NP-MRD: Showing NP-Card for Strictosidine (NP0070475)

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Record Information

Version

2.0

Created at

2022-04-28 15:52:32 UTC

Updated at

2022-04-28 15:52:32 UTC

NP-MRD ID

NP0070475

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Strictosidine

Description

Methyl (2S,3R,4R)-3-ethenyl-4-{[(1S)-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-1-yl]methyl}-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. Strictosidine is found in Alstonia scholaris , Alstonia angustiloba, Rhazya orientalis, Camptotheca acuminata, Catharanthus roseus , Cephalanthus occidentalis, Chimarrhis turbinata, Chonemorpha grandiflora, Cinchona ledgeriana, Cinchona officinalis , Cinchona robusta, Tabernaemontana divaricata, Ervatamia officinalis , Nothapodytes foetida, Nothapodytes nimmoniana, Ophiorrhiza pumila, Ophiorrhiza rugosa var. prostrata, Palicourea acuminata, Palicourea cyanococca, Palicourea tsakiana, Palicourea winkleri, Rauvolfia serpentina , Rehmannia glutinosa , Rhazya stricta Decaisne. , Stenostomum acreanum, Strempeliopsis strempelioides, Strychnos mellodora, Strychnos nux-vomica , Strychnos spinosa, Tabernaemontana heyneana and Tabernaemontana litoralis. Based on a literature review very few articles have been published on methyl (2S,3R,4R)-3-ethenyl-4-{[(1S)-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-1-yl]methyl}-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282217522D          

 38 42  0  0  1  0            999 V2000
    2.6014   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    0.2410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084   -0.3721    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6633   -1.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4703   -1.3283    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7252   -2.1129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5322   -2.2844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0842   -1.6713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8293   -0.8867    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0223   -0.7152    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7674    0.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3194    0.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3813   -0.2736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1883   -0.4451    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7403    0.1680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5473   -0.0036    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.8022   -0.7882    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2502   -1.4013    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4432   -1.2298    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8912   -1.8429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5051   -2.1859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6092   -0.9597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0993    0.6095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1732   -2.7260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3662   -2.5545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4281   -3.5106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2351   -3.6821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339   -0.6855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694    1.1971    0.0000 C   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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  2  0  0  0  0
 12 16  1  6  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  1  0  0  0
 21 24  1  6  0  0  0
 20 25  1  1  0  0  0
 19 26  1  6  0  0  0
 26 27  1  0  0  0  0
  9 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
  2 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
  1 34  1  0  0  0  0
 33 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 32 38  2  0  0  0  0
M  END

     RDKit          3D

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   -5.8004    1.0827   -0.2660 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6561    2.2097   -0.8113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8291    1.6703   -1.3391 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.5199   -0.4943   -0.0162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8555   -0.6069    1.6123 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6834   -1.0120    2.6574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6478    0.1695    2.0985 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8696   -0.5707    2.9621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9811   -0.5971    1.4116 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8304   -0.9834   -0.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4760   -0.0461    1.5394 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5962   -0.6388    1.9765 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8593   -1.3979    3.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1162   -1.9285    3.3569 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1577   -1.7100    2.4802 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8956   -0.9455    1.3492 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6387   -0.4128    1.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9726    0.3024   -1.9022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7574    1.5976   -3.1835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7565    2.3638   -2.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5618    1.8345    0.2483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2301   -0.6163   -0.2819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9890   -0.2860    0.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5390    0.4346   -1.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9831    2.9228   -0.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1002    2.8063   -1.5435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1744    2.2375   -2.0597 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.1391   -0.6996   -0.9133 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7392   -0.1946   -2.6846 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0359    1.4990   -3.1100 H   0  0  0  0  0  0  0  0  0  0  0  0
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 37 72  1  0
M  END


  Mrv1652304282217522D          

 38 42  0  0  1  0            999 V2000
    2.6014   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    0.2410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084   -0.3721    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6633   -1.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4703   -1.3283    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7252   -2.1129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5322   -2.2844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0842   -1.6713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8293   -0.8867    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0223   -0.7152    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7674    0.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3194    0.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3813   -0.2736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2351   -3.6821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339   -0.6855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694    1.1971    0.0000 C   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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  2  0  0  0  0
 12 16  1  6  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  1  0  0  0
 21 24  1  6  0  0  0
 20 25  1  1  0  0  0
 19 26  1  6  0  0  0
 26 27  1  0  0  0  0
  9 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
  2 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
  1 34  1  0  0  0  0
 33 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 32 38  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0070475

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](C=C)[C@H]1C[C@@H]1NCCC2=C1NC1=CC=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C27H34N2O9/c1-3-13-16(10-19-21-15(8-9-28-19)14-6-4-5-7-18(14)29-21)17(25(34)35-2)12-36-26(13)38-27-24(33)23(32)22(31)20(11-30)37-27/h3-7,12-13,16,19-20,22-24,26-33H,1,8-11H2,2H3/t13-,16-,19+,20-,22-,23+,24-,26+,27+/m1/s1

> <INCHI_KEY>
XBAMJZTXGWPTRM-YNUCFGNCSA-N

> <FORMULA>
C27H34N2O9

> <MOLECULAR_WEIGHT>
530.574

> <EXACT_MASS>
530.226430683

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
55.72257457104719

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2S,3R,4R)-3-ethenyl-4-{[(1S)-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-1-yl]methyl}-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate

> <ALOGPS_LOGP>
0.88

> <JCHEM_LOGP>
0.5208186083333349

> <ALOGPS_LOGS>
-3.08

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.19852044430446

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.20751973384191

> <JCHEM_PKA_STRONGEST_BASIC>
9.342001657830965

> <JCHEM_POLAR_SURFACE_AREA>
162.73

> <JCHEM_REFRACTIVITY>
134.69779999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.41e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (4R,5R,6S)-5-ethenyl-4-[(1S)-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-1-ylmethyl]-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4H-pyran-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       4.856  -0.374   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.380   1.090   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.410   2.235   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.917   1.914   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       7.393   0.450   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       6.362  -0.695   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.838  -2.159   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.344  -2.479   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.820  -3.944   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.327  -4.264   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      11.357  -3.120   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.881  -1.655   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.375  -1.335   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.899   0.130   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.930   1.274   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      11.912  -0.511   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      13.418  -0.831   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      14.449   0.314   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      15.955  -0.007   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.431  -1.471   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.400  -2.616   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.894  -2.296   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      12.864  -3.440   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      15.876  -4.080   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      17.937  -1.791   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      16.985   1.138   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      18.492   0.818   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.790  -5.089   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.284  -4.768   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       8.266  -6.553   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       9.772  -6.873   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.840   1.090   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.364  -0.374   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0       3.610  -1.280   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0       0.858  -0.695   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.173   0.450   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.303   1.914   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       1.810   2.235   0.000  0.00  0.00           C+0
CONECT    1    2    6   34                                                  
CONECT    2    1    3   32                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10   28                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12    8   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   12   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   26                                                  
CONECT   20   19   21   25                                                  
CONECT   21   20   22   24                                                  
CONECT   22   21   17   23                                                  
CONECT   23   22                                                            
CONECT   24   21                                                            
CONECT   25   20                                                            
CONECT   26   19   27                                                       
CONECT   27   26                                                            
CONECT   28    9   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30                                                            
CONECT   32    2   33   38                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33    1                                                       
CONECT   35   33   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   32                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Value	Source
Methyl (2S,3R,4R)-3-ethenyl-4-{[(1S)-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-1-yl]methyl}-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylic acid	Generator

Chemical Formula

C₂₇H₃₄N₂O₉

Average Mass

530.5740 Da

Monoisotopic Mass

530.22643 Da

IUPAC Name

methyl (2S,3R,4R)-3-ethenyl-4-{[(1S)-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-1-yl]methyl}-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate

Traditional Name

methyl (4R,5R,6S)-5-ethenyl-4-[(1S)-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-1-ylmethyl]-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4H-pyran-3-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](C=C)[C@H]1C[C@@H]1NCCC2=C1NC1=CC=CC=C21

InChI Identifier

InChI=1S/C27H34N2O9/c1-3-13-16(10-19-21-15(8-9-28-19)14-6-4-5-7-18(14)29-21)17(25(34)35-2)12-36-26(13)38-27-24(33)23(32)22(31)20(11-30)37-27/h3-7,12-13,16,19-20,22-24,26-33H,1,8-11H2,2H3/t13-,16-,19+,20-,22-,23+,24-,26+,27+/m1/s1

InChI Key

XBAMJZTXGWPTRM-YNUCFGNCSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Alstonia Alstonia scholaris	Plant	KNApSAcK
Alstonia angustiloba	Plant	KNApSAcK
Amsonia orientalis	Plant	KNApSAcK
Camptotheca acuminata	Plant	KNApSAcK
Catharanthus roseus	Plant	KNApSAcK
Cephalanthus occidentalis	LOTUS Database	35616633
Chimarrhis turbinata	Plant	KNApSAcK
Chonemorpha grandiflora	Plant	KNApSAcK
Cinchona calisaya	Plant	KNApSAcK
Cinchona officinalis	Plant	KNApSAcK
Cinchona robusta	Plant	KNApSAcK
Ervatamia coronaria	LOTUS Database	35616633
Ervatamia officinalis	Plant	KNApSAcK
Nothapodytes foetida	Plant	KNApSAcK
Nothapodytes nimmoniana	Plant	KNApSAcK
Ophiorrhiza pumila	Plant	KNApSAcK
Ophiorrhiza rugosa var. prostrata	Plant	KNApSAcK
Palicourea acuminata	Plant	KNApSAcK
Palicourea cyanococca	Plant	KNApSAcK
Palicourea tsakiana	Plant	KNApSAcK
Palicourea winkleri	Plant	KNApSAcK
Rauvolfia serpentina	Plant	KNApSAcK
Rehmannia glutinosa	Plant	KNApSAcK
Rhazya stricta Decaisne.	Plant	KNApSAcK
Stenostomum acreanum	LOTUS Database	35616633
Strempeliopsis strempelioides	Plant	KNApSAcK
Strychnos mellodora	Plant	KNApSAcK
Strychnos nux-vomica L.	Plant	KNApSAcK
Strychnos spinosa	LOTUS Database	35616633
Tabernaemontana heyneana	Plant	KNApSAcK
Tabernaemontana litoralis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Harman
Pyridoindole
Beta-carboline
O-glycosyl compound
Secoiridoid-skeleton
Glycosyl compound
3-alkylindole
Monoterpenoid
Aromatic monoterpenoid
Alkaloid or derivatives
Indole or derivatives
Indole
Aralkylamine
Sugar acid
Benzenoid
Oxane
Monosaccharide
Heteroaromatic compound
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Pyrrole
Secondary alcohol
Carboxylic acid ester
Amino acid or derivatives
Oxacycle
Azacycle
Organoheterocyclic compound
Secondary amine
Polyol
Monocarboxylic acid or derivatives
Secondary aliphatic amine
Carboxylic acid derivative
Acetal
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	0.88	ALOGPS
logP	0.52	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	9.34	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	162.73 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	134.7 m³·mol⁻¹	ChemAxon
Polarizability	55.72 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

28945012

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

154497529

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Strictosidine (NP0070475)

MOL for NP0070475 (Strictosidine)

3D MOL for NP0070475 (Strictosidine)

3D SDF for NP0070475 (Strictosidine)

3D-SDF for NP0070475 (Strictosidine)

PDB for NP0070475 (Strictosidine)

3D PDB for NP0070475 (Strictosidine)

SMILES for NP0070475 (Strictosidine)

INCHI for NP0070475 (Strictosidine)

Structure for NP0070475 (Strictosidine)

3D Structure for NP0070475 (Strictosidine)