NP-MRD: Showing NP-Card for Isoascaridol (NP0085893)

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Record Information

Version

2.0

Created at

2022-04-29 06:19:43 UTC

Updated at

2022-04-29 06:19:43 UTC

NP-MRD ID

NP0085893

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isoascaridol

Description

ISOASCARIDOLE belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms. Isoascaridol is found in Dysphania ambrosioides and Senecio vulgaris . Isoascaridol was first documented in 2017 (PMID: 28504841). Based on a literature review a small amount of articles have been published on ISOASCARIDOLE (PMID: 32239617) (PMID: 32061727) (PMID: 30618281).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292208192D          

 14 16  0  0  1  0            999 V2000
    2.9046    1.4757    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9046    0.6507    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3171   -0.0638    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7296    0.6507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0316   -0.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0316   -1.3013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7460   -0.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9046   -0.7783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0796   -0.7783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6671   -0.0638    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9526   -0.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0796    0.6507    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0796    1.4757    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546    0.6507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  6  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 10 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0085893

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12O[C@]1(C)CC[C@@]1(O[C@]21[H])C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C10H16O2/c1-6(2)10-5-4-9(3)7(11-9)8(10)12-10/h6-8H,4-5H2,1-3H3/t7-,8+,9+,10+/m0/s1

> <INCHI_KEY>
LEZWCCRTFNBOBU-SGIHWFKDSA-N

> <FORMULA>
C10H16O2

> <MOLECULAR_WEIGHT>
168.236

> <EXACT_MASS>
168.115029755

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
18.806978223044474

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,4R,7R)-4-methyl-7-(propan-2-yl)-3,8-dioxatricyclo[5.1.0.0^{2,4}]octane

> <ALOGPS_LOGP>
1.74

> <JCHEM_LOGP>
1.828038344666667

> <ALOGPS_LOGS>
-1.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9451587143071634

> <JCHEM_POLAR_SURFACE_AREA>
25.06

> <JCHEM_REFRACTIVITY>
44.611799999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.97e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,4R,7R)-4-isopropyl-7-methyl-3,8-dioxatricyclo[5.1.0.0^{2,4}]octane

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  H   UNK     0       5.422   2.755   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       5.422   1.215   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.192  -0.119   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.962   1.215   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.526  -0.889   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.526  -2.429   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.859  -0.119   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.422  -1.453   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.882  -1.453   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.112  -0.119   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.778  -0.889   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.882   1.215   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0       3.882   2.755   0.000  0.00  0.00           H+0
HETATM   14  O   UNK     0       2.342   1.215   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   12                                             
CONECT    3    2    4    5    8                                             
CONECT    4    3    2                                                       
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    3    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   14                                             
CONECT   11   10                                                            
CONECT   12   10    2   13   14                                             
CONECT   13   12                                                            
CONECT   14   12   10                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   32    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₀H₁₆O₂

Average Mass

168.2360 Da

Monoisotopic Mass

168.11503 Da

IUPAC Name

(1R,2S,4R,7R)-4-methyl-7-(propan-2-yl)-3,8-dioxatricyclo[5.1.0.0^{2,4}]octane

Traditional Name

(1S,2R,4R,7R)-4-isopropyl-7-methyl-3,8-dioxatricyclo[5.1.0.0^{2,4}]octane

CAS Registry Number

Not Available

SMILES

[H][C@@]12O[C@]1(C)CC[C@@]1(O[C@]21[H])C(C)C

InChI Identifier

InChI=1S/C10H16O2/c1-6(2)10-5-4-9(3)7(11-9)8(10)12-10/h6-8H,4-5H2,1-3H3/t7-,8+,9+,10+/m0/s1

InChI Key

LEZWCCRTFNBOBU-SGIHWFKDSA-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
Dysphania ambrosioides	LOTUS Database	35616633
Senecio vulgaris	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxepanes

Sub Class

Not Available

Direct Parent

Oxepanes

Alternative Parents

Substituents

Oxepane
Oxacycle
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
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
logP	1.74	ALOGPS
logP	1.83	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	25.06 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	44.61 m³·mol⁻¹	ChemAxon
Polarizability	18.81 Å³	ChemAxon
Number of Rings	3	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

C00055938

Chemspider ID

31115335

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12314661

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Aminkhani A, Sharifi S, Ekhtiyari S: Achillea filipendulina Lam.: Chemical Constituents and Antimicrobial Activities of Essential Oil of Stem, Leaf, and Flower. Chem Biodivers. 2020 May;17(5):e2000133. doi: 10.1002/cbdv.202000133. Epub 2020 Apr 29. [PubMed:32239617 ]
Benelli G, Pavela R, Cianfaglione K, Sender J, Danuta U, Maslanko W, Canale A, Barboni L, Petrelli R, Zeppa L, Aguzzi C, Maggi F: Ascaridole-rich essential oil from marsh rosemary (Ledum palustre) growing in Poland exerts insecticidal activity on mosquitoes, moths and flies without serious effects on non-target organisms and human cells. Food Chem Toxicol. 2020 Apr;138:111184. doi: 10.1016/j.fct.2020.111184. Epub 2020 Feb 13. [PubMed:32061727 ]
Qadir M, Maurya AK, Waza AA, Agnihotri VK, Shah WA: Chemical composition, antioxidant and cytotoxic activity of Artemisia gmelinii essential oil growing wild in Kashmir valley. Nat Prod Res. 2020 Nov;34(22):3289-3294. doi: 10.1080/14786419.2018.1557178. Epub 2019 Jan 8. [PubMed:30618281 ]
Soares MH, Dias HJ, Vieira TM, de Souza MGM, Cruz AFF, Badoco FR, Nicolella HD, Cunha WR, Groppo M, Martins CHG, Tavares DC, Magalhaes LG, Crotti AEM: Chemical Composition, Antibacterial, Schistosomicidal, and Cytotoxic Activities of the Essential Oil of Dysphania ambrosioides (L.) Mosyakin & Clemants (Chenopodiaceae). Chem Biodivers. 2017 Aug;14(8). doi: 10.1002/cbdv.201700149. Epub 2017 Jul 29. [PubMed:28504841 ]

Showing NP-Card for Isoascaridol (NP0085893)

MOL for NP0085893 (Isoascaridol)

3D MOL for NP0085893 (Isoascaridol)

3D SDF for NP0085893 (Isoascaridol)

3D-SDF for NP0085893 (Isoascaridol)

PDB for NP0085893 (Isoascaridol)

3D PDB for NP0085893 (Isoascaridol)

SMILES for NP0085893 (Isoascaridol)

INCHI for NP0085893 (Isoascaridol)

Structure for NP0085893 (Isoascaridol)

3D Structure for NP0085893 (Isoascaridol)