NP-MRD: Showing NP-Card for (3r,9r,10s,11r,14r,15r)-10-ethyl-9-hydroxy-14-methyl-3-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.0⁴,¹⁶.0¹¹,¹⁵]hexadec-1(16)-en-13-one (NP0327975)

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Record Information

Version

2.0

Created at

2022-09-12 11:01:51 UTC

Updated at

2022-09-12 11:01:52 UTC

NP-MRD ID

NP0327975

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,9r,10s,11r,14r,15r)-10-ethyl-9-hydroxy-14-methyl-3-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.0⁴,¹⁶.0¹¹,¹⁵]hexadec-1(16)-en-13-one

Description

(3R,9R,10S,11R,14R,15R)-10-ethyl-9-hydroxy-14-methyl-3-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.0⁴,¹⁶.0¹¹,¹⁵]Hexadec-1(16)-en-13-one belongs to the class of organic compounds known as stichoneurine-type alkaloids. These are stemona alkaloids with a structure that typically contains a 3-methyloxolan-2-one and a 5-propyloxolan-2-one moieties that are attached to the characteristic pyrrolo[1,2-a]azepine skeleton at the C3 and C9 position, respectively. (3r,9r,10s,11r,14r,15r)-10-ethyl-9-hydroxy-14-methyl-3-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.0⁴,¹⁶.0¹¹,¹⁵]hexadec-1(16)-en-13-one is found in Stemona tuberosa. It was first documented in 2022 (PMID: 36130844). Based on a literature review a significant number of articles have been published on (3R,9R,10S,11R,14R,15R)-10-ethyl-9-hydroxy-14-methyl-3-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.0⁴,¹⁶.0¹¹,¹⁵]Hexadec-1(16)-en-13-one (PMID: 36130843) (PMID: 36130842) (PMID: 36130841) (PMID: 36130840).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122213012D          

 28 32  0  0  1  0            999 V2000
    1.5063   -1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7792   -1.2601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7532   -0.4355    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4601   -0.0102    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2492   -0.2509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7220    0.4252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5468    0.4401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2251    1.0837    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4658    1.8728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4452    0.8147    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7234    1.2142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0165    0.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6065    1.3297    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4178    1.1799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8065    0.4522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4799   -0.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6839   -0.5224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0180   -0.0354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0450   -0.8580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2846    2.0893    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7099    2.7963    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5318    2.8677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7179    3.6714    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4775    3.9933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0110    4.0967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9396    4.9186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3880    3.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5373    2.0179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 12 18  1  0  0  0  0
  3 18  1  0  0  0  0
 18 19  1  1  0  0  0
 13 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 21 27  1  6  0  0  0
 20 28  1  0  0  0  0
 11 28  1  0  0  0  0
M  END

     RDKit          3D

 59 63  0  0  0  0  0  0  0  0999 V2000
   -4.6821    1.3167    0.6283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6476    0.6630    1.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4879    0.0663    0.7336 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9333   -1.0161   -0.2443 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6568   -1.9473    0.5222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1501   -3.2010    0.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7393   -4.2783    0.5102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7813   -3.0448   -0.2361 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7962   -3.2173    0.8570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7888   -1.6968   -0.8931 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5162   -0.9791   -0.8698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4150    0.2774   -0.4772 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8907    0.7770   -0.7400 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3593    2.1453   -0.8309 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1542    3.0117   -1.1484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9366    2.2921   -1.8686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1040    1.9052   -0.9475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5327    1.0314    0.1415 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0293    1.8325    1.1657 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8039   -0.3402   -0.9318 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5707   -0.6129    0.3412 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4913    0.5328    0.6939 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7661   -0.1792    1.1196 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9853    0.6933    0.9025 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7618   -1.3323    0.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7565   -1.8579   -0.4110 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4351   -1.7218    0.0652 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8371   -1.4514   -1.2536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5226    2.4337    0.6603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6727    1.1850    1.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8318    0.9365   -0.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2604    1.3822    2.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1115   -0.1647    2.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9014   -0.5021    1.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6471   -0.6030   -0.9906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6314   -3.8621   -0.9731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3106   -3.6377    1.7457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3189   -2.2745    1.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0050   -3.9880    0.6126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0891   -1.8933   -1.9677 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1422    2.2692   -1.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7401    2.4847    0.1739 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5384    3.8482   -1.8025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2595    3.5150   -0.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3303    2.8588   -2.7562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5641    1.3237   -2.3089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8047    1.3449   -1.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4896    2.8411   -0.5450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0812    1.3297    2.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5409   -0.1565   -1.7348 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8750   -0.8515    1.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7224    1.1823   -0.1701 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1268    1.1169    1.5658 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7242   -0.4966    2.1792 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8478    0.1380    1.3276 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7984    1.6603    1.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1071    0.8555   -0.1993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1440   -2.3343   -0.6875 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9101   -1.6099   -2.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
 13 20  1  0
 20 28  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 25 27  1  0
 18  3  1  0
 27 21  1  0
 10  4  1  0
 28 11  1  0
 18 12  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  3 34  1  1
  4 35  1  6
  8 36  1  6
  9 37  1  0
  9 38  1  0
  9 39  1  0
 10 40  1  6
 14 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  0
 17 48  1  0
 19 49  1  0
 20 50  1  6
 28 58  1  0
 28 59  1  0
 21 51  1  1
 22 52  1  0
 22 53  1  0
 23 54  1  1
 24 55  1  0
 24 56  1  0
 24 57  1  0
M  END


  Mrv1652309122213012D          

 28 32  0  0  1  0            999 V2000
    1.5063   -1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7792   -1.2601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7532   -0.4355    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4601   -0.0102    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2492   -0.2509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7220    0.4252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5468    0.4401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2251    1.0837    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4658    1.8728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4452    0.8147    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7234    1.2142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0165    0.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6065    1.3297    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4178    1.1799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8065    0.4522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4799   -0.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6839   -0.5224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0180   -0.0354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0450   -0.8580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2846    2.0893    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7099    2.7963    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5318    2.8677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7179    3.6714    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4775    3.9933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0110    4.0967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9396    4.9186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3880    3.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5373    2.0179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 12 18  1  0  0  0  0
  3 18  1  0  0  0  0
 18 19  1  1  0  0  0
 13 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 21 27  1  6  0  0  0
 20 28  1  0  0  0  0
 11 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0327975

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H]1[C@@H]2OC(=O)[C@H](C)[C@@H]2C2=C3N(CCCC[C@@]13O)[C@H](C2)[C@@H]1C[C@H](C)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C22H31NO5/c1-4-14-18-17(12(3)21(25)28-18)13-10-15(16-9-11(2)20(24)27-16)23-8-6-5-7-22(14,26)19(13)23/h11-12,14-18,26H,4-10H2,1-3H3/t11-,12+,14-,15+,16-,17+,18-,22+/m0/s1

> <INCHI_KEY>
FXLCCDTUQJLMJF-CRVJWMJXSA-N

> <FORMULA>
C22H31NO5

> <MOLECULAR_WEIGHT>
389.492

> <EXACT_MASS>
389.220223102

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
41.68425760748943

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,9R,10S,11R,14R,15R)-10-ethyl-9-hydroxy-14-methyl-3-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.0^{4,16}.0^{11,15}]hexadec-1(16)-en-13-one

> <JCHEM_LOGP>
1.9279266226666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.690006790665642

> <JCHEM_PKA_STRONGEST_BASIC>
10.919458522032446

> <JCHEM_POLAR_SURFACE_AREA>
76.07000000000001

> <JCHEM_REFRACTIVITY>
103.15679999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3R,9R,10S,11R,14R,15R)-10-ethyl-9-hydroxy-14-methyl-3-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.0^{4,16}.0^{11,15}]hexadec-1(16)-en-13-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       2.812  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.454  -2.352   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.406  -0.813   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.726  -0.019   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.198  -0.468   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.081   0.794   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.621   0.821   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.153   2.023   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.603   3.496   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.698   1.521   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.350   2.267   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.031   1.473   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -1.132   2.482   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      -2.646   2.202   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.372   0.844   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.762  -0.570   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.277  -0.975   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.034  -0.066   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.084  -1.602   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.531   3.900   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.325   5.220   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.859   5.353   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.207   6.853   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.625   7.454   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.887   7.647   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.754   9.181   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -0.724   6.638   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.003   3.767   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    4   11                                                  
CONECT   11   10   12   28                                                  
CONECT   12   11   13   18                                                  
CONECT   13   12   14   20                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   12    3   19                                             
CONECT   19   18                                                            
CONECT   20   13   21   28                                                  
CONECT   21   20   22   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   21                                                       
CONECT   28   20   11                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₁NO₅

Average Mass

389.4920 Da

Monoisotopic Mass

389.22022 Da

IUPAC Name

(3R,9R,10S,11R,14R,15R)-10-ethyl-9-hydroxy-14-methyl-3-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.0^{4,16}.0^{11,15}]hexadec-1(16)-en-13-one

Traditional Name

(3R,9R,10S,11R,14R,15R)-10-ethyl-9-hydroxy-14-methyl-3-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.0^{4,16}.0^{11,15}]hexadec-1(16)-en-13-one

CAS Registry Number

Not Available

SMILES

CC[C@H]1[C@@H]2OC(=O)[C@H](C)[C@@H]2C2=C3N(CCCC[C@@]13O)[C@H](C2)[C@@H]1C[C@H](C)C(=O)O1

InChI Identifier

InChI=1S/C22H31NO5/c1-4-14-18-17(12(3)21(25)28-18)13-10-15(16-9-11(2)20(24)27-16)23-8-6-5-7-22(14,26)19(13)23/h11-12,14-18,26H,4-10H2,1-3H3/t11-,12+,14-,15+,16-,17+,18-,22+/m0/s1

InChI Key

FXLCCDTUQJLMJF-CRVJWMJXSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Stemona tuberosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stichoneurine-type alkaloids. These are stemona alkaloids with a structure that typically contains a 3-methyloxolan-2-one and a 5-propyloxolan-2-one moieties that are attached to the characteristic pyrrolo[1,2-a]azepine skeleton at the C3 and C9 position, respectively.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Stemona alkaloids

Sub Class

Stemoamide-type alkaloids

Direct Parent

Stichoneurine-type alkaloids

Alternative Parents

Substituents

Stichoneurine-type alkaloid
Stenine backbone
Indole or derivatives
Azepane
Gamma butyrolactone
Dicarboxylic acid or derivatives
Tetrahydrofuran
Tertiary alcohol
Pyrroline
Tertiary aliphatic amine
Tertiary amine
Lactone
Carboxylic acid ester
Amino acid or derivatives
Oxacycle
Azacycle
Organoheterocyclic compound
Enamine
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
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	1.93	ChemAxon
pKa (Strongest Acidic)	13.69	ChemAxon
pKa (Strongest Basic)	10.92	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	76.07 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	103.16 m³·mol⁻¹	ChemAxon
Polarizability	41.68 Å³	ChemAxon
Number of Rings	5	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

162917486

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Cani I, Righini M, Cenni P, Foschi M: Teaching NeuroImage: Partially Reversible Widespread Leukoencephalopathy Associated With Atypical Hemolytic Uremic Syndrome. Neurology. 2022 Sep 21. pii: WNL.0000000000201378. doi: 10.1212/WNL.0000000000201378. [PubMed:36130844 ]
Sasaki R, Morimoto S, Ozawa F, Okano H, Yoshida M, Ishiura H, Tsuji S, Kuzuhara S, Kokubo Y: APOE Alleles With Tau and Abeta Pathology In Patients With Amyotrophic Lateral Sclerosis and Parkinsonism-Dementia Complex in the Kii Peninsula. Neurology. 2022 Sep 21. pii: WNL.0000000000201156. doi: 10.1212/WNL.0000000000201156. [PubMed:36130843 ]
Zhang Z, Wang M, Gill D, Liu X: Genetically Predicted Smoking and Alcohol Consumption and Functional Outcome After Ischemic Stroke. Neurology. 2022 Sep 21. pii: WNL.0000000000201291. doi: 10.1212/WNL.0000000000201291. [PubMed:36130842 ]
Khamis S, Mitakidou MR, Champion M, Goyal S, Jones RL, Siddiqui A, Sabanathan S, Hedderly T, Lin JP, Jungbluth H, Papandreou A: Clinical Reasoning: A Teenage Girl With Progressive Hyperkinetic Movements, Seizures, and Encephalopathy. Neurology. 2022 Sep 21. pii: WNL.0000000000201385. doi: 10.1212/WNL.0000000000201385. [PubMed:36130841 ]
Rosenberg A, Ohlund-Wistbacka U, Hall A, Bonnard A, Hagman G, Ryden M, Thunborg C, Wiggenraad F, Sandebring-Matton A, Solomon A, Kivipelto M: beta-Amyloid, Tau, Neurodegeneration Classification and Eligibility for Anti-amyloid Treatment in a Memory Clinic Population. Neurology. 2022 Sep 21. pii: WNL.0000000000201043. doi: 10.1212/WNL.0000000000201043. [PubMed:36130840 ]
LOTUS database [Link]

Showing NP-Card for (3r,9r,10s,11r,14r,15r)-10-ethyl-9-hydroxy-14-methyl-3-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.0⁴,¹⁶.0¹¹,¹⁵]hexadec-1(16)-en-13-one (NP0327975)

MOL for NP0327975 ((3r,9r,10s,11r,14r,15r)-10-ethyl-9-hydroxy-14-methyl-3-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.0⁴,¹⁶.0¹¹,¹⁵]hexadec-1(16)-en-13-one)

3D MOL for NP0327975 ((3r,9r,10s,11r,14r,15r)-10-ethyl-9-hydroxy-14-methyl-3-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.0⁴,¹⁶.0¹¹,¹⁵]hexadec-1(16)-en-13-one)

3D SDF for NP0327975 ((3r,9r,10s,11r,14r,15r)-10-ethyl-9-hydroxy-14-methyl-3-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.0⁴,¹⁶.0¹¹,¹⁵]hexadec-1(16)-en-13-one)

3D-SDF for NP0327975 ((3r,9r,10s,11r,14r,15r)-10-ethyl-9-hydroxy-14-methyl-3-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.0⁴,¹⁶.0¹¹,¹⁵]hexadec-1(16)-en-13-one)

PDB for NP0327975 ((3r,9r,10s,11r,14r,15r)-10-ethyl-9-hydroxy-14-methyl-3-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.0⁴,¹⁶.0¹¹,¹⁵]hexadec-1(16)-en-13-one)

3D PDB for NP0327975 ((3r,9r,10s,11r,14r,15r)-10-ethyl-9-hydroxy-14-methyl-3-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.0⁴,¹⁶.0¹¹,¹⁵]hexadec-1(16)-en-13-one)

SMILES for NP0327975 ((3r,9r,10s,11r,14r,15r)-10-ethyl-9-hydroxy-14-methyl-3-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.0⁴,¹⁶.0¹¹,¹⁵]hexadec-1(16)-en-13-one)

INCHI for NP0327975 ((3r,9r,10s,11r,14r,15r)-10-ethyl-9-hydroxy-14-methyl-3-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.0⁴,¹⁶.0¹¹,¹⁵]hexadec-1(16)-en-13-one)

Structure for NP0327975 ((3r,9r,10s,11r,14r,15r)-10-ethyl-9-hydroxy-14-methyl-3-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.0⁴,¹⁶.0¹¹,¹⁵]hexadec-1(16)-en-13-one)

3D Structure for NP0327975 ((3r,9r,10s,11r,14r,15r)-10-ethyl-9-hydroxy-14-methyl-3-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.0⁴,¹⁶.0¹¹,¹⁵]hexadec-1(16)-en-13-one)