NP-MRD: Showing NP-Card for (+)-Taxusin (NP0074778)

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Record Information

Version

2.0

Created at

2022-04-28 20:06:15 UTC

Updated at

2025-05-21 20:00:32 UTC

NP-MRD ID

NP0074778

Natural Product DOI

https://doi.org/10.57994/4025

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Taxusin

Description

Taxusin 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. (+)-Taxusin is found in Taxus baccata , Taxus brevifolia , Taxus cuspidata , Taxus floridana, Taxus fuana, Taxus mairei , Taxus wallichiana and Taxus yunnanensis. (+)-Taxusin was first documented in 2008 (PMID: 19122848). Based on a literature review a small amount of articles have been published on taxusin (PMID: 33622251) (PMID: 30223770) (PMID: 26826823) (PMID: 19501040).

Structure

MOL 3D MOL SDF PDB SMILES InChI


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  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
  3 34  1  0  0  0  0
  3 35  1  0  0  0  0
  1 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0074778

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1CC[C@]2(C)[C@H](C[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/C28H40O8/c1-14-21-12-20-13-23(34-17(4)30)15(2)24(27(20,7)8)25(35-18(5)31)26(36-19(6)32)28(21,9)11-10-22(14)33-16(3)29/h20-23,25-26H,1,10-13H2,2-9H3/t20-,21-,22+,23+,25-,26+,28-/m1/s1

> <INCHI_KEY>
SKJSIVQEPKBFTJ-HUWILPJBSA-N

> <FORMULA>
C28H40O8

> <MOLECULAR_WEIGHT>
504.62

> <EXACT_MASS>
504.272318248

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
53.84553469740055

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
4.01

> <JCHEM_LOGP>
2.9282206003333346

> <ALOGPS_LOGS>
-5.66

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.412399127382139

> <JCHEM_POLAR_SURFACE_AREA>
105.20000000000002

> <JCHEM_REFRACTIVITY>
130.5179

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.11e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3R,5S,8R,9R,10R,13S)-5,9,10-tris(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                                 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      13.026   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  C   UNK     0       9.764   1.897   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.510   0.776   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      14.062   3.080   0.000  0.00  0.00           C+0
CONECT    1    2    6   36                                                  
CONECT    2    1    3   15                                                  
CONECT    3    2    4   34   35                                             
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                                                       
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    3                                                            
CONECT   35    3                                                            
CONECT   36    1                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Value	Source
(+)-Taxusin	ChEBI
Taxa-4(20),11-diene-5alpha,9alpha,10beta,13alpha-tetrayl tetraacetate	ChEBI
Taxa-4(20),11-diene-5a,9a,10b,13a-tetrayl tetraacetate	Generator
Taxa-4(20),11-diene-5a,9a,10b,13a-tetrayl tetraacetic acid	Generator
Taxa-4(20),11-diene-5alpha,9alpha,10beta,13alpha-tetrayl tetraacetic acid	Generator
Taxa-4(20),11-diene-5α,9α,10β,13α-tetrayl tetraacetate	Generator
Taxa-4(20),11-diene-5α,9α,10β,13α-tetrayl tetraacetic acid	Generator

Chemical Formula

C₂₈H₄₀O₈

Average Mass

504.6200 Da

Monoisotopic Mass

504.27232 Da

IUPAC Name

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

Traditional Name

(1R,3R,5S,8R,9R,10R,13S)-5,9,10-tris(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[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/C28H40O8/c1-14-21-12-20-13-23(34-17(4)30)15(2)24(27(20,7)8)25(35-18(5)31)26(36-19(6)32)28(21,9)11-10-22(14)33-16(3)29/h20-23,25-26H,1,10-13H2,2-9H3/t20-,21-,22+,23+,25-,26+,28-/m1/s1

InChI Key

SKJSIVQEPKBFTJ-HUWILPJBSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCl3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-10-21	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-10-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-10-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-10-21	View Spectrum
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-10-21	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-10-21	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-10-21	View Spectrum

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 baccata	Plant	KNApSAcK
Taxus brevifolia	Plant	KNApSAcK
Taxus cuspidata	Plant	KNApSAcK
Taxus floridana	Plant	KNApSAcK
Taxus fuana	Plant	KNApSAcK
Taxus mairei	Plant	KNApSAcK
Taxus wallichiana	Plant	KNApSAcK
Taxus wallichiana var. yunnanensis	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
Tetracarboxylic 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

acetate ester (CHEBI:63664 )
carbotricyclic compound (CHEBI:63664 )
taxane diterpenoid (CHEBI:63664 )

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	4.01	ALOGPS
logP	2.93	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Basic)	-6.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	105.2 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	130.52 m³·mol⁻¹	ChemAxon
Polarizability	53.85 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

C00036221

Chemspider ID

146810

KEGG Compound ID

C20152

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Taxusin

METLIN ID

Not Available

PubChem Compound

167825

PDB ID

Not Available

ChEBI ID

63664

Good Scents ID

Not Available

References

General References

Yu C, Zhang C, Xu X, Huang J, Chen Y, Luo X, Wang H, Shen C: Omic analysis of the endangered Taxaceae species Pseudotaxus chienii revealed the differences in taxol biosynthesis pathway between Pseudotaxus and Taxus yunnanensis trees. BMC Plant Biol. 2021 Feb 19;21(1):104. doi: 10.1186/s12870-021-02883-0. [PubMed:33622251 ]
Yu C, Luo X, Zhan X, Hao J, Zhang L, L Song YB, Shen C, Dong M: Comparative metabolomics reveals the metabolic variations between two endangered Taxus species (T. fuana and T. yunnanensis) in the Himalayas. BMC Plant Biol. 2018 Sep 17;18(1):197. doi: 10.1186/s12870-018-1412-4. [PubMed:30223770 ]
Asif M, Rizwani GH, Zahid H, Khan Z, Qasim R: Pharmacognostic studies on Taxus baccata L.: A brilliant source of Anti-cancer agents. Pak J Pharm Sci. 2016 Jan;29(1):105-9. [PubMed:26826823 ]
Hampel D, Mau CJ, Croteau RB: Taxol biosynthesis: Identification and characterization of two acetyl CoA:taxoid-O-acetyl transferases that divert pathway flux away from Taxol production. Arch Biochem Biophys. 2009 Jul 15;487(2):91-7. doi: 10.1016/j.abb.2009.05.018. Epub 2009 Jun 6. [PubMed:19501040 ]
Li H, Horiguchi T, Croteau R, Williams RM: Studies on Taxol Biosynthesis: Preparation of Taxadiene-diol- and triol-Derivatives by Deoxygenation of Taxusin. Tetrahedron. 2008;64(27):6561-6567. doi: 10.1016/j.tet.2008.04.008. [PubMed:19122848 ]

Showing NP-Card for (+)-Taxusin (NP0074778)

MOL for NP0074778 ((+)-Taxusin)

3D MOL for NP0074778 ((+)-Taxusin)

3D SDF for NP0074778 ((+)-Taxusin)

3D-SDF for NP0074778 ((+)-Taxusin)

PDB for NP0074778 ((+)-Taxusin)

3D PDB for NP0074778 ((+)-Taxusin)

SMILES for NP0074778 ((+)-Taxusin)

INCHI for NP0074778 ((+)-Taxusin)

Structure for NP0074778 ((+)-Taxusin)

3D Structure for NP0074778 ((+)-Taxusin)