NP-MRD: Showing NP-Card for [(3r,3ar,4s,5r,11ar)-5-(acetyloxy)-4-hydroxy-10-methyl-2-oxo-3-(piperidin-1-ylmethyl)-3h,3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylpropanoate (NP0292342)

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Record Information

Version

2.0

Created at

2022-09-09 23:49:30 UTC

Updated at

2022-09-09 23:49:30 UTC

NP-MRD ID

NP0292342

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(3r,3ar,4s,5r,11ar)-5-(acetyloxy)-4-hydroxy-10-methyl-2-oxo-3-(piperidin-1-ylmethyl)-3h,3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylpropanoate

Description

[(3R,3aR,4S,5R,11aR)-5-(acetyloxy)-4-hydroxy-10-methyl-2-oxo-3-[(piperidin-1-yl)methyl]-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-yl]methyl 2-methylpropanoate belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. [(3r,3ar,4s,5r,11ar)-5-(acetyloxy)-4-hydroxy-10-methyl-2-oxo-3-(piperidin-1-ylmethyl)-3h,3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylpropanoate is found in Blainvillea acmella. Based on a literature review very few articles have been published on [(3R,3aR,4S,5R,11aR)-5-(acetyloxy)-4-hydroxy-10-methyl-2-oxo-3-[(piperidin-1-yl)methyl]-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-yl]methyl 2-methylpropanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102201492D          

 34 36  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309102201492D          

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 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
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 26 31  1  0  0  0  0
 32 24  1  6  0  0  0
 20 32  1  0  0  0  0
 32 33  1  0  0  0  0
  5 33  1  0  0  0  0
 33 34  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0292342

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=O)OC\C1=C/CC\C(C)=C\[C@H]2OC(=O)[C@@H](CN3CCCCC3)[C@@H]2[C@H](O)[C@@H]1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H39NO7/c1-16(2)25(30)32-15-19-10-8-9-17(3)13-21-22(23(29)24(19)33-18(4)28)20(26(31)34-21)14-27-11-6-5-7-12-27/h10,13,16,20-24,29H,5-9,11-12,14-15H2,1-4H3/b17-13+,19-10+/t20-,21+,22-,23-,24+/m0/s1

> <INCHI_KEY>
KUHXICRUCMAUAH-CVMQHTFVSA-N

> <FORMULA>
C26H39NO7

> <MOLECULAR_WEIGHT>
477.598

> <EXACT_MASS>
477.2726526

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
51.84216817699756

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(3R,3aR,4S,5R,11aR)-5-(acetyloxy)-4-hydroxy-10-methyl-2-oxo-3-[(piperidin-1-yl)methyl]-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-yl]methyl 2-methylpropanoate

> <JCHEM_LOGP>
2.5336972939999978

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.730872982851135

> <JCHEM_PKA_STRONGEST_BASIC>
8.92731066777289

> <JCHEM_POLAR_SURFACE_AREA>
102.37

> <JCHEM_REFRACTIVITY>
127.84379999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(3R,3aR,4S,5R,11aR)-5-(acetyloxy)-4-hydroxy-10-methyl-2-oxo-3-(piperidin-1-ylmethyl)-3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-yl]methyl 2-methylpropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -6.637  -0.469   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.168  -0.931   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -4.834  -2.434   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -4.034   0.110   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.564  -0.352   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.430   0.689   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.341  -0.352   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.872   1.848   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.341   1.386   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.016  -0.119   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.778   1.848   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.919   0.814   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.102   3.353   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.764   2.193   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.630   3.234   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.839   2.772   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.174   1.269   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.643   0.807   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.039   0.227   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.374  -1.276   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.715  -2.033   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.409  -3.542   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.450  -4.677   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.121  -3.718   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.879  -5.059   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0      -0.096  -6.385   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0       1.444  -6.371   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.227  -7.697   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.469  -9.038   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.071  -9.052   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.853  -7.726   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.761  -2.317   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.230  -1.855   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -3.365  -2.896   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   33                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    6   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   32                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   32                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   26                                                       
CONECT   32   24   20   33                                                  
CONECT   33   32    5   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Value	Source
[(3R,3AR,4S,5R,11ar)-5-(acetyloxy)-4-hydroxy-10-methyl-2-oxo-3-[(piperidin-1-yl)methyl]-2H,3H,3ah,4H,5H,8H,9H,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylpropanoic acid	Generator

Chemical Formula

C₂₆H₃₉NO₇

Average Mass

477.5980 Da

Monoisotopic Mass

477.27265 Da

IUPAC Name

[(3R,3aR,4S,5R,11aR)-5-(acetyloxy)-4-hydroxy-10-methyl-2-oxo-3-[(piperidin-1-yl)methyl]-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-yl]methyl 2-methylpropanoate

Traditional Name

[(3R,3aR,4S,5R,11aR)-5-(acetyloxy)-4-hydroxy-10-methyl-2-oxo-3-(piperidin-1-ylmethyl)-3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-yl]methyl 2-methylpropanoate

CAS Registry Number

Not Available

SMILES

CC(C)C(=O)OC\C1=C/CC\C(C)=C\[C@H]2OC(=O)[C@@H](CN3CCCCC3)[C@@H]2[C@H](O)[C@@H]1OC(C)=O

InChI Identifier

InChI=1S/C26H39NO7/c1-16(2)25(30)32-15-19-10-8-9-17(3)13-21-22(23(29)24(19)33-18(4)28)20(26(31)34-21)14-27-11-6-5-7-12-27/h10,13,16,20-24,29H,5-9,11-12,14-15H2,1-4H3/b17-13+,19-10+/t20-,21+,22-,23-,24+/m0/s1

InChI Key

KUHXICRUCMAUAH-CVMQHTFVSA-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
Blainvillea acmella	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Germacrane sesquiterpenoid
Sesquiterpenoid
Tricarboxylic acid or derivatives
Gamma butyrolactone
Piperidine
Tetrahydrofuran
Amino acid or derivatives
Carboxylic acid ester
Lactone
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Oxacycle
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Alcohol
Organic oxide
Organooxygen compound
Organonitrogen compound
Amine
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
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	2.53	ChemAxon
pKa (Strongest Acidic)	13.73	ChemAxon
pKa (Strongest Basic)	8.93	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	102.37 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	127.84 m³·mol⁻¹	ChemAxon
Polarizability	51.84 Å³	ChemAxon
Number of Rings	3	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

163010942

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(3r,3ar,4s,5r,11ar)-5-(acetyloxy)-4-hydroxy-10-methyl-2-oxo-3-(piperidin-1-ylmethyl)-3h,3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylpropanoate (NP0292342)

MOL for NP0292342 ([(3r,3ar,4s,5r,11ar)-5-(acetyloxy)-4-hydroxy-10-methyl-2-oxo-3-(piperidin-1-ylmethyl)-3h,3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylpropanoate)

3D MOL for NP0292342 ([(3r,3ar,4s,5r,11ar)-5-(acetyloxy)-4-hydroxy-10-methyl-2-oxo-3-(piperidin-1-ylmethyl)-3h,3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylpropanoate)

3D SDF for NP0292342 ([(3r,3ar,4s,5r,11ar)-5-(acetyloxy)-4-hydroxy-10-methyl-2-oxo-3-(piperidin-1-ylmethyl)-3h,3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylpropanoate)

3D-SDF for NP0292342 ([(3r,3ar,4s,5r,11ar)-5-(acetyloxy)-4-hydroxy-10-methyl-2-oxo-3-(piperidin-1-ylmethyl)-3h,3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylpropanoate)

PDB for NP0292342 ([(3r,3ar,4s,5r,11ar)-5-(acetyloxy)-4-hydroxy-10-methyl-2-oxo-3-(piperidin-1-ylmethyl)-3h,3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylpropanoate)

3D PDB for NP0292342 ([(3r,3ar,4s,5r,11ar)-5-(acetyloxy)-4-hydroxy-10-methyl-2-oxo-3-(piperidin-1-ylmethyl)-3h,3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylpropanoate)

SMILES for NP0292342 ([(3r,3ar,4s,5r,11ar)-5-(acetyloxy)-4-hydroxy-10-methyl-2-oxo-3-(piperidin-1-ylmethyl)-3h,3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylpropanoate)

INCHI for NP0292342 ([(3r,3ar,4s,5r,11ar)-5-(acetyloxy)-4-hydroxy-10-methyl-2-oxo-3-(piperidin-1-ylmethyl)-3h,3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylpropanoate)

Structure for NP0292342 ([(3r,3ar,4s,5r,11ar)-5-(acetyloxy)-4-hydroxy-10-methyl-2-oxo-3-(piperidin-1-ylmethyl)-3h,3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylpropanoate)

3D Structure for NP0292342 ([(3r,3ar,4s,5r,11ar)-5-(acetyloxy)-4-hydroxy-10-methyl-2-oxo-3-(piperidin-1-ylmethyl)-3h,3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylpropanoate)