NP-MRD: Showing NP-Card for Trixikingolide isovalerate (NP0064705)

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Record Information

Version

2.0

Created at

2022-04-28 08:53:49 UTC

Updated at

2022-04-28 08:53:49 UTC

NP-MRD ID

NP0064705

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Trixikingolide isovalerate

Description

(1S,5S,6S,9S,10R,13S,15R)-10-methyl-11-oxo-4,12-dioxapentacyclo[7.7.0.0¹,⁶.0²,¹³.0¹⁰,¹⁵]Hexadec-2-en-5-yl (2R)-2-methylbutanoate belongs to the class of organic compounds known as lactones. These are cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. Trixikingolide isovalerate is found in Trixis wrightii. Based on a literature review very few articles have been published on (1S,5S,6S,9S,10R,13S,15R)-10-methyl-11-oxo-4,12-dioxapentacyclo[7.7.0.0¹,⁶.0²,¹³.0¹⁰,¹⁵]Hexadec-2-en-5-yl (2R)-2-methylbutanoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282210532D          

 25 29  0  0  1  0            999 V2000
    2.4742    1.0038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6578    0.8471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5398    0.0105    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3650   -0.3767    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9037    0.2759    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6558   -0.1424    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5387   -1.3258    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4622   -0.6975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8438   -1.5254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9443   -0.5545    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1727   -1.1680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4554   -1.6325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7423   -1.2341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7690   -0.4111    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0663    0.0210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6594   -0.3715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6823   -1.1961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3621    0.0607    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0878   -0.3318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7905    0.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3392    0.8854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0494   -0.9677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3892   -0.2961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1328    0.0613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9441    0.6306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  5  1  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  4  8  1  1  0  0  0
  7  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  1  0  0  0
 10 22  1  0  0  0  0
 22 23  1  0  0  0  0
  6 23  1  0  0  0  0
 23 24  2  0  0  0  0
  6 25  1  1  0  0  0
M  END


  Mrv1652304282210532D          

 25 29  0  0  1  0            999 V2000
    2.4742    1.0038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6578    0.8471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5398    0.0105    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3650   -0.3767    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9037    0.2759    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6558   -0.1424    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5387   -1.3258    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4622   -0.6975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8438   -1.5254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9443   -0.5545    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1727   -1.1680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4554   -1.6325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7423   -1.2341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7690   -0.4111    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0663    0.0210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6594   -0.3715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6823   -1.1961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3621    0.0607    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0878   -0.3318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7905    0.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3392    0.8854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0494   -0.9677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3892   -0.2961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1328    0.0613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9441    0.6306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  5  1  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  4  8  1  1  0  0  0
  7  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  1  0  0  0
 10 22  1  0  0  0  0
 22 23  1  0  0  0  0
  6 23  1  0  0  0  0
 23 24  2  0  0  0  0
  6 25  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0064705

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H](C)C(=O)O[C@@H]1OC=C2[C@@H]3C[C@H]4C[C@]22[C@@H]1CC[C@@H]2[C@]4(C)C(=O)O3

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O5/c1-4-10(2)16(21)25-17-12-5-6-15-19(3)11-7-14(24-18(19)22)13(9-23-17)20(12,15)8-11/h9-12,14-15,17H,4-8H2,1-3H3/t10-,11+,12-,14+,15-,17+,19-,20+/m1/s1

> <INCHI_KEY>
NQPYPEJSUJSTMT-YFVNVMRDSA-N

> <FORMULA>
C20H26O5

> <MOLECULAR_WEIGHT>
346.423

> <EXACT_MASS>
346.178023937

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
26.6206534502518

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,5S,6S,9S,10R,13S,15R)-10-methyl-11-oxo-4,12-dioxapentacyclo[7.7.0.0^{1,6}.0^{2,13}.0^{10,15}]hexadec-2-en-5-yl (2R)-2-methylbutanoate

> <ALOGPS_LOGP>
2.93

> <JCHEM_LOGP>
3.1173531396666667

> <ALOGPS_LOGS>
-4.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.891429351242481

> <JCHEM_POLAR_SURFACE_AREA>
61.830000000000005

> <JCHEM_REFRACTIVITY>
88.72070000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.49e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,5S,6S,9S,10R,13S,15R)-10-methyl-11-oxo-4,12-dioxapentacyclo[7.7.0.0^{1,6}.0^{2,13}.0^{10,15}]hexadec-2-en-5-yl (2R)-2-methylbutanoate

> <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       4.618   1.874   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.095   1.581   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.874   0.020   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.415  -0.703   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.420   0.515   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.824  -0.266   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.606  -2.475   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.463  -1.302   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.308  -2.847   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.496  -1.035   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.056  -2.180   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.717  -3.047   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.386  -2.304   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.436  -0.767   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.124   0.039   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.231  -0.693   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.274  -2.233   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.543   0.113   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.897  -0.619   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.209   0.187   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.500   1.653   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.559  -1.806   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.193  -0.553   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.581   0.114   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.362   1.177   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5    8   11                                             
CONECT    5    4    1    6                                                  
CONECT    6    5    7   23   25                                             
CONECT    7    6    8    9                                                  
CONECT    8    7    4                                                       
CONECT    9    7   10                                                       
CONECT   10    9   11   22                                                  
CONECT   11   10    4   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    3   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18                                                            
CONECT   22   10   23                                                       
CONECT   23   22    6   24                                                  
CONECT   24   23                                                            
CONECT   25    6                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

View in JSmol

Synonyms

Value	Source
(1S,5S,6S,9S,10R,13S,15R)-10-Methyl-11-oxo-4,12-dioxapentacyclo[7.7.0.0,.0,.0,]hexadec-2-en-5-yl (2R)-2-methylbutanoic acid	Generator

Chemical Formula

C₂₀H₂₆O₅

Average Mass

346.4230 Da

Monoisotopic Mass

346.17802 Da

IUPAC Name

(1S,5S,6S,9S,10R,13S,15R)-10-methyl-11-oxo-4,12-dioxapentacyclo[7.7.0.0^{1,6}.0^{2,13}.0^{10,15}]hexadec-2-en-5-yl (2R)-2-methylbutanoate

Traditional Name

(1S,5S,6S,9S,10R,13S,15R)-10-methyl-11-oxo-4,12-dioxapentacyclo[7.7.0.0^{1,6}.0^{2,13}.0^{10,15}]hexadec-2-en-5-yl (2R)-2-methylbutanoate

CAS Registry Number

Not Available

SMILES

CC[C@@H](C)C(=O)O[C@@H]1OC=C2[C@@H]3C[C@H]4C[C@]22[C@@H]1CC[C@@H]2[C@]4(C)C(=O)O3

InChI Identifier

InChI=1S/C20H26O5/c1-4-10(2)16(21)25-17-12-5-6-15-19(3)11-7-14(24-18(19)22)13(9-23-17)20(12,15)8-11/h9-12,14-15,17H,4-8H2,1-3H3/t10-,11+,12-,14+,15-,17+,19-,20+/m1/s1

InChI Key

NQPYPEJSUJSTMT-YFVNVMRDSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Trixis wrightii	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lactones. These are cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Not Available

Direct Parent

Lactones

Alternative Parents

Substituents

Caprolactone
Oxepane
Delta_valerolactone
Fatty acid ester
Delta valerolactone
Fatty acyl
Oxane
Dicarboxylic acid or derivatives
Lactone
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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
logP	2.93	ALOGPS
logP	3.12	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	61.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	88.72 m³·mol⁻¹	ChemAxon
Polarizability	26.62 Å³	ChemAxon
Number of Rings	5	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

162995194

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Trixikingolide isovalerate (NP0064705)

MOL for NP0064705 (Trixikingolide isovalerate)

3D MOL for NP0064705 (Trixikingolide isovalerate)

3D SDF for NP0064705 (Trixikingolide isovalerate)

3D-SDF for NP0064705 (Trixikingolide isovalerate)

PDB for NP0064705 (Trixikingolide isovalerate)

3D PDB for NP0064705 (Trixikingolide isovalerate)

SMILES for NP0064705 (Trixikingolide isovalerate)

INCHI for NP0064705 (Trixikingolide isovalerate)

Structure for NP0064705 (Trixikingolide isovalerate)

3D Structure for NP0064705 (Trixikingolide isovalerate)