NP-MRD: Showing NP-Card for (1r,2r,5r,7r,8r,9r,10r,13r,16s,17r)-11-ethyl-7-hydroxy-16-methoxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one (NP0301044)

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Record Information

Version

2.0

Created at

2022-09-10 13:46:39 UTC

Updated at

2022-09-10 13:46:39 UTC

NP-MRD ID

NP0301044

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,5r,7r,8r,9r,10r,13r,16s,17r)-11-ethyl-7-hydroxy-16-methoxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one

Description

Liangshanone belongs to the class of organic compounds known as napelline-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the napelline skeleton, which is a hexacyclic compound, with an additional C-20-C-7 bond in the kaurane-type. (1r,2r,5r,7r,8r,9r,10r,13r,16s,17r)-11-ethyl-7-hydroxy-16-methoxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one is found in Aconitum liangshanicum. (1r,2r,5r,7r,8r,9r,10r,13r,16s,17r)-11-ethyl-7-hydroxy-16-methoxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one was first documented in 2020 (PMID: 32902096). Based on a literature review a small amount of articles have been published on Liangshanone (PMID: 33351595) (PMID: 35948501).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102215462D          

 27 32  0  0  1  0            999 V2000
    4.8996    0.8640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1695    1.2483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0556    2.1378    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4540    1.8577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7591    1.4525    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3931    0.8495    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2757    0.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1549    0.8474    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6856    0.1874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0421    0.7006    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2438    0.5895    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7872   -0.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3164    1.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0326    2.2132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7876    2.3648    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0494    3.1471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5027    3.7650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3522    1.7493    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3037    1.2488    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4139    1.6551    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2523    2.4641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5292    2.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2089    0.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2280    2.1352    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6873    2.8903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5654    2.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9598    3.6080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  1  0  0  0
  5  8  1  0  0  0  0
  8  9  1  1  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 10  1  1  0  0  0
 18 19  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 11 23  1  0  0  0  0
 18 24  1  0  0  0  0
  5 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
  3 26  1  0  0  0  0
 26 27  2  0  0  0  0
M  END

     RDKit          3D

 60 65  0  0  0  0  0  0  0  0999 V2000
    5.1369    1.0715   -1.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0033    0.7433   -0.6435 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8346   -0.0115    0.6565 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5616    0.6889    1.1588 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7269    0.5991   -0.0716 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6471    1.0700   -1.1614 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4875    0.3443   -2.3457 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4850    1.3947    0.0781 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2465    1.3493   -1.2276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9034   -0.0380   -1.2977 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3482    0.1729   -1.0163 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9907    0.7711   -2.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0745   -1.1155   -0.6853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4651   -1.6511    0.5892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9986   -1.9449    0.2496 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4908   -2.7928    1.1884 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4111   -4.1118    0.7458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2847   -0.7225   -0.0655 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3626    0.4095    0.9085 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5884    1.0111    1.1642 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4260    2.3125    1.7791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7186    2.6522    2.5261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5462    1.1087    0.1360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1769   -0.7987   -0.3421 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9819   -1.7781    0.4141 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4299   -1.4057    0.4002 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3113   -2.2161    0.1830 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1082    1.6106   -2.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0974    0.7934   -0.7845 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6773    0.1089    1.3301 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7589    1.7565    1.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1589    0.1939    2.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5166    2.1533   -1.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0617   -0.4472   -2.4045 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5654    2.3630    0.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4358    1.4291   -2.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9838    2.1598   -1.3503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6634   -0.5574   -2.2197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2381    1.2389   -2.9333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7279    1.5371   -1.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4801   -0.0373   -2.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9422   -1.8824   -1.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1237   -0.8612   -0.4788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6145   -1.0664    1.4794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9948   -2.6373    0.7686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1236   -2.5540   -0.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4244   -4.5100    0.4886 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1424   -4.1822   -0.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0358   -4.7809    1.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1379    0.1218    1.8318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5953    2.2658    2.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3178    3.0760    0.9863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2789    1.7380    2.7995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3959    3.2280    1.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4771    3.2748    3.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5567    0.8756    0.5853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6663    2.1802   -0.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3116   -1.0435   -1.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7000   -1.8905    1.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9691   -2.7669   -0.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 21  1  0
 21 20  1  0
 20 23  1  0
 23 11  1  0
 11 12  1  6
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 18 15  1  1
 18 10  1  0
 10  9  1  0
  9  8  1  0
  8 19  1  0
  8  5  1  0
  5  4  1  1
  4  3  1  0
  3  2  1  0
  2  1  2  3
  2  6  1  0
  6  7  1  0
  3 26  1  0
 26 27  2  0
 26 25  1  0
 25 24  1  0
 19 20  1  0
  6  5  1  0
 10 11  1  0
 24  5  1  0
 19 18  1  0
 24 18  1  0
 22 53  1  0
 22 54  1  0
 22 55  1  0
 21 51  1  0
 21 52  1  0
 23 56  1  0
 23 57  1  0
 12 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  6
 17 47  1  0
 17 48  1  0
 17 49  1  0
 10 38  1  6
  9 36  1  0
  9 37  1  0
  8 35  1  1
 19 50  1  1
  4 31  1  0
  4 32  1  0
  3 30  1  1
  1 28  1  0
  1 29  1  0
  6 33  1  6
  7 34  1  0
 25 59  1  0
 25 60  1  0
 24 58  1  6
M  END


  Mrv1652309102215462D          

 27 32  0  0  1  0            999 V2000
    4.8996    0.8640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1695    1.2483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0556    2.1378    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4540    1.8577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7591    1.4525    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3931    0.8495    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2757    0.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1549    0.8474    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6856    0.1874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0421    0.7006    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2438    0.5895    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7872   -0.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3164    1.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0326    2.2132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7876    2.3648    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0494    3.1471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5027    3.7650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3522    1.7493    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3037    1.2488    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4139    1.6551    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2523    2.4641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5292    2.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2089    0.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2280    2.1352    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6873    2.8903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5654    2.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9598    3.6080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  1  0  0  0
  5  8  1  0  0  0  0
  8  9  1  1  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 10  1  1  0  0  0
 18 19  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 11 23  1  0  0  0  0
 18 24  1  0  0  0  0
  5 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
  3 26  1  0  0  0  0
 26 27  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0301044

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1C[C@]2(C)CC[C@H](OC)[C@@]34[C@@H]2C[C@@H]([C@@H]13)[C@]12C[C@H](C(=C)[C@H]1O)C(=O)C[C@@H]42

> <INCHI_IDENTIFIER>
InChI=1S/C23H33NO3/c1-5-24-11-21(3)7-6-18(27-4)23-16(21)8-14(19(23)24)22-10-13(12(2)20(22)26)15(25)9-17(22)23/h13-14,16-20,26H,2,5-11H2,1,3-4H3/t13-,14+,16-,17-,18+,19-,20-,21+,22+,23+/m1/s1

> <INCHI_KEY>
NVVRRHYGTUDOIZ-RJYZSOOHSA-N

> <FORMULA>
C23H33NO3

> <MOLECULAR_WEIGHT>
371.521

> <EXACT_MASS>
371.246043927

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
42.12972097102627

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,5R,7R,8R,9R,10R,13R,16S,17R)-11-ethyl-7-hydroxy-16-methoxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1^{5,8}.0^{1,10}.0^{2,8}.0^{13,17}]nonadecan-4-one

> <JCHEM_LOGP>
1.5595270443333331

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.392411079066807

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.588226423446883

> <JCHEM_PKA_STRONGEST_BASIC>
9.609167236090752

> <JCHEM_POLAR_SURFACE_AREA>
49.77

> <JCHEM_REFRACTIVITY>
103.51459999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5R,7R,8R,9R,10R,13R,16S,17R)-11-ethyl-7-hydroxy-16-methoxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1^{5,8}.0^{1,10}.0^{2,8}.0^{13,17}]nonadecan-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       9.146   1.613   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.783   2.330   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.570   3.991   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.447   3.468   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.150   2.711   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.334   1.586   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.115   0.061   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.022   1.582   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.146   0.350   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.945   1.308   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.455   1.100   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.469  -0.058   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.591   2.683   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.061   4.131   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.470   4.414   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.959   5.875   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.938   7.028   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.524   3.265   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.433   2.331   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       0.773   3.090   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       0.471   4.600   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.988   5.093   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.390   1.836   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.159   3.986   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.016   5.395   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.655   5.382   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       7.392   6.735   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4   26                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8   24                                             
CONECT    6    5    2    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9   19                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   18                                                  
CONECT   11   10   12   13   23                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   10   19   24                                             
CONECT   19   18    8   20                                                  
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   11                                                       
CONECT   24   18    5   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25    3   27                                                  
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₃NO₃

Average Mass

371.5210 Da

Monoisotopic Mass

371.24604 Da

IUPAC Name

(1R,2R,5R,7R,8R,9R,10R,13R,16S,17R)-11-ethyl-7-hydroxy-16-methoxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1^{5,8}.0^{1,10}.0^{2,8}.0^{13,17}]nonadecan-4-one

Traditional Name

(1R,2R,5R,7R,8R,9R,10R,13R,16S,17R)-11-ethyl-7-hydroxy-16-methoxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1^{5,8}.0^{1,10}.0^{2,8}.0^{13,17}]nonadecan-4-one

CAS Registry Number

Not Available

SMILES

CCN1C[C@]2(C)CC[C@H](OC)[C@@]34[C@@H]2C[C@@H]([C@@H]13)[C@]12C[C@H](C(=C)[C@H]1O)C(=O)C[C@@H]42

InChI Identifier

InChI=1S/C23H33NO3/c1-5-24-11-21(3)7-6-18(27-4)23-16(21)8-14(19(23)24)22-10-13(12(2)20(22)26)15(25)9-17(22)23/h13-14,16-20,26H,2,5-11H2,1,3-4H3/t13-,14+,16-,17-,18+,19-,20-,21+,22+,23+/m1/s1

InChI Key

NVVRRHYGTUDOIZ-RJYZSOOHSA-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
Aconitum liangshanicum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as napelline-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the napelline skeleton, which is a hexacyclic compound, with an additional C-20-C-7 bond in the kaurane-type.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Napelline-type diterpenoid alkaloids

Alternative Parents

Substituents

Napelline-type diterpenoid alkaloid
Alkaloid or derivatives
Azepane
Piperidine
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Ketone
Azacycle
Organoheterocyclic compound
Ether
Dialkyl ether
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	1.56	ChemAxon
pKa (Strongest Acidic)	13.59	ChemAxon
pKa (Strongest Basic)	9.61	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.77 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	103.51 m³·mol⁻¹	ChemAxon
Polarizability	42.13 Å³	ChemAxon
Number of Rings	6	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

C00024929

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

101604997

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liu XY, Wang FP, Qin Y: Synthesis of Three-Dimensionally Fascinating Diterpenoid Alkaloids and Related Diterpenes. Acc Chem Res. 2021 Jan 5;54(1):22-34. doi: 10.1021/acs.accounts.0c00720. Epub 2020 Dec 22. [PubMed:33351595 ]
Jin S, Zhao X, Ma D: Divergent Total Syntheses of Napelline-Type C20-Diterpenoid Alkaloids: (-)-Napelline, (+)-Dehydronapelline, (-)-Songorine, (-)-Songoramine, (-)-Acoapetaldine D, and (-)-Liangshanone. J Am Chem Soc. 2022 Aug 24;144(33):15355-15362. doi: 10.1021/jacs.2c06738. Epub 2022 Aug 10. [PubMed:35948501 ]
Huang HX, Mi F, Li C, He H, Wang FP, Liu XY, Qin Y: Total Synthesis of Liangshanone. Angew Chem Int Ed Engl. 2020 Dec 21;59(52):23609-23614. doi: 10.1002/anie.202011923. Epub 2020 Oct 15. [PubMed:32902096 ]
LOTUS database [Link]

Showing NP-Card for (1r,2r,5r,7r,8r,9r,10r,13r,16s,17r)-11-ethyl-7-hydroxy-16-methoxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one (NP0301044)

MOL for NP0301044 ((1r,2r,5r,7r,8r,9r,10r,13r,16s,17r)-11-ethyl-7-hydroxy-16-methoxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one)

3D MOL for NP0301044 ((1r,2r,5r,7r,8r,9r,10r,13r,16s,17r)-11-ethyl-7-hydroxy-16-methoxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one)

3D SDF for NP0301044 ((1r,2r,5r,7r,8r,9r,10r,13r,16s,17r)-11-ethyl-7-hydroxy-16-methoxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one)

3D-SDF for NP0301044 ((1r,2r,5r,7r,8r,9r,10r,13r,16s,17r)-11-ethyl-7-hydroxy-16-methoxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one)

PDB for NP0301044 ((1r,2r,5r,7r,8r,9r,10r,13r,16s,17r)-11-ethyl-7-hydroxy-16-methoxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one)

3D PDB for NP0301044 ((1r,2r,5r,7r,8r,9r,10r,13r,16s,17r)-11-ethyl-7-hydroxy-16-methoxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one)

SMILES for NP0301044 ((1r,2r,5r,7r,8r,9r,10r,13r,16s,17r)-11-ethyl-7-hydroxy-16-methoxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one)

INCHI for NP0301044 ((1r,2r,5r,7r,8r,9r,10r,13r,16s,17r)-11-ethyl-7-hydroxy-16-methoxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one)

Structure for NP0301044 ((1r,2r,5r,7r,8r,9r,10r,13r,16s,17r)-11-ethyl-7-hydroxy-16-methoxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one)

3D Structure for NP0301044 ((1r,2r,5r,7r,8r,9r,10r,13r,16s,17r)-11-ethyl-7-hydroxy-16-methoxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one)