NP-MRD: Showing NP-Card for 2alpha-Acetoxytaxusin (NP0078190)

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Record Information

Version

2.0

Created at

2022-04-28 23:18:39 UTC

Updated at

2022-04-28 23:18:39 UTC

NP-MRD ID

NP0078190

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2alpha-Acetoxytaxusin

Description

2Alpha-Acetoxytaxusin 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. 2alpha-Acetoxytaxusin is found in Taxus cuspidata . 2alpha-Acetoxytaxusin was first documented in 2004 (PMID: 14738387). Based on a literature review very few articles have been published on 2alpha-Acetoxytaxusin (PMID: 25924478).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292201182D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304292201182D          

 40 42  0  0  1  0            999 V2000
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    3.5697   -0.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7224   -1.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1655   -0.6531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3870   -0.3800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7612   -0.9177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2343    0.4307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7949    1.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7467   -1.1164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3561   -1.6725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1424   -1.4228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1792   -2.4783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2308    1.0162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0945    0.4155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5332    1.6499    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  1  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  4 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
 14 15  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 14 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 13 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 12 27  1  6  0  0  0
 27 28  2  0  0  0  0
 26 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 13 33  1  6  0  0  0
 11 34  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  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>
NP0078190

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1CC[C@]2(C)[C@H]([C@H](OC(C)=O)[C@@H]3C[C@H](OC(C)=O)C(C)=C([C@@H](OC(C)=O)[C@@H]2OC(C)=O)C3(C)C)C1=C

> <INCHI_IDENTIFIER>
InChI=1S/C30H42O10/c1-14-22(36-16(3)31)11-12-30(10)25(14)26(38-18(5)33)21-13-23(37-17(4)32)15(2)24(29(21,8)9)27(39-19(6)34)28(30)40-20(7)35/h21-23,25-28H,1,11-13H2,2-10H3/t21-,22-,23-,25-,26+,27+,28-,30+/m0/s1

> <INCHI_KEY>
CNWPSHAWQVTMLN-RQHYBHECSA-N

> <FORMULA>
C30H42O10

> <MOLECULAR_WEIGHT>
562.656

> <EXACT_MASS>
562.277797552

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
58.73780526162509

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,3R,5S,8R,9R,10R,13S)-2,5,9,10-tetrakis(acetyloxy)-8,12,15,15-tetramethyl-4-methylidenetricyclo[9.3.1.0^{3,8}]pentadec-11-en-13-yl acetate

> <ALOGPS_LOGP>
3.38

> <JCHEM_LOGP>
2.1385349436666674

> <ALOGPS_LOGS>
-5.14

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.313503910320797

> <JCHEM_POLAR_SURFACE_AREA>
131.50000000000003

> <JCHEM_REFRACTIVITY>
141.1849

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.07e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,3R,5S,8R,9R,10R,13S)-2,5,9,10-tetrakis(acetyloxy)-8,12,15,15-tetramethyl-4-methylidenetricyclo[9.3.1.0^{3,8}]pentadec-11-en-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      13.026   1.940   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.434   2.363   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.030   1.020   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.815  -0.366   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.434  -0.671   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.582   0.441   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      15.084   0.100   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      16.130   1.230   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      17.632   0.890   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      15.674   2.701   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.191  -0.580   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.832   0.278   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.547   1.791   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.465   3.070   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.061   3.257   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.413   4.757   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.290   5.811   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       7.816   5.365   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.641   7.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.683   4.397   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.144   4.383   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.385   3.043   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.362   5.710   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.093   2.301   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.925   1.298   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.210  -0.216   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.663  -0.725   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.949  -2.239   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.042  -1.219   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.589  -0.709   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.421  -1.713   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.304   0.804   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.084   3.260   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       8.860  -2.084   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       9.998  -3.122   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      11.466  -2.656   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       9.668  -4.626   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.764   1.897   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       9.510   0.776   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      14.062   3.080   0.000  0.00  0.00           C+0
CONECT    1    2    6   40                                                  
CONECT    2    1    3   15                                                  
CONECT    3    2    4   38   39                                             
CONECT    4    3    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    4   12   34                                                  
CONECT   12   11   13   27                                                  
CONECT   13   12   14   24   33                                             
CONECT   14   13   15   20                                                  
CONECT   15   14    2   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   14   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   13   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26   12   28                                                  
CONECT   28   27                                                            
CONECT   29   26   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   13                                                            
CONECT   34   11   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38    3                                                            
CONECT   39    3                                                            
CONECT   40    1                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   84    0
END

View in JSmol

Synonyms

Value	Source
2a-Acetoxytaxusin	Generator
2Α-acetoxytaxusin	Generator

Chemical Formula

C₃₀H₄₂O₁₀

Average Mass

562.6560 Da

Monoisotopic Mass

562.27780 Da

IUPAC Name

(1R,2R,3R,5S,8R,9R,10R,13S)-2,5,9,10-tetrakis(acetyloxy)-8,12,15,15-tetramethyl-4-methylidenetricyclo[9.3.1.0^{3,8}]pentadec-11-en-13-yl acetate

Traditional Name

(1R,2R,3R,5S,8R,9R,10R,13S)-2,5,9,10-tetrakis(acetyloxy)-8,12,15,15-tetramethyl-4-methylidenetricyclo[9.3.1.0^{3,8}]pentadec-11-en-13-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1CC[C@]2(C)[C@H]([C@H](OC(C)=O)[C@@H]3C[C@H](OC(C)=O)C(C)=C([C@@H](OC(C)=O)[C@@H]2OC(C)=O)C3(C)C)C1=C

InChI Identifier

InChI=1S/C30H42O10/c1-14-22(36-16(3)31)11-12-30(10)25(14)26(38-18(5)33)21-13-23(37-17(4)32)15(2)24(29(21,8)9)27(39-19(6)34)28(30)40-20(7)35/h21-23,25-28H,1,11-13H2,2-10H3/t21-,22-,23-,25-,26+,27+,28-,30+/m0/s1

InChI Key

CNWPSHAWQVTMLN-RQHYBHECSA-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 cuspidata	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
Pentacarboxylic acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	3.38	ALOGPS
logP	2.14	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	131.5 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	141.18 m³·mol⁻¹	ChemAxon
Polarizability	58.74 Å³	ChemAxon
Number of Rings	3	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

C00042087

Chemspider ID

10295453

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15227268

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bai XY, Lu JM, Zhou YY, Zhu ZR, Jiang RW, Zhang W: [Chemical constituents of Taxus chinensis var. mairei cell cultures]. Yao Xue Xue Bao. 2015 Jan;50(1):70-4. [PubMed:25924478 ]
Bai J, Kitabatake M, Toyoizumi K, Fu L, Zhang S, Dai J, Sakai J, Hirose K, Yamori T, Tomida A, Tsuruo T, Ando M: Production of biologically active taxoids by a callus culture of Taxus cuspidata. J Nat Prod. 2004 Jan;67(1):58-63. doi: 10.1021/np0301083. [PubMed:14738387 ]

Showing NP-Card for 2alpha-Acetoxytaxusin (NP0078190)

MOL for NP0078190 (2alpha-Acetoxytaxusin)

3D MOL for NP0078190 (2alpha-Acetoxytaxusin)

3D SDF for NP0078190 (2alpha-Acetoxytaxusin)

3D-SDF for NP0078190 (2alpha-Acetoxytaxusin)

PDB for NP0078190 (2alpha-Acetoxytaxusin)

3D PDB for NP0078190 (2alpha-Acetoxytaxusin)

SMILES for NP0078190 (2alpha-Acetoxytaxusin)

INCHI for NP0078190 (2alpha-Acetoxytaxusin)

Structure for NP0078190 (2alpha-Acetoxytaxusin)

3D Structure for NP0078190 (2alpha-Acetoxytaxusin)