NP-MRD: Showing NP-Card for (1s,2s,6s,9s,10s,11r,12r,13s,15s,19s,22s,23s)-10,12,13,14,23-pentahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-22-yl (2z)-2-methylbut-2-enoate (NP0274123)

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Record Information

Version

2.0

Created at

2022-09-08 21:23:46 UTC

Updated at

2022-09-08 21:23:46 UTC

NP-MRD ID

NP0274123

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,6s,9s,10s,11r,12r,13s,15s,19s,22s,23s)-10,12,13,14,23-pentahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-22-yl (2z)-2-methylbut-2-enoate

Description

Angeloylzygadenine belongs to the class of organic compounds known as cerveratrum-type alkaloids. These are steroidal alkaloids containing the cevane (23-methyl-4- azahexacyclo[12.11.0.0^{2,11}.0^{4,9}.0^{15,24}.0^{18,23}]Pentacosane) moiety, which is a six ring system. Cerveratrum alkaloids have 7-9 oxygen atoms and occur as free alkamines or esters of simple aliphatic or aromatic acids. (1s,2s,6s,9s,10s,11r,12r,13s,15s,19s,22s,23s)-10,12,13,14,23-pentahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-22-yl (2z)-2-methylbut-2-enoate is found in Salvia nemorosa, Veratrum formosanum, Veratrum maackii, Veratrum oblongum and Veratrum taliense. (1s,2s,6s,9s,10s,11r,12r,13s,15s,19s,22s,23s)-10,12,13,14,23-pentahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-22-yl (2z)-2-methylbut-2-enoate was first documented in 2009 (PMID: 20222419). Based on a literature review very few articles have been published on Angeloylzygadenine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082223232D          

 41 47  0  0  1  0            999 V2000
   -2.9021   -0.9184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1639   -1.7008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6173   -2.3187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8791   -3.1010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8088   -2.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2622   -2.7721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5471   -1.3718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7386   -1.2073    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.6947   -1.5581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9737    1.1077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
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 17 40  1  0  0  0  0
 40 41  1  1  0  0  0
M  END

     RDKit          3D

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 41 90  1  0
M  END


  Mrv1652309082223232D          

 41 47  0  0  1  0            999 V2000
   -2.9021   -0.9184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1639   -1.7008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6173   -2.3187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8791   -3.1010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8088   -2.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2622   -2.7721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5471   -1.3718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7386   -1.2073    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1181   -1.7643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6947   -1.5581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8710   -0.7114    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5847   -1.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1706   -0.0173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2111    0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9737    1.1077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5661    0.5428    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3702    0.7100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9113    1.3956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7300   -0.0324    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1244   -0.6106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3187   -0.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3834   -0.9243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3910   -0.4649    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6337    0.3235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5528   -0.0921    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9125   -0.8345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7354   -0.8942    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0951   -1.6366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9179   -1.6963    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2777   -2.4388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3811   -1.0136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0213   -0.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1985   -0.2115    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8388    0.5310    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6324    0.7563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7546    1.3517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0159    0.5907    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6562    1.3331    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1193    2.0159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8333    1.3928    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4736    2.1352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 16 21  1  0  0  0  0
 11 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 13 23  1  0  0  0  0
  8 23  1  0  0  0  0
 23 24  1  1  0  0  0
 19 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 27  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  6  0  0  0
 37 34  1  6  0  0  0
 25 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  6  0  0  0
 38 40  1  0  0  0  0
 17 40  1  0  0  0  0
 40 41  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0274123

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(\C)C(=O)O[C@H]1CC[C@@]2(C)C3CC[C@H]4C5(O)[C@@H](CC24O[C@]13O)[C@@H]1CN2C[C@@H](C)CC[C@H]2[C@@](C)(O)[C@H]1[C@@H](O)[C@@H]5O

> <INCHI_IDENTIFIER>
InChI=1S/C32H49NO8/c1-6-17(3)27(36)40-23-11-12-28(4)20-8-9-21-30(28,41-32(20,23)39)13-19-18-15-33-14-16(2)7-10-22(33)29(5,37)24(18)25(34)26(35)31(19,21)38/h6,16,18-26,34-35,37-39H,7-15H2,1-5H3/b17-6-/t16-,18-,19-,20?,21+,22-,23-,24+,25+,26-,28-,29+,30?,31?,32-/m0/s1

> <INCHI_KEY>
VZBCOPRNVQLISP-PSQKXIODSA-N

> <FORMULA>
C32H49NO8

> <MOLECULAR_WEIGHT>
575.743

> <EXACT_MASS>
575.345817542

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
90

> <JCHEM_AVERAGE_POLARIZABILITY>
63.7626546793237

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,6S,9S,10S,11R,12R,13S,15S,19S,22S,23S)-10,12,13,14,23-pentahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0^{2,11}.0^{4,9}.0^{15,25}.0^{18,23}.0^{19,25}]hexacosan-22-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_LOGP>
1.8321434199999993

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.778747710198047

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.885224464754183

> <JCHEM_PKA_STRONGEST_BASIC>
7.971230948711923

> <JCHEM_POLAR_SURFACE_AREA>
139.92000000000002

> <JCHEM_REFRACTIVITY>
150.4995

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,6S,9S,10S,11R,12R,13S,15S,19S,22S,23S)-10,12,13,14,23-pentahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0^{2,11}.0^{4,9}.0^{15,25}.0^{18,23}.0^{19,25}]hexacosan-22-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.417  -1.714   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.906  -3.175   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.886  -4.328   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.374  -5.789   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.376  -4.021   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.356  -5.175   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -2.888  -2.561   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.379  -2.254   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.220  -3.293   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.297  -2.909   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.626  -1.328   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.958  -2.100   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.319  -0.032   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.394   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.818   2.068   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.923   1.013   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.424   1.325   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.568   2.605   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.096  -0.060   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.965  -1.140   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.462  -0.587   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.716  -1.725   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.730  -0.868   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.183   0.604   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.632  -0.172   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.303  -1.558   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0       8.839  -1.669   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0       9.511  -3.055   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.047  -3.166   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.718  -4.552   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.911  -1.892   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.240  -0.506   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.704  -0.395   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.032   0.991   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.514   1.412   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       8.875   2.523   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       7.496   1.103   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.825   2.488   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       7.689   3.763   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       5.289   2.600   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       4.617   3.986   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   23                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   21                                             
CONECT   12   11                                                            
CONECT   13   11   14   23                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18   19   40                                             
CONECT   18   17                                                            
CONECT   19   17   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16   11   22                                             
CONECT   22   21   23                                                       
CONECT   23   22   13    8   24                                             
CONECT   24   23                                                            
CONECT   25   19   26   37                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   33                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   27   34                                                  
CONECT   34   33   35   36   37                                             
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   34   25   38                                                  
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   17   41                                                  
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   94    0
END

View in JSmol

Synonyms

Value	Source
Angeloyl-zygadenine	MeSH

Chemical Formula

C₃₂H₄₉NO₈

Average Mass

575.7430 Da

Monoisotopic Mass

575.34582 Da

IUPAC Name

(1S,2S,6S,9S,10S,11R,12R,13S,15S,19S,22S,23S)-10,12,13,14,23-pentahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0^{2,11}.0^{4,9}.0^{15,25}.0^{18,23}.0^{19,25}]hexacosan-22-yl (2Z)-2-methylbut-2-enoate

Traditional Name

CAS Registry Number

Not Available

SMILES

C\C=C(\C)C(=O)O[C@H]1CC[C@@]2(C)C3CC[C@H]4C5(O)[C@@H](CC24O[C@]13O)[C@@H]1CN2C[C@@H](C)CC[C@H]2[C@@](C)(O)[C@H]1[C@@H](O)[C@@H]5O

InChI Identifier

InChI=1S/C32H49NO8/c1-6-17(3)27(36)40-23-11-12-28(4)20-8-9-21-30(28,41-32(20,23)39)13-19-18-15-33-14-16(2)7-10-22(33)29(5,37)24(18)25(34)26(35)31(19,21)38/h6,16,18-26,34-35,37-39H,7-15H2,1-5H3/b17-6-/t16-,18-,19-,20?,21+,22-,23-,24+,25+,26-,28-,29+,30?,31?,32-/m0/s1

InChI Key

VZBCOPRNVQLISP-PSQKXIODSA-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
Salvia nemorosa	LOTUS Database	35616633
Veratrum formosanum	LOTUS Database	35616633
Veratrum maackii	LOTUS Database	35616633
Veratrum oblongum	LOTUS Database	35616633
Veratrum taliense	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cerveratrum-type alkaloids. These are steroidal alkaloids containing the cevane (23-methyl-4- azahexacyclo[12.11.0.0^{2,11}.0^{4,9}.0^{15,24}.0^{18,23}]Pentacosane) moiety, which is a six ring system. Cerveratrum alkaloids have 7-9 oxygen atoms and occur as free alkamines or esters of simple aliphatic or aromatic acids.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal alkaloids

Direct Parent

Cerveratrum-type alkaloids

Alternative Parents

Substituents

Cerveratrum-type alkaloid
Azasteroid
Quinolizidine
Alkaloid or derivatives
Oxepane
Fatty acid ester
Fatty acyl
Piperidine
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Hemiacetal
Carboxylic acid ester
Amino acid or derivatives
1,2-aminoalcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
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	1.83	ChemAxon
pKa (Strongest Acidic)	10.89	ChemAxon
pKa (Strongest Basic)	7.97	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	139.92 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	150.5 m³·mol⁻¹	ChemAxon
Polarizability	63.76 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

C00027858

Chemspider ID

4945330

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6441115

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhao L, Ou Z, Wang K, Fu H: [Steroidal alkaloids of from Veratrum dahuricum]. Zhongguo Zhong Yao Za Zhi. 2009 Dec;34(23):3039-42. [PubMed:20222419 ]
LOTUS database [Link]

Showing NP-Card for (1s,2s,6s,9s,10s,11r,12r,13s,15s,19s,22s,23s)-10,12,13,14,23-pentahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-22-yl (2z)-2-methylbut-2-enoate (NP0274123)

MOL for NP0274123 ((1s,2s,6s,9s,10s,11r,12r,13s,15s,19s,22s,23s)-10,12,13,14,23-pentahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-22-yl (2z)-2-methylbut-2-enoate)

3D MOL for NP0274123 ((1s,2s,6s,9s,10s,11r,12r,13s,15s,19s,22s,23s)-10,12,13,14,23-pentahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-22-yl (2z)-2-methylbut-2-enoate)

3D SDF for NP0274123 ((1s,2s,6s,9s,10s,11r,12r,13s,15s,19s,22s,23s)-10,12,13,14,23-pentahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-22-yl (2z)-2-methylbut-2-enoate)

3D-SDF for NP0274123 ((1s,2s,6s,9s,10s,11r,12r,13s,15s,19s,22s,23s)-10,12,13,14,23-pentahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-22-yl (2z)-2-methylbut-2-enoate)

PDB for NP0274123 ((1s,2s,6s,9s,10s,11r,12r,13s,15s,19s,22s,23s)-10,12,13,14,23-pentahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-22-yl (2z)-2-methylbut-2-enoate)

3D PDB for NP0274123 ((1s,2s,6s,9s,10s,11r,12r,13s,15s,19s,22s,23s)-10,12,13,14,23-pentahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-22-yl (2z)-2-methylbut-2-enoate)

SMILES for NP0274123 ((1s,2s,6s,9s,10s,11r,12r,13s,15s,19s,22s,23s)-10,12,13,14,23-pentahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-22-yl (2z)-2-methylbut-2-enoate)

INCHI for NP0274123 ((1s,2s,6s,9s,10s,11r,12r,13s,15s,19s,22s,23s)-10,12,13,14,23-pentahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-22-yl (2z)-2-methylbut-2-enoate)

Structure for NP0274123 ((1s,2s,6s,9s,10s,11r,12r,13s,15s,19s,22s,23s)-10,12,13,14,23-pentahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-22-yl (2z)-2-methylbut-2-enoate)

3D Structure for NP0274123 ((1s,2s,6s,9s,10s,11r,12r,13s,15s,19s,22s,23s)-10,12,13,14,23-pentahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-22-yl (2z)-2-methylbut-2-enoate)