NP-MRD: Showing NP-Card for (1s,3s,5r,8r,9s,10s,11r,14s,17r,18r,19s)-5-methyl-12-methylidene-7-azahexacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁹,¹⁴.0¹⁴,¹⁸]nonadecane-3,10,19-triol (NP0153314)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 09:56:49 UTC

Updated at

2022-09-02 09:56:49 UTC

NP-MRD ID

NP0153314

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3s,5r,8r,9s,10s,11r,14s,17r,18r,19s)-5-methyl-12-methylidene-7-azahexacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁹,¹⁴.0¹⁴,¹⁸]nonadecane-3,10,19-triol

Description

(1S,3S,5R,8R,9S,10S,11R,14S,17R,18R,19S)-5-methyl-12-methylidene-7-azahexacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁹,¹⁴.0¹⁴,¹⁸]Nonadecane-3,10,19-triol belongs to the class of organic compounds known as hetidine-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hetidine skeleton, which is a hexacyclic compound with an additional C-20-C-14 bond in the atisine-type. (1s,3s,5r,8r,9s,10s,11r,14s,17r,18r,19s)-5-methyl-12-methylidene-7-azahexacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁹,¹⁴.0¹⁴,¹⁸]nonadecane-3,10,19-triol is found in Delphinium peregrinum. Based on a literature review very few articles have been published on (1S,3S,5R,8R,9S,10S,11R,14S,17R,18R,19S)-5-methyl-12-methylidene-7-azahexacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁹,¹⁴.0¹⁴,¹⁸]Nonadecane-3,10,19-triol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022211562D          

 24 29  0  0  1  0            999 V2000
   -0.9852    0.4716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1698    0.3459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4368    0.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2507    0.6342    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7447    1.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6018    1.3319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0934    0.6256    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7237   -0.0403    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6330    0.3112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4811    0.2109    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1686    0.6669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2516   -0.5822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4452   -0.2823    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8733   -0.9876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3390   -1.1366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5848   -1.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2127   -0.7479    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4566   -0.3316    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8433   -0.9513    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8665   -1.7760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2252   -0.3932    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9531    0.0324    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9288    0.8570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8786    0.1799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  6  0  0  0
  8 17  1  0  0  0  0
 18 17  1  1  0  0  0
  4 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21  2  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24  4  1  6  0  0  0
  8 24  1  0  0  0  0
M  END

     RDKit          3D

 53 58  0  0  0  0  0  0  0  0999 V2000
    4.9333   -0.1038   -0.6971 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6486   -0.0488   -0.4359 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8551    1.2020   -0.4306 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4253    0.8400   -0.0852 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6454    2.0823    0.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6954    2.1163   -0.5353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3984    0.8197   -0.6327 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5269   -0.3917   -0.3497 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2534   -1.5845   -0.8733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6988   -1.3063   -1.2592 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3444   -2.5670   -1.2891 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4350   -0.4592   -0.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6293    0.7054    0.2338 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4454    1.9949    0.2028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3007    0.4007    1.6770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8928    0.4783    1.8457 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1278   -0.4604    1.0851 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3267    0.0213    1.1968 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2951   -1.1018    1.2777 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3197   -0.8996    2.2012 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9034   -1.2879   -0.1214 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6667   -1.4118   -1.0295 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0163   -2.5455   -0.5389 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8284   -0.1754   -1.0412 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5256    0.7894   -0.9353 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4739   -1.0286   -0.6914 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2309    1.8234    0.4006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8364    1.7126   -1.3931 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2217    2.9797   -0.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5265    2.3027    1.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3535    2.8150    0.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6188    2.6341   -1.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7510    0.6937   -1.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7759   -1.8731   -1.8580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2790   -2.4118   -0.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7745   -0.9473   -2.3281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9602   -3.1316   -0.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3168   -0.0207   -0.8140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8617   -1.0756    0.5348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4964    1.6795    0.4695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1348    2.6560    1.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4055    2.4899   -0.7709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7268   -0.5748    2.0165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7585    1.1603    2.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5574    0.6604    2.7926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1774   -1.4948    1.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4764    0.6823    2.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7387   -2.0371    1.4940 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4936    0.0392    2.3913 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4791   -2.2051   -0.2076 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0453   -1.6247   -2.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0767   -3.2875   -1.2009 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7076    0.2774   -2.0257 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  1
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24  4  1  0
  4  5  1  1
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  6
  9 10  1  0
 10 11  1  0
 10 12  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  7 13  1  0
 12 13  1  0
  8 17  1  0
  4 18  1  0
  2 21  1  0
  8 24  1  0
 14 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 17 46  1  1
 18 47  1  1
 19 48  1  1
 20 49  1  0
 21 50  1  1
 22 51  1  6
 23 52  1  0
 24 53  1  6
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  6
  9 34  1  0
  9 35  1  0
 10 36  1  6
 11 37  1  0
 12 38  1  0
 12 39  1  0
  3 27  1  0
  3 28  1  0
  1 25  1  0
  1 26  1  0
M  END


  Mrv1652309022211562D          

 24 29  0  0  1  0            999 V2000
   -0.9852    0.4716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1698    0.3459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4368    0.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2507    0.6342    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7447    1.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6018    1.3319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0934    0.6256    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7237   -0.0403    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6330    0.3112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4811    0.2109    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1686    0.6669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2516   -0.5822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4452   -0.2823    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8733   -0.9876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3390   -1.1366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5848   -1.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2127   -0.7479    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4566   -0.3316    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8433   -0.9513    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8665   -1.7760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2252   -0.3932    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9531    0.0324    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9288    0.8570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8786    0.1799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  6  0  0  0
  8 17  1  0  0  0  0
 18 17  1  1  0  0  0
  4 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21  2  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24  4  1  6  0  0  0
  8 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0153314

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12CN[C@@H]3[C@H]4[C@H](O)[C@H]5[C@@H](O)[C@@H]6[C@]4(CC[C@H]1[C@]36C[C@@H](O)C2)CC5=C

> <INCHI_IDENTIFIER>
InChI=1S/C20H29NO3/c1-9-5-19-4-3-11-18(2)6-10(22)7-20(11)16(19)15(24)12(9)14(23)13(19)17(20)21-8-18/h10-17,21-24H,1,3-8H2,2H3/t10-,11+,12-,13+,14+,15+,16+,17+,18-,19+,20-/m0/s1

> <INCHI_KEY>
XNFQUGPVHYJHHZ-PMCSWTMGSA-N

> <FORMULA>
C20H29NO3

> <MOLECULAR_WEIGHT>
331.456

> <EXACT_MASS>
331.214743798

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
36.66667861611894

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3S,5R,8R,9S,10S,11R,14S,17R,18R,19S)-5-methyl-12-methylidene-7-azahexacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{9,14}.0^{14,18}]nonadecane-3,10,19-triol

> <ALOGPS_LOGP>
0.20

> <JCHEM_LOGP>
-0.5156248009999995

> <ALOGPS_LOGS>
-2.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.763659050619019

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.152787475392664

> <JCHEM_PKA_STRONGEST_BASIC>
9.782879760729392

> <JCHEM_POLAR_SURFACE_AREA>
72.72

> <JCHEM_REFRACTIVITY>
89.8327

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.14e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3S,5R,8R,9S,10S,11R,14S,17R,18R,19S)-5-methyl-12-methylidene-7-azahexacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{9,14}.0^{14,18}]nonadecane-3,10,19-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.839   0.880   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.317   0.646   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.815   1.752   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.335   1.184   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.257   2.527   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.857   2.486   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.774   1.168   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.084  -0.075   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.782   0.581   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.365   0.394   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.648   1.245   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.936  -1.087   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.431  -0.527   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.230  -1.843   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.233  -2.122   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       4.825  -2.806   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       4.130  -1.396   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.719  -0.619   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.574  -1.776   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.617  -3.315   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.420  -0.734   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.779   0.060   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.734   1.600   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.507   0.336   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   18   24                                             
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9   17   24                                             
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    7   14   15                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    8   18                                                  
CONECT   18   17    4   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    2   22                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22    4    8                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₉NO₃

Average Mass

331.4560 Da

Monoisotopic Mass

331.21474 Da

IUPAC Name

(1S,3S,5R,8R,9S,10S,11R,14S,17R,18R,19S)-5-methyl-12-methylidene-7-azahexacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{9,14}.0^{14,18}]nonadecane-3,10,19-triol

Traditional Name

(1S,3S,5R,8R,9S,10S,11R,14S,17R,18R,19S)-5-methyl-12-methylidene-7-azahexacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{9,14}.0^{14,18}]nonadecane-3,10,19-triol

CAS Registry Number

Not Available

SMILES

C[C@]12CN[C@@H]3[C@H]4[C@H](O)[C@H]5[C@@H](O)[C@@H]6[C@]4(CC[C@H]1[C@]36C[C@@H](O)C2)CC5=C

InChI Identifier

InChI=1S/C20H29NO3/c1-9-5-19-4-3-11-18(2)6-10(22)7-20(11)16(19)15(24)12(9)14(23)13(19)17(20)21-8-18/h10-17,21-24H,1,3-8H2,2H3/t10-,11+,12-,13+,14+,15+,16+,17+,18-,19+,20-/m0/s1

InChI Key

XNFQUGPVHYJHHZ-PMCSWTMGSA-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
Delphinium peregrinum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hetidine-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hetidine skeleton, which is a hexacyclic compound with an additional C-20-C-14 bond in the atisine-type.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Hetidine-type diterpenoid alkaloids

Alternative Parents

Substituents

Hetidine-type diterpenoid alkaloid
Alkaloid or derivatives
Piperidine
Cyclic alcohol
Secondary alcohol
Organoheterocyclic compound
Secondary amine
Polyol
Secondary aliphatic amine
Azacycle
Hydrocarbon derivative
Organopnictogen compound
Alcohol
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Amine
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	0.2	ALOGPS
logP	-0.52	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	14.15	ChemAxon
pKa (Strongest Basic)	9.78	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	72.72 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	89.83 m³·mol⁻¹	ChemAxon
Polarizability	36.67 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

162973443

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3s,5r,8r,9s,10s,11r,14s,17r,18r,19s)-5-methyl-12-methylidene-7-azahexacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁹,¹⁴.0¹⁴,¹⁸]nonadecane-3,10,19-triol (NP0153314)

MOL for NP0153314 ((1s,3s,5r,8r,9s,10s,11r,14s,17r,18r,19s)-5-methyl-12-methylidene-7-azahexacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁹,¹⁴.0¹⁴,¹⁸]nonadecane-3,10,19-triol)

3D MOL for NP0153314 ((1s,3s,5r,8r,9s,10s,11r,14s,17r,18r,19s)-5-methyl-12-methylidene-7-azahexacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁹,¹⁴.0¹⁴,¹⁸]nonadecane-3,10,19-triol)

3D SDF for NP0153314 ((1s,3s,5r,8r,9s,10s,11r,14s,17r,18r,19s)-5-methyl-12-methylidene-7-azahexacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁹,¹⁴.0¹⁴,¹⁸]nonadecane-3,10,19-triol)

3D-SDF for NP0153314 ((1s,3s,5r,8r,9s,10s,11r,14s,17r,18r,19s)-5-methyl-12-methylidene-7-azahexacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁹,¹⁴.0¹⁴,¹⁸]nonadecane-3,10,19-triol)

PDB for NP0153314 ((1s,3s,5r,8r,9s,10s,11r,14s,17r,18r,19s)-5-methyl-12-methylidene-7-azahexacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁹,¹⁴.0¹⁴,¹⁸]nonadecane-3,10,19-triol)

3D PDB for NP0153314 ((1s,3s,5r,8r,9s,10s,11r,14s,17r,18r,19s)-5-methyl-12-methylidene-7-azahexacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁹,¹⁴.0¹⁴,¹⁸]nonadecane-3,10,19-triol)

SMILES for NP0153314 ((1s,3s,5r,8r,9s,10s,11r,14s,17r,18r,19s)-5-methyl-12-methylidene-7-azahexacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁹,¹⁴.0¹⁴,¹⁸]nonadecane-3,10,19-triol)

INCHI for NP0153314 ((1s,3s,5r,8r,9s,10s,11r,14s,17r,18r,19s)-5-methyl-12-methylidene-7-azahexacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁹,¹⁴.0¹⁴,¹⁸]nonadecane-3,10,19-triol)

Structure for NP0153314 ((1s,3s,5r,8r,9s,10s,11r,14s,17r,18r,19s)-5-methyl-12-methylidene-7-azahexacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁹,¹⁴.0¹⁴,¹⁸]nonadecane-3,10,19-triol)

3D Structure for NP0153314 ((1s,3s,5r,8r,9s,10s,11r,14s,17r,18r,19s)-5-methyl-12-methylidene-7-azahexacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁹,¹⁴.0¹⁴,¹⁸]nonadecane-3,10,19-triol)