NP-MRD: Showing NP-Card for (1s,2s,4r,8r,9s,10z,12r)-11-(hydroxymethyl)-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-5,10,13-trien-2-yl (2e)-3-(1-methylimidazol-4-yl)prop-2-enoate (NP0241469)

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Record Information

Version

2.0

Created at

2022-09-07 01:33:28 UTC

Updated at

2022-09-07 01:33:29 UTC

NP-MRD ID

NP0241469

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,4r,8r,9s,10z,12r)-11-(hydroxymethyl)-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-5,10,13-trien-2-yl (2e)-3-(1-methylimidazol-4-yl)prop-2-enoate

Description

Eleutherobin aglycon belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (1s,2s,4r,8r,9s,10z,12r)-11-(hydroxymethyl)-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-5,10,13-trien-2-yl (2e)-3-(1-methylimidazol-4-yl)prop-2-enoate is found in Erythropodium caribaeorum. Based on a literature review very few articles have been published on eleutherobin aglycon.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072203332D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309072203332D          

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 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 27 31  1  0  0  0  0
 22 31  1  0  0  0  0
 31 32  1  6  0  0  0
 32 33  2  0  0  0  0
  3 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0241469

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@]12O[C@@](C)(C=C1)[C@H](C[C@@H]1[C@H](\C=C2\CO)[C@H](CC=C1C)C(C)C)OC(=O)\C=C\C1=CN(C)C=N1

> <INCHI_IDENTIFIER>
InChI=1S/C28H38N2O5/c1-18(2)22-9-7-19(3)23-14-25(34-26(32)10-8-21-15-30(5)17-29-21)27(4)11-12-28(33-6,35-27)20(16-31)13-24(22)23/h7-8,10-13,15,17-18,22-25,31H,9,14,16H2,1-6H3/b10-8+,20-13-/t22-,23+,24-,25+,27+,28-/m1/s1

> <INCHI_KEY>
KRKBJGWABZAQHV-MMFKBRBESA-N

> <FORMULA>
C28H38N2O5

> <MOLECULAR_WEIGHT>
482.621

> <EXACT_MASS>
482.278072332

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
53.632530836815604

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,4R,8R,9S,10Z,12R)-11-(hydroxymethyl)-12-methoxy-1,5-dimethyl-8-(propan-2-yl)-15-oxatricyclo[10.2.1.0^{4,9}]pentadeca-5,10,13-trien-2-yl (2E)-3-(1-methyl-1H-imidazol-4-yl)prop-2-enoate

> <JCHEM_LOGP>
4.471791834666664

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.99918362165835

> <JCHEM_PKA_STRONGEST_BASIC>
5.946668508371407

> <JCHEM_POLAR_SURFACE_AREA>
82.81

> <JCHEM_REFRACTIVITY>
138.4509

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,4R,8R,9S,10Z,12R)-11-(hydroxymethyl)-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0^{4,9}]pentadeca-5,10,13-trien-2-yl (2E)-3-(1-methylimidazol-4-yl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      11.119   1.191   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.588   1.030   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.682   2.276   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.588   3.522   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.588   5.062   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.682   6.308   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.588   7.554   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.178   4.292   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       7.218   6.784   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.218   8.324   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       8.551   9.094   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.885   8.324   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.551  10.634   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.218  11.404   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.218  12.944   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.972  13.849   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       6.448  15.314   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       5.543  16.560   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.988  15.314   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       8.464  13.849   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       5.753   6.308   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.848   5.062   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.514   5.832   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.514   7.372   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.181   5.062   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.181   3.522   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.514   2.752   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.514   1.212   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.848   0.442   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.181   0.442   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.848   3.522   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.753   2.276   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.218   1.800   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.218   0.260   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       8.551  -0.510   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8   33                                             
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6    3                                                       
CONECT    9    6   10   21                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   15                                                       
CONECT   21    9   22                                                       
CONECT   22   21   23   31                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   31                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   27   22   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32    3   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₈N₂O₅

Average Mass

482.6210 Da

Monoisotopic Mass

482.27807 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CO[C@@]12O[C@@](C)(C=C1)[C@H](C[C@@H]1[C@H](\C=C2\CO)[C@H](CC=C1C)C(C)C)OC(=O)\C=C\C1=CN(C)C=N1

InChI Identifier

InChI=1S/C28H38N2O5/c1-18(2)22-9-7-19(3)23-14-25(34-26(32)10-8-21-15-30(5)17-29-21)27(4)11-12-28(33-6,35-27)20(16-31)13-24(22)23/h7-8,10-13,15,17-18,22-25,31H,9,14,16H2,1-6H3/b10-8+,20-13-/t22-,23+,24-,25+,27+,28-/m1/s1

InChI Key

KRKBJGWABZAQHV-MMFKBRBESA-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, 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
Erythropodium caribaeorum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Imidazolyl carboxylic acid derivative
Ketal
Fatty acid ester
N-substituted imidazole
Fatty acyl
Azole
Dihydrofuran
Imidazole
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Acetal
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Primary alcohol
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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

Not Available

Chemspider ID

8430168

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10254683

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2s,4r,8r,9s,10z,12r)-11-(hydroxymethyl)-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-5,10,13-trien-2-yl (2e)-3-(1-methylimidazol-4-yl)prop-2-enoate (NP0241469)

MOL for NP0241469 ((1s,2s,4r,8r,9s,10z,12r)-11-(hydroxymethyl)-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-5,10,13-trien-2-yl (2e)-3-(1-methylimidazol-4-yl)prop-2-enoate)

3D MOL for NP0241469 ((1s,2s,4r,8r,9s,10z,12r)-11-(hydroxymethyl)-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-5,10,13-trien-2-yl (2e)-3-(1-methylimidazol-4-yl)prop-2-enoate)

3D SDF for NP0241469 ((1s,2s,4r,8r,9s,10z,12r)-11-(hydroxymethyl)-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-5,10,13-trien-2-yl (2e)-3-(1-methylimidazol-4-yl)prop-2-enoate)

3D-SDF for NP0241469 ((1s,2s,4r,8r,9s,10z,12r)-11-(hydroxymethyl)-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-5,10,13-trien-2-yl (2e)-3-(1-methylimidazol-4-yl)prop-2-enoate)

PDB for NP0241469 ((1s,2s,4r,8r,9s,10z,12r)-11-(hydroxymethyl)-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-5,10,13-trien-2-yl (2e)-3-(1-methylimidazol-4-yl)prop-2-enoate)

3D PDB for NP0241469 ((1s,2s,4r,8r,9s,10z,12r)-11-(hydroxymethyl)-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-5,10,13-trien-2-yl (2e)-3-(1-methylimidazol-4-yl)prop-2-enoate)

SMILES for NP0241469 ((1s,2s,4r,8r,9s,10z,12r)-11-(hydroxymethyl)-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-5,10,13-trien-2-yl (2e)-3-(1-methylimidazol-4-yl)prop-2-enoate)

INCHI for NP0241469 ((1s,2s,4r,8r,9s,10z,12r)-11-(hydroxymethyl)-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-5,10,13-trien-2-yl (2e)-3-(1-methylimidazol-4-yl)prop-2-enoate)

Structure for NP0241469 ((1s,2s,4r,8r,9s,10z,12r)-11-(hydroxymethyl)-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-5,10,13-trien-2-yl (2e)-3-(1-methylimidazol-4-yl)prop-2-enoate)

3D Structure for NP0241469 ((1s,2s,4r,8r,9s,10z,12r)-11-(hydroxymethyl)-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-5,10,13-trien-2-yl (2e)-3-(1-methylimidazol-4-yl)prop-2-enoate)