NP-MRD: Showing NP-Card for (1r,2r,7r,8s,9r,10r,13r,16s,17r)-11-ethyl-7,16-dihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one (NP0194548)

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Record Information

Version

2.0

Created at

2022-09-04 12:13:25 UTC

Updated at

2022-09-04 12:13:25 UTC

NP-MRD ID

NP0194548

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

(1R,2R,7R,8S,9R,10R,13R,16S,17R)-11-ethyl-7,16-dihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]Nonadecan-4-one 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,7r,8s,9r,10r,13r,16s,17r)-11-ethyl-7,16-dihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one is found in Aconitum baicalense, Aconitum firmum, Aconitum leucostomum, Aconitum napellus and Brachycaudus aconiti. Based on a literature review very few articles have been published on (1R,2R,7R,8S,9R,10R,13R,16S,17R)-11-ethyl-7,16-dihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]Nonadecan-4-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042214132D          

 26 31  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  0  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  1  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
    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  0  0  0  0
  5  4  1  1  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
 15 17  1  0  0  0  0
 17 10  1  1  0  0  0
 17 18  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 11 22  1  0  0  0  0
 17 23  1  0  0  0  0
  5 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
  3 25  1  0  0  0  0
 25 26  2  0  0  0  0
M  END

     RDKit          3D

 57 62  0  0  0  0  0  0  0  0999 V2000
    4.9774    1.2535   -0.0403 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8948    0.5465   -0.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7947   -0.8315   -0.6647 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5995   -0.5860   -1.6108 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6634   -0.0302   -0.6023 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5059    0.8829    0.2420 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1914    2.2228   -0.0821 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342    0.6504   -1.0283 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4440   -0.3156   -1.7798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1327   -1.1921   -0.7432 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5546   -0.7922   -0.5255 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3177   -1.0746   -1.8014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0806   -1.6251    0.6388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3060   -1.1678    1.8612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8342   -1.3907    1.7425 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2247   -0.7426    2.8248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2693   -0.8810    0.4955 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2734    0.6374    0.3475 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5146    1.2492    0.3829 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4024    2.6170   -0.1113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5415    3.4675    0.4051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6337    0.6507   -0.2031 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1043   -1.2392    0.1461 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0866   -1.6325    1.1693 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4038   -1.6836    0.4827 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2275   -2.4784    0.8833 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9462    0.8471   -0.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0444    2.2638    0.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6633   -1.1998   -1.1768 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2961   -1.5707   -2.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9360    0.1367   -2.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3776    0.7906    1.3233 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0207    2.7752    0.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5034    1.6412   -1.4387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1946    0.2508   -2.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2105   -0.9548   -2.3879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0285   -2.2621   -0.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7287   -0.1098   -2.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6560   -1.4657   -2.6059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1561   -1.7505   -1.5909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1410   -1.4417    0.8450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8083   -2.6719    0.4598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5776   -0.1195    2.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7099   -1.7916    2.7129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6265   -2.4762    1.8122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3543   -1.3498    3.6179 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3876    1.0754    1.1156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4261    2.5766   -1.2187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4122    3.0555    0.1703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2776    3.6496   -0.4273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0029    2.9849    1.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1787    4.4770    0.6857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9648    1.2200   -1.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5088    0.7847    0.5017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0673   -2.1210   -0.5717 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8563   -2.6969    1.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0893   -1.0619    2.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  1  0
 20 19  1  0
 19 22  1  0
 22 11  1  0
 11 12  1  6
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 17 15  1  1
 17 10  1  0
 10  9  1  0
  9  8  1  0
  8 18  1  0
  8  5  1  0
  5  4  1  6
  4  3  1  0
  3  2  1  0
  2  1  2  3
  2  6  1  0
  6  7  1  0
  3 25  1  0
 25 26  2  0
 25 24  1  0
 24 23  1  0
 18 19  1  0
  6  5  1  0
 10 11  1  0
 23  5  1  0
 18 17  1  0
 23 17  1  0
 21 50  1  0
 21 51  1  0
 21 52  1  0
 20 48  1  0
 20 49  1  0
 22 53  1  0
 22 54  1  0
 12 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  1
 16 46  1  0
 10 37  1  6
  9 35  1  0
  9 36  1  0
  8 34  1  6
 18 47  1  1
  4 30  1  0
  4 31  1  0
  3 29  1  6
  1 27  1  0
  1 28  1  0
  6 32  1  1
  7 33  1  0
 24 56  1  0
 24 57  1  0
 23 55  1  6
M  END


  Mrv1652309042214132D          

 26 31  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  0  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  1  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
    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  0  0  0  0
  5  4  1  1  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
 15 17  1  0  0  0  0
 17 10  1  1  0  0  0
 17 18  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 11 22  1  0  0  0  0
 17 23  1  0  0  0  0
  5 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
  3 25  1  0  0  0  0
 25 26  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0194548

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H31NO3/c1-4-23-10-20(3)6-5-17(25)22-15(20)7-13(18(22)23)21-9-12(11(2)19(21)26)14(24)8-16(21)22/h12-13,15-19,25-26H,2,4-10H2,1,3H3/t12?,13-,15+,16+,17-,18+,19+,20-,21+,22-/m0/s1

> <INCHI_KEY>
CBOSLVQFGANWTL-NNPHXHKDSA-N

> <FORMULA>
C22H31NO3

> <MOLECULAR_WEIGHT>
357.494

> <EXACT_MASS>
357.230393862

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
40.19565406669943

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,7R,8S,9R,10R,13R,16S,17R)-11-ethyl-7,16-dihydroxy-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>
0.9164005406666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.60407977105563

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.549812198075081

> <JCHEM_PKA_STRONGEST_BASIC>
9.25465854689705

> <JCHEM_POLAR_SURFACE_AREA>
60.77

> <JCHEM_REFRACTIVITY>
98.76339999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,7R,8S,9R,10R,13R,16S,17R)-11-ethyl-7,16-dihydroxy-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                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-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       2.524   3.265   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.433   2.331   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       0.773   3.090   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       0.471   4.600   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.988   5.093   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.390   1.836   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.159   3.986   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.016   5.395   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.655   5.382   0.000  0.00  0.00           C+0
HETATM   26  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   25                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8   23                                             
CONECT    6    5    2    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9   18                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12   13   22                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   10   18   23                                             
CONECT   18   17    8   19                                                  
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19   11                                                       
CONECT   23   17    5   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24    3   26                                                  
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₁NO₃

Average Mass

357.4940 Da

Monoisotopic Mass

357.23039 Da

IUPAC Name

(1R,2R,7R,8S,9R,10R,13R,16S,17R)-11-ethyl-7,16-dihydroxy-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,7R,8S,9R,10R,13R,16S,17R)-11-ethyl-7,16-dihydroxy-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](O)[C@@]34[C@@H]2C[C@@H]([C@@H]13)[C@@]12CC(C(=C)[C@H]1O)C(=O)C[C@@H]42

InChI Identifier

InChI=1S/C22H31NO3/c1-4-23-10-20(3)6-5-17(25)22-15(20)7-13(18(22)23)21-9-12(11(2)19(21)26)14(24)8-16(21)22/h12-13,15-19,25-26H,2,4-10H2,1,3H3/t12?,13-,15+,16+,17-,18+,19+,20-,21+,22-/m0/s1

InChI Key

CBOSLVQFGANWTL-NNPHXHKDSA-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 baicalense	LOTUS Database	35616633
Aconitum firmum	LOTUS Database	35616633
Aconitum leucostomum	LOTUS Database	35616633
Aconitum napellus	LOTUS Database	35616633
Brachycaudus aconiti	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
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	0.92	ChemAxon
pKa (Strongest Acidic)	13.55	ChemAxon
pKa (Strongest Basic)	9.25	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	60.77 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	98.76 m³·mol⁻¹	ChemAxon
Polarizability	40.2 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

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

163187592

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2r,7r,8s,9r,10r,13r,16s,17r)-11-ethyl-7,16-dihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one (NP0194548)

MOL for NP0194548 ((1r,2r,7r,8s,9r,10r,13r,16s,17r)-11-ethyl-7,16-dihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one)

3D MOL for NP0194548 ((1r,2r,7r,8s,9r,10r,13r,16s,17r)-11-ethyl-7,16-dihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one)

3D SDF for NP0194548 ((1r,2r,7r,8s,9r,10r,13r,16s,17r)-11-ethyl-7,16-dihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one)

3D-SDF for NP0194548 ((1r,2r,7r,8s,9r,10r,13r,16s,17r)-11-ethyl-7,16-dihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one)

PDB for NP0194548 ((1r,2r,7r,8s,9r,10r,13r,16s,17r)-11-ethyl-7,16-dihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one)

3D PDB for NP0194548 ((1r,2r,7r,8s,9r,10r,13r,16s,17r)-11-ethyl-7,16-dihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one)

SMILES for NP0194548 ((1r,2r,7r,8s,9r,10r,13r,16s,17r)-11-ethyl-7,16-dihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one)

INCHI for NP0194548 ((1r,2r,7r,8s,9r,10r,13r,16s,17r)-11-ethyl-7,16-dihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one)

Structure for NP0194548 ((1r,2r,7r,8s,9r,10r,13r,16s,17r)-11-ethyl-7,16-dihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one)

3D Structure for NP0194548 ((1r,2r,7r,8s,9r,10r,13r,16s,17r)-11-ethyl-7,16-dihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one)