NP-MRD: Showing NP-Card for 11-(hydroxymethyl)-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-5,10,13-trien-2-yl 3-(1-methylimidazol-4-yl)prop-2-enoate (NP0194443)

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Record Information

Version

2.0

Created at

2022-09-04 12:05:57 UTC

Updated at

2022-09-04 12:05:57 UTC

NP-MRD ID

NP0194443

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

11-(Hydroxymethyl)-12-methoxy-1,5-dimethyl-8-(propan-2-yl)-15-oxatricyclo[10.2.1.0⁴,⁹]Pentadeca-5,10,13-trien-2-yl 3-(1-methyl-1H-imidazol-4-yl)prop-2-enoate belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 11-(hydroxymethyl)-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-5,10,13-trien-2-yl 3-(1-methylimidazol-4-yl)prop-2-enoate is found in Erythropodium caribaeorum. 11-(Hydroxymethyl)-12-methoxy-1,5-dimethyl-8-(propan-2-yl)-15-oxatricyclo[10.2.1.0⁴,⁹]Pentadeca-5,10,13-trien-2-yl 3-(1-methyl-1H-imidazol-4-yl)prop-2-enoate is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241506542D          

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M  END

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M  END


  Mrv1533004241506542D          

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 13 14  2  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
  9 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 28 26  1  4  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 30 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0194443

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC12OC(C)(C=C1)C(CC1C(C=C2CO)C(CC=C1C)C(C)C)OC(=O)C=CC1=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

> <INCHI_KEY>
KRKBJGWABZAQHV-UHFFFAOYSA-N

> <FORMULA>
C28H38N2O5

> <MOLECULAR_WEIGHT>
482.621

> <EXACT_MASS>
482.278072332

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
53.15779368878598

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
11-(hydroxymethyl)-12-methoxy-1,5-dimethyl-8-(propan-2-yl)-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-5,10,13-trien-2-yl 3-(1-methyl-1H-imidazol-4-yl)prop-2-enoate

> <ALOGPS_LOGP>
3.99

> <JCHEM_LOGP>
4.471791834666664

> <ALOGPS_LOGS>
-5.18

> <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>
82.81000000000002

> <JCHEM_REFRACTIVITY>
138.45089999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.20e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       8.961  -0.376   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  O   UNK     0       8.178   4.292   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.682   6.308   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.588   7.554   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.588   5.062   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.588   3.522   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.218   6.784   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.753   6.308   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.848   5.062   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.848   3.522   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.753   2.276   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.218   1.800   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.218   0.260   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.884  -0.510   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.514   2.752   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.181   3.522   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.181   5.062   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.514   5.832   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.514   7.372   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.514   1.212   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.181   0.442   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.848   0.442   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.218   8.324   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.884   9.094   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.550   8.324   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.884  10.634   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.550  11.404   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.550  12.944   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.305  13.849   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0       3.780  15.314   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0       2.875  16.560   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.320  15.314   0.000  0.00  0.00           C+0
HETATM   35  N   UNK     0       5.796  13.849   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8   14                                             
CONECT    4    3    5                                                       
CONECT    5    4    6    7    9                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    3                                                       
CONECT    9    5   10   25                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   20                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13    3   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   12   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   11   21                                                  
CONECT   21   20                                                            
CONECT   22   17   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25    9   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   30                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
11-(Hydroxymethyl)-12-methoxy-1,5-dimethyl-8-(propan-2-yl)-15-oxatricyclo[10.2.1.0,]pentadeca-5,10,13-trien-2-yl 3-(1-methyl-1H-imidazol-4-yl)prop-2-enoic acid	Generator
11-(Hydroxymethyl)-12-methoxy-1,5-dimethyl-8-(propan-2-yl)-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-5,10,13-trien-2-yl 3-(1-methyl-1H-imidazol-4-yl)prop-2-enoic acid	Generator

Chemical Formula

C₂₈H₃₈N₂O₅

Average Mass

482.6210 Da

Monoisotopic Mass

482.27807 Da

IUPAC Name

11-(hydroxymethyl)-12-methoxy-1,5-dimethyl-8-(propan-2-yl)-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-5,10,13-trien-2-yl 3-(1-methyl-1H-imidazol-4-yl)prop-2-enoate

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC12OC(C)(C=C1)C(CC1C(C=C2CO)C(CC=C1C)C(C)C)OC(=O)C=CC1=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

InChI Key

KRKBJGWABZAQHV-UHFFFAOYSA-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
logP	3.99	ALOGPS
logP	4.47	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	15	ChemAxon
pKa (Strongest Basic)	5.95	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	82.81 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	138.45 m³·mol⁻¹	ChemAxon
Polarizability	53.16 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

LOTUS database [Link]

Showing NP-Card for 11-(hydroxymethyl)-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-5,10,13-trien-2-yl 3-(1-methylimidazol-4-yl)prop-2-enoate (NP0194443)

MOL for NP0194443 (11-(hydroxymethyl)-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-5,10,13-trien-2-yl 3-(1-methylimidazol-4-yl)prop-2-enoate)

3D MOL for NP0194443 (11-(hydroxymethyl)-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-5,10,13-trien-2-yl 3-(1-methylimidazol-4-yl)prop-2-enoate)

3D SDF for NP0194443 (11-(hydroxymethyl)-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-5,10,13-trien-2-yl 3-(1-methylimidazol-4-yl)prop-2-enoate)

3D-SDF for NP0194443 (11-(hydroxymethyl)-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-5,10,13-trien-2-yl 3-(1-methylimidazol-4-yl)prop-2-enoate)

PDB for NP0194443 (11-(hydroxymethyl)-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-5,10,13-trien-2-yl 3-(1-methylimidazol-4-yl)prop-2-enoate)

3D PDB for NP0194443 (11-(hydroxymethyl)-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-5,10,13-trien-2-yl 3-(1-methylimidazol-4-yl)prop-2-enoate)

SMILES for NP0194443 (11-(hydroxymethyl)-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-5,10,13-trien-2-yl 3-(1-methylimidazol-4-yl)prop-2-enoate)

INCHI for NP0194443 (11-(hydroxymethyl)-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-5,10,13-trien-2-yl 3-(1-methylimidazol-4-yl)prop-2-enoate)

Structure for NP0194443 (11-(hydroxymethyl)-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-5,10,13-trien-2-yl 3-(1-methylimidazol-4-yl)prop-2-enoate)

3D Structure for NP0194443 (11-(hydroxymethyl)-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-5,10,13-trien-2-yl 3-(1-methylimidazol-4-yl)prop-2-enoate)