NP-MRD: Showing NP-Card for 5a,13a-diacetoxy-taxadiene (NP0350849)

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Record Information

Version

2.0

Created at

2025-03-17 04:45:37 UTC

Updated at

2025-03-19 00:02:24 UTC

NP-MRD ID

NP0350849

Natural Product DOI

https://doi.org/10.57994/3834

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5a,13a-diacetoxy-taxadiene

Description

Based on a literature review very few articles have been published on 5a,13a-diacetoxy-taxadiene.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 06142304522D          

 30 32  0  0  1  0            999 V2000
    3.6521    2.5897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4344    2.3275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6505    1.6079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5036    1.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0585    1.2241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8015    2.6377    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6061    2.8203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1665    2.2148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9710    2.3973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9223    1.4268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1862    3.2336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8419    1.7534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3188    3.0700    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2959    3.8947    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4488    3.1846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7208    2.7250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5680    1.9143    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3202    1.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0601    1.2294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9152    1.1290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7812    3.5478    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0950    3.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3165    2.9895    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6907    3.5271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8434    4.3379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2177    4.8755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6219    4.6110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1638    2.1788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7896    1.6411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2477    4.0734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  6  4  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  6 11  1  0  0  0  0
  2 12  1  0  0  0  0
 13  2  1  0  0  0  0
 13 11  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 16 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
  3 20  1  0  0  0  0
 16 21  1  6  0  0  0
 16 22  1  0  0  0  0
 23 22  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  0  0  0  0
 17 29  1  0  0  0  0
 22 30  2  0  0  0  0
M  END


  Mrv2104 06142304522D          

 30 32  0  0  1  0            999 V2000
    3.6521    2.5897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4344    2.3275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6505    1.6079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5036    1.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0585    1.2241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8015    2.6377    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6061    2.8203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1665    2.2148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9710    2.3973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9223    1.4268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1862    3.2336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8419    1.7534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3188    3.0700    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2959    3.8947    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4488    3.1846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7208    2.7250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5680    1.9143    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3202    1.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0601    1.2294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9152    1.1290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7812    3.5478    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0950    3.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3165    2.9895    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6907    3.5271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8434    4.3379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2177    4.8755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6219    4.6110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1638    2.1788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7896    1.6411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2477    4.0734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  6  4  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  6 11  1  0  0  0  0
  2 12  1  0  0  0  0
 13  2  1  0  0  0  0
 13 11  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 16 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
  3 20  1  0  0  0  0
 16 21  1  6  0  0  0
 16 22  1  0  0  0  0
 23 22  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  0  0  0  0
 17 29  1  0  0  0  0
 22 30  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0350849

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12C[C@H](OC(C)=O)C(C)=C(CC[C@]3(C)CC[C@H](OC(C)=O)C(=C)[C@@]3([H])C1)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C24H36O4/c1-14-19-8-10-24(7)11-9-21(27-16(3)25)15(2)20(24)12-18(23(19,5)6)13-22(14)28-17(4)26/h18,20-22H,2,8-13H2,1,3-7H3/t18-,20-,21+,22+,24-/m1/s1

> <INCHI_KEY>
BZUPLNZFHUMLOU-VILWBRSESA-N

> <FORMULA>
C24H36O4

> <MOLECULAR_WEIGHT>
388.548

> <EXACT_MASS>
388.261359639

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
43.90536401515965

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
4.195776993666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.712832575159883

> <JCHEM_POLAR_SURFACE_AREA>
52.6

> <JCHEM_REFRACTIVITY>
109.4919

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3S,5S,8R,13S)-5-(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                                 14-JUN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-JUN-23         0                                  
HETATM    1  C   UNK     0       6.817   4.834   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.277   4.345   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.681   3.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.273   3.425   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.309   2.285   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.830   4.924   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      12.331   5.265   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      13.377   4.134   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.879   4.475   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      12.922   2.663   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.681   6.036   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.171   3.273   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.062   5.731   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0       8.019   7.270   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0       6.438   5.945   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.079   5.087   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.794   3.573   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.331   2.104   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.712   2.295   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.308   2.108   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0       5.192   6.623   0.000  0.00  0.00           H+0
HETATM   22  C   UNK     0       3.911   6.090   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.457   5.580   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.289   6.584   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.574   8.097   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.406   9.101   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.028   8.607   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.172   4.067   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.341   3.063   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.196   7.604   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12   13                                             
CONECT    3    2    4   20                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    6   13                                                       
CONECT   12    2                                                            
CONECT   13    2   11   14   15                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   21   22                                             
CONECT   17   16   18   19   29                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19    3                                                       
CONECT   21   16                                                            
CONECT   22   16   23   30                                                  
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   23   29                                                       
CONECT   29   28   17                                                       
CONECT   30   22                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₆O₄

Average Mass

388.5480 Da

Monoisotopic Mass

388.26136 Da

IUPAC Name

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

Traditional Name

(1R,3S,5S,8R,13S)-5-(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

[H][C@]12C[C@H](OC(C)=O)C(C)=C(CC[C@]3(C)CC[C@H](OC(C)=O)C(=C)[C@@]3([H])C1)C2(C)C

InChI Identifier

InChI=1S/C24H36O4/c1-14-19-8-10-24(7)11-9-21(27-16(3)25)15(2)20(24)12-18(23(19,5)6)13-22(14)28-17(4)26/h18,20-22H,2,8-13H2,1,3-7H3/t18-,20-,21+,22+,24-/m1/s1

InChI Key

BZUPLNZFHUMLOU-VILWBRSESA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2025-03-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCl3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2025-03-17	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2025-03-17	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2025-03-17	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2025-03-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2025-03-17	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Classification

Not classified

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	4.2	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	109.49 m³·mol⁻¹	ChemAxon
Polarizability	43.91 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

Not Available

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 5a,13a-diacetoxy-taxadiene (NP0350849)

MOL for NP0350849 (5a,13a-diacetoxy-taxadiene)

3D MOL for NP0350849 (5a,13a-diacetoxy-taxadiene)

3D SDF for NP0350849 (5a,13a-diacetoxy-taxadiene)

3D-SDF for NP0350849 (5a,13a-diacetoxy-taxadiene)

PDB for NP0350849 (5a,13a-diacetoxy-taxadiene)

3D PDB for NP0350849 (5a,13a-diacetoxy-taxadiene)

SMILES for NP0350849 (5a,13a-diacetoxy-taxadiene)

INCHI for NP0350849 (5a,13a-diacetoxy-taxadiene)

Structure for NP0350849 (5a,13a-diacetoxy-taxadiene)

3D Structure for NP0350849 (5a,13a-diacetoxy-taxadiene)