NP-MRD: Showing NP-Card for (2r,3r,5s,8r,9r,10r)-2,5,9-trihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0³,⁸]pentadec-11-en-10-yl acetate (NP0233823)

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Record Information

Version

2.0

Created at

2022-09-06 15:34:04 UTC

Updated at

2022-09-06 15:34:04 UTC

NP-MRD ID

NP0233823

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r,5s,8r,9r,10r)-2,5,9-trihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0³,⁸]pentadec-11-en-10-yl acetate

Description

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

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062217342D          

 28 30  0  0  1  0            999 V2000
    4.8045    2.3012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9601    1.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7396    1.2207    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3634    1.7606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8952    0.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2713   -0.1294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4919    0.1410    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7373   -0.6467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3363    0.9512    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6109    1.4262    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7929    2.2309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7457    1.3088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8928    1.4608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2975    0.8606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4927    1.0419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5779    0.0631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0158   -0.5407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4136   -0.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1449   -0.6424    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9587   -1.4461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5617   -2.0092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3508   -1.7685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3755   -2.8129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9942   -0.5374    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4116   -1.2491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6447    0.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3216    0.0854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4585    0.6930    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  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9  2  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 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
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  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
  7 24  1  0  0  0  0
 24 25  1  1  0  0  0
 18 26  1  0  0  0  0
 12 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
M  END


  Mrv1652309062217342D          

 28 30  0  0  1  0            999 V2000
    4.8045    2.3012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9601    1.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7396    1.2207    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3634    1.7606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8952    0.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2713   -0.1294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4919    0.1410    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7373   -0.6467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3363    0.9512    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6109    1.4262    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7929    2.2309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7457    1.3088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8928    1.4608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2975    0.8606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4927    1.0419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5779    0.0631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0158   -0.5407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4136   -0.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1449   -0.6424    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9587   -1.4461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5617   -2.0092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3508   -1.7685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3755   -2.8129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9942   -0.5374    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4116   -1.2491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6447    0.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3216    0.0854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4585    0.6930    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  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9  2  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 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
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  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
  7 24  1  0  0  0  0
 24 25  1  1  0  0  0
 18 26  1  0  0  0  0
 12 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0233823

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1[C@H](O)[C@]2(C)CC[C@H](O)C(=C)[C@H]2[C@H](O)C2CC(=O)C(C)=C1C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C22H32O6/c1-10-14(24)7-8-22(6)16(10)18(26)13-9-15(25)11(2)17(21(13,4)5)19(20(22)27)28-12(3)23/h13-14,16,18-20,24,26-27H,1,7-9H2,2-6H3/t13?,14-,16-,18+,19+,20-,22+/m0/s1

> <INCHI_KEY>
XFEUMJJMSJHHTG-YQSHZWRQSA-N

> <FORMULA>
C22H32O6

> <MOLECULAR_WEIGHT>
392.492

> <EXACT_MASS>
392.21988875

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
41.52918716089284

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
0.9375610079999994

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.355098196690317

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.552128576914058

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9649876651637266

> <JCHEM_POLAR_SURFACE_AREA>
104.06000000000002

> <JCHEM_REFRACTIVITY>
103.75660000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       8.968   4.296   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.259   2.783   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.714   2.279   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      11.878   3.286   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      11.004   0.766   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.840  -0.241   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.385   0.263   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.843  -1.207   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.094   1.775   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.740   2.662   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.080   4.164   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.125   2.443   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.533   2.727   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.422   1.606   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.920   1.945   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.945   0.118   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.896  -1.009   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.505  -0.309   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.870  -1.199   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.523  -2.699   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.648  -3.750   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.122  -3.301   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.301  -5.251   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       7.456  -1.003   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.235  -2.332   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.937   1.040   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.200   0.159   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.456   1.294   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   24                                             
CONECT    8    7                                                            
CONECT    9    7    2   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   26                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   26                                                  
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   19    7   25                                                  
CONECT   25   24                                                            
CONECT   26   18   12   27   28                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₂₂H₃₂O₆

Average Mass

392.4920 Da

Monoisotopic Mass

392.21989 Da

IUPAC Name

(2R,3R,5S,8R,9R,10R)-2,5,9-trihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0^{3,8}]pentadec-11-en-10-yl acetate

Traditional Name

(2R,3R,5S,8R,9R,10R)-2,5,9-trihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0^{3,8}]pentadec-11-en-10-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1[C@H](O)[C@]2(C)CC[C@H](O)C(=C)[C@H]2[C@H](O)C2CC(=O)C(C)=C1C2(C)C

InChI Identifier

InChI=1S/C22H32O6/c1-10-14(24)7-8-22(6)16(10)18(26)13-9-15(25)11(2)17(21(13,4)5)19(20(22)27)28-12(3)23/h13-14,16,18-20,24,26-27H,1,7-9H2,2-6H3/t13?,14-,16-,18+,19+,20-,22+/m0/s1

InChI Key

XFEUMJJMSJHHTG-YQSHZWRQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Taxus baccata	LOTUS Database	35616633
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
Cyclohexenone
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Carboxylic acid ester
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	0.94	ChemAxon
pKa (Strongest Acidic)	13.55	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	103.76 m³·mol⁻¹	ChemAxon
Polarizability	41.53 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

4479360

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5321688

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3r,5s,8r,9r,10r)-2,5,9-trihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0³,⁸]pentadec-11-en-10-yl acetate (NP0233823)

MOL for NP0233823 ((2r,3r,5s,8r,9r,10r)-2,5,9-trihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0³,⁸]pentadec-11-en-10-yl acetate)

3D MOL for NP0233823 ((2r,3r,5s,8r,9r,10r)-2,5,9-trihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0³,⁸]pentadec-11-en-10-yl acetate)

3D SDF for NP0233823 ((2r,3r,5s,8r,9r,10r)-2,5,9-trihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0³,⁸]pentadec-11-en-10-yl acetate)

3D-SDF for NP0233823 ((2r,3r,5s,8r,9r,10r)-2,5,9-trihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0³,⁸]pentadec-11-en-10-yl acetate)

PDB for NP0233823 ((2r,3r,5s,8r,9r,10r)-2,5,9-trihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0³,⁸]pentadec-11-en-10-yl acetate)

3D PDB for NP0233823 ((2r,3r,5s,8r,9r,10r)-2,5,9-trihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0³,⁸]pentadec-11-en-10-yl acetate)

SMILES for NP0233823 ((2r,3r,5s,8r,9r,10r)-2,5,9-trihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0³,⁸]pentadec-11-en-10-yl acetate)

INCHI for NP0233823 ((2r,3r,5s,8r,9r,10r)-2,5,9-trihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0³,⁸]pentadec-11-en-10-yl acetate)

Structure for NP0233823 ((2r,3r,5s,8r,9r,10r)-2,5,9-trihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0³,⁸]pentadec-11-en-10-yl acetate)

3D Structure for NP0233823 ((2r,3r,5s,8r,9r,10r)-2,5,9-trihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0³,⁸]pentadec-11-en-10-yl acetate)