NP-MRD: Showing NP-Card for 12-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one (NP0296331)

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Record Information

Version

2.0

Created at

2022-09-10 05:50:50 UTC

Updated at

2022-09-10 05:50:50 UTC

NP-MRD ID

NP0296331

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one

Description

Ervoside belongs to the class of organic compounds known as indolonaphthyridine alkaloids. These are a numerous and relatively straightforward subgroup of the b-carbolines, e.G. Canthin-6-one, in which an additional C3 unit is attached between C-1 and the indole nitrogen to form an additional ring. The group includes a few dimeric examples, such as Haplophytine. 12-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one was first documented in 2011 (PMID: 22279378). Based on a literature review very few articles have been published on Ervoside (PMID: 34368407).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102207502D          

 29 33  0  0  1  0            999 V2000
    2.1150   -0.4031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8600    0.3816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0531    0.5531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7981    1.3377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3502    1.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3172    2.9353    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9847    3.4202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7383    3.0847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8246    2.2642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4920    1.7793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2990    1.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8510    1.3377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6580    1.5092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2100    0.8961    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0170    1.0677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5690    0.4546    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3760    0.6261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6309    1.4107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3141   -0.3301    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8661   -0.9431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5071   -0.5016    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2522   -1.2862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9551    0.1115    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1481   -0.0600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5961    0.5531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7891    0.3816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2371    0.9946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4121    0.9946    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1571    1.7793    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  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  2  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  1  0  0  0
 12 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 10 27  2  0  0  0  0
 27 28  1  0  0  0  0
  2 28  1  0  0  0  0
 28 29  1  0  0  0  0
  5 29  1  0  0  0  0
  9 29  2  0  0  0  0
M  END

     RDKit          3D

 47 51  0  0  0  0  0  0  0  0999 V2000
    4.8040    2.8876    1.3713 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1038    1.8113    0.8166 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4313    1.4160    0.6140 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7484    0.2246   -0.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7110   -0.5662   -0.4088 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8879   -1.7594   -1.0239 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8067   -2.4857   -1.3995 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4989   -2.0463   -1.1741 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3176   -0.8431   -0.5538 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2468   -0.0694   -0.1559 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8804   -0.2598   -0.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0376    0.6983    0.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3113    0.5879    0.1797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0157   -0.4562   -0.3594 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8202   -0.0411   -1.4213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0397    0.4604   -1.0631 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9681    1.7727   -0.3101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2433    2.2312    0.0247 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9406   -0.5471   -0.3625 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8844   -1.0898   -1.2304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1097   -1.6980    0.1790 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8129   -2.2775    1.2351 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8381   -1.1362    0.7224 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1002   -2.1576    1.3397 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5530    1.8534    0.8340 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8978    2.0475    0.9353 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7377    1.0778    0.4361 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0934    1.0173    0.4062 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4352   -0.1372   -0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2058    2.0966    0.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7567   -0.0618   -0.1468 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8943   -3.4380   -1.8904 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6275   -2.5971   -1.4590 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5671   -1.1814   -0.7309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3685   -1.2522   -0.7694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5655    0.7135   -2.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2868    1.7694    0.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5630    2.5237   -1.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2628    3.2278    0.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4810   -0.0736    0.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2455   -0.3748   -1.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9383   -2.4814   -0.5685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2424   -1.5075    1.7261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0723   -0.4062    1.5225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2900   -3.0434    0.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1220    2.6245    1.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2792    2.9466    1.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10 27  2  0
 27 26  1  0
 26 25  2  0
 27 28  1  0
 28 29  1  0
 29  9  2  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
 14 23  1  0
 23 24  1  0
 23 21  1  0
 21 22  1  0
 21 19  1  0
 19 20  1  0
 19 16  1  0
 25 12  1  0
  2 28  1  0
  9 10  1  0
  5 29  1  0
 18 39  1  0
 17 37  1  0
 17 38  1  0
 16 36  1  6
 14 35  1  6
 11 34  1  0
 26 47  1  0
 25 46  1  0
  8 33  1  0
  7 32  1  0
  4 31  1  0
  3 30  1  0
 23 44  1  1
 24 45  1  0
 21 42  1  6
 22 43  1  0
 19 40  1  1
 20 41  1  0
M  END


  Mrv1652309102207502D          

 29 33  0  0  1  0            999 V2000
    2.1150   -0.4031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8600    0.3816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0531    0.5531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7981    1.3377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3502    1.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3172    2.9353    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9847    3.4202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7383    3.0847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8246    2.2642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4920    1.7793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2990    1.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8510    1.3377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6580    1.5092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2100    0.8961    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0170    1.0677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5690    0.4546    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3760    0.6261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6309    1.4107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3141   -0.3301    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8661   -0.9431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5071   -0.5016    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2522   -1.2862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9551    0.1115    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1481   -0.0600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5961    0.5531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7891    0.3816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2371    0.9946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4121    0.9946    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1571    1.7793    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  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  2  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  1  0  0  0
 12 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 10 27  2  0  0  0  0
 27 28  1  0  0  0  0
  2 28  1  0  0  0  0
 28 29  1  0  0  0  0
  5 29  1  0  0  0  0
  9 29  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0296331

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC3=C(C=C2)N2C4=C3C=CN=C4C=CC2=O)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H18N2O7/c23-8-14-17(25)18(26)19(27)20(29-14)28-9-1-3-13-11(7-9)10-5-6-21-12-2-4-15(24)22(13)16(10)12/h1-7,14,17-20,23,25-27H,8H2/t14-,17-,18+,19-,20-/m1/s1

> <INCHI_KEY>
MZSAQIYKZGAUDD-LWUBGYQZSA-N

> <FORMULA>
C20H18N2O7

> <MOLECULAR_WEIGHT>
398.371

> <EXACT_MASS>
398.111400928

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
39.20498401030628

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
12-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,6-diazatetracyclo[7.6.1.0^{5,16}.0^{10,15}]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one

> <JCHEM_LOGP>
-0.7587637769999998

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.196091299863198

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.200141367678604

> <JCHEM_PKA_STRONGEST_BASIC>
4.011367348595813

> <JCHEM_POLAR_SURFACE_AREA>
134.27

> <JCHEM_REFRACTIVITY>
98.62200000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
12-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,6-diazatetracyclo[7.6.1.0^{5,16}.0^{10,15}]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  O   UNK     0       3.948  -0.752   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.472   0.712   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.966   1.032   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.490   2.497   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.520   3.641   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       2.459   5.479   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       3.705   6.384   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.112   5.758   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.273   4.226   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.518   3.321   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.025   3.641   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.055   2.497   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      10.562   2.817   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      11.592   1.673   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      13.098   1.993   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      14.129   0.849   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.635   1.169   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      16.111   2.633   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      13.653  -0.616   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      14.683  -1.761   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      12.147  -0.936   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      11.671  -2.401   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      11.116   0.208   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.610  -0.112   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.579   1.032   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.073   0.712   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.043   1.857   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       4.503   1.857   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0       4.027   3.321   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   28                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   29                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   29                                                  
CONECT   10    9   11   27                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   25                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   23                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   14   24                                                  
CONECT   24   23                                                            
CONECT   25   12   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   10   28                                                  
CONECT   28   27    2   29                                                  
CONECT   29   28    5    9                                                  
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₁₈N₂O₇

Average Mass

398.3710 Da

Monoisotopic Mass

398.11140 Da

IUPAC Name

12-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,6-diazatetracyclo[7.6.1.0^{5,16}.0^{10,15}]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one

Traditional Name

12-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,6-diazatetracyclo[7.6.1.0^{5,16}.0^{10,15}]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=CC3=C(C=C2)N2C4=C3C=CN=C4C=CC2=O)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C20H18N2O7/c23-8-14-17(25)18(26)19(27)20(29-14)28-9-1-3-13-11(7-9)10-5-6-21-12-2-4-15(24)22(13)16(10)12/h1-7,14,17-20,23,25-27H,8H2/t14-,17-,18+,19-,20-/m1/s1

InChI Key

MZSAQIYKZGAUDD-LWUBGYQZSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolonaphthyridine alkaloids. These are a numerous and relatively straightforward subgroup of the b-carbolines, e.G. Canthin-6-one, in which an additional C3 unit is attached between C-1 and the indole nitrogen to form an additional ring. The group includes a few dimeric examples, such as Haplophytine.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Indolonaphthyridine alkaloids

Sub Class

Not Available

Direct Parent

Indolonaphthyridine alkaloids

Alternative Parents

Substituents

Indolo[3,2-1de][1,5]naphthyridine
Phenolic glycoside
Beta-carboline
Pyridoindole
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Diazanaphthalene
Naphthyridine
Indole
Pyrrolopyridine
Indole or derivatives
Indolizine
Pyridinone
Pyridine
Benzenoid
Oxane
Monosaccharide
Pyrrole
Heteroaromatic compound
Lactam
Secondary alcohol
Organoheterocyclic compound
Azacycle
Acetal
Oxacycle
Polyol
Organooxygen compound
Organonitrogen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Primary 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	-0.76	ChemAxon
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	4.01	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	134.27 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	98.62 m³·mol⁻¹	ChemAxon
Polarizability	39.2 Å³	ChemAxon
Number of Rings	5	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

10392024

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15109283

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sherin DR, Sharanya N, Manojkumar TK: Potential drug leads for SARS-CoV2 from phytochemicals of Aerva lanata: a Machine Learning approach. Virusdisease. 2021 Dec;32(4):757-765. doi: 10.1007/s13337-021-00732-0. Epub 2021 Jul 31. [PubMed:34368407 ]
Goyal M, Pareek A, Nagori BP, Sasmal D: Aerva lanata: A review on phytochemistry and pharmacological aspects. Pharmacogn Rev. 2011 Jul;5(10):195-8. doi: 10.4103/0973-7847.91120. [PubMed:22279378 ]
LOTUS database [Link]

Showing NP-Card for 12-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one (NP0296331)

MOL for NP0296331 (12-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one)

3D MOL for NP0296331 (12-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one)

3D SDF for NP0296331 (12-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one)

3D-SDF for NP0296331 (12-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one)

PDB for NP0296331 (12-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one)

3D PDB for NP0296331 (12-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one)

SMILES for NP0296331 (12-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one)

INCHI for NP0296331 (12-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one)

Structure for NP0296331 (12-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one)

3D Structure for NP0296331 (12-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one)