NP-MRD: Showing NP-Card for 14beta-hydroxy-13,14-dihydronorsecurinine (NP0039070)

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Record Information

Version

2.0

Created at

2021-06-20 21:36:10 UTC

Updated at

2021-06-30 00:12:12 UTC

NP-MRD ID

NP0039070

Secondary Accession Numbers

None

Natural Product Identification

Common Name

14beta-hydroxy-13,14-dihydronorsecurinine

Provided By

JEOL Database JEOL Logo

Description

15Beta-Hydroxy-14,15-dihydro-6-norsecurinan-11-one belongs to the class of organic compounds known as pyrrolizidines. Pyrrolizidines are compounds containing a pyrrolizidine, which is a bicyclic ring system made up of two fused pyrrolidine ring sharing a nitrogen atom. 14beta-hydroxy-13,14-dihydronorsecurinine is found in Flueggea leucopyra. 14beta-hydroxy-13,14-dihydronorsecurinine was first documented in 2010 (Wang, G.-c., et al.). Based on a literature review very few articles have been published on 15beta-Hydroxy-14,15-dihydro-6-norsecurinan-11-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123363D          

 31 34  0  0  0  0            999 V2000
    2.2867   -4.9613    1.1380 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9660   -3.7943    1.0110 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4445   -2.9514    2.0913 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2310   -1.7543    1.5551 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6851   -0.4982    2.1529 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1596    0.3070    1.1340 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0737    1.6985    1.4530 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2810    0.1076   -0.3523 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3299   -1.3831   -0.6766 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5775   -1.7618    0.1062 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0315   -3.0752   -0.1478 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5547   -0.6309   -0.2637 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3682   -0.8453   -1.5368 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3765    0.5295   -2.1732 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9706    1.0235   -1.8917 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6921    0.5780   -0.5140 N   0  0  1  0  0  0  0  0  0  0  0  0
    1.2895   -3.2948    3.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5229    0.1190    2.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0793   -0.7131    3.0410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2111    0.0117    1.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7626    1.9999    1.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4041    0.6661   -1.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4562   -1.5750   -1.7488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5685   -1.9241   -0.3571 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2435   -0.4044    0.5603 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8882   -1.5629   -2.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3804   -1.2029   -1.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1190    1.1730   -1.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6006    0.4903   -3.2430 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8983    2.1122   -1.9722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2806    0.5802   -2.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
  2 11  1  0  0  0  0
 10 11  1  6  0  0  0
  6  5  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  0  0  0  0
 10  4  1  0  0  0  0
 12 25  1  1  0  0  0
 16  8  1  0  0  0  0
  2  1  2  0  0  0  0
 12 10  1  0  0  0  0
  6  7  1  0  0  0  0
 16 12  1  0  0  0  0
  8  6  1  0  0  0  0
  4  5  1  0  0  0  0
  4  3  2  0  0  0  0
  3  2  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
  8 22  1  6  0  0  0
  6 20  1  6  0  0  0
  5 18  1  0  0  0  0
  5 19  1  0  0  0  0
  3 17  1  0  0  0  0
  9 23  1  0  0  0  0
  9 24  1  0  0  0  0
  7 21  1  0  0  0  0
 13 26  1  0  0  0  0
 13 27  1  0  0  0  0
 14 28  1  0  0  0  0
 14 29  1  0  0  0  0
 15 30  1  0  0  0  0
 15 31  1  0  0  0  0
M  END

     RDKit          3D

 31 34  0  0  0  0  0  0  0  0999 V2000
    2.2867   -4.9613    1.1380 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9660   -3.7943    1.0110 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4445   -2.9514    2.0913 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2310   -1.7543    1.5551 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6851   -0.4982    2.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1596    0.3070    1.1340 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0737    1.6985    1.4530 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2810    0.1076   -0.3523 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3299   -1.3831   -0.6766 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5775   -1.7618    0.1062 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0315   -3.0752   -0.1478 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5547   -0.6309   -0.2637 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3682   -0.8453   -1.5368 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3765    0.5295   -2.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9706    1.0235   -1.8917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6921    0.5780   -0.5140 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2895   -3.2948    3.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5229    0.1190    2.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0793   -0.7131    3.0410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2111    0.0117    1.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7626    1.9999    1.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4041    0.6661   -1.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4562   -1.5750   -1.7488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5685   -1.9241   -0.3571 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2435   -0.4044    0.5603 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8882   -1.5629   -2.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3804   -1.2029   -1.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1190    1.1730   -1.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6006    0.4903   -3.2430 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8983    2.1122   -1.9722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2806    0.5802   -2.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
  2 11  1  0
 10 11  1  6
  6  5  1  0
  8  9  1  0
 10  9  1  0
 10  4  1  0
 12 25  1  1
 16  8  1  0
  2  1  2  0
 12 10  1  0
  6  7  1  0
 16 12  1  0
  8  6  1  0
  4  5  1  0
  4  3  2  0
  3  2  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  8 22  1  6
  6 20  1  6
  5 18  1  0
  5 19  1  0
  3 17  1  0
  9 23  1  0
  9 24  1  0
  7 21  1  0
 13 26  1  0
 13 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
M  END


  Mrv1652306202123363D          

 31 34  0  0  0  0            999 V2000
    2.2867   -4.9613    1.1380 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9660   -3.7943    1.0110 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4445   -2.9514    2.0913 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2310   -1.7543    1.5551 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6851   -0.4982    2.1529 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1596    0.3070    1.1340 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0737    1.6985    1.4530 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2810    0.1076   -0.3523 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3299   -1.3831   -0.6766 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5775   -1.7618    0.1062 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0315   -3.0752   -0.1478 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5547   -0.6309   -0.2637 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3682   -0.8453   -1.5368 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3765    0.5295   -2.1732 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9706    1.0235   -1.8917 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6921    0.5780   -0.5140 N   0  0  1  0  0  0  0  0  0  0  0  0
    1.2895   -3.2948    3.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5229    0.1190    2.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0793   -0.7131    3.0410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2111    0.0117    1.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7626    1.9999    1.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4041    0.6661   -1.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4562   -1.5750   -1.7488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5685   -1.9241   -0.3571 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2435   -0.4044    0.5603 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8882   -1.5629   -2.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3804   -1.2029   -1.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1190    1.1730   -1.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6006    0.4903   -3.2430 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8983    2.1122   -1.9722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2806    0.5802   -2.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
  2 11  1  0  0  0  0
 10 11  1  6  0  0  0
  6  5  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  0  0  0  0
 10  4  1  0  0  0  0
 12 25  1  1  0  0  0
 16  8  1  0  0  0  0
  2  1  2  0  0  0  0
 12 10  1  0  0  0  0
  6  7  1  0  0  0  0
 16 12  1  0  0  0  0
  8  6  1  0  0  0  0
  4  5  1  0  0  0  0
  4  3  2  0  0  0  0
  3  2  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
  8 22  1  6  0  0  0
  6 20  1  6  0  0  0
  5 18  1  0  0  0  0
  5 19  1  0  0  0  0
  3 17  1  0  0  0  0
  9 23  1  0  0  0  0
  9 24  1  0  0  0  0
  7 21  1  0  0  0  0
 13 26  1  0  0  0  0
 13 27  1  0  0  0  0
 14 28  1  0  0  0  0
 14 29  1  0  0  0  0
 15 30  1  0  0  0  0
 15 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0039070

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])C([H])([H])C2=C([H])C(=O)O[C@@]22C([H])([H])[C@]1([H])N1C([H])([H])C([H])([H])C([H])([H])[C@]21[H]

> <INCHI_IDENTIFIER>
InChI=1S/C12H15NO3/c14-9-4-7-5-11(15)16-12(7)6-8(9)13-3-1-2-10(12)13/h5,8-10,14H,1-4,6H2/t8-,9+,10+,12-/m0/s1

> <INCHI_KEY>
WZQDMBYSKYYFPZ-XNDJQWLSSA-N

> <FORMULA>
C12H15NO3

> <MOLECULAR_WEIGHT>
221.256

> <EXACT_MASS>
221.105193347

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
22.529513415538474

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,7R,8S,13R)-7-hydroxy-2-oxa-9-azatetracyclo[6.5.1.0^{1,5}.0^{9,13}]tetradec-4-en-3-one

> <ALOGPS_LOGP>
0.19

> <JCHEM_LOGP>
0.0920557436666671

> <ALOGPS_LOGS>
0.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.440329887274732

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.104608273124974

> <JCHEM_PKA_STRONGEST_BASIC>
9.487028668749339

> <JCHEM_POLAR_SURFACE_AREA>
49.77

> <JCHEM_REFRACTIVITY>
57.117000000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.28e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,7R,8S,13R)-7-hydroxy-2-oxa-9-azatetracyclo[6.5.1.0^{1,5}.0^{9,13}]tetradec-4-en-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 31 34  0  0  0  0  0  0  0  0999 V2000
    2.2867   -4.9613    1.1380 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9660   -3.7943    1.0110 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4445   -2.9514    2.0913 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2310   -1.7543    1.5551 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6851   -0.4982    2.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1596    0.3070    1.1340 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0737    1.6985    1.4530 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2810    0.1076   -0.3523 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3299   -1.3831   -0.6766 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5775   -1.7618    0.1062 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0315   -3.0752   -0.1478 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5547   -0.6309   -0.2637 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3682   -0.8453   -1.5368 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3765    0.5295   -2.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9706    1.0235   -1.8917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6921    0.5780   -0.5140 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2895   -3.2948    3.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5229    0.1190    2.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0793   -0.7131    3.0410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2111    0.0117    1.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7626    1.9999    1.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4041    0.6661   -1.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4562   -1.5750   -1.7488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5685   -1.9241   -0.3571 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2435   -0.4044    0.5603 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8882   -1.5629   -2.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3804   -1.2029   -1.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1190    1.1730   -1.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6006    0.4903   -3.2430 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8983    2.1122   -1.9722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2806    0.5802   -2.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
  2 11  1  0
 10 11  1  6
  6  5  1  0
  8  9  1  0
 10  9  1  0
 10  4  1  0
 12 25  1  1
 16  8  1  0
  2  1  2  0
 12 10  1  0
  6  7  1  0
 16 12  1  0
  8  6  1  0
  4  5  1  0
  4  3  2  0
  3  2  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  8 22  1  6
  6 20  1  6
  5 18  1  0
  5 19  1  0
  3 17  1  0
  9 23  1  0
  9 24  1  0
  7 21  1  0
 13 26  1  0
 13 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  O   UNK     0       2.287  -4.961   1.138  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.966  -3.794   1.011  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.444  -2.951   2.091  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.231  -1.754   1.555  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.685  -0.498   2.153  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.160   0.307   1.134  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.074   1.698   1.453  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.281   0.108  -0.352  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.330  -1.383  -0.677  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.577  -1.762   0.106  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.031  -3.075  -0.148  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.555  -0.631  -0.264  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.368  -0.845  -1.537  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.377   0.530  -2.173  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.971   1.024  -1.892  0.00  0.00           C+0
HETATM   16  N   UNK     0       1.692   0.578  -0.514  0.00  0.00           N+0
HETATM   17  H   UNK     0       1.290  -3.295   3.098  0.00  0.00           H+0
HETATM   18  H   UNK     0       1.523   0.119   2.502  0.00  0.00           H+0
HETATM   19  H   UNK     0       0.079  -0.713   3.041  0.00  0.00           H+0
HETATM   20  H   UNK     0      -1.211   0.012   1.232  0.00  0.00           H+0
HETATM   21  H   UNK     0       0.763   2.000   1.042  0.00  0.00           H+0
HETATM   22  H   UNK     0      -0.404   0.666  -1.001  0.00  0.00           H+0
HETATM   23  H   UNK     0       0.456  -1.575  -1.749  0.00  0.00           H+0
HETATM   24  H   UNK     0      -0.569  -1.924  -0.357  0.00  0.00           H+0
HETATM   25  H   UNK     0       3.244  -0.404   0.560  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.888  -1.563  -2.212  0.00  0.00           H+0
HETATM   27  H   UNK     0       4.380  -1.203  -1.325  0.00  0.00           H+0
HETATM   28  H   UNK     0       4.119   1.173  -1.686  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.601   0.490  -3.243  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.898   2.112  -1.972  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.281   0.580  -2.621  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2   11    1    3                                                  
CONECT    3    4    2   17                                                  
CONECT    4   10    5    3                                                  
CONECT    5    6    4   18   19                                             
CONECT    6    5    7    8   20                                             
CONECT    7    6   21                                                       
CONECT    8    9   16    6   22                                             
CONECT    9    8   10   23   24                                             
CONECT   10   11    9    4   12                                             
CONECT   11    2   10                                                       
CONECT   12   25   10   16   13                                             
CONECT   13   12   14   26   27                                             
CONECT   14   13   15   28   29                                             
CONECT   15   14   16   30   31                                             
CONECT   16    8   12   15                                                  
CONECT   17    3                                                            
CONECT   18    5                                                            
CONECT   19    5                                                            
CONECT   20    6                                                            
CONECT   21    7                                                            
CONECT   22    8                                                            
CONECT   23    9                                                            
CONECT   24    9                                                            
CONECT   25   12                                                            
CONECT   26   13                                                            
CONECT   27   13                                                            
CONECT   28   14                                                            
CONECT   29   14                                                            
CONECT   30   15                                                            
CONECT   31   15                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

RDKit          3D

31 34  0  0  0  0  0  0  0  0999 V2000
    2.2867   -4.9613    1.1380 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9660   -3.7943    1.0110 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4445   -2.9514    2.0913 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2310   -1.7543    1.5551 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6851   -0.4982    2.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1596    0.3070    1.1340 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0737    1.6985    1.4530 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2810    0.1076   -0.3523 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3299   -1.3831   -0.6766 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5775   -1.7618    0.1062 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0315   -3.0752   -0.1478 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5547   -0.6309   -0.2637 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3682   -0.8453   -1.5368 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3765    0.5295   -2.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9706    1.0235   -1.8917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6921    0.5780   -0.5140 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2895   -3.2948    3.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5229    0.1190    2.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0793   -0.7131    3.0410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2111    0.0117    1.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7626    1.9999    1.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4041    0.6661   -1.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4562   -1.5750   -1.7488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5685   -1.9241   -0.3571 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2435   -0.4044    0.5603 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8882   -1.5629   -2.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3804   -1.2029   -1.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1190    1.1730   -1.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6006    0.4903   -3.2430 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8983    2.1122   -1.9722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2806    0.5802   -2.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
  2 11  1  0
 10 11  1  6
  6  5  1  0
  8  9  1  0
 10  9  1  0
 10  4  1  0
 12 25  1  1
 16  8  1  0
  2  1  2  0
 12 10  1  0
  6  7  1  0
 16 12  1  0
  8  6  1  0
  4  5  1  0
  4  3  2  0
  3  2  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  8 22  1  6
  6 20  1  6
  5 18  1  0
  5 19  1  0
  3 17  1  0
  9 23  1  0
  9 24  1  0
  7 21  1  0
 13 26  1  0
 13 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
M  END

View in JSmol

Synonyms

Value	Source
15b-Hydroxy-14,15-dihydro-6-norsecurinan-11-one	Generator
15Β-hydroxy-14,15-dihydro-6-norsecurinan-11-one	Generator

Chemical Formula

C₁₂H₁₅NO₃

Average Mass

221.2560 Da

Monoisotopic Mass

221.10519 Da

IUPAC Name

(1S,7R,8S,13R)-7-hydroxy-2-oxa-9-azatetracyclo[6.5.1.0^{1,5}.0^{9,13}]tetradec-4-en-3-one

Traditional Name

(1S,7R,8S,13R)-7-hydroxy-2-oxa-9-azatetracyclo[6.5.1.0^{1,5}.0^{9,13}]tetradec-4-en-3-one

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])C([H])([H])C2=C([H])C(=O)O[C@@]22C([H])([H])[C@]1([H])N1C([H])([H])C([H])([H])C([H])([H])[C@]21[H]

InChI Identifier

InChI=1S/C12H15NO3/c14-9-4-7-5-11(15)16-12(7)6-8(9)13-3-1-2-10(12)13/h5,8-10,14H,1-4,6H2/t8-,9+,10+,12-/m0/s1

InChI Key

WZQDMBYSKYYFPZ-XNDJQWLSSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, 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
Flueggea leucopyra	JEOL database	Wang, G.-c., et al, Chem. Pharm. Bull. 58, 390 (2010)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrolizidines. Pyrrolizidines are compounds containing a pyrrolizidine, which is a bicyclic ring system made up of two fused pyrrolidine ring sharing a nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolizidines

Sub Class

Not Available

Direct Parent

Pyrrolizidines

Alternative Parents

Substituents

Pyrrolizidine
Azepane
N-alkylpyrrolidine
2-furanone
Dihydrofuran
Cyclic alcohol
Pyrrolidine
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
1,2-aminoalcohol
Lactone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Azacycle
Oxacycle
Carboxylic acid derivative
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
Alcohol
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	0.19	ALOGPS
logP	0.092	ChemAxon
logS	0.01	ALOGPS
pKa (Strongest Acidic)	14.1	ChemAxon
pKa (Strongest Basic)	9.49	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.77 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	57.12 m³·mol⁻¹	ChemAxon
Polarizability	22.53 Å³	ChemAxon
Number of Rings	4	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

45258549

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang, G.-c., et al. (2010). Wang, G.-c., et al, Chem. Pharm. Bull. 58, 390 (2010). Chem. Pharm. Bull..

Showing NP-Card for 14beta-hydroxy-13,14-dihydronorsecurinine (NP0039070)

MOL for NP0039070 (14beta-hydroxy-13,14-dihydronorsecurinine)

3D MOL for NP0039070 (14beta-hydroxy-13,14-dihydronorsecurinine)

3D SDF for NP0039070 (14beta-hydroxy-13,14-dihydronorsecurinine)

3D-SDF for NP0039070 (14beta-hydroxy-13,14-dihydronorsecurinine)

PDB for NP0039070 (14beta-hydroxy-13,14-dihydronorsecurinine)

3D PDB for NP0039070 (14beta-hydroxy-13,14-dihydronorsecurinine)

SMILES for NP0039070 (14beta-hydroxy-13,14-dihydronorsecurinine)

INCHI for NP0039070 (14beta-hydroxy-13,14-dihydronorsecurinine)

Structure for NP0039070 (14beta-hydroxy-13,14-dihydronorsecurinine)

3D Structure for NP0039070 (14beta-hydroxy-13,14-dihydronorsecurinine)