NP-MRD: Showing NP-Card for Isolinderanolide (NP0337410)

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Record Information

Version

2.0

Created at

2024-09-11 10:44:08 UTC

Updated at

2024-09-11 10:44:09 UTC

NP-MRD ID

NP0337410

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isolinderanolide

Description

Isolinderanolide belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen. Isolinderanolide was first documented in 2019 (PMID: 31467511). Based on a literature review a small amount of articles have been published on Isolinderanolide (PMID: 30668381) (PMID: 34254435) (PMID: 35461015) (PMID: 34224703).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05262313162D          

 24 24  0  0  0  0            999 V2000
   -5.0172    1.9821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3695    1.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3695    0.6865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0172    0.2017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0172   -0.6883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2084   -0.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9642    0.2831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1554    0.4442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5890   -0.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7786    0.0390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2936   -0.6070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5361   -1.3343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9698   -1.9821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1610   -1.8210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0814   -1.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8901   -0.8495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4564   -1.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2653   -1.3343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5078   -0.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3183   -0.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5608    0.4442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0741    1.0920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2653    1.0920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5608    1.7395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2 24  1  0  0  0  0
  3  4  1  0  0  0  0
  3 21  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0337410

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCC\C=C1\C(O)C(=C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1/C21H36O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-19-20(22)18(2)24-21(19)23/h17,20,22H,2-16H2,1H3/b19-17-

> <INCHI_KEY>
HFEZVKMFKXUREP-ZPHPHTNENA-N

> <FORMULA>
C21H36O3

> <MOLECULAR_WEIGHT>
336.516

> <EXACT_MASS>
336.266445019

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
43.1454526383974

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3Z)-3-hexadecylidene-4-hydroxy-5-methylideneoxolan-2-one

> <JCHEM_LOGP>
6.745998268000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.966794011565566

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.310322436738188

> <JCHEM_PKA_STRONGEST_BASIC>
-3.664244015179754

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
100.74369999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3Z)-3-hexadecylidene-4-hydroxy-5-methylideneoxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0      -9.365   3.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.156   2.795   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.156   1.281   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -9.365   0.377   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.365  -1.285   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.856  -0.981   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.400   0.528   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.890   0.829   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.833  -0.228   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.320   0.073   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.415  -1.133   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.867  -2.491   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.810  -3.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.301  -3.399   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.152  -1.890   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.662  -1.586   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.719  -2.795   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.229  -2.491   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.681  -0.981   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.194  -0.681   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.647   0.829   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.738   2.038   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -4.229   2.038   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -6.647   3.247   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   24                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3                                                            
CONECT    5    6                                                            
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21    3   20   22                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24    2   22                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₃₆O₃

Average Mass

336.5160 Da

Monoisotopic Mass

336.26645 Da

IUPAC Name

(3Z)-3-hexadecylidene-4-hydroxy-5-methylideneoxolan-2-one

Traditional Name

(3Z)-3-hexadecylidene-4-hydroxy-5-methylideneoxolan-2-one

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCC\C=C1\C(O)C(=C)OC1=O

InChI Identifier

InChI=1/C21H36O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-19-20(22)18(2)24-21(19)23/h17,20,22H,2-16H2,1H3/b19-17-

InChI Key

HFEZVKMFKXUREP-ZPHPHTNENA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrahydrofurans

Sub Class

Not Available

Direct Parent

Tetrahydrofurans

Alternative Parents

Substituents

Enol ester
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Lactone
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Carbonyl group
Organooxygen compound
Organic oxygen compound
Alcohol
Organic oxide
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	6.75	ChemAxon
pKa (Strongest Acidic)	11.31	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	100.74 m³·mol⁻¹	ChemAxon
Polarizability	43.15 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

da Costa-Silva TA, Conserva GAA, Galisteo AJ Jr, Tempone AG, Lago JHG: Antileishmanial activity and immunomodulatory effect of secosubamolide, a butanolide isolated from Nectandra oppositifolia (Lauraceae). J Venom Anim Toxins Incl Trop Dis. 2019 Aug 19;25:e20190008. doi: 10.1590/1678-9199-JVATITD-2019-0008. eCollection 2019. [PubMed:31467511 ]
Conserva GAA, da Costa-Silva TA, Amaral M, Antar GM, Neves BJ, Andrade CH, Tempone AG, Lago JHG: Butenolides from Nectandra oppositifolia (Lauraceae) displayed anti-Trypanosoma cruzi activity via deregulation of mitochondria. Phytomedicine. 2019 Feb 15;54:302-307. doi: 10.1016/j.phymed.2018.09.236. Epub 2018 Oct 9. [PubMed:30668381 ]
Reis IMA, Umehara E, Conceicao RS, de M Oliveira L, Coelho Dos S Junior M, Costa-Silva TA, Amaral M, Tempone AG, Branco A, Lago JHG: gamma-Lactones from Persea americana and Persea fulva - in Vitro and in Silico Evaluation of Trypanosoma cruzi Activity. Chem Biodivers. 2021 Sep;18(9):e2100362. doi: 10.1002/cbdv.202100362. Epub 2021 Jul 29. [PubMed:34254435 ]
Rosa ME, Alves Conserva GA, Passero LFD, Lago JHG, Caseli L: Unsaturated lipids modulating the interaction of the antileishmanial isolinderanolide E with models of cellular membranes. Bioorg Chem. 2022 Jul;124:105814. doi: 10.1016/j.bioorg.2022.105814. Epub 2022 Apr 18. [PubMed:35461015 ]
Rosa ME, Alves Conserva GA, Lago JHG, Caseli L: Interaction of isolinderanolide E obtained from Nectandra oppositifolia with biomembrane models. Biochim Biophys Acta Biomembr. 2021 Oct 1;1863(10):183690. doi: 10.1016/j.bbamem.2021.183690. Epub 2021 Jul 2. [PubMed:34224703 ]

Showing NP-Card for Isolinderanolide (NP0337410)

MOL for NP0337410 (Isolinderanolide)

3D MOL for NP0337410 (Isolinderanolide)

3D SDF for NP0337410 (Isolinderanolide)

3D-SDF for NP0337410 (Isolinderanolide)

PDB for NP0337410 (Isolinderanolide)

3D PDB for NP0337410 (Isolinderanolide)

SMILES for NP0337410 (Isolinderanolide)

INCHI for NP0337410 (Isolinderanolide)

Structure for NP0337410 (Isolinderanolide)

3D Structure for NP0337410 (Isolinderanolide)