NP-MRD: Showing NP-Card for stemona-lactam R (NP0042549)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2021-06-21 00:10:53 UTC

Updated at

2021-06-30 00:17:41 UTC

NP-MRD ID

NP0042549

Secondary Accession Numbers

None

Natural Product Identification

Common Name

stemona-lactam R

Provided By

JEOL Database JEOL Logo

Description

(9R)-3'beta-Hydroxy-4'alpha-methyl-1,5,6,7,8,9abeta-hexahydrospiro[9H-pyrrolo[1,2-a]azepine-9,2'(3'H)-furan]-3,5'(2H,4'H)-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. stemona-lactam R is found in Stemona tuberosa. stemona-lactam R was first documented in 2013 (Hitotsuyanagi, Y., et al.). Based on a literature review very few articles have been published on (9R)-3'beta-Hydroxy-4'alpha-methyl-1,5,6,7,8,9abeta-hexahydrospiro[9H-pyrrolo[1,2-a]azepine-9,2'(3'H)-furan]-3,5'(2H,4'H)-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102103D          

 37 39  0  0  0  0            999 V2000
   -2.9680    1.1817   -1.4274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7997   -0.0984   -0.6256 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2202    0.0635    0.8073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2069    0.6648    1.1977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3385   -0.5658    1.6370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3419   -1.2799    0.8696 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7876   -2.7572    0.7070 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4199   -3.4018    1.9476 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4729   -3.6706    3.1134 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7698   -2.4293    3.6446 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2658   -1.9919    2.7312 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6026   -2.3439    2.8682 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0980   -3.0213    3.7525 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3580   -1.7038    1.7339 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2554   -1.4269    0.7185 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0288   -1.1319    1.5851 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3440   -0.4992   -0.4605 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8785   -1.2731   -1.5551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4578    2.0257   -0.9498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5682    1.0663   -2.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0273    1.4480   -1.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3889   -0.9001   -1.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9573   -3.3751    0.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5570   -2.8131   -0.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2661   -2.7978    2.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8508   -4.3644    1.6428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7325   -4.4224    2.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0582   -4.1151    3.9277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2954   -2.6844    4.5992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4631   -1.6051    3.8371 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1187   -2.3790    1.3353 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8210   -0.7789    2.0912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1018   -2.3226    0.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5159   -0.5996    0.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1080   -0.1078    1.9774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7151    0.3970   -0.3775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9495   -0.7365   -2.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0  0  0  0
 16 11  1  0  0  0  0
  2  3  1  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  1  0  0  0
 11 12  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7  6  1  0  0  0  0
 16 35  1  1  0  0  0
 12 13  2  0  0  0  0
  6 16  1  0  0  0  0
  7  8  1  0  0  0  0
  6 17  1  0  0  0  0
 16 15  1  0  0  0  0
  8  9  1  0  0  0  0
  3  4  2  0  0  0  0
 17  2  1  0  0  0  0
  2  1  1  0  0  0  0
 11 10  1  0  0  0  0
 17 18  1  0  0  0  0
 17 36  1  1  0  0  0
  2 22  1  6  0  0  0
  7 23  1  0  0  0  0
  7 24  1  0  0  0  0
  8 25  1  0  0  0  0
  8 26  1  0  0  0  0
  9 27  1  0  0  0  0
  9 28  1  0  0  0  0
 10 29  1  0  0  0  0
 10 30  1  0  0  0  0
 14 31  1  0  0  0  0
 14 32  1  0  0  0  0
 15 33  1  0  0  0  0
 15 34  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
 18 37  1  0  0  0  0
M  END

     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
   -2.9680    1.1817   -1.4274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7997   -0.0984   -0.6256 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2202    0.0635    0.8073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2069    0.6648    1.1977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3385   -0.5658    1.6370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3419   -1.2799    0.8696 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7876   -2.7572    0.7070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4199   -3.4018    1.9476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4729   -3.6706    3.1134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7698   -2.4293    3.6446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2658   -1.9919    2.7312 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6026   -2.3439    2.8682 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0980   -3.0213    3.7525 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3580   -1.7038    1.7339 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2554   -1.4269    0.7185 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0288   -1.1319    1.5851 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3440   -0.4992   -0.4605 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8785   -1.2731   -1.5551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4578    2.0257   -0.9498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5682    1.0663   -2.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0273    1.4480   -1.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3889   -0.9001   -1.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9573   -3.3751    0.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5570   -2.8131   -0.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2661   -2.7978    2.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8508   -4.3644    1.6428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7325   -4.4224    2.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0582   -4.1151    3.9277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2954   -2.6844    4.5992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4631   -1.6051    3.8371 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1187   -2.3790    1.3353 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8210   -0.7789    2.0912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1018   -2.3226    0.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5159   -0.5996    0.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1080   -0.1078    1.9774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7151    0.3970   -0.3775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9495   -0.7365   -2.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
 16 11  1  0
  2  3  1  0
  3  5  1  0
  6  5  1  1
 11 12  1  0
 12 14  1  0
 14 15  1  0
  7  6  1  0
 16 35  1  1
 12 13  2  0
  6 16  1  0
  7  8  1  0
  6 17  1  0
 16 15  1  0
  8  9  1  0
  3  4  2  0
 17  2  1  0
  2  1  1  0
 11 10  1  0
 17 18  1  0
 17 36  1  1
  2 22  1  6
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
 18 37  1  0
M  END


  Mrv1652306212102103D          

 37 39  0  0  0  0            999 V2000
   -2.9680    1.1817   -1.4274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7997   -0.0984   -0.6256 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2202    0.0635    0.8073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2069    0.6648    1.1977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3385   -0.5658    1.6370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3419   -1.2799    0.8696 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7876   -2.7572    0.7070 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4199   -3.4018    1.9476 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4729   -3.6706    3.1134 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7698   -2.4293    3.6446 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2658   -1.9919    2.7312 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6026   -2.3439    2.8682 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0980   -3.0213    3.7525 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3580   -1.7038    1.7339 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2554   -1.4269    0.7185 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0288   -1.1319    1.5851 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3440   -0.4992   -0.4605 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8785   -1.2731   -1.5551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4578    2.0257   -0.9498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5682    1.0663   -2.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0273    1.4480   -1.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3889   -0.9001   -1.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9573   -3.3751    0.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5570   -2.8131   -0.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2661   -2.7978    2.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8508   -4.3644    1.6428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7325   -4.4224    2.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0582   -4.1151    3.9277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2954   -2.6844    4.5992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4631   -1.6051    3.8371 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1187   -2.3790    1.3353 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8210   -0.7789    2.0912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1018   -2.3226    0.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5159   -0.5996    0.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1080   -0.1078    1.9774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7151    0.3970   -0.3775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9495   -0.7365   -2.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0  0  0  0
 16 11  1  0  0  0  0
  2  3  1  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  1  0  0  0
 11 12  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7  6  1  0  0  0  0
 16 35  1  1  0  0  0
 12 13  2  0  0  0  0
  6 16  1  0  0  0  0
  7  8  1  0  0  0  0
  6 17  1  0  0  0  0
 16 15  1  0  0  0  0
  8  9  1  0  0  0  0
  3  4  2  0  0  0  0
 17  2  1  0  0  0  0
  2  1  1  0  0  0  0
 11 10  1  0  0  0  0
 17 18  1  0  0  0  0
 17 36  1  1  0  0  0
  2 22  1  6  0  0  0
  7 23  1  0  0  0  0
  7 24  1  0  0  0  0
  8 25  1  0  0  0  0
  8 26  1  0  0  0  0
  9 27  1  0  0  0  0
  9 28  1  0  0  0  0
 10 29  1  0  0  0  0
 10 30  1  0  0  0  0
 14 31  1  0  0  0  0
 14 32  1  0  0  0  0
 15 33  1  0  0  0  0
 15 34  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
 18 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042549

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])[C@@]([H])(C(=O)O[C@@]11C([H])([H])C([H])([H])C([H])([H])C([H])([H])N2C(=O)C([H])([H])C([H])([H])[C@@]12[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C13H19NO4/c1-8-11(16)13(18-12(8)17)6-2-3-7-14-9(13)4-5-10(14)15/h8-9,11,16H,2-7H2,1H3/t8-,9-,11-,13+/m0/s1

> <INCHI_KEY>
FPBTZQXLGBERTH-LKAMGYQZSA-N

> <FORMULA>
C13H19NO4

> <MOLECULAR_WEIGHT>
253.298

> <EXACT_MASS>
253.131408096

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
26.11376983336372

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.34

> <JCHEM_LOGP>
0.1397522463333336

> <ALOGPS_LOGS>
-0.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.461799403789033

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7629914183995908

> <JCHEM_POLAR_SURFACE_AREA>
66.84

> <JCHEM_REFRACTIVITY>
62.6477

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.97e+02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
   -2.9680    1.1817   -1.4274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7997   -0.0984   -0.6256 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2202    0.0635    0.8073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2069    0.6648    1.1977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3385   -0.5658    1.6370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3419   -1.2799    0.8696 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7876   -2.7572    0.7070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4199   -3.4018    1.9476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4729   -3.6706    3.1134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7698   -2.4293    3.6446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2658   -1.9919    2.7312 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6026   -2.3439    2.8682 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0980   -3.0213    3.7525 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3580   -1.7038    1.7339 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2554   -1.4269    0.7185 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0288   -1.1319    1.5851 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3440   -0.4992   -0.4605 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8785   -1.2731   -1.5551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4578    2.0257   -0.9498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5682    1.0663   -2.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0273    1.4480   -1.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3889   -0.9001   -1.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9573   -3.3751    0.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5570   -2.8131   -0.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2661   -2.7978    2.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8508   -4.3644    1.6428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7325   -4.4224    2.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0582   -4.1151    3.9277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2954   -2.6844    4.5992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4631   -1.6051    3.8371 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1187   -2.3790    1.3353 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8210   -0.7789    2.0912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1018   -2.3226    0.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5159   -0.5996    0.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1080   -0.1078    1.9774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7151    0.3970   -0.3775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9495   -0.7365   -2.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
 16 11  1  0
  2  3  1  0
  3  5  1  0
  6  5  1  1
 11 12  1  0
 12 14  1  0
 14 15  1  0
  7  6  1  0
 16 35  1  1
 12 13  2  0
  6 16  1  0
  7  8  1  0
  6 17  1  0
 16 15  1  0
  8  9  1  0
  3  4  2  0
 17  2  1  0
  2  1  1  0
 11 10  1  0
 17 18  1  0
 17 36  1  1
  2 22  1  6
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
 18 37  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.968   1.182  -1.427  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.800  -0.098  -0.626  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.220   0.064   0.807  0.00  0.00           C+0
HETATM    4  O   UNK     0      -4.207   0.665   1.198  0.00  0.00           O+0
HETATM    5  O   UNK     0      -2.338  -0.566   1.637  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.342  -1.280   0.870  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.788  -2.757   0.707  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.420  -3.402   1.948  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.473  -3.671   3.113  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.770  -2.429   3.645  0.00  0.00           C+0
HETATM   11  N   UNK     0       0.266  -1.992   2.731  0.00  0.00           N+0
HETATM   12  C   UNK     0       1.603  -2.344   2.868  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.098  -3.021   3.753  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.358  -1.704   1.734  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.255  -1.427   0.719  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.029  -1.132   1.585  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.344  -0.499  -0.461  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.879  -1.273  -1.555  0.00  0.00           O+0
HETATM   19  H   UNK     0      -2.458   2.026  -0.950  0.00  0.00           H+0
HETATM   20  H   UNK     0      -2.568   1.066  -2.440  0.00  0.00           H+0
HETATM   21  H   UNK     0      -4.027   1.448  -1.510  0.00  0.00           H+0
HETATM   22  H   UNK     0      -3.389  -0.900  -1.084  0.00  0.00           H+0
HETATM   23  H   UNK     0      -0.957  -3.375   0.346  0.00  0.00           H+0
HETATM   24  H   UNK     0      -2.557  -2.813  -0.074  0.00  0.00           H+0
HETATM   25  H   UNK     0      -3.266  -2.798   2.296  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.851  -4.364   1.643  0.00  0.00           H+0
HETATM   27  H   UNK     0      -0.733  -4.422   2.813  0.00  0.00           H+0
HETATM   28  H   UNK     0      -2.058  -4.115   3.928  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.295  -2.684   4.599  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.463  -1.605   3.837  0.00  0.00           H+0
HETATM   31  H   UNK     0       3.119  -2.379   1.335  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.821  -0.779   2.091  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.102  -2.323   0.105  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.516  -0.600   0.052  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.108  -0.108   1.977  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.715   0.397  -0.378  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.950  -0.737  -2.365  0.00  0.00           H+0
CONECT    1    2   19   20   21                                             
CONECT    2    3   17    1   22                                             
CONECT    3    2    5    4                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   16   17                                             
CONECT    7    6    8   23   24                                             
CONECT    8    7    9   25   26                                             
CONECT    9   10    8   27   28                                             
CONECT   10    9   11   29   30                                             
CONECT   11   16   12   10                                                  
CONECT   12   11   14   13                                                  
CONECT   13   12                                                            
CONECT   14   12   15   31   32                                             
CONECT   15   14   16   33   34                                             
CONECT   16   11   35    6   15                                             
CONECT   17    6    2   18   36                                             
CONECT   18   17   37                                                       
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    2                                                            
CONECT   23    7                                                            
CONECT   24    7                                                            
CONECT   25    8                                                            
CONECT   26    8                                                            
CONECT   27    9                                                            
CONECT   28    9                                                            
CONECT   29   10                                                            
CONECT   30   10                                                            
CONECT   31   14                                                            
CONECT   32   14                                                            
CONECT   33   15                                                            
CONECT   34   15                                                            
CONECT   35   16                                                            
CONECT   36   17                                                            
CONECT   37   18                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

RDKit          3D

37 39  0  0  0  0  0  0  0  0999 V2000
   -2.9680    1.1817   -1.4274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7997   -0.0984   -0.6256 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2202    0.0635    0.8073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2069    0.6648    1.1977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3385   -0.5658    1.6370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3419   -1.2799    0.8696 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7876   -2.7572    0.7070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4199   -3.4018    1.9476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4729   -3.6706    3.1134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7698   -2.4293    3.6446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2658   -1.9919    2.7312 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6026   -2.3439    2.8682 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0980   -3.0213    3.7525 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3580   -1.7038    1.7339 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2554   -1.4269    0.7185 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0288   -1.1319    1.5851 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3440   -0.4992   -0.4605 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8785   -1.2731   -1.5551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4578    2.0257   -0.9498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5682    1.0663   -2.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0273    1.4480   -1.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3889   -0.9001   -1.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9573   -3.3751    0.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5570   -2.8131   -0.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2661   -2.7978    2.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8508   -4.3644    1.6428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7325   -4.4224    2.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0582   -4.1151    3.9277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2954   -2.6844    4.5992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4631   -1.6051    3.8371 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1187   -2.3790    1.3353 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8210   -0.7789    2.0912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1018   -2.3226    0.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5159   -0.5996    0.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1080   -0.1078    1.9774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7151    0.3970   -0.3775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9495   -0.7365   -2.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
 16 11  1  0
  2  3  1  0
  3  5  1  0
  6  5  1  1
 11 12  1  0
 12 14  1  0
 14 15  1  0
  7  6  1  0
 16 35  1  1
 12 13  2  0
  6 16  1  0
  7  8  1  0
  6 17  1  0
 16 15  1  0
  8  9  1  0
  3  4  2  0
 17  2  1  0
  2  1  1  0
 11 10  1  0
 17 18  1  0
 17 36  1  1
  2 22  1  6
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
 18 37  1  0
M  END

View in JSmol

Synonyms

Value	Source
(9R)-3'b-Hydroxy-4'a-methyl-1,5,6,7,8,9abeta-hexahydrospiro[9H-pyrrolo[1,2-a]azepine-9,2'(3'H)-furan]-3,5'(2H,4'H)-dione	Generator
(9R)-3'Β-hydroxy-4'α-methyl-1,5,6,7,8,9abeta-hexahydrospiro[9H-pyrrolo[1,2-a]azepine-9,2'(3'H)-furan]-3,5'(2H,4'H)-dione	Generator

Chemical Formula

C₁₃H₁₉NO₄

Average Mass

253.2980 Da

Monoisotopic Mass

253.13141 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])[C@@]([H])(C(=O)O[C@@]11C([H])([H])C([H])([H])C([H])([H])C([H])([H])N2C(=O)C([H])([H])C([H])([H])[C@@]12[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C13H19NO4/c1-8-11(16)13(18-12(8)17)6-2-3-7-14-9(13)4-5-10(14)15/h8-9,11,16H,2-7H2,1H3/t8-,9-,11-,13+/m0/s1

InChI Key

FPBTZQXLGBERTH-LKAMGYQZSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Stemona tuberosa	JEOL database	Hitotsuyanagi, Y., et al, Tetrahedron 69, 6297 (2013)

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
Oxolane
Pyrrolidine
Tertiary carboxylic acid amide
Carboxamide group
Carboxylic acid ester
Lactam
Lactone
Secondary alcohol
Monocarboxylic acid or derivatives
Azacycle
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Alcohol
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Organic oxygen compound
Organic oxide
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	0.34	ALOGPS
logP	0.14	ChemAxon
logS	-0.11	ALOGPS
pKa (Strongest Acidic)	13.46	ChemAxon
pKa (Strongest Basic)	-0.76	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	66.84 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	62.65 m³·mol⁻¹	ChemAxon
Polarizability	26.11 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

101449916

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hitotsuyanagi, Y., et al. (2013). Hitotsuyanagi, Y., et al, Tetrahedron 69, 6297 (2013). Tetrahedron.

Showing NP-Card for stemona-lactam R (NP0042549)

MOL for NP0042549 (stemona-lactam R)

3D MOL for NP0042549 (stemona-lactam R)

3D SDF for NP0042549 (stemona-lactam R)

3D-SDF for NP0042549 (stemona-lactam R)

PDB for NP0042549 (stemona-lactam R)

3D PDB for NP0042549 (stemona-lactam R)

SMILES for NP0042549 (stemona-lactam R)

INCHI for NP0042549 (stemona-lactam R)

Structure for NP0042549 (stemona-lactam R)

3D Structure for NP0042549 (stemona-lactam R)