NP-MRD: Showing NP-Card for 11beta-Acetoxy-5alpha-tigloyloxysilphinen-3-one (NP0064763)

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Record Information

Version

2.0

Created at

2022-04-28 09:02:43 UTC

Updated at

2022-04-28 09:02:43 UTC

NP-MRD ID

NP0064763

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11beta-Acetoxy-5alpha-tigloyloxysilphinen-3-one

Description

(1R,5R,6S,8R,9R,11R)-9-[(1-hydroxyethenyl)oxy]-5,7,7,11-tetramethyl-4-oxotricyclo[6.3.0.0¹,⁵]Undec-2-en-6-yl (2E)-2-methylbut-2-enoate belongs to the class of organic compounds known as angular triquinanes. These are triquinane with a structure based on a [6.3.0.0^1,5] Undecane carbon skeleton. 11beta-Acetoxy-5alpha-tigloyloxysilphinen-3-one is found in Cineraria geifolia. Based on a literature review very few articles have been published on (1R,5R,6S,8R,9R,11R)-9-[(1-hydroxyethenyl)oxy]-5,7,7,11-tetramethyl-4-oxotricyclo[6.3.0.0¹,⁵]Undec-2-en-6-yl (2E)-2-methylbut-2-enoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282211032D          

 27 29  0  0  1  0            999 V2000
   -0.1956   -1.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6294   -1.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8843   -0.4506    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2169    0.0343    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4506   -0.4506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2352   -0.1956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4718    0.8190    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2968    0.8190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5517    0.0343    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2192   -0.4506    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9642   -1.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1392   -1.2352    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6543   -1.9026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0038   -0.1956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6169   -0.7477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4015   -0.4927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4454   -1.5546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3916    1.6385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0469    1.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0131    1.4864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3224    2.2401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1429    2.3263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1625    2.9075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1731    3.6612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3118    4.3286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9830    2.8213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4506    0.5193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  5  6  2  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  3  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
  3 12  1  0  0  0  0
 12 13  1  1  0  0  0
 10 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  8 18  1  0  0  0  0
  8 19  1  0  0  0  0
  7 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
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
  4 27  1  6  0  0  0
M  END


  Mrv1652304282211032D          

 27 29  0  0  1  0            999 V2000
   -0.1956   -1.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6294   -1.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8843   -0.4506    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2169    0.0343    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4506   -0.4506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2352   -0.1956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4718    0.8190    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2968    0.8190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5517    0.0343    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2192   -0.4506    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9642   -1.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1392   -1.2352    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6543   -1.9026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0038   -0.1956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6169   -0.7477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4015   -0.4927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4454   -1.5546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3916    1.6385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0469    1.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0131    1.4864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3224    2.2401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1429    2.3263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1625    2.9075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1731    3.6612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3118    4.3286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9830    2.8213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4506    0.5193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  5  6  2  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  3  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
  3 12  1  0  0  0  0
 12 13  1  1  0  0  0
 10 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  8 18  1  0  0  0  0
  8 19  1  0  0  0  0
  7 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
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
  4 27  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0064763

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(/C)C(=O)O[C@H]1C(C)(C)[C@@H]2[C@@H](C[C@@H](C)[C@@]22C=CC(=O)[C@@]12C)OC(O)=C

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O5/c1-8-12(2)18(25)27-19-20(5,6)17-15(26-14(4)23)11-13(3)22(17)10-9-16(24)21(19,22)7/h8-10,13,15,17,19,23H,4,11H2,1-3,5-7H3/b12-8+/t13-,15-,17+,19+,21+,22+/m1/s1

> <INCHI_KEY>
BDSWFNVYPZVFAO-YTHCPPIISA-N

> <FORMULA>
C22H30O5

> <MOLECULAR_WEIGHT>
374.477

> <EXACT_MASS>
374.209324066

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
40.38125998791479

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,5R,6S,8R,9R,11R)-9-[(1-hydroxyethenyl)oxy]-5,7,7,11-tetramethyl-4-oxotricyclo[6.3.0.0^{1,5}]undec-2-en-6-yl (2E)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
4.28

> <JCHEM_LOGP>
5.105457121333334

> <ALOGPS_LOGS>
-4.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.231108355777954

> <JCHEM_PKA_STRONGEST_BASIC>
-4.821890816110536

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
113.06309999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.46e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5R,6S,8R,9R,11R)-9-[(1-hydroxyethenyl)oxy]-5,7,7,11-tetramethyl-4-oxotricyclo[6.3.0.0^{1,5}]undec-2-en-6-yl (2E)-2-methylbut-2-enoate

> <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      -0.365  -2.306   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.175  -2.306   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.651  -0.841   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.405   0.064   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.841  -0.841   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.306  -0.365   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.881   1.529   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.421   1.529   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.897   0.064   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.142  -0.841   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.667  -2.306   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.127  -2.306   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.221  -3.552   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.607  -0.365   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.752  -1.396   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.216  -0.920   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.431  -2.902   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.598   3.059   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.821   2.170   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.024   2.775   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.602   4.181   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.133   4.342   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.303   5.427   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.323   6.834   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.582   8.080   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.835   5.266   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.841   0.969   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    9   12                                             
CONECT    4    3    5    7   27                                             
CONECT    5    4    1    6                                                  
CONECT    6    5                                                            
CONECT    7    4    8   20                                                  
CONECT    8    7    9   18   19                                             
CONECT    9    8    3   10                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11    3   13                                                  
CONECT   13   12                                                            
CONECT   14   10   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    8                                                            
CONECT   19    8                                                            
CONECT   20    7   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23                                                            
CONECT   27    4                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Value	Source
(1R,5R,6S,8R,9R,11R)-9-[(1-Hydroxyethenyl)oxy]-5,7,7,11-tetramethyl-4-oxotricyclo[6.3.0.0,]undec-2-en-6-yl (2E)-2-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₂H₃₀O₅

Average Mass

374.4770 Da

Monoisotopic Mass

374.20932 Da

IUPAC Name

(1R,5R,6S,8R,9R,11R)-9-[(1-hydroxyethenyl)oxy]-5,7,7,11-tetramethyl-4-oxotricyclo[6.3.0.0^{1,5}]undec-2-en-6-yl (2E)-2-methylbut-2-enoate

Traditional Name

(1R,5R,6S,8R,9R,11R)-9-[(1-hydroxyethenyl)oxy]-5,7,7,11-tetramethyl-4-oxotricyclo[6.3.0.0^{1,5}]undec-2-en-6-yl (2E)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

C\C=C(/C)C(=O)O[C@H]1C(C)(C)[C@@H]2[C@@H](C[C@@H](C)[C@@]22C=CC(=O)[C@@]12C)OC(O)=C

InChI Identifier

InChI=1S/C22H30O5/c1-8-12(2)18(25)27-19-20(5,6)17-15(26-14(4)23)11-13(3)22(17)10-9-16(24)21(19,22)7/h8-10,13,15,17,19,23H,4,11H2,1-3,5-7H3/b12-8+/t13-,15-,17+,19+,21+,22+/m1/s1

InChI Key

BDSWFNVYPZVFAO-YTHCPPIISA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cineraria geifolia	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as angular triquinanes. These are triquinane with a structure based on a [6.3.0.0^1,5] Undecane carbon skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Angular triquinanes

Alternative Parents

Substituents

Angular triquinane sesquiterpenoid
Fatty acid ester
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Ketone
Ketene acetal or derivatives
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	4.28	ALOGPS
logP	5.11	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	7.23	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	113.06 m³·mol⁻¹	ChemAxon
Polarizability	40.38 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

163103484

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 11beta-Acetoxy-5alpha-tigloyloxysilphinen-3-one (NP0064763)

MOL for NP0064763 (11beta-Acetoxy-5alpha-tigloyloxysilphinen-3-one)

3D MOL for NP0064763 (11beta-Acetoxy-5alpha-tigloyloxysilphinen-3-one)

3D SDF for NP0064763 (11beta-Acetoxy-5alpha-tigloyloxysilphinen-3-one)

3D-SDF for NP0064763 (11beta-Acetoxy-5alpha-tigloyloxysilphinen-3-one)

PDB for NP0064763 (11beta-Acetoxy-5alpha-tigloyloxysilphinen-3-one)

3D PDB for NP0064763 (11beta-Acetoxy-5alpha-tigloyloxysilphinen-3-one)

SMILES for NP0064763 (11beta-Acetoxy-5alpha-tigloyloxysilphinen-3-one)

INCHI for NP0064763 (11beta-Acetoxy-5alpha-tigloyloxysilphinen-3-one)

Structure for NP0064763 (11beta-Acetoxy-5alpha-tigloyloxysilphinen-3-one)

3D Structure for NP0064763 (11beta-Acetoxy-5alpha-tigloyloxysilphinen-3-one)