NP-MRD: Showing NP-Card for (1r,3r,4r,10s,14r,15r,17r,18s)-18-[(acetyloxy)methyl]-17-hydroxy-3-(methoxycarbonyl)-14-methyl-12λ⁵-azahexacyclo[10.6.1.1¹,⁴.0¹⁰,¹⁸.0¹⁵,¹⁹.0⁷,²⁰]icosa-7(20),12(19)-dien-12-ylium (NP0180453)

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Record Information

Version

2.0

Created at

2022-09-03 18:48:54 UTC

Updated at

2022-09-03 18:48:54 UTC

NP-MRD ID

NP0180453

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3r,4r,10s,14r,15r,17r,18s)-18-[(acetyloxy)methyl]-17-hydroxy-3-(methoxycarbonyl)-14-methyl-12λ⁵-azahexacyclo[10.6.1.1¹,⁴.0¹⁰,¹⁸.0¹⁵,¹⁹.0⁷,²⁰]icosa-7(20),12(19)-dien-12-ylium

Description

Daphnezomine J belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. (1r,3r,4r,10s,14r,15r,17r,18s)-18-[(acetyloxy)methyl]-17-hydroxy-3-(methoxycarbonyl)-14-methyl-12λ⁵-azahexacyclo[10.6.1.1¹,⁴.0¹⁰,¹⁸.0¹⁵,¹⁹.0⁷,²⁰]icosa-7(20),12(19)-dien-12-ylium is found in Daphniphyllum macropodum. Based on a literature review very few articles have been published on Daphnezomine J.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032220482D          

 31 36  0  0  1  0            999 V2000
   -0.0584   -2.8697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0482   -2.0333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6081   -1.4866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3102   -2.0015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5307   -0.5908    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1093   -0.0179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9526    0.8697    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1102    0.7067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5508    1.1967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4810    2.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2077    2.5529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0411    2.3611    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8059    1.9019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1038    1.0384    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.6526    0.5394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6371    0.7660    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7407    1.5760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1632    2.1738    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2008    3.0679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2275    1.7858    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3328    1.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0729    1.2353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1586    1.2267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8057    1.8386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7584    0.4249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7870   -0.0622    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4723   -0.5782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9847   -0.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2069    0.6383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9540   -0.1578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1328   -0.1154    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  7 15  1  0  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
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  7 20  1  0  0  0  0
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 22 23  1  0  0  0  0
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  9 29  1  0  0  0  0
 29 30  1  0  0  0  0
 31 30  1  1  0  0  0
  8 31  1  0  0  0  0
  5 31  1  0  0  0  0
M  CHG  1  14   1
M  END

     RDKit          3D

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   -0.6134    0.7093    1.8513 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9816   -0.6853    2.2908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6217   -1.4633    1.2274 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.3293   -1.1139    0.0651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3830   -1.1960   -0.9324 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7314    0.3099   -1.0755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0972    1.1701   -0.0356 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9450    1.1055    1.1004 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6553    0.9764    0.3670 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1371    2.1241   -0.1104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3442    3.3481    0.4316 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2155    4.5716    0.1486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3560    5.8142    0.7646 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2001    4.6286   -0.6243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4074   -1.9896   -0.1777 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6858   -3.2343   -0.9971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5998   -2.4916    1.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7872   -1.8764    1.5303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7045   -2.4990    0.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3605   -2.1210   -0.3413 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3223   -0.4636   -1.9458 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5818    1.0399   -2.5808 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0272    0.8805   -0.8271 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9326   -2.2734   -2.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9177    0.6133   -1.8243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4149   -0.4725   -2.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7422    0.9195    2.3320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9651   -0.1689    3.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8900    2.1925    2.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3568    1.4033    3.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4244    1.3784    2.2780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1724   -1.2463    2.7882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861   -0.6594    3.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1164   -1.5551   -1.9033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8215    0.3638   -0.9471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4789    0.6919   -2.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2653    2.2321   -0.4027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1904    1.9735    1.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2213    2.0204   -0.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1063    2.2335   -1.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2969    6.1825    1.5902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4009    5.6557    1.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4116    6.5750   -0.0666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2997   -1.4462    0.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7390   -3.5659   -0.8967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9764   -4.0624   -0.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5387   -3.0319   -2.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2568   -2.6611    1.9085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0732   -3.4331    0.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5619   -2.8640   -0.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
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  3  5  1  0
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  8  9  2  0
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 29 30  1  0
 30 31  1  0
  9 10  1  0
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 14 15  2  0
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 17 18  1  0
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 18 20  1  0
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 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 16 26  1  0
 26 27  1  0
 26 28  1  0
 31  5  1  0
 20 12  1  0
 15  7  1  0
 20  7  1  0
 31  8  1  0
 28 14  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  5 35  1  6
  6 36  1  0
  6 37  1  0
 29 61  1  0
 29 62  1  0
 30 63  1  0
 30 64  1  0
 31 65  1  6
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  1
 13 43  1  0
 13 44  1  0
 16 45  1  6
 17 46  1  0
 17 47  1  0
 18 48  1  6
 19 49  1  0
 21 50  1  0
 21 51  1  0
 24 52  1  0
 24 53  1  0
 24 54  1  0
 26 55  1  1
 27 56  1  0
 27 57  1  0
 27 58  1  0
 28 59  1  0
 28 60  1  0
M  CHG  1  14   1
M  END


  Mrv1652309032220482D          

 31 36  0  0  1  0            999 V2000
   -0.0584   -2.8697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0482   -2.0333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6081   -1.4866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3102   -2.0015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5307   -0.5908    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1093   -0.0179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9526    0.8697    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.4810    2.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0411    2.3611    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8059    1.9019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1038    1.0384    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.6526    0.5394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6371    0.7660    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7407    1.5760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1632    2.1738    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2008    3.0679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2275    1.7858    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3328    1.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0729    1.2353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1586    1.2267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8057    1.8386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7584    0.4249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7870   -0.0622    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4723   -0.5782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9847   -0.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2069    0.6383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9540   -0.1578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1328   -0.1154    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  1  0  0  0
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 14 28  1  0  0  0  0
  9 29  1  0  0  0  0
 29 30  1  0  0  0  0
 31 30  1  1  0  0  0
  8 31  1  0  0  0  0
  5 31  1  0  0  0  0
M  CHG  1  14   1
M  END
> <DATABASE_ID>
NP0180453

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@H]1C[C@]23C4=C(CC[C@H]14)CC[C@@H]1C[N+]4=C2[C@H](C[C@@H](O)[C@]31COC(C)=O)[C@@H](C)C4

> <INCHI_IDENTIFIER>
InChI=1S/C25H34NO5/c1-13-10-26-11-16-6-4-15-5-7-17-19(23(29)30-3)9-24(21(15)17)22(26)18(13)8-20(28)25(16,24)12-31-14(2)27/h13,16-20,28H,4-12H2,1-3H3/q+1/t13-,16+,17+,18+,19+,20+,24-,25+/m0/s1

> <INCHI_KEY>
HDERSXCBGZDBCI-CZQHBCSPSA-N

> <FORMULA>
C25H34NO5

> <MOLECULAR_WEIGHT>
428.548

> <EXACT_MASS>
428.243149619

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
46.97418154956032

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3R,4R,10S,14R,15R,17R,18S)-18-[(acetyloxy)methyl]-17-hydroxy-3-(methoxycarbonyl)-14-methyl-12lambda5-azahexacyclo[10.6.1.1^{1,4}.0^{10,18}.0^{15,19}.0^{7,20}]icosa-7(20),12(19)-dien-12-ylium

> <JCHEM_LOGP>
-2.1274714104717463

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.534192956007935

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0025440010421294

> <JCHEM_POLAR_SURFACE_AREA>
75.84

> <JCHEM_REFRACTIVITY>
125.54279999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3R,4R,10S,14R,15R,17R,18S)-18-[(acetyloxy)methyl]-17-hydroxy-3-(methoxycarbonyl)-14-methyl-12lambda5-azahexacyclo[10.6.1.1^{1,4}.0^{10,18}.0^{15,19}.0^{7,20}]icosa-7(20),12(19)-dien-12-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.109  -5.357   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.090  -3.796   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.135  -2.775   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.446  -3.736   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.991  -1.103   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.071  -0.033   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.778   1.623   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.206   1.319   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.028   2.234   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.898   3.823   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.388   4.765   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.943   4.407   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.371   3.550   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       3.927   1.938   0.000  0.00  0.00           N+1
HETATM   15  C   UNK     0       3.085   1.007   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.923   1.430   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.116   2.942   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.038   4.058   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.108   5.727   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.291   3.334   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.621   3.670   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.136   2.306   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.163   2.290   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.371   3.432   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -3.282   0.793   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.202  -0.116   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.482  -1.079   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.705  -0.024   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.253   1.192   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.781  -0.295   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.248  -0.215   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   31                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   15   20                                             
CONECT    8    7    9   31                                                  
CONECT    9    8   10   29                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   28                                                  
CONECT   15   14    7   16                                                  
CONECT   16   15   17   26                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   12    7   21                                             
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   16   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   14                                                       
CONECT   29    9   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30    8    5                                                  
MASTER        0    0    0    0    0    0    0    0   31    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₄NO₅

Average Mass

428.5480 Da

Monoisotopic Mass

428.24315 Da

IUPAC Name

(1R,3R,4R,10S,14R,15R,17R,18S)-18-[(acetyloxy)methyl]-17-hydroxy-3-(methoxycarbonyl)-14-methyl-12lambda5-azahexacyclo[10.6.1.1^{1,4}.0^{10,18}.0^{15,19}.0^{7,20}]icosa-7(20),12(19)-dien-12-ylium

Traditional Name

(1R,3R,4R,10S,14R,15R,17R,18S)-18-[(acetyloxy)methyl]-17-hydroxy-3-(methoxycarbonyl)-14-methyl-12lambda5-azahexacyclo[10.6.1.1^{1,4}.0^{10,18}.0^{15,19}.0^{7,20}]icosa-7(20),12(19)-dien-12-ylium

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@H]1C[C@]23C4=C(CC[C@H]14)CC[C@@H]1C[N+]4=C2[C@H](C[C@@H](O)[C@]31COC(C)=O)[C@@H](C)C4

InChI Identifier

InChI=1S/C25H34NO5/c1-13-10-26-11-16-6-4-15-5-7-17-19(23(29)30-3)9-24(21(15)17)22(26)18(13)8-20(28)25(16,24)12-31-14(2)27/h13,16-20,28H,4-12H2,1-3H3/q+1/t13-,16+,17+,18+,19+,20+,24-,25+/m0/s1

InChI Key

HDERSXCBGZDBCI-CZQHBCSPSA-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
Daphniphyllum macropodum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Not Available

Direct Parent

Indoles and derivatives

Alternative Parents

Substituents

Indole or derivatives
Tetrahydropyridine
Dicarboxylic acid or derivatives
Methyl ester
Pyrroline
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Azacycle
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Organic cation
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	-2.1	ChemAxon
pKa (Strongest Acidic)	14.53	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	75.84 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	125.54 m³·mol⁻¹	ChemAxon
Polarizability	46.97 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

101025777

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3r,4r,10s,14r,15r,17r,18s)-18-[(acetyloxy)methyl]-17-hydroxy-3-(methoxycarbonyl)-14-methyl-12λ⁵-azahexacyclo[10.6.1.1¹,⁴.0¹⁰,¹⁸.0¹⁵,¹⁹.0⁷,²⁰]icosa-7(20),12(19)-dien-12-ylium (NP0180453)

MOL for NP0180453 ((1r,3r,4r,10s,14r,15r,17r,18s)-18-[(acetyloxy)methyl]-17-hydroxy-3-(methoxycarbonyl)-14-methyl-12λ⁵-azahexacyclo[10.6.1.1¹,⁴.0¹⁰,¹⁸.0¹⁵,¹⁹.0⁷,²⁰]icosa-7(20),12(19)-dien-12-ylium)

3D MOL for NP0180453 ((1r,3r,4r,10s,14r,15r,17r,18s)-18-[(acetyloxy)methyl]-17-hydroxy-3-(methoxycarbonyl)-14-methyl-12λ⁵-azahexacyclo[10.6.1.1¹,⁴.0¹⁰,¹⁸.0¹⁵,¹⁹.0⁷,²⁰]icosa-7(20),12(19)-dien-12-ylium)

3D SDF for NP0180453 ((1r,3r,4r,10s,14r,15r,17r,18s)-18-[(acetyloxy)methyl]-17-hydroxy-3-(methoxycarbonyl)-14-methyl-12λ⁵-azahexacyclo[10.6.1.1¹,⁴.0¹⁰,¹⁸.0¹⁵,¹⁹.0⁷,²⁰]icosa-7(20),12(19)-dien-12-ylium)

3D-SDF for NP0180453 ((1r,3r,4r,10s,14r,15r,17r,18s)-18-[(acetyloxy)methyl]-17-hydroxy-3-(methoxycarbonyl)-14-methyl-12λ⁵-azahexacyclo[10.6.1.1¹,⁴.0¹⁰,¹⁸.0¹⁵,¹⁹.0⁷,²⁰]icosa-7(20),12(19)-dien-12-ylium)

PDB for NP0180453 ((1r,3r,4r,10s,14r,15r,17r,18s)-18-[(acetyloxy)methyl]-17-hydroxy-3-(methoxycarbonyl)-14-methyl-12λ⁵-azahexacyclo[10.6.1.1¹,⁴.0¹⁰,¹⁸.0¹⁵,¹⁹.0⁷,²⁰]icosa-7(20),12(19)-dien-12-ylium)

3D PDB for NP0180453 ((1r,3r,4r,10s,14r,15r,17r,18s)-18-[(acetyloxy)methyl]-17-hydroxy-3-(methoxycarbonyl)-14-methyl-12λ⁵-azahexacyclo[10.6.1.1¹,⁴.0¹⁰,¹⁸.0¹⁵,¹⁹.0⁷,²⁰]icosa-7(20),12(19)-dien-12-ylium)

SMILES for NP0180453 ((1r,3r,4r,10s,14r,15r,17r,18s)-18-[(acetyloxy)methyl]-17-hydroxy-3-(methoxycarbonyl)-14-methyl-12λ⁵-azahexacyclo[10.6.1.1¹,⁴.0¹⁰,¹⁸.0¹⁵,¹⁹.0⁷,²⁰]icosa-7(20),12(19)-dien-12-ylium)

INCHI for NP0180453 ((1r,3r,4r,10s,14r,15r,17r,18s)-18-[(acetyloxy)methyl]-17-hydroxy-3-(methoxycarbonyl)-14-methyl-12λ⁵-azahexacyclo[10.6.1.1¹,⁴.0¹⁰,¹⁸.0¹⁵,¹⁹.0⁷,²⁰]icosa-7(20),12(19)-dien-12-ylium)

Structure for NP0180453 ((1r,3r,4r,10s,14r,15r,17r,18s)-18-[(acetyloxy)methyl]-17-hydroxy-3-(methoxycarbonyl)-14-methyl-12λ⁵-azahexacyclo[10.6.1.1¹,⁴.0¹⁰,¹⁸.0¹⁵,¹⁹.0⁷,²⁰]icosa-7(20),12(19)-dien-12-ylium)

3D Structure for NP0180453 ((1r,3r,4r,10s,14r,15r,17r,18s)-18-[(acetyloxy)methyl]-17-hydroxy-3-(methoxycarbonyl)-14-methyl-12λ⁵-azahexacyclo[10.6.1.1¹,⁴.0¹⁰,¹⁸.0¹⁵,¹⁹.0⁷,²⁰]icosa-7(20),12(19)-dien-12-ylium)