NP-MRD: Showing NP-Card for (1s,2z,4r,8r,9r,11r)-1-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-9-yl 2-methylpropanoate (NP0325849)

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Record Information

Version

2.0

Created at

2022-09-12 06:55:29 UTC

Updated at

2022-09-12 06:55:29 UTC

NP-MRD ID

NP0325849

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2z,4r,8r,9r,11r)-1-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-9-yl 2-methylpropanoate

Description

(1S,2Z,4R,8R,9R,11R)-1-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]Tetradeca-2,12-dien-9-yl 2-methylpropanoate belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. (1s,2z,4r,8r,9r,11r)-1-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-9-yl 2-methylpropanoate is found in Tithonia diversifolia. Based on a literature review very few articles have been published on (1S,2Z,4R,8R,9R,11R)-1-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]Tetradeca-2,12-dien-9-yl 2-methylpropanoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309122208552D          

 25 27  0  0  1  0            999 V2000
    5.4278   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1729   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6578    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4828    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1729    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3883    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9034    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1187    1.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1187    2.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3341    1.4924    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8492    2.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8492    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8492   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3341   -0.6674    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8492   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1187   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9034   -0.6674    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3883   -1.3349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0527   -2.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5376   -2.7560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2322   -2.1748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8967   -2.9285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7473   -1.5074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3883   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6041    0.4125    0.0000 O   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  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 17 24  1  0  0  0  0
 24  2  1  6  0  0  0
  6 24  1  0  0  0  0
 14 25  1  0  0  0  0
 10 25  1  0  0  0  0
M  END


  Mrv1652309122208552D          

 25 27  0  0  1  0            999 V2000
    5.4278   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1729   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6578    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4828    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1729    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3883    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9034    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1187    1.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1187    2.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3341    1.4924    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8492    2.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8492    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8492   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3341   -0.6674    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8492   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1187   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9034   -0.6674    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3883   -1.3349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0527   -2.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5376   -2.7560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2322   -2.1748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8967   -2.9285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7473   -1.5074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3883   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6041    0.4125    0.0000 O   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  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 17 24  1  0  0  0  0
 24  2  1  6  0  0  0
  6 24  1  0  0  0  0
 14 25  1  0  0  0  0
 10 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0325849

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=O)O[C@@H]1C[C@@]2(C)O[C@@](O)(C=C2)\C(C)=C/[C@H]2OC(=O)C(=C)[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C19H24O6/c1-10(2)16(20)24-14-9-18(5)6-7-19(22,25-18)11(3)8-13-15(14)12(4)17(21)23-13/h6-8,10,13-15,22H,4,9H2,1-3,5H3/b11-8-/t13-,14-,15+,18+,19+/m1/s1

> <INCHI_KEY>
XJUPOHKZSDZNBE-UMXFGWAOSA-N

> <FORMULA>
C19H24O6

> <MOLECULAR_WEIGHT>
348.395

> <EXACT_MASS>
348.157288493

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
36.48996710946749

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2Z,4R,8R,9R,11R)-1-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradeca-2,12-dien-9-yl 2-methylpropanoate

> <JCHEM_LOGP>
2.786378629666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.085995801317956

> <JCHEM_PKA_STRONGEST_BASIC>
-4.4513629749549795

> <JCHEM_POLAR_SURFACE_AREA>
82.06000000000002

> <JCHEM_REFRACTIVITY>
91.0168

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2Z,4R,8R,9R,11R)-1-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradeca-2,12-dien-9-yl 2-methylpropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      10.132  -1.941   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.656  -0.476   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.561   0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      12.101   0.770   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       9.656   2.016   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       8.191   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.286   2.786   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.822   3.262   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.822   4.802   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.357   2.786   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.452   4.032   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.452   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.452  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.357  -1.246   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.452  -2.492   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.822  -1.722   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.286  -1.246   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.191  -2.492   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.565  -3.899   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.470  -5.145   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.034  -4.060   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.407  -5.466   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.128  -2.814   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.191  -0.000   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.861   0.770   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   24                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   24                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12   25                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   25                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   17    2    6                                                  
CONECT   25   14   10                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Value	Source
(1S,2Z,4R,8R,9R,11R)-1-Hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0,]tetradeca-2,12-dien-9-yl 2-methylpropanoic acid	Generator

Chemical Formula

C₁₉H₂₄O₆

Average Mass

348.3950 Da

Monoisotopic Mass

348.15729 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)C(=O)O[C@@H]1C[C@@]2(C)O[C@@](O)(C=C2)\C(C)=C/[C@H]2OC(=O)C(=C)[C@H]12

InChI Identifier

InChI=1S/C19H24O6/c1-10(2)16(20)24-14-9-18(5)6-7-19(22,25-18)11(3)8-13-15(14)12(4)17(21)23-13/h6-8,10,13-15,22H,4,9H2,1-3,5H3/b11-8-/t13-,14-,15+,18+,19+/m1/s1

InChI Key

XJUPOHKZSDZNBE-UMXFGWAOSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Tithonia diversifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Dicarboxylic acid or derivatives
Gamma butyrolactone
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Hemiacetal
Carboxylic acid derivative
Oxacycle
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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

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

163007420

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2z,4r,8r,9r,11r)-1-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-9-yl 2-methylpropanoate (NP0325849)

MOL for NP0325849 ((1s,2z,4r,8r,9r,11r)-1-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-9-yl 2-methylpropanoate)

3D MOL for NP0325849 ((1s,2z,4r,8r,9r,11r)-1-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-9-yl 2-methylpropanoate)

3D SDF for NP0325849 ((1s,2z,4r,8r,9r,11r)-1-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-9-yl 2-methylpropanoate)

3D-SDF for NP0325849 ((1s,2z,4r,8r,9r,11r)-1-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-9-yl 2-methylpropanoate)

PDB for NP0325849 ((1s,2z,4r,8r,9r,11r)-1-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-9-yl 2-methylpropanoate)

3D PDB for NP0325849 ((1s,2z,4r,8r,9r,11r)-1-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-9-yl 2-methylpropanoate)

SMILES for NP0325849 ((1s,2z,4r,8r,9r,11r)-1-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-9-yl 2-methylpropanoate)

INCHI for NP0325849 ((1s,2z,4r,8r,9r,11r)-1-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-9-yl 2-methylpropanoate)

Structure for NP0325849 ((1s,2z,4r,8r,9r,11r)-1-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-9-yl 2-methylpropanoate)

3D Structure for NP0325849 ((1s,2z,4r,8r,9r,11r)-1-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-9-yl 2-methylpropanoate)