NP-MRD: Showing NP-Card for (6r,9s,13r)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-en-16-yl acetate (NP0244405)

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Record Information

Version

2.0

Created at

2022-09-07 05:11:34 UTC

Updated at

2022-09-07 05:11:34 UTC

NP-MRD ID

NP0244405

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6r,9s,13r)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-en-16-yl acetate

Description

Spirosol-5-en-3-yl acetate belongs to the class of organic compounds known as spirosolanes and derivatives. These are steroidal alkaloids with a structure containing a spirosolane skeleton. Siporosolane is a polycyclic compound that is characterized by a 1-oxa-6-azaspiro[4.5]Decane moiety where the oxolane ring is fused to a docosahydronaphth[2,1:4',5']Indene ring system. Spirosolane arises from the conversion of a cholestane side-chain into a bicyclic system containing a piperidine and a tetrahydrofuran ring. (6r,9s,13r)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-en-16-yl acetate is found in Solanum umbelliferum. Based on a literature review very few articles have been published on Spirosol-5-en-3-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072207112D          

 33 38  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309072207112D          

 33 38  0  0  1  0            999 V2000
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  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 18 24  1  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 16 27  1  0  0  0  0
 27 28  1  0  0  0  0
 14 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 13 32  1  0  0  0  0
  8 32  1  0  0  0  0
 10 33  1  0  0  0  0
  5 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0244405

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2C(CC3C4CC=C5CC(CC[C@]5(C)C4CC[C@]23C)OC(C)=O)O[C@]11CCC(C)CN1

> <INCHI_IDENTIFIER>
InChI=1S/C29H45NO3/c1-17-8-13-29(30-16-17)18(2)26-25(33-29)15-24-22-7-6-20-14-21(32-19(3)31)9-11-27(20,4)23(22)10-12-28(24,26)5/h6,17-18,21-26,30H,7-16H2,1-5H3/t17?,18?,21?,22?,23?,24?,25?,26?,27-,28-,29+/m0/s1

> <INCHI_KEY>
MCQNPWNREVNWDQ-YYQHPOQZSA-N

> <FORMULA>
C29H45NO3

> <MOLECULAR_WEIGHT>
455.683

> <EXACT_MASS>
455.339944313

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
53.70855447673879

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6R,9S,13R)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane-6,2'-piperidin]-18-en-16-yl acetate

> <JCHEM_LOGP>
5.051002957666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.541647885597499

> <JCHEM_POLAR_SURFACE_AREA>
47.56

> <JCHEM_REFRACTIVITY>
131.0983

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(6R,9S,13R)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane-6,2'-piperidin]-18-en-16-yl acetate

> <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       0.031   0.105   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.569   0.015   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.415   1.302   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.260  -1.361   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.797  -1.451   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.489  -2.827   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.026  -2.916   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.872  -1.629   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.563  -3.006   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.181  -0.253   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.027   1.033   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.565   0.944   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.256  -0.432   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.793  -0.522   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.888   0.561   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.256  -0.146   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      14.779   0.086   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      15.470  -1.290   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.446  -0.099   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.966  -0.349   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      18.509  -1.790   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      20.029  -2.039   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      17.533  -2.981   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0      16.014  -2.731   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0      14.375  -2.373   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.607  -3.895   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.007  -1.666   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.484  -1.898   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.316  -3.194   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.638  -3.185   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.101  -3.095   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.410  -1.719   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.644  -0.164   0.000  0.00  0.00           C+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                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   32                                             
CONECT    9    8                                                            
CONECT   10    8   11   33                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   32                                                  
CONECT   14   13   15   28                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   27                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   24   25                                             
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   18                                                       
CONECT   25   18   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   16   28                                                  
CONECT   28   27   14   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   13    8                                                  
CONECT   33   10    5                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   76    0
END

View in JSmol

Synonyms

Value	Source
Spirosol-5-en-3-yl acetic acid	Generator

Chemical Formula

C₂₉H₄₅NO₃

Average Mass

455.6830 Da

Monoisotopic Mass

455.33994 Da

IUPAC Name

(6R,9S,13R)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane-6,2'-piperidin]-18-en-16-yl acetate

Traditional Name

(6R,9S,13R)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane-6,2'-piperidin]-18-en-16-yl acetate

CAS Registry Number

Not Available

SMILES

CC1C2C(CC3C4CC=C5CC(CC[C@]5(C)C4CC[C@]23C)OC(C)=O)O[C@]11CCC(C)CN1

InChI Identifier

InChI=1S/C29H45NO3/c1-17-8-13-29(30-16-17)18(2)26-25(33-29)15-24-22-7-6-20-14-21(32-19(3)31)9-11-27(20,4)23(22)10-12-28(24,26)5/h6,17-18,21-26,30H,7-16H2,1-5H3/t17?,18?,21?,22?,23?,24?,25?,26?,27-,28-,29+/m0/s1

InChI Key

MCQNPWNREVNWDQ-YYQHPOQZSA-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
Solanum umbelliferum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as spirosolanes and derivatives. These are steroidal alkaloids with a structure containing a spirosolane skeleton. Siporosolane is a polycyclic compound that is characterized by a 1-oxa-6-azaspiro[4.5]Decane moiety where the oxolane ring is fused to a docosahydronaphth[2,1:4',5']Indene ring system. Spirosolane arises from the conversion of a cholestane side-chain into a bicyclic system containing a piperidine and a tetrahydrofuran ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal alkaloids

Direct Parent

Spirosolanes and derivatives

Alternative Parents

Substituents

Spirosolane skeleton
Steroid ester
Delta-5-steroid
Azasteroid
Azaspirodecane
Alkaloid or derivatives
Piperidine
Tetrahydrofuran
Hemiaminal
Carboxylic acid ester
Amino acid or derivatives
Oxacycle
Azacycle
Organoheterocyclic compound
Secondary amine
Monocarboxylic acid or derivatives
Secondary aliphatic amine
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
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	5.05	ChemAxon
pKa (Strongest Basic)	9.54	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	47.56 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	131.1 m³·mol⁻¹	ChemAxon
Polarizability	53.71 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

139291958

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (6r,9s,13r)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-en-16-yl acetate (NP0244405)

MOL for NP0244405 ((6r,9s,13r)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-en-16-yl acetate)

3D MOL for NP0244405 ((6r,9s,13r)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-en-16-yl acetate)

3D SDF for NP0244405 ((6r,9s,13r)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-en-16-yl acetate)

3D-SDF for NP0244405 ((6r,9s,13r)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-en-16-yl acetate)

PDB for NP0244405 ((6r,9s,13r)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-en-16-yl acetate)

3D PDB for NP0244405 ((6r,9s,13r)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-en-16-yl acetate)

SMILES for NP0244405 ((6r,9s,13r)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-en-16-yl acetate)

INCHI for NP0244405 ((6r,9s,13r)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-en-16-yl acetate)

Structure for NP0244405 ((6r,9s,13r)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-en-16-yl acetate)

3D Structure for NP0244405 ((6r,9s,13r)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-en-16-yl acetate)