NP-MRD: Showing NP-Card for n-(3-{1,14-dimethyl-6-methylidene-8,16,18-trioxapentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicos-10-en-17-yl}propyl)ethanimidic acid (NP0203638)

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Record Information

Version

2.0

Created at

2022-09-04 23:08:34 UTC

Updated at

2022-09-04 23:08:35 UTC

NP-MRD ID

NP0203638

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-(3-{1,14-dimethyl-6-methylidene-8,16,18-trioxapentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicos-10-en-17-yl}propyl)ethanimidic acid

Description

N-(3-{1,14-dimethyl-6-methylidene-8,16,18-trioxapentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]Henicos-10-en-17-yl}propyl)ethanimidic acid belongs to the class of organic compounds known as oxasteroids and derivatives. These are steroid derivatives where a carbon atom of the steroid is replaced by an oxygen atom. n-(3-{1,14-dimethyl-6-methylidene-8,16,18-trioxapentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicos-10-en-17-yl}propyl)ethanimidic acid is found in Isodon rubescens. N-(3-{1,14-dimethyl-6-methylidene-8,16,18-trioxapentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]Henicos-10-en-17-yl}propyl)ethanimidic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161514112D          

 31 35  0  0  0  0            999 V2000
   -3.0754   -1.0878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6738   -1.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0972   -2.5166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8489   -1.8210    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4474   -2.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6225   -2.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2209   -3.2749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6040   -3.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0056   -4.0081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8305   -4.0207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2538   -3.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6554   -4.0332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8523   -2.5919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2756   -1.8838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1005   -1.8963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5021   -2.6170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5535   -3.3627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0961   -3.9842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8548   -3.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7811   -2.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3052   -4.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0274   -2.5793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  2  4  1  0  0  0  0
  4  5  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
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 15 16  1  0  0  0  0
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 11 30  1  0  0  0  0
 16 30  1  0  0  0  0
 13 31  1  0  0  0  0
  8 31  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004161514112D          

 31 35  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0203638

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)NCCCC1OCC2(C)C(CCC3(C)C4CCC5C(OCC5=C)C4=CCC23)O1

> <INCHI_IDENTIFIER>
InChI=1S/C26H39NO4/c1-16-14-29-24-18(16)7-9-20-19(24)8-10-21-25(20,3)12-11-22-26(21,4)15-30-23(31-22)6-5-13-27-17(2)28/h8,18,20-24H,1,5-7,9-15H2,2-4H3,(H,27,28)

> <INCHI_KEY>
XQWVHKVUIDMQBH-UHFFFAOYSA-N

> <FORMULA>
C26H39NO4

> <MOLECULAR_WEIGHT>
429.601

> <EXACT_MASS>
429.28790874

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
50.276321595325

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-(3-{1,14-dimethyl-6-methylidene-8,16,18-trioxapentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicos-10-en-17-yl}propyl)acetamide

> <ALOGPS_LOGP>
3.43

> <JCHEM_LOGP>
2.8463888593333335

> <ALOGPS_LOGS>
-5.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.77392047585186

> <JCHEM_PKA_STRONGEST_BASIC>
-1.4143695468287425

> <JCHEM_POLAR_SURFACE_AREA>
56.790000000000006

> <JCHEM_REFRACTIVITY>
120.70279999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.47e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-(3-{1,14-dimethyl-6-methylidene-8,16,18-trioxapentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicos-10-en-17-yl}propyl)acetamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      -5.741  -2.031   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.991  -3.376   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -5.781  -4.698   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      -3.451  -3.399   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -2.702  -4.745   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.162  -4.768   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.412  -6.113   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.128  -6.137   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.877  -7.482   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.417  -7.505   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.207  -6.183   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.957  -7.529   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.458  -4.838   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.248  -3.516   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.788  -3.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.537  -4.885   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.327  -3.563   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.077  -4.908   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.867  -3.587   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.407  -3.610   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.157  -4.955   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.366  -6.277   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      11.379  -7.437   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      12.796  -6.832   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.658  -5.298   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.818  -4.285   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.827  -6.254   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.036  -7.575   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.497  -7.552   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.747  -6.207   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.918  -4.815   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   31                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   30                                             
CONECT   12   11                                                            
CONECT   13   11   14   31                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   30                                             
CONECT   17   16                                                            
CONECT   18   16   19   27                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   25                                                  
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   21   26                                                  
CONECT   26   25                                                            
CONECT   27   22   18   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   11   16                                                  
CONECT   31   13    8                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Value	Source
N-(3-{1,14-dimethyl-6-methylidene-8,16,18-trioxapentacyclo[11.8.0.0,.0,.0,]henicos-10-en-17-yl}propyl)ethanimidate	Generator
N-(3-{1,14-dimethyl-6-methylidene-8,16,18-trioxapentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicos-10-en-17-yl}propyl)ethanimidate	Generator

Chemical Formula

C₂₆H₃₉NO₄

Average Mass

429.6010 Da

Monoisotopic Mass

429.28791 Da

IUPAC Name

N-(3-{1,14-dimethyl-6-methylidene-8,16,18-trioxapentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicos-10-en-17-yl}propyl)acetamide

Traditional Name

N-(3-{1,14-dimethyl-6-methylidene-8,16,18-trioxapentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicos-10-en-17-yl}propyl)acetamide

CAS Registry Number

Not Available

SMILES

CC(=O)NCCCC1OCC2(C)C(CCC3(C)C4CCC5C(OCC5=C)C4=CCC23)O1

InChI Identifier

InChI=1S/C26H39NO4/c1-16-14-29-24-18(16)7-9-20-19(24)8-10-21-25(20,3)12-11-22-26(21,4)15-30-23(31-22)6-5-13-27-17(2)28/h8,18,20-24H,1,5-7,9-15H2,2-4H3,(H,27,28)

InChI Key

XQWVHKVUIDMQBH-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
Isodon rubescens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxasteroids and derivatives. These are steroid derivatives where a carbon atom of the steroid is replaced by an oxygen atom.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Oxasteroids and derivatives

Direct Parent

Oxasteroids and derivatives

Alternative Parents

Substituents

Delta-7-steroid
15-oxasteroid
Naphthofuran
Meta-dioxane
Acetamide
Tetrahydrofuran
Carboxamide group
Secondary carboxylic acid amide
Acetal
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Carbonyl group
Organopnictogen compound
Organic oxide
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen 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	3.43	ALOGPS
logP	2.85	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	15.77	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	56.79 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	120.7 m³·mol⁻¹	ChemAxon
Polarizability	50.28 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

85081638

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-(3-{1,14-dimethyl-6-methylidene-8,16,18-trioxapentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicos-10-en-17-yl}propyl)ethanimidic acid (NP0203638)

MOL for NP0203638 (n-(3-{1,14-dimethyl-6-methylidene-8,16,18-trioxapentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicos-10-en-17-yl}propyl)ethanimidic acid)

3D MOL for NP0203638 (n-(3-{1,14-dimethyl-6-methylidene-8,16,18-trioxapentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicos-10-en-17-yl}propyl)ethanimidic acid)

3D SDF for NP0203638 (n-(3-{1,14-dimethyl-6-methylidene-8,16,18-trioxapentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicos-10-en-17-yl}propyl)ethanimidic acid)

3D-SDF for NP0203638 (n-(3-{1,14-dimethyl-6-methylidene-8,16,18-trioxapentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicos-10-en-17-yl}propyl)ethanimidic acid)

PDB for NP0203638 (n-(3-{1,14-dimethyl-6-methylidene-8,16,18-trioxapentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicos-10-en-17-yl}propyl)ethanimidic acid)

3D PDB for NP0203638 (n-(3-{1,14-dimethyl-6-methylidene-8,16,18-trioxapentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicos-10-en-17-yl}propyl)ethanimidic acid)

SMILES for NP0203638 (n-(3-{1,14-dimethyl-6-methylidene-8,16,18-trioxapentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicos-10-en-17-yl}propyl)ethanimidic acid)

INCHI for NP0203638 (n-(3-{1,14-dimethyl-6-methylidene-8,16,18-trioxapentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicos-10-en-17-yl}propyl)ethanimidic acid)

Structure for NP0203638 (n-(3-{1,14-dimethyl-6-methylidene-8,16,18-trioxapentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicos-10-en-17-yl}propyl)ethanimidic acid)

3D Structure for NP0203638 (n-(3-{1,14-dimethyl-6-methylidene-8,16,18-trioxapentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicos-10-en-17-yl}propyl)ethanimidic acid)