NP-MRD: Showing NP-Card for (+)-Iridodial (NP0051772)

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Record Information

Version

2.0

Created at

2022-04-27 23:00:43 UTC

Updated at

2022-04-27 23:00:43 UTC

NP-MRD ID

NP0051772

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Iridodial

Description

(+)-Iridodial lactol, also known as nepetalactol, belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open. Thus, (+)-iridodial lactol is considered to be an isoprenoid. (+)-Iridodial is found in Centaurium erythraea , Cornus officinalis , Iridomyrmex spp., Lonicera japonica , Myoporum sp., Rehmannia glutinosa , Schizaphis graminum and Sertia mussotii. Based on a literature review very few articles have been published on (+)-iridodial lactol.

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  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.846   3.481   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.121  -2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.121   3.850   0.000  0.00  0.00           O+0
CONECT    1    2    6   12                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8    5                                                       
CONECT   10    7                                                            
CONECT   11    4                                                            
CONECT   12    1                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol

Synonyms

Value	Source
(+)-cis-trans-Nepetalactol	ChEBI
(+)-Iridodial	ChEBI
cis-trans-Iridodial lactol	Kegg
(+)-cis,trans-Nepetalactol	Kegg
(4AS,7S,7ar)-4,7-dimethyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-1-ol	Kegg
(1R,4AS,7S,7ar)-nepetalactol	MeSH
Nepetalactol	MeSH

Chemical Formula

C₁₀H₁₆O₂

Average Mass

168.2360 Da

Monoisotopic Mass

168.11503 Da

IUPAC Name

(1R,4aS,7S,7aR)-4,7-dimethyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-1-ol

Traditional Name

(+)-iridodial

CAS Registry Number

Not Available

SMILES

C[C@H]1CC[C@H]2[C@@H]1[C@H](O)OC=C2C

InChI Identifier

InChI=1S/C10H16O2/c1-6-3-4-8-7(2)5-12-10(11)9(6)8/h5-6,8-11H,3-4H2,1-2H3/t6-,8+,9+,10+/m0/s1

InChI Key

OJGPEAXUHQRLNC-JZKKDOLYSA-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
Centaurium erythraea	Plant	KNApSAcK
Cornus officinalis	Plant	KNApSAcK
Iridomyrmex spp.	Animalia	KNApSAcK
Lonicera japonica	Plant	KNApSAcK
Myoporum sp.	Plant	KNApSAcK
Rehmannia glutinosa	Plant	KNApSAcK
Schizaphis graminum	LOTUS Database	35616633
Sertia mussotii	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Iridoids and derivatives

Alternative Parents

Substituents

Iridoid-skeleton
Bicyclic monoterpenoid
Hemiacetal
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

lactol (CHEBI:26 )
iridoid monoterpenoid (CHEBI:26 )
Iridoid, 10-alkyliridoid and secoiridoid monoterpenoids (C09804 )
Cyclic monoterpenes (C09804 )
Iridoid, 10-alkyliridoid and secoiridoid monoterpenoids (LMPR0102070017 )

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	1.41	ALOGPS
logP	1.67	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	12.1	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	46.98 m³·mol⁻¹	ChemAxon
Polarizability	18.81 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

C00003085

Chemspider ID

390878

KEGG Compound ID

C09804

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442438

PDB ID

Not Available

ChEBI ID

Good Scents ID

rw1422691

References

General References

Not Available

Showing NP-Card for (+)-Iridodial (NP0051772)

MOL for NP0051772 ((+)-Iridodial)

3D MOL for NP0051772 ((+)-Iridodial)

3D SDF for NP0051772 ((+)-Iridodial)

3D-SDF for NP0051772 ((+)-Iridodial)

PDB for NP0051772 ((+)-Iridodial)

3D PDB for NP0051772 ((+)-Iridodial)

SMILES for NP0051772 ((+)-Iridodial)

INCHI for NP0051772 ((+)-Iridodial)

Structure for NP0051772 ((+)-Iridodial)

3D Structure for NP0051772 ((+)-Iridodial)