NP-MRD: Showing NP-Card for (+)-Taxinine NN-7 (NP0075825)

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Record Information

Version

2.0

Created at

2022-04-28 21:03:09 UTC

Updated at

2022-04-28 21:03:09 UTC

NP-MRD ID

NP0075825

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Taxinine NN-7

Description

Taxinine NN-7 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. (+)-Taxinine NN-7 is found in Taxus cuspidata . (+)-Taxinine NN-7 was first documented in 2000 (PMID: 11014276). Based on a literature review very few articles have been published on taxinine NN-7.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282223032D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304282223032D          

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   -2.0397    2.3016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8841    3.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1047    3.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4808    2.8424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7950   -0.9133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1158   -1.5134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5229   -2.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3479   -2.2371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1050   -2.9423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5738   -1.7093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3627   -1.9507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9662   -1.3881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5481   -2.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0976    0.4251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2318   -0.1760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  6  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
 12 13  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  1  6  0  0  0
 12 15  1  1  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 11 19  1  0  0  0  0
 17 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 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  1  0  0  0
 10 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
  9 36  1  1  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
  5 40  1  0  0  0  0
  5 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0075825

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1[C@H](OC(C)=O)[C@]2(C)CC[C@H](OC(=O)\C=C\C3=CC=CC=C3)C(=C)[C@H]2[C@H](O)[C@@H]2CC(=O)C(C)=C1C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C33H40O8/c1-18-24(36)17-23-29(38)27-19(2)25(41-26(37)14-13-22-11-9-8-10-12-22)15-16-33(27,7)31(40-21(4)35)30(39-20(3)34)28(18)32(23,5)6/h8-14,23,25,27,29-31,38H,2,15-17H2,1,3-7H3/b14-13+/t23-,25-,27-,29+,30+,31-,33+/m0/s1

> <INCHI_KEY>
SPZFWGXRAFVTPQ-ZQXBODBKSA-N

> <FORMULA>
C33H40O8

> <MOLECULAR_WEIGHT>
564.675

> <EXACT_MASS>
564.272318248

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
60.17970589515558

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,3R,5S,8R,9R,10R)-9,10-bis(acetyloxy)-2-hydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0^{3,8}]pentadec-11-en-5-yl (2E)-3-phenylprop-2-enoate

> <ALOGPS_LOGP>
3.40

> <JCHEM_LOGP>
4.412577136333333

> <ALOGPS_LOGS>
-5.56

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.265889020161474

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.558013282087074

> <JCHEM_PKA_STRONGEST_BASIC>
-2.991930046575076

> <JCHEM_POLAR_SURFACE_AREA>
116.20000000000002

> <JCHEM_REFRACTIVITY>
152.47580000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.57e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,3R,5S,8R,9R,10R)-9,10-bis(acetyloxy)-2-hydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0^{3,8}]pentadec-11-en-5-yl (2E)-3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      13.589   1.114   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      15.092   1.449   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      12.444   2.230   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.824   1.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.035   0.544   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.434  -0.801   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.028  -0.383   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.060  -1.527   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.058  -1.690   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.463  -1.497   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.545  -0.235   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.835   1.277   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.201   2.150   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.869   3.654   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.671   2.285   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.961   3.797   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.216   1.780   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.925   0.268   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.090  -0.740   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.051   2.788   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.596   2.283   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.306   0.770   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.432   3.291   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.023   2.786   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.188   3.793   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.643   3.289   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.807   4.296   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.517   5.809   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.062   6.313   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.897   5.306   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.084  -1.705   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       7.683  -2.825   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       8.443  -4.164   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       9.983  -4.176   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       7.663  -5.492   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      10.404  -3.191   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      11.877  -3.641   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      13.003  -2.591   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      12.223  -5.142   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       9.516   0.794   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       9.766  -0.329   0.000  0.00  0.00           C+0
CONECT    1    2    3    7                                                  
CONECT    2    1                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6   40   41                                             
CONECT    6    5    7    9                                                  
CONECT    7    6    1    8                                                  
CONECT    8    7                                                            
CONECT    9    6   10   36                                                  
CONECT   10    9   11   32                                                  
CONECT   11   10   12   19   31                                             
CONECT   12   11   13   15                                                  
CONECT   13   12    4   14                                                  
CONECT   14   13                                                            
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18   11                                                       
CONECT   20   17   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   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                                                            
CONECT   32   10   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36    9   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40    5                                                            
CONECT   41    5                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₄₀O₈

Average Mass

564.6750 Da

Monoisotopic Mass

564.27232 Da

IUPAC Name

(1R,2R,3R,5S,8R,9R,10R)-9,10-bis(acetyloxy)-2-hydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0^{3,8}]pentadec-11-en-5-yl (2E)-3-phenylprop-2-enoate

Traditional Name

(1R,2R,3R,5S,8R,9R,10R)-9,10-bis(acetyloxy)-2-hydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0^{3,8}]pentadec-11-en-5-yl (2E)-3-phenylprop-2-enoate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1[C@H](OC(C)=O)[C@]2(C)CC[C@H](OC(=O)\C=C\C3=CC=CC=C3)C(=C)[C@H]2[C@H](O)[C@@H]2CC(=O)C(C)=C1C2(C)C

InChI Identifier

InChI=1S/C33H40O8/c1-18-24(36)17-23-29(38)27-19(2)25(41-26(37)14-13-22-11-9-8-10-12-22)15-16-33(27,7)31(40-21(4)35)30(39-20(3)34)28(18)32(23,5)6/h8-14,23,25,27,29-31,38H,2,15-17H2,1,3-7H3/b14-13+/t23-,25-,27-,29+,30+,31-,33+/m0/s1

InChI Key

SPZFWGXRAFVTPQ-ZQXBODBKSA-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
Cinnamic acid or derivatives
Cinnamic acid ester
Tricarboxylic acid or derivatives
Styrene
Cyclohexenone
Fatty acid ester
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Cyclic ketone
Carboxylic acid ester
Ketone
Secondary alcohol
Carboxylic acid derivative
Alcohol
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Carbonyl group
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic 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	3.4	ALOGPS
logP	4.41	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	14.56	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	116.2 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	152.48 m³·mol⁻¹	ChemAxon
Polarizability	60.18 Å³	ChemAxon
Number of Rings	4	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

C00037889

Chemspider ID

8873529

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10698187

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kosugi K, Sakai J, Zhang S, Watanabe Y, Sasaki H, Suzuki T, Hagiwara H, Hirata N, Hirose K, Ando M, Tomida A, Tsuruo T: Neutral taxoids from Taxus cuspidata as modulators of multidrug-resistant tumor cells. Phytochemistry. 2000 Aug;54(8):839-45. doi: 10.1016/s0031-9422(00)00108-4. [PubMed:11014276 ]

Showing NP-Card for (+)-Taxinine NN-7 (NP0075825)

MOL for NP0075825 ((+)-Taxinine NN-7)

3D MOL for NP0075825 ((+)-Taxinine NN-7)

3D SDF for NP0075825 ((+)-Taxinine NN-7)

3D-SDF for NP0075825 ((+)-Taxinine NN-7)

PDB for NP0075825 ((+)-Taxinine NN-7)

3D PDB for NP0075825 ((+)-Taxinine NN-7)

SMILES for NP0075825 ((+)-Taxinine NN-7)

INCHI for NP0075825 ((+)-Taxinine NN-7)

Structure for NP0075825 ((+)-Taxinine NN-7)

3D Structure for NP0075825 ((+)-Taxinine NN-7)