NP-MRD: Showing NP-Card for (1r,2r,5s,8r,10s,11r,12s)-2,9-bis(acetyloxy)-5,11-dihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-13-oxotricyclo[9.3.1.0³,⁸]pentadec-3-en-10-yl acetate (NP0158894)

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Record Information

Version

2.0

Created at

2022-09-02 16:33:30 UTC

Updated at

2022-09-02 16:33:30 UTC

NP-MRD ID

NP0158894

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,5s,8r,10s,11r,12s)-2,9-bis(acetyloxy)-5,11-dihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-13-oxotricyclo[9.3.1.0³,⁸]pentadec-3-en-10-yl acetate

Description

(1R,2R,5S,8R,10S,11R,12S)-2,9-bis(acetyloxy)-5,11-dihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-13-oxotricyclo[9.3.1.0³,⁸]Pentadec-3-en-10-yl acetate 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. (1r,2r,5s,8r,10s,11r,12s)-2,9-bis(acetyloxy)-5,11-dihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-13-oxotricyclo[9.3.1.0³,⁸]pentadec-3-en-10-yl acetate is found in Taxus cuspidata. Based on a literature review very few articles have been published on (1R,2R,5S,8R,10S,11R,12S)-2,9-bis(acetyloxy)-5,11-dihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-13-oxotricyclo[9.3.1.0³,⁸]Pentadec-3-en-10-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022218332D          

 36 38  0  0  1  0            999 V2000
    4.4184    3.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309022218332D          

 36 38  0  0  1  0            999 V2000
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    4.7327    1.4679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6441    0.2709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4585    0.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3184    0.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  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
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 19 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 24 32  1  0  0  0  0
  5 32  1  0  0  0  0
 32 33  1  1  0  0  0
 18 34  1  0  0  0  0
 11 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0158894

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C(=O)C[C@H]2[C@@H](OC(C)=O)C3=C(CO)[C@@H](O)CC[C@@]3(C)C(OC(C)=O)[C@H](OC(C)=O)[C@]1(O)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C26H38O10/c1-12-19(32)10-17-21(34-13(2)28)20-16(11-27)18(31)8-9-25(20,7)22(35-14(3)29)23(36-15(4)30)26(12,33)24(17,5)6/h12,17-18,21-23,27,31,33H,8-11H2,1-7H3/t12-,17+,18+,21-,22?,23+,25-,26+/m1/s1

> <INCHI_KEY>
ZMMCRUZQJGEEQT-XEPMOVRHSA-N

> <FORMULA>
C26H38O10

> <MOLECULAR_WEIGHT>
510.58

> <EXACT_MASS>
510.246497424

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
51.77481209349882

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.01

> <JCHEM_LOGP>
-0.13881181400000056

> <ALOGPS_LOGS>
-2.94

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.425831551171303

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.011077495201313

> <JCHEM_PKA_STRONGEST_BASIC>
-2.773341892904255

> <JCHEM_POLAR_SURFACE_AREA>
156.66

> <JCHEM_REFRACTIVITY>
125.174

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.90e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       8.248   6.556   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.466   5.229   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.926   5.242   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       8.225   3.889   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.444   2.562   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.857   2.749   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.502   4.248   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.026   4.689   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.671   6.188   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.906   3.632   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.497   1.852   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.858   3.253   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.939   1.417   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.884   2.539   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.424  -0.074   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.923  -0.421   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.541  -1.189   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.132  -0.897   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.748  -1.107   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.085  -2.610   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.952  -3.653   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.290  -5.156   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.483  -3.194   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.091  -0.243   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.261  -1.245   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.979  -2.759   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      10.149  -3.760   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      10.714  -0.732   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      11.883  -1.734   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      10.996   0.781   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.826   1.783   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.374   1.271   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.834   2.740   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.936   0.506   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.456   0.260   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.194   1.393   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   32                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    6   12   13   34                                             
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   34                                                  
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   19   25   32                                                  
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   24    5   33                                             
CONECT   33   32                                                            
CONECT   34   18   11   35   36                                             
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Value	Source
(1R,2R,5S,8R,10S,11R,12S)-2,9-Bis(acetyloxy)-5,11-dihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-13-oxotricyclo[9.3.1.0,]pentadec-3-en-10-yl acetic acid	Generator

Chemical Formula

C₂₆H₃₈O₁₀

Average Mass

510.5800 Da

Monoisotopic Mass

510.24650 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@@H]1C(=O)C[C@H]2[C@@H](OC(C)=O)C3=C(CO)[C@@H](O)CC[C@@]3(C)C(OC(C)=O)[C@H](OC(C)=O)[C@]1(O)C2(C)C

InChI Identifier

InChI=1S/C26H38O10/c1-12-19(32)10-17-21(34-13(2)28)20-16(11-27)18(31)8-9-25(20,7)22(35-14(3)29)23(36-15(4)30)26(12,33)24(17,5)6/h12,17-18,21-23,27,31,33H,8-11H2,1-7H3/t12-,17+,18+,21-,22?,23+,25-,26+/m1/s1

InChI Key

ZMMCRUZQJGEEQT-XEPMOVRHSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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	LOTUS Database	35616633

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
Tricarboxylic acid or derivatives
Tertiary alcohol
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
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	1.01	ALOGPS
logS	-2.9	ALOGPS

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

4479358

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5321686

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2r,5s,8r,10s,11r,12s)-2,9-bis(acetyloxy)-5,11-dihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-13-oxotricyclo[9.3.1.0³,⁸]pentadec-3-en-10-yl acetate (NP0158894)

MOL for NP0158894 ((1r,2r,5s,8r,10s,11r,12s)-2,9-bis(acetyloxy)-5,11-dihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-13-oxotricyclo[9.3.1.0³,⁸]pentadec-3-en-10-yl acetate)

3D MOL for NP0158894 ((1r,2r,5s,8r,10s,11r,12s)-2,9-bis(acetyloxy)-5,11-dihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-13-oxotricyclo[9.3.1.0³,⁸]pentadec-3-en-10-yl acetate)

3D SDF for NP0158894 ((1r,2r,5s,8r,10s,11r,12s)-2,9-bis(acetyloxy)-5,11-dihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-13-oxotricyclo[9.3.1.0³,⁸]pentadec-3-en-10-yl acetate)

3D-SDF for NP0158894 ((1r,2r,5s,8r,10s,11r,12s)-2,9-bis(acetyloxy)-5,11-dihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-13-oxotricyclo[9.3.1.0³,⁸]pentadec-3-en-10-yl acetate)

PDB for NP0158894 ((1r,2r,5s,8r,10s,11r,12s)-2,9-bis(acetyloxy)-5,11-dihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-13-oxotricyclo[9.3.1.0³,⁸]pentadec-3-en-10-yl acetate)

3D PDB for NP0158894 ((1r,2r,5s,8r,10s,11r,12s)-2,9-bis(acetyloxy)-5,11-dihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-13-oxotricyclo[9.3.1.0³,⁸]pentadec-3-en-10-yl acetate)

SMILES for NP0158894 ((1r,2r,5s,8r,10s,11r,12s)-2,9-bis(acetyloxy)-5,11-dihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-13-oxotricyclo[9.3.1.0³,⁸]pentadec-3-en-10-yl acetate)

INCHI for NP0158894 ((1r,2r,5s,8r,10s,11r,12s)-2,9-bis(acetyloxy)-5,11-dihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-13-oxotricyclo[9.3.1.0³,⁸]pentadec-3-en-10-yl acetate)

Structure for NP0158894 ((1r,2r,5s,8r,10s,11r,12s)-2,9-bis(acetyloxy)-5,11-dihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-13-oxotricyclo[9.3.1.0³,⁸]pentadec-3-en-10-yl acetate)

3D Structure for NP0158894 ((1r,2r,5s,8r,10s,11r,12s)-2,9-bis(acetyloxy)-5,11-dihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-13-oxotricyclo[9.3.1.0³,⁸]pentadec-3-en-10-yl acetate)