NP-MRD: Showing NP-Card for tuberostemospiroline (NP0042821)

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Record Information

Version

1.0

Created at

2021-06-21 00:23:33 UTC

Updated at

2021-06-30 00:18:08 UTC

NP-MRD ID

NP0042821

Secondary Accession Numbers

None

Natural Product Identification

Common Name

tuberostemospiroline

Provided By

JEOL Database JEOL Logo

Description

Tuberostemospiroline 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. tuberostemospiroline is found in Stemona tuberosa. It was first documented in 2013 (PMID: 24088701). Based on a literature review a small amount of articles have been published on Tuberostemospiroline (PMID: 33848039) (PMID: 25145296).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102233D          

 36 38  0  0  0  0            999 V2000
   -4.0510    2.4957    1.4320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1237    1.7451    0.4949 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8418    2.5032    0.2028 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4234    1.9562   -1.1678 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5978    3.0072   -1.9447 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6668    2.9152   -3.4746 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0323    1.7137   -4.1018 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4879    0.3702   -3.6126 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0353    0.1036   -2.2624 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0918   -0.6543   -1.9727 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8408   -1.1935   -2.7689 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2145   -0.7275   -0.4745 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3748    0.4586   -0.0154 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7273    0.5616   -1.0722 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7048    1.7863   -1.8182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6926    1.5976   -0.8915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8476    1.3258   -1.1706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3549    3.4608    1.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9646    1.9193    1.6132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5663    2.6777    2.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9068    0.7456    0.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0901    2.3915    0.9882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0687    3.5758    0.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4460    3.0040   -1.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9849    4.0059   -1.7017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7119    2.9434   -3.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2024    3.8206   -3.8868 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1122    1.7877   -3.9220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1097    1.7688   -5.1880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5793    0.3031   -3.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0882   -0.4136   -4.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7956   -1.6776   -0.1292 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2562   -0.6358   -0.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9991    1.3602   -0.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0187    0.3069    0.9943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4835   -0.2102   -0.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
  4 15  1  6  0  0  0
 15 16  1  0  0  0  0
  4  5  1  0  0  0  0
  2  1  1  0  0  0  0
  8  7  1  0  0  0  0
 16 17  2  0  0  0  0
 14  9  1  0  0  0  0
  6  7  1  0  0  0  0
 16  2  1  0  0  0  0
  4 14  1  0  0  0  0
  9  8  1  0  0  0  0
  9 10  1  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
  5  6  1  0  0  0  0
 14 36  1  1  0  0  0
  2  3  1  0  0  0  0
 10 11  2  0  0  0  0
  4  3  1  0  0  0  0
  5 24  1  0  0  0  0
  5 25  1  0  0  0  0
  8 30  1  0  0  0  0
  8 31  1  0  0  0  0
  6 26  1  0  0  0  0
  6 27  1  0  0  0  0
  7 28  1  0  0  0  0
  7 29  1  0  0  0  0
  2 21  1  1  0  0  0
  3 22  1  0  0  0  0
  3 23  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
 12 32  1  0  0  0  0
 12 33  1  0  0  0  0
 13 34  1  0  0  0  0
 13 35  1  0  0  0  0
M  END

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
   -4.0510    2.4957    1.4320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1237    1.7451    0.4949 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8418    2.5032    0.2028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4234    1.9562   -1.1678 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5978    3.0072   -1.9447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6668    2.9152   -3.4746 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0323    1.7137   -4.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4879    0.3702   -3.6126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0353    0.1036   -2.2624 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0918   -0.6543   -1.9727 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8408   -1.1935   -2.7689 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2145   -0.7275   -0.4745 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3748    0.4586   -0.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7273    0.5616   -1.0722 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7048    1.7863   -1.8182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6926    1.5976   -0.8915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8476    1.3258   -1.1706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3549    3.4608    1.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9646    1.9193    1.6132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5663    2.6777    2.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9068    0.7456    0.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0901    2.3915    0.9882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0687    3.5758    0.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4460    3.0040   -1.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9849    4.0059   -1.7017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7119    2.9434   -3.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2024    3.8206   -3.8868 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1122    1.7877   -3.9220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1097    1.7688   -5.1880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5793    0.3031   -3.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0882   -0.4136   -4.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7956   -1.6776   -0.1292 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2562   -0.6358   -0.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9991    1.3602   -0.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0187    0.3069    0.9943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4835   -0.2102   -0.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
  4 15  1  6
 15 16  1  0
  4  5  1  0
  2  1  1  0
  8  7  1  0
 16 17  2  0
 14  9  1  0
  6  7  1  0
 16  2  1  0
  4 14  1  0
  9  8  1  0
  9 10  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
  5  6  1  0
 14 36  1  1
  2  3  1  0
 10 11  2  0
  4  3  1  0
  5 24  1  0
  5 25  1  0
  8 30  1  0
  8 31  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  2 21  1  1
  3 22  1  0
  3 23  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
M  END


  Mrv1652306212102233D          

 36 38  0  0  0  0            999 V2000
   -4.0510    2.4957    1.4320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1237    1.7451    0.4949 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8418    2.5032    0.2028 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4234    1.9562   -1.1678 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5978    3.0072   -1.9447 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6668    2.9152   -3.4746 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0323    1.7137   -4.1018 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4879    0.3702   -3.6126 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0353    0.1036   -2.2624 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0918   -0.6543   -1.9727 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8408   -1.1935   -2.7689 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2145   -0.7275   -0.4745 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3748    0.4586   -0.0154 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7273    0.5616   -1.0722 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7048    1.7863   -1.8182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6926    1.5976   -0.8915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8476    1.3258   -1.1706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3549    3.4608    1.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9646    1.9193    1.6132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5663    2.6777    2.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9068    0.7456    0.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0901    2.3915    0.9882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0687    3.5758    0.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4460    3.0040   -1.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9849    4.0059   -1.7017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7119    2.9434   -3.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2024    3.8206   -3.8868 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1122    1.7877   -3.9220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1097    1.7688   -5.1880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5793    0.3031   -3.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0882   -0.4136   -4.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7956   -1.6776   -0.1292 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2562   -0.6358   -0.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9991    1.3602   -0.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0187    0.3069    0.9943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4835   -0.2102   -0.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
  4 15  1  6  0  0  0
 15 16  1  0  0  0  0
  4  5  1  0  0  0  0
  2  1  1  0  0  0  0
  8  7  1  0  0  0  0
 16 17  2  0  0  0  0
 14  9  1  0  0  0  0
  6  7  1  0  0  0  0
 16  2  1  0  0  0  0
  4 14  1  0  0  0  0
  9  8  1  0  0  0  0
  9 10  1  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
  5  6  1  0  0  0  0
 14 36  1  1  0  0  0
  2  3  1  0  0  0  0
 10 11  2  0  0  0  0
  4  3  1  0  0  0  0
  5 24  1  0  0  0  0
  5 25  1  0  0  0  0
  8 30  1  0  0  0  0
  8 31  1  0  0  0  0
  6 26  1  0  0  0  0
  6 27  1  0  0  0  0
  7 28  1  0  0  0  0
  7 29  1  0  0  0  0
  2 21  1  1  0  0  0
  3 22  1  0  0  0  0
  3 23  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
 12 32  1  0  0  0  0
 12 33  1  0  0  0  0
 13 34  1  0  0  0  0
 13 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042821

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C([H])([H])[C@@]1([H])C(=O)O[C@]2(C1([H])[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])N1C(=O)C([H])([H])C([H])([H])[C@@]21[H]

> <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+/m1/s1

> <INCHI_KEY>
BNTLJWHMOCJBCZ-NRUUGDAUSA-N

> <FORMULA>
C13H19NO3

> <MOLECULAR_WEIGHT>
237.299

> <EXACT_MASS>
237.136493476

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
25.2555031395367

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.09

> <JCHEM_LOGP>
1.0587483933333326

> <ALOGPS_LOGS>
-1.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7617957371698444

> <JCHEM_POLAR_SURFACE_AREA>
46.61

> <JCHEM_REFRACTIVITY>
61.44020000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.28e+01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
   -4.0510    2.4957    1.4320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1237    1.7451    0.4949 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8418    2.5032    0.2028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4234    1.9562   -1.1678 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5978    3.0072   -1.9447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6668    2.9152   -3.4746 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0323    1.7137   -4.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4879    0.3702   -3.6126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0353    0.1036   -2.2624 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0918   -0.6543   -1.9727 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8408   -1.1935   -2.7689 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2145   -0.7275   -0.4745 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3748    0.4586   -0.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7273    0.5616   -1.0722 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7048    1.7863   -1.8182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6926    1.5976   -0.8915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8476    1.3258   -1.1706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3549    3.4608    1.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9646    1.9193    1.6132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5663    2.6777    2.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9068    0.7456    0.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0901    2.3915    0.9882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0687    3.5758    0.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4460    3.0040   -1.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9849    4.0059   -1.7017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7119    2.9434   -3.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2024    3.8206   -3.8868 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1122    1.7877   -3.9220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1097    1.7688   -5.1880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5793    0.3031   -3.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0882   -0.4136   -4.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7956   -1.6776   -0.1292 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2562   -0.6358   -0.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9991    1.3602   -0.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0187    0.3069    0.9943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4835   -0.2102   -0.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
  4 15  1  6
 15 16  1  0
  4  5  1  0
  2  1  1  0
  8  7  1  0
 16 17  2  0
 14  9  1  0
  6  7  1  0
 16  2  1  0
  4 14  1  0
  9  8  1  0
  9 10  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
  5  6  1  0
 14 36  1  1
  2  3  1  0
 10 11  2  0
  4  3  1  0
  5 24  1  0
  5 25  1  0
  8 30  1  0
  8 31  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  2 21  1  1
  3 22  1  0
  3 23  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  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      -4.051   2.496   1.432  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.124   1.745   0.495  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.842   2.503   0.203  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.423   1.956  -1.168  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.598   3.007  -1.945  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.667   2.915  -3.475  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.032   1.714  -4.102  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.488   0.370  -3.613  0.00  0.00           C+0
HETATM    9  N   UNK     0      -0.035   0.104  -2.262  0.00  0.00           N+0
HETATM   10  C   UNK     0       1.092  -0.654  -1.973  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.841  -1.194  -2.769  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.214  -0.728  -0.475  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.375   0.459  -0.015  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.727   0.562  -1.072  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.705   1.786  -1.818  0.00  0.00           O+0
HETATM   16  C   UNK     0      -3.693   1.598  -0.892  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.848   1.326  -1.171  0.00  0.00           O+0
HETATM   18  H   UNK     0      -4.355   3.461   1.012  0.00  0.00           H+0
HETATM   19  H   UNK     0      -4.965   1.919   1.613  0.00  0.00           H+0
HETATM   20  H   UNK     0      -3.566   2.678   2.397  0.00  0.00           H+0
HETATM   21  H   UNK     0      -2.907   0.746   0.887  0.00  0.00           H+0
HETATM   22  H   UNK     0      -1.090   2.392   0.988  0.00  0.00           H+0
HETATM   23  H   UNK     0      -2.069   3.576   0.135  0.00  0.00           H+0
HETATM   24  H   UNK     0       0.446   3.004  -1.610  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.985   4.006  -1.702  0.00  0.00           H+0
HETATM   26  H   UNK     0      -1.712   2.943  -3.806  0.00  0.00           H+0
HETATM   27  H   UNK     0      -0.202   3.821  -3.887  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.112   1.788  -3.922  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.110   1.769  -5.188  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.579   0.303  -3.654  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.088  -0.414  -4.266  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.796  -1.678  -0.129  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.256  -0.636  -0.159  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.999   1.360  -0.006  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.019   0.307   0.994  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.484  -0.210  -0.874  0.00  0.00           H+0
CONECT    1    2   18   19   20                                             
CONECT    2    1   16    3   21                                             
CONECT    3    2    4   22   23                                             
CONECT    4   15    5   14    3                                             
CONECT    5    4    6   24   25                                             
CONECT    6    7    5   26   27                                             
CONECT    7    8    6   28   29                                             
CONECT    8    7    9   30   31                                             
CONECT    9   14    8   10                                                  
CONECT   10    9   12   11                                                  
CONECT   11   10                                                            
CONECT   12   10   13   32   33                                             
CONECT   13   12   14   34   35                                             
CONECT   14    9    4   13   36                                             
CONECT   15    4   16                                                       
CONECT   16   15   17    2                                                  
CONECT   17   16                                                            
CONECT   18    1                                                            
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    2                                                            
CONECT   22    3                                                            
CONECT   23    3                                                            
CONECT   24    5                                                            
CONECT   25    5                                                            
CONECT   26    6                                                            
CONECT   27    6                                                            
CONECT   28    7                                                            
CONECT   29    7                                                            
CONECT   30    8                                                            
CONECT   31    8                                                            
CONECT   32   12                                                            
CONECT   33   12                                                            
CONECT   34   13                                                            
CONECT   35   13                                                            
CONECT   36   14                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

RDKit          3D

36 38  0  0  0  0  0  0  0  0999 V2000
   -4.0510    2.4957    1.4320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1237    1.7451    0.4949 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8418    2.5032    0.2028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4234    1.9562   -1.1678 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5978    3.0072   -1.9447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6668    2.9152   -3.4746 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0323    1.7137   -4.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4879    0.3702   -3.6126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0353    0.1036   -2.2624 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0918   -0.6543   -1.9727 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8408   -1.1935   -2.7689 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2145   -0.7275   -0.4745 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3748    0.4586   -0.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7273    0.5616   -1.0722 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7048    1.7863   -1.8182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6926    1.5976   -0.8915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8476    1.3258   -1.1706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3549    3.4608    1.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9646    1.9193    1.6132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5663    2.6777    2.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9068    0.7456    0.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0901    2.3915    0.9882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0687    3.5758    0.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4460    3.0040   -1.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9849    4.0059   -1.7017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7119    2.9434   -3.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2024    3.8206   -3.8868 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1122    1.7877   -3.9220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1097    1.7688   -5.1880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5793    0.3031   -3.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0882   -0.4136   -4.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7956   -1.6776   -0.1292 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2562   -0.6358   -0.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9991    1.3602   -0.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0187    0.3069    0.9943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4835   -0.2102   -0.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
  4 15  1  6
 15 16  1  0
  4  5  1  0
  2  1  1  0
  8  7  1  0
 16 17  2  0
 14  9  1  0
  6  7  1  0
 16  2  1  0
  4 14  1  0
  9  8  1  0
  9 10  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
  5  6  1  0
 14 36  1  1
  2  3  1  0
 10 11  2  0
  4  3  1  0
  5 24  1  0
  5 25  1  0
  8 30  1  0
  8 31  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  2 21  1  1
  3 22  1  0
  3 23  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₉NO₃

Average Mass

237.2990 Da

Monoisotopic Mass

237.13649 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

[H]C([H])([H])[C@@]1([H])C(=O)O[C@]2(C1([H])[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])N1C(=O)C([H])([H])C([H])([H])[C@@]21[H]

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+/m1/s1

InChI Key

BNTLJWHMOCJBCZ-NRUUGDAUSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, 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	Fukaya, H., et al., Chem. Pharm. Bull. 61, 1085 (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
Organoheterocyclic compound
Azacycle
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Organonitrogen compound
Organooxygen 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	1.09	ALOGPS
logP	1.06	ChemAxon
logS	-1	ALOGPS
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	25.26 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

72696119

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Guo Z, Bao R, Li Y, Li Y, Zhang J, Tang Y: Tailored Synthesis of Skeletally Diverse Stemona Alkaloids through Chemoselective Dyotropic Rearrangements of beta-Lactones. Angew Chem Int Ed Engl. 2021 Jun 21;60(26):14545-14553. doi: 10.1002/anie.202102614. Epub 2021 May 26. [PubMed:33848039 ]
Fu J, Shen H, Chang Y, Li C, Gong J, Yang Z: Concise stereoselective synthesis of oxaspirocycles with 1-tosyl-1,2,3-triazoles: application to the total syntheses of (+/-)-Tuberostemospiroline and (+/-)-stemona-lactam R. Chemistry. 2014 Sep 26;20(40):12881-8. doi: 10.1002/chem.201403756. Epub 2014 Aug 21. [PubMed:25145296 ]
Fukaya H, Hitotsuyanagi Y, Aoyagi Y, Shu Z, Komatsu K, Takeya K: Absolute structures of stemona-lactam S and tuberostemospiroline, alkaloids from stemona tuberosa. Chem Pharm Bull (Tokyo). 2013;61(10):1085-9. doi: 10.1248/cpb.c13-00454. [PubMed:24088701 ]
Fukaya, H., et al. (2013). Fukaya, H., et al., Chem. Pharm. Bull. 61, 1085 (2013). Chem. Pharm. Bull..

Showing NP-Card for tuberostemospiroline (NP0042821)

MOL for NP0042821 (tuberostemospiroline)

3D MOL for NP0042821 (tuberostemospiroline)

3D SDF for NP0042821 (tuberostemospiroline)

3D-SDF for NP0042821 (tuberostemospiroline)

PDB for NP0042821 (tuberostemospiroline)

3D PDB for NP0042821 (tuberostemospiroline)

SMILES for NP0042821 (tuberostemospiroline)

INCHI for NP0042821 (tuberostemospiroline)

Structure for NP0042821 (tuberostemospiroline)

3D Structure for NP0042821 (tuberostemospiroline)