NP-MRD: Showing NP-Card for taxadiene (NP0332339)

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Record Information

Version

2.0

Created at

2024-01-05 04:00:52 UTC

Updated at

2024-09-03 04:18:51 UTC

NP-MRD ID

NP0332339

Natural Product DOI

https://doi.org/10.57994/1541

Secondary Accession Numbers

None

Natural Product Identification

Common Name

taxadiene

Description

Taxa-4,11-diene 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. Thus, taxa-4,11-diene is considered to be an isoprenoid. taxadiene was first documented in 2007 (PMID: 17309272). Based on a literature review very few articles have been published on taxa-4,11-diene (PMID: 30842758).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304272223562D          

 20 22  0  0  1  0            999 V2000
    4.6519    1.6363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4864    1.8691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7625    2.6681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1640    3.2651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3120    3.1086    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4169    2.3574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6025    2.4890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7426    1.8821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4462    3.2214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7263    2.7586    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5750    1.9476    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7970    1.6731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1703    2.2096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3216    3.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0996    3.2951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2509    4.1061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0733    1.2557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9232    1.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3283    1.1603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0517    1.2683    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
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  5  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
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  1  0  0  0
 15 16  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
  1 18  1  0  0  0  0
 11 19  1  1  0  0  0
  2 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332339

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C2CC[C@]3(C)CCC=C(C)[C@H]3C[C@H](CC1)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C20H32/c1-14-7-6-11-20(5)12-10-17-15(2)8-9-16(13-18(14)20)19(17,3)4/h7,16,18H,6,8-13H2,1-5H3/t16-,18+,20-/m0/s1

> <INCHI_KEY>
FRJSECSOXKQMOD-HQRMLTQVSA-N

> <FORMULA>
C20H32

> <MOLECULAR_WEIGHT>
272.476

> <EXACT_MASS>
272.25040103

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
34.06993445891196

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3S,8S)-4,8,12,15,15-pentamethyltricyclo[9.3.1.0^{3,8}]pentadeca-4,11-diene

> <ALOGPS_LOGP>
7.06

> <JCHEM_LOGP>
5.717214636666666

> <ALOGPS_LOGS>
-4.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
89.2304

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.32e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3S,8S)-4,8,12,15,15-pentamethyltricyclo[9.3.1.0^{3,8}]pentadeca-4,11-diene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 27-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-22         0                                  
HETATM    1  C   UNK     0       8.684   3.054   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.241   3.489   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.757   4.980   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.640   6.095   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.049   5.803   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.245   4.401   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.725   4.646   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.986   3.513   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.433   6.013   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.089   5.149   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.807   3.635   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.354   3.123   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.185   4.125   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.467   5.639   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.919   6.151   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.202   7.665   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.737   2.344   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.323   2.157   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.346   2.166   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.297   2.368   0.000  0.00  0.00           C+0
CONECT    1    2    6   18                                                  
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    1    7    8                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12   17   19                                             
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10   16                                                  
CONECT   16   15                                                            
CONECT   17   11   18                                                       
CONECT   18   17    1                                                       
CONECT   19   11                                                            
CONECT   20    2                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
Taxa-4(5),11(12)-diene	ChEBI
4(20),11(12)-Taxadiene	MeSH
Taxa-4(5),11(12)diene	MeSH
Taxadiene	MeSH

Chemical Formula

C₂₀H₃₂

Average Mass

272.4760 Da

Monoisotopic Mass

272.25040 Da

IUPAC Name

(1S,3S,8S)-4,8,12,15,15-pentamethyltricyclo[9.3.1.0^{3,8}]pentadeca-4,11-diene

Traditional Name

(1S,3S,8S)-4,8,12,15,15-pentamethyltricyclo[9.3.1.0^{3,8}]pentadeca-4,11-diene

CAS Registry Number

Not Available

SMILES

CC1=C2CC[C@]3(C)CCC=C(C)[C@H]3C[C@H](CC1)C2(C)C

InChI Identifier

InChI=1S/C20H32/c1-14-7-6-11-20(5)12-10-17-15(2)8-9-16(13-18(14)20)19(17,3)4/h7,16,18H,6,8-13H2,1-5H3/t16-,18+,20-/m0/s1

InChI Key

FRJSECSOXKQMOD-HQRMLTQVSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-27	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-27	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-26	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-26	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-05	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-05	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Branched unsaturated hydrocarbon
Polycyclic hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

diterpene (CHEBI:30037 )
Taxane and Abeotaxane diterpenoids (C11894 )
Taxanes (C11894 )
Taxane and Abeotaxane diterpenoids (LMPR0104390002 )

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	7.06	ALOGPS
logP	5.72	ChemAxon
logS	-4.9	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	89.23 m³·mol⁻¹	ChemAxon
Polarizability	34.07 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	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

C00000900

Chemspider ID

391697

KEGG Compound ID

C11894

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Taxadiene

METLIN ID

Not Available

PubChem Compound

443484

PDB ID

Not Available

ChEBI ID

30037

Good Scents ID

Not Available

References

General References

Abdallah II, Pramastya H, van Merkerk R, Sukrasno, Quax WJ: Metabolic Engineering of Bacillus subtilis Toward Taxadiene Biosynthesis as the First Committed Step for Taxol Production. Front Microbiol. 2019 Feb 20;10:218. doi: 10.3389/fmicb.2019.00218. eCollection 2019. [PubMed:30842758 ]
Gutta P, Tantillo DJ: A promiscuous proton in taxadiene biosynthesis? Org Lett. 2007 Mar 15;9(6):1069-71. doi: 10.1021/ol070007m. Epub 2007 Feb 20. [PubMed:17309272 ]

Showing NP-Card for taxadiene (NP0332339)

MOL for NP0332339 (taxadiene)

3D MOL for NP0332339 (taxadiene)

3D SDF for NP0332339 (taxadiene)

3D-SDF for NP0332339 (taxadiene)

PDB for NP0332339 (taxadiene)

3D PDB for NP0332339 (taxadiene)

SMILES for NP0332339 (taxadiene)

INCHI for NP0332339 (taxadiene)

Structure for NP0332339 (taxadiene)

3D Structure for NP0332339 (taxadiene)