NP-MRD: Showing NP-Card for 15-ethyl-9,17-dihydroxy-11-methyl-7-(4-methyl-5-oxooxolan-2-yl)-13,16-dioxa-6,18-diazapentacyclo[7.6.4.0¹,¹⁹.0⁶,¹⁹.0¹⁰,¹⁴]nonadec-17-en-12-one (NP0154543)

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Record Information

Version

2.0

Created at

2022-09-02 11:28:29 UTC

Updated at

2022-09-02 11:28:29 UTC

NP-MRD ID

NP0154543

Secondary Accession Numbers

None

Natural Product Identification

Common Name

15-ethyl-9,17-dihydroxy-11-methyl-7-(4-methyl-5-oxooxolan-2-yl)-13,16-dioxa-6,18-diazapentacyclo[7.6.4.0¹,¹⁹.0⁶,¹⁹.0¹⁰,¹⁴]nonadec-17-en-12-one

Description

15-Ethyl-9,17-dihydroxy-11-methyl-7-(4-methyl-5-oxooxolan-2-yl)-13,16-dioxa-6,18-diazapentacyclo[7.6.4.0¹,¹⁹.0⁶,¹⁹.0¹⁰,¹⁴]Nonadec-17-en-12-one belongs to the class of organic compounds known as stichoneurine-type alkaloids. These are stemona alkaloids with a structure that typically contains a 3-methyloxolan-2-one and a 5-propyloxolan-2-one moieties that are attached to the characteristic pyrrolo[1,2-a]azepine skeleton at the C3 and C9 position, respectively. 15-ethyl-9,17-dihydroxy-11-methyl-7-(4-methyl-5-oxooxolan-2-yl)-13,16-dioxa-6,18-diazapentacyclo[7.6.4.0¹,¹⁹.0⁶,¹⁹.0¹⁰,¹⁴]nonadec-17-en-12-one is found in Stemona sessilifolia. 15-Ethyl-9,17-dihydroxy-11-methyl-7-(4-methyl-5-oxooxolan-2-yl)-13,16-dioxa-6,18-diazapentacyclo[7.6.4.0¹,¹⁹.0⁶,¹⁹.0¹⁰,¹⁴]Nonadec-17-en-12-one is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251502352D          

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M  END

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M  END


  Mrv1533004251502352D          

 32 37  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0154543

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1C2OC(=O)C(C)C2C2(O)CC(C3CC(C)C(=O)O3)N3CCCCC11OC(=O)NC231

> <INCHI_IDENTIFIER>
InChI=1S/C23H32N2O7/c1-4-13-17-16(12(3)19(27)31-17)21(29)10-14(15-9-11(2)18(26)30-15)25-8-6-5-7-22(13)23(21,25)24-20(28)32-22/h11-17,29H,4-10H2,1-3H3,(H,24,28)

> <INCHI_KEY>
DZBQBBBCGRUNIN-UHFFFAOYSA-N

> <FORMULA>
C23H32N2O7

> <MOLECULAR_WEIGHT>
448.516

> <EXACT_MASS>
448.220951378

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
46.034902976690034

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
15-ethyl-9-hydroxy-11-methyl-7-(4-methyl-5-oxooxolan-2-yl)-13,16-dioxa-6,18-diazapentacyclo[7.6.4.0¹,¹⁹.0⁶,¹⁹.0¹⁰,¹⁴]nonadecane-12,17-dione

> <ALOGPS_LOGP>
1.06

> <JCHEM_LOGP>
1.929360435666666

> <ALOGPS_LOGS>
-1.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.23746433948548

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.744433566634964

> <JCHEM_PKA_STRONGEST_BASIC>
7.862630522089893

> <JCHEM_POLAR_SURFACE_AREA>
114.4

> <JCHEM_REFRACTIVITY>
109.09259999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.62e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15-ethyl-9-hydroxy-11-methyl-7-(4-methyl-5-oxooxolan-2-yl)-13,16-dioxa-6,18-diazapentacyclo[7.6.4.0¹,¹⁹.0⁶,¹⁹.0¹⁰,¹⁴]nonadecane-12,17-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       8.533   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.199   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.199   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.533   1.540   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       9.997   2.016   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      10.902   0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      12.442   0.770   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.997  -0.476   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.473  -1.941   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.533   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.199  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.445  -1.675   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.879  -2.276   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.347  -2.437   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.588  -3.777   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.225  -5.179   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.089  -6.218   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.262  -7.749   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.749  -5.459   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.347  -6.097   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       3.057  -3.950   0.000  0.00  0.00           O+0
HETATM   22  N   UNK     0       4.661  -0.960   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       3.160  -0.617   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.492   0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.160   2.157   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.661   2.500   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.865   1.540   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.401   2.016   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.495   0.770   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.955   0.770   0.000  0.00  0.00           O+0
HETATM   31  N   UNK     0       4.401  -0.476   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0       5.865   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   27                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    4   11                                                  
CONECT   11   10   12   13   32                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   22                                                  
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   15                                                       
CONECT   22   14   23   32                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26    3   28   32                                             
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   11   22   27                                             
MASTER        0    0    0    0    0    0    0    0   32    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₂N₂O₇

Average Mass

448.5160 Da

Monoisotopic Mass

448.22095 Da

IUPAC Name

15-ethyl-9-hydroxy-11-methyl-7-(4-methyl-5-oxooxolan-2-yl)-13,16-dioxa-6,18-diazapentacyclo[7.6.4.0¹,¹⁹.0⁶,¹⁹.0¹⁰,¹⁴]nonadecane-12,17-dione

Traditional Name

15-ethyl-9-hydroxy-11-methyl-7-(4-methyl-5-oxooxolan-2-yl)-13,16-dioxa-6,18-diazapentacyclo[7.6.4.0¹,¹⁹.0⁶,¹⁹.0¹⁰,¹⁴]nonadecane-12,17-dione

CAS Registry Number

Not Available

SMILES

CCC1C2OC(=O)C(C)C2C2(O)CC(C3CC(C)C(=O)O3)N3CCCCC11OC(=O)NC231

InChI Identifier

InChI=1S/C23H32N2O7/c1-4-13-17-16(12(3)19(27)31-17)21(29)10-14(15-9-11(2)18(26)30-15)25-8-6-5-7-22(13)23(21,25)24-20(28)32-22/h11-17,29H,4-10H2,1-3H3,(H,24,28)

InChI Key

DZBQBBBCGRUNIN-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
Stemona sessilifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stichoneurine-type alkaloids. These are stemona alkaloids with a structure that typically contains a 3-methyloxolan-2-one and a 5-propyloxolan-2-one moieties that are attached to the characteristic pyrrolo[1,2-a]azepine skeleton at the C3 and C9 position, respectively.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Stemona alkaloids

Sub Class

Stemoamide-type alkaloids

Direct Parent

Stichoneurine-type alkaloids

Alternative Parents

Substituents

Stichoneurine-type alkaloid
Stenine backbone
Indole or derivatives
Azepane
Dicarboxylic acid or derivatives
Gamma butyrolactone
Oxazolidinone
N-alkylpyrrolidine
Cyclic alcohol
Oxazolidine
Pyrrolidine
Carbamic acid ester
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Lactone
Carbonic acid derivative
Azacycle
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic nitrogen compound
Organopnictogen 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	1.06	ALOGPS
logP	1.93	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	11.74	ChemAxon
pKa (Strongest Basic)	7.86	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	114.4 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	109.09 m³·mol⁻¹	ChemAxon
Polarizability	46.03 Å³	ChemAxon
Number of Rings	6	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

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 15-ethyl-9,17-dihydroxy-11-methyl-7-(4-methyl-5-oxooxolan-2-yl)-13,16-dioxa-6,18-diazapentacyclo[7.6.4.0¹,¹⁹.0⁶,¹⁹.0¹⁰,¹⁴]nonadec-17-en-12-one (NP0154543)

MOL for NP0154543 (15-ethyl-9,17-dihydroxy-11-methyl-7-(4-methyl-5-oxooxolan-2-yl)-13,16-dioxa-6,18-diazapentacyclo[7.6.4.0¹,¹⁹.0⁶,¹⁹.0¹⁰,¹⁴]nonadec-17-en-12-one)

3D MOL for NP0154543 (15-ethyl-9,17-dihydroxy-11-methyl-7-(4-methyl-5-oxooxolan-2-yl)-13,16-dioxa-6,18-diazapentacyclo[7.6.4.0¹,¹⁹.0⁶,¹⁹.0¹⁰,¹⁴]nonadec-17-en-12-one)

3D SDF for NP0154543 (15-ethyl-9,17-dihydroxy-11-methyl-7-(4-methyl-5-oxooxolan-2-yl)-13,16-dioxa-6,18-diazapentacyclo[7.6.4.0¹,¹⁹.0⁶,¹⁹.0¹⁰,¹⁴]nonadec-17-en-12-one)

3D-SDF for NP0154543 (15-ethyl-9,17-dihydroxy-11-methyl-7-(4-methyl-5-oxooxolan-2-yl)-13,16-dioxa-6,18-diazapentacyclo[7.6.4.0¹,¹⁹.0⁶,¹⁹.0¹⁰,¹⁴]nonadec-17-en-12-one)

PDB for NP0154543 (15-ethyl-9,17-dihydroxy-11-methyl-7-(4-methyl-5-oxooxolan-2-yl)-13,16-dioxa-6,18-diazapentacyclo[7.6.4.0¹,¹⁹.0⁶,¹⁹.0¹⁰,¹⁴]nonadec-17-en-12-one)

3D PDB for NP0154543 (15-ethyl-9,17-dihydroxy-11-methyl-7-(4-methyl-5-oxooxolan-2-yl)-13,16-dioxa-6,18-diazapentacyclo[7.6.4.0¹,¹⁹.0⁶,¹⁹.0¹⁰,¹⁴]nonadec-17-en-12-one)

SMILES for NP0154543 (15-ethyl-9,17-dihydroxy-11-methyl-7-(4-methyl-5-oxooxolan-2-yl)-13,16-dioxa-6,18-diazapentacyclo[7.6.4.0¹,¹⁹.0⁶,¹⁹.0¹⁰,¹⁴]nonadec-17-en-12-one)

INCHI for NP0154543 (15-ethyl-9,17-dihydroxy-11-methyl-7-(4-methyl-5-oxooxolan-2-yl)-13,16-dioxa-6,18-diazapentacyclo[7.6.4.0¹,¹⁹.0⁶,¹⁹.0¹⁰,¹⁴]nonadec-17-en-12-one)

Structure for NP0154543 (15-ethyl-9,17-dihydroxy-11-methyl-7-(4-methyl-5-oxooxolan-2-yl)-13,16-dioxa-6,18-diazapentacyclo[7.6.4.0¹,¹⁹.0⁶,¹⁹.0¹⁰,¹⁴]nonadec-17-en-12-one)

3D Structure for NP0154543 (15-ethyl-9,17-dihydroxy-11-methyl-7-(4-methyl-5-oxooxolan-2-yl)-13,16-dioxa-6,18-diazapentacyclo[7.6.4.0¹,¹⁹.0⁶,¹⁹.0¹⁰,¹⁴]nonadec-17-en-12-one)