NP-MRD: Showing NP-Card for Iridomyrmecin (NP0051773)

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Record Information

Version

2.0

Created at

2022-04-27 23:00:47 UTC

Updated at

2022-04-27 23:00:47 UTC

NP-MRD ID

NP0051773

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Iridomyrmecin

Description

Iridomyrmecin belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Iridomyrmecin is found in Actinida polygama, Actinidia polygama , Iridomyrmex humilis and Nepeta erecta. Iridomyrmecin was first documented in 2016 (PMID: 30452153). Based on a literature review a significant number of articles have been published on Iridomyrmecin (PMID: 29766719) (PMID: 29367727) (PMID: 31250873) (PMID: 33302371) (PMID: 32812277) (PMID: 30756216).

Structure

MOL 3D MOL SDF PDB SMILES InChI

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       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.454   1.540   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.788  -0.770   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.846   3.481   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.121  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   12                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    1    8                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    6                                                       
CONECT   11    8                                                            
CONECT   12    5                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₀H₁₆O₂

Average Mass

168.2360 Da

Monoisotopic Mass

168.11503 Da

IUPAC Name

(4S,4aS,7S,7aR)-4,7-dimethyl-octahydrocyclopenta[c]pyran-3-one

Traditional Name

iridomyrmecin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C10H16O2/c1-6-3-4-8-7(2)10(11)12-5-9(6)8/h6-9H,3-5H2,1-2H3/t6-,7-,8+,9+/m0/s1

InChI Key

LYEFRAMOOLOUKA-RBXMUDONSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Actinida polygama	-	KNApSAcK
Actinidia polygama	Plant	KNApSAcK
Iridomyrmex humilis	Animalia	KNApSAcK
Nepeta erecta	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Iridoid-skeleton
Bicyclic monoterpenoid
Monoterpenoid
Delta valerolactone
Delta_valerolactone
Oxane
Carboxylic acid ester
Lactone
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

terpene lactone (CHEBI:5967 )
Iridoids (C09786 )

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	2.09	ALOGPS
logP	2.06	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	45.85 m³·mol⁻¹	ChemAxon
Polarizability	18.63 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

C00003086

Chemspider ID

390867

KEGG Compound ID

C09786

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Iridomyrmecin

METLIN ID

Not Available

PubChem Compound

442427

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

rw1086001

References

General References

Khan HPA, Das D, Chakraborty TK: Application of Cp2TiCl-Promoted Radical Cyclization: A Unified Strategy for the Syntheses of Iridoid Monoterpenes. J Org Chem. 2018 Jun 1;83(11):6086-6092. doi: 10.1021/acs.joc.8b00752. Epub 2018 May 22. [PubMed:29766719 ]
Welzel KF, Lee SH, Dossey AT, Chauhan KR, Choe DH: Verification of Argentine ant defensive compounds and their behavioral effects on heterospecific competitors and conspecific nestmates. Sci Rep. 2018 Jan 24;8(1):1477. doi: 10.1038/s41598-018-19435-6. [PubMed:29367727 ]
Salam A, Ray S, Zaid MA, Kumar D, Khan T: Total syntheses of several iridolactones and the putative structure of noriridoid scholarein A: an intramolecular Pauson-Khand reaction based one-stop synthetic solution. Org Biomol Chem. 2019 Jul 17;17(28):6831-6842. doi: 10.1039/c9ob00855a. [PubMed:31250873 ]
Maccaro JJ, Whyte BA, Tsutsui ND: The Ant Who Cried Wolf? Short-Term Repeated Exposure to Alarm Pheromone Reduces Behavioral Response in Argentine Ants. Insects. 2020 Dec 8;11(12). pii: insects11120871. doi: 10.3390/insects11120871. [PubMed:33302371 ]
Alvarez-Blanco P, Cerda X, Hefetz A, Boulay R, Berto-Moran A, Diaz-Paniagua C, Lenoir A, Billen J, Liedtke HC, Chauhan KR, Bhagavathy G, Angulo E: Effects of the Argentine ant venom on terrestrial amphibians. Conserv Biol. 2021 Feb;35(1):216-226. doi: 10.1111/cobi.13604. Epub 2020 Aug 18. [PubMed:32812277 ]
Bottinger LC, Hofferberth J, Ruther J, Stokl J: Semiochemicals Mediating Defense, Intraspecific Competition, and Mate Finding in Leptopilina ryukyuensis and L. japonica (Hymenoptera: Figitidae), Parasitoids of Drosophila. J Chem Ecol. 2019 Mar;45(3):241-252. doi: 10.1007/s10886-019-01052-w. Epub 2019 Feb 13. [PubMed:30756216 ]
Pfeiffer L, Ruther J, Hofferberth J, Stokl J: Interference of chemical defence and sexual communication can shape the evolution of chemical signals. Sci Rep. 2018 Jan 10;8(1):321. doi: 10.1038/s41598-017-18376-w. [PubMed:29321506 ]
Adachi M, Miyazawa Y, Nishikawa T: Improved Syntheses of (+)-Iridomyrmecin and (-)-Isoiridomyrmecin, Major Components of Matatabilactone. Nat Prod Commun. 2016 Jul;11(7):883-886. [PubMed:30452153 ]
Stokl J, Herzner G: Morphology and ultrastructure of the allomone and sex-pheromone producing mandibular gland of the parasitoid wasp Leptopilina heterotoma (Hymenoptera: Figitidae). Arthropod Struct Dev. 2016 Jul;45(4):333-40. doi: 10.1016/j.asd.2016.06.003. Epub 2016 Jul 4. [PubMed:27349419 ]

Showing NP-Card for Iridomyrmecin (NP0051773)

MOL for NP0051773 (Iridomyrmecin)

3D MOL for NP0051773 (Iridomyrmecin)

3D SDF for NP0051773 (Iridomyrmecin)

3D-SDF for NP0051773 (Iridomyrmecin)

PDB for NP0051773 (Iridomyrmecin)

3D PDB for NP0051773 (Iridomyrmecin)

SMILES for NP0051773 (Iridomyrmecin)

INCHI for NP0051773 (Iridomyrmecin)

Structure for NP0051773 (Iridomyrmecin)

3D Structure for NP0051773 (Iridomyrmecin)