NP-MRD: Showing NP-Card for (2s,4s,9'ar)-4-methyl-hexahydro-1'h-spiro[oxolane-2,9'-pyrrolo[1,2-a]azepine]-3',5-dione (NP0244874)

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Record Information

Version

2.0

Created at

2022-09-07 05:46:04 UTC

Updated at

2022-09-07 05:46:04 UTC

NP-MRD ID

NP0244874

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,4s,9'ar)-4-methyl-hexahydro-1'h-spiro[oxolane-2,9'-pyrrolo[1,2-a]azepine]-3',5-dione

Description

(2S,4S,9'aR)-4-methyl-octahydrospiro[oxolane-2,9'-pyrrolo[1,2-a]azepine]-3',5-dione belongs to the class of organic compounds known as tuberostemospironine-type alkaloids. These are alkaloids with a structure that is characterized by a 2H-spiro[furan-2,9A[9H]pyrrolo[1,2-a]azepin]-\n5-one nucleus which displays a spiro gamma-lactone at C-9 of the basic ring. (2s,4s,9'ar)-4-methyl-hexahydro-1'h-spiro[oxolane-2,9'-pyrrolo[1,2-a]azepine]-3',5-dione is found in Stemona tuberosa. Based on a literature review very few articles have been published on (2S,4S,9'aR)-4-methyl-octahydrospiro[oxolane-2,9'-pyrrolo[1,2-a]azepine]-3',5-dione.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309072207462D          

 17 19  0  0  1  0            999 V2000
    5.5695    0.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7574   -0.0822    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3972   -0.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5800   -0.7113    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8676   -1.4845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4423   -2.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6245   -2.2998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0299   -1.7279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1063   -0.9065    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4628   -0.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6669   -0.6073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7550    0.3813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5790    0.3419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7961   -0.4540    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4351    0.1009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1627    0.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2759    1.3069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  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  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14  9  1  6  0  0  0
  4 14  1  0  0  0  0
  4 15  1  6  0  0  0
 15 16  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0244874

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C[C@]2(CCCCN3[C@@H]2CCC3=O)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H19NO3/c1-9-8-13(17-12(9)16)6-2-3-7-14-10(13)4-5-11(14)15/h9-10H,2-8H2,1H3/t9-,10+,13-/m0/s1

> <INCHI_KEY>
BNTLJWHMOCJBCZ-CWSCBRNRSA-N

> <FORMULA>
C13H19NO3

> <MOLECULAR_WEIGHT>
237.299

> <EXACT_MASS>
237.136493476

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
25.052296027392316

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,4S,9'aR)-4-methyl-octahydrospiro[oxolane-2,9'-pyrrolo[1,2-a]azepine]-3',5-dione

> <JCHEM_LOGP>
1.0587483933333326

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.761795737169844

> <JCHEM_POLAR_SURFACE_AREA>
46.61

> <JCHEM_REFRACTIVITY>
61.44020000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4S,9'aR)-4-methyl-hexahydro-1'H-spiro[oxolane-2,9'-pyrrolo[1,2-a]azepine]-3',5-dione

> <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      10.396   0.117   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.880  -0.153   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.208  -1.539   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.683  -1.328   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.220  -2.771   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.426  -4.091   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.899  -4.293   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.789  -3.225   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       3.932  -1.692   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       2.731  -0.728   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.245  -1.134   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.276   0.712   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.814   0.638   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.219  -0.848   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.412   0.188   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       7.770   0.914   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.982   2.439   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   14   15                                             
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9    4                                                  
CONECT   15    4   16                                                       
CONECT   16   15    2   17                                                  
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₉NO₃

Average Mass

237.2990 Da

Monoisotopic Mass

237.13649 Da

IUPAC Name

(2S,4S,9'aR)-4-methyl-octahydrospiro[oxolane-2,9'-pyrrolo[1,2-a]azepine]-3',5-dione

Traditional Name

(2S,4S,9'aR)-4-methyl-hexahydro-1'H-spiro[oxolane-2,9'-pyrrolo[1,2-a]azepine]-3',5-dione

CAS Registry Number

Not Available

SMILES

C[C@H]1C[C@]2(CCCCN3[C@@H]2CCC3=O)OC1=O

InChI Identifier

InChI=1S/C13H19NO3/c1-9-8-13(17-12(9)16)6-2-3-7-14-10(13)4-5-11(14)15/h9-10H,2-8H2,1H3/t9-,10+,13-/m0/s1

InChI Key

BNTLJWHMOCJBCZ-CWSCBRNRSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Stemona tuberosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tuberostemospironine-type alkaloids. These are alkaloids with a structure that is characterized by a 2H-spiro[furan-2,9A[9H]pyrrolo[1,2-a]azepin]-\n5-one nucleus which displays a spiro gamma-lactone at C-9 of the basic ring.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Stemona alkaloids

Sub Class

Tuberostemospironine-type alkaloids

Direct Parent

Tuberostemospironine-type alkaloids

Alternative Parents

Substituents

Tuberostemospironine backbone
Pyrroloazepine
Azepane
Gamma butyrolactone
Pyrrolidone
2-pyrrolidone
N-alkylpyrrolidine
Pyrrolidine
Tertiary carboxylic acid amide
Tetrahydrofuran
Carboxamide group
Carboxylic acid ester
Lactam
Lactone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
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	ChemAxon
pKa (Strongest Basic)	-0.76	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	46.61 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	61.44 m³·mol⁻¹	ChemAxon
Polarizability	25.05 Å³	ChemAxon
Number of Rings	3	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

163186228

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,4s,9'ar)-4-methyl-hexahydro-1'h-spiro[oxolane-2,9'-pyrrolo[1,2-a]azepine]-3',5-dione (NP0244874)

MOL for NP0244874 ((2s,4s,9'ar)-4-methyl-hexahydro-1'h-spiro[oxolane-2,9'-pyrrolo[1,2-a]azepine]-3',5-dione)

3D MOL for NP0244874 ((2s,4s,9'ar)-4-methyl-hexahydro-1'h-spiro[oxolane-2,9'-pyrrolo[1,2-a]azepine]-3',5-dione)

3D SDF for NP0244874 ((2s,4s,9'ar)-4-methyl-hexahydro-1'h-spiro[oxolane-2,9'-pyrrolo[1,2-a]azepine]-3',5-dione)

3D-SDF for NP0244874 ((2s,4s,9'ar)-4-methyl-hexahydro-1'h-spiro[oxolane-2,9'-pyrrolo[1,2-a]azepine]-3',5-dione)

PDB for NP0244874 ((2s,4s,9'ar)-4-methyl-hexahydro-1'h-spiro[oxolane-2,9'-pyrrolo[1,2-a]azepine]-3',5-dione)

3D PDB for NP0244874 ((2s,4s,9'ar)-4-methyl-hexahydro-1'h-spiro[oxolane-2,9'-pyrrolo[1,2-a]azepine]-3',5-dione)

SMILES for NP0244874 ((2s,4s,9'ar)-4-methyl-hexahydro-1'h-spiro[oxolane-2,9'-pyrrolo[1,2-a]azepine]-3',5-dione)

INCHI for NP0244874 ((2s,4s,9'ar)-4-methyl-hexahydro-1'h-spiro[oxolane-2,9'-pyrrolo[1,2-a]azepine]-3',5-dione)

Structure for NP0244874 ((2s,4s,9'ar)-4-methyl-hexahydro-1'h-spiro[oxolane-2,9'-pyrrolo[1,2-a]azepine]-3',5-dione)

3D Structure for NP0244874 ((2s,4s,9'ar)-4-methyl-hexahydro-1'h-spiro[oxolane-2,9'-pyrrolo[1,2-a]azepine]-3',5-dione)