NP-MRD: Showing NP-Card for Isololiolide (NP0141222)

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Record Information

Version

1.0

Created at

2022-06-29 22:18:22 UTC

Updated at

2022-06-29 22:18:22 UTC

NP-MRD ID

NP0141222

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isololiolide

Description

Isololiolide belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Isololiolide is found in Acanthosyris paulo-alvinii, Calyptocarpus vialis, Cichorium intybus, Dictyopteris divaricata, Excoecaria cochinchinensis, Melilotus messanensis, Monteverdia apurimacensis, Peperomia heyneana, Potentilla anserina, Salvia divinorum, Undaria pinnatifida and Viburnum dilatatum. It was first documented in 2016 (PMID: 27064014). Based on a literature review a significant number of articles have been published on isololiolide (PMID: 33926330) (PMID: 33179569) (PMID: 31136901) (PMID: 27981801).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 31  0  0  0  0  0  0  0  0999 V2000
   -1.4797   -0.4946    1.3007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0835   -0.3259   -0.1280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1050   -0.9850   -1.0502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0875    1.1450   -0.4826 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0914    1.8961    0.0445 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0187    3.2345   -0.3955 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776    1.2902   -0.4306 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4777   -0.1197    0.0531 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5742   -0.1583    1.5834 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5755   -0.8585   -0.3772 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1474   -2.0240   -0.9602 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8617   -2.9728   -1.4516 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6851   -1.9901   -0.9201 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2733   -0.8963   -0.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8505   -1.2390    1.8242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5464    0.4818    1.8302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5149   -0.9522    1.3138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8280   -2.0296   -1.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2111   -0.4144   -2.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1181   -1.0090   -0.5572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1006    1.2332   -1.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0096    1.6188   -0.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0150    1.9684    1.1477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7888    3.6788   -0.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4232    1.3654   -1.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2143    1.8770    0.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8130    0.4417    2.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5690    0.2452    1.8977 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5425   -1.2173    1.8826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0645   -2.7892   -1.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  1
  8  7  1  0
  7  5  1  0
  5  6  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  1  0
  2 14  1  0
 14 13  2  0
 13 11  1  0
 11 12  2  0
 11 10  1  0
 14  8  1  0
 10  8  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
  7 25  1  0
  7 26  1  0
  5 23  1  1
  6 24  1  0
  4 21  1  0
  4 22  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  3 20  1  0
 13 30  1  0
M  END

HEADER    PROTEIN                                 30-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUN-22         0                                  
HETATM    1  C   UNK     0       3.429   0.999   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.320  -1.303   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.126  -0.057   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.647  -4.203   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.201  -4.203   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.591   0.237   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7   11                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   12   13                                             
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    2                                                       
CONECT   12    6                                                            
CONECT   13    6                                                            
CONECT   14    4                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₆O₃

Average Mass

196.2460 Da

Monoisotopic Mass

196.10994 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@]12C[C@@H](O)CC(C)(C)C1=CC(=O)O2

InChI Identifier

InChI=1S/C11H16O3/c1-10(2)5-7(12)6-11(3)8(10)4-9(13)14-11/h4,7,12H,5-6H2,1-3H3/t7-,11-/m0/s1

InChI Key

XEVQXKKKAVVSMW-CPCISQLKSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.303707098 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150.960649616 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Acanthosyris paulo-alvinii	LOTUS Database	35616633
Calyptocarpus vialis	LOTUS Database	35616633
Cichorium intybus	LOTUS Database	35616633
Dictyopteris divaricata	LOTUS Database	35616633
Excoecaria cochinchinensis	LOTUS Database	35616633
Melilotus messanensis	LOTUS Database	35616633
Monteverdia apurimacensis	LOTUS Database	35616633
Peperomia heyneana	LOTUS Database	35616633
Potentilla anserina	LOTUS Database	35616633
Salvia divinorum	LOTUS Database	35616633
Undaria pinnatifida	LOTUS Database	35616633
Viburnum dilatatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Not Available

Direct Parent

Benzofurans

Alternative Parents

Substituents

Benzofuran
2-furanone
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Secondary alcohol
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organooxygen compound
Organic oxygen 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

C00019146

Chemspider ID

9194965

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11019783

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Xu W, Wang J, Ju B, Lan X, Ying X, Stien D: Seven compounds from Portulaca oleracea L. and their anticholinesterase activities. Nat Prod Res. 2022 May;36(10):2547-2553. doi: 10.1080/14786419.2021.1916928. Epub 2021 Apr 30. [PubMed:33926330 ]
Baruah VJ, Paul R, Gogoi D, Mazumder N, Chakraborty S, Das A, Mondal TK, Sarmah B: Integrated computational approach toward discovery of multi-targeted natural products from Thumbai (Leucas aspera) for attuning NKT cells. J Biomol Struct Dyn. 2022 Apr;40(7):2893-2907. doi: 10.1080/07391102.2020.1844056. Epub 2020 Nov 12. [PubMed:33179569 ]
Lima ML, Romanelli MM, Borborema SET, Johns DM, Migotto AE, Lago JHG, Tempone AG: Antitrypanosomal activity of isololiolide isolated from the marine hydroid Macrorhynchia philippina (Cnidaria, Hydrozoa). Bioorg Chem. 2019 Aug;89:103002. doi: 10.1016/j.bioorg.2019.103002. Epub 2019 May 20. [PubMed:31136901 ]
Salem AB, Di Giuseppe G, Anesi A, Hammami S, Mighri Z, Guella G: Natural Products among Brown Algae: The Case of Cystoseira schiffneri Hamel (Sargassaceae, Phaeophyceae). Chem Biodivers. 2017 Apr;14(4). doi: 10.1002/cbdv.201600333. Epub 2017 Mar 20. [PubMed:27981801 ]
Vizetto-Duarte C, Custodio L, Gangadhar KN, Lago JH, Dias C, Matos AM, Neng N, Nogueira JM, Barreira L, Albericio F, Rauter AP, Varela J: Isololiolide, a carotenoid metabolite isolated from the brown alga Cystoseira tamariscifolia, is cytotoxic and able to induce apoptosis in hepatocarcinoma cells through caspase-3 activation, decreased Bcl-2 levels, increased p53 expression and PARP cleavage. Phytomedicine. 2016 May 15;23(5):550-7. doi: 10.1016/j.phymed.2016.02.008. Epub 2016 Feb 26. [PubMed:27064014 ]

Showing NP-Card for Isololiolide (NP0141222)

MOL for NP0141222 (Isololiolide)

3D MOL for NP0141222 (Isololiolide)

3D SDF for NP0141222 (Isololiolide)

3D-SDF for NP0141222 (Isololiolide)

PDB for NP0141222 (Isololiolide)

3D PDB for NP0141222 (Isololiolide)

SMILES for NP0141222 (Isololiolide)

INCHI for NP0141222 (Isololiolide)

Structure for NP0141222 (Isololiolide)

3D Structure for NP0141222 (Isololiolide)