)\[C@H](OC(C)=O)C(=C1C)C2(C)C

InChI Identifier

InChI=1S/C28H40O11/c1-13-23(36-15(3)30)10-20-22(35)9-19(12-29)21(34)11-24(37-16(4)31)14(2)26(38-17(5)32)27(39-18(6)33)25(13)28(20,7)8/h9,20-24,27,29,34-35H,10-12H2,1-8H3/b19-9+,26-14-/t20-,21-,22-,23-,24-,27+/m0/s1

InChI Key

DEWSERBDPFVHMP-CCFPQACYSA-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 chinensis	Plant	KNApSAcK
Taxus mairei	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

3,8-seco-taxane diterpenoid
Tetracarboxylic acid or derivatives
Enol ester
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	1.15	ALOGPS
logP	-0.63	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	14.13	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	165.89 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	139.64 m³·mol⁻¹	ChemAxon
Polarizability	56.97 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00040838

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

101702748

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Shi QW, Oritani T, Sugiyama T, Kiyota H: Three novel bicyclic 3,8-secotaxane diterpenoids from the needles of the chinese yew, taxus chinensis var. mairei J Nat Prod. 1998 Nov;61(11):1437-40. doi: 10.1021/np980213q. [PubMed:9834176 ]
Fang WS, Fang QC, Liang XT: Bicyclic taxoids from needles of Taxus chinensis. Planta Med. 1996 Dec;62(6):567-9. doi: 10.1055/s-2006-957975. [PubMed:17252502 ]

Showing NP-Card for 5-Deacetyltaxachitriene B (NP0077485)

MOL for NP0077485 (5-Deacetyltaxachitriene B)

3D MOL for NP0077485 (5-Deacetyltaxachitriene B)

3D SDF for NP0077485 (5-Deacetyltaxachitriene B)

3D-SDF for NP0077485 (5-Deacetyltaxachitriene B)

PDB for NP0077485 (5-Deacetyltaxachitriene B)

3D PDB for NP0077485 (5-Deacetyltaxachitriene B)

SMILES for NP0077485 (5-Deacetyltaxachitriene B)

INCHI for NP0077485 (5-Deacetyltaxachitriene B)

Structure for NP0077485 (5-Deacetyltaxachitriene B)

3D Structure for NP0077485 (5-Deacetyltaxachitriene B)