NP-MRD: Showing NP-Card for (3as,4r,9r,10as)-6-amino-10,10-dihydroxy-4-[(c-hydroxycarbonimidoyloxy)methyl]-2-imino-9-(sulfooxy)-1h,3h,3ah,4h,8h,9h-pyrrolo[1,2-c]purin-5-ium-5-olate (NP0251554)

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Record Information

Version

2.0

Created at

2022-09-07 14:46:52 UTC

Updated at

2022-09-07 14:46:53 UTC

NP-MRD ID

NP0251554

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3as,4r,9r,10as)-6-amino-10,10-dihydroxy-4-[(c-hydroxycarbonimidoyloxy)methyl]-2-imino-9-(sulfooxy)-1h,3h,3ah,4h,8h,9h-pyrrolo[1,2-c]purin-5-ium-5-olate

Description

Gonyautoxin-1 belongs to the class of organic compounds known as saxitoxins, gonyautoxins, and derivatives. Saxitoxins, gonyautoxins, and derivatives are compounds with a structure based on a 2,6-diamino-4-methyl-pyrrolo[1,2-c]purin-10-ol skeleton. (3as,4r,9r,10as)-6-amino-10,10-dihydroxy-4-[(c-hydroxycarbonimidoyloxy)methyl]-2-imino-9-(sulfooxy)-1h,3h,3ah,4h,8h,9h-pyrrolo[1,2-c]purin-5-ium-5-olate was first documented in 2022 (PMID: 35364510). Based on a literature review very few articles have been published on gonyautoxin-1.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072216462D          

 27 29  0  0  1  0            999 V2000
   -0.1712   -0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    2.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.6021    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4663   -2.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6458   -2.4162    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2333   -3.1306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6458   -3.8451    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0583   -4.5596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9313   -4.2576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3603   -3.4326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3102   -1.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5958   -2.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8253   -0.9950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 N   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
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  2  0  0  0  0
 19 22  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
  4 26  1  0  0  0  0
 26 15  1  1  0  0  0
 26 27  1  0  0  0  0
  2 27  1  0  0  0  0
M  CHG  2  11   1  12  -1
M  END

     RDKit          3D

 44 46  0  0  0  0  0  0  0  0999 V2000
   -0.7921    1.0564   -4.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2357    0.2368   -3.9215 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1503   -0.0823   -2.6752 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6196   -1.2169   -2.2278 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6452   -1.1408   -0.7944 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8965   -0.3542   -0.4001 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0804   -0.8681   -1.0973 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1808   -0.0489   -1.0805 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9629    0.3593   -0.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0780    1.6534    0.4235 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6426   -0.6431    0.4781 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2754   -0.5119    1.2573 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9256   -0.1097    0.9878 N   0  0  0  0  0  4  0  0  0  0  0  0
    3.0454   -0.1982    1.8135 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.7858    0.2462    1.5651 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8472    0.5010    2.9775 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4040    0.3395    0.8382 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6606    0.9860    1.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6402   -0.1011    0.6161 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5524    0.4373   -0.2664 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1003    0.1045    0.2969 S   0  0  0  0  0  6  0  0  0  0  0  0
   -5.5325    1.2165    1.2390 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0056    0.0217   -0.8972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0802   -1.3632    1.0985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8111   -1.1240   -0.1566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5319   -2.2453    0.5908 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4110   -1.4426   -1.3728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5677   -0.3249   -0.4319 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7492    0.5626   -1.5499 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0504   -1.9217   -2.8437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6226   -2.1217   -0.3375 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6738    0.6782   -0.8894 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3335   -1.9225   -0.7362 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7744   -1.0150   -2.1889 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4531    1.8607    1.3180 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6887    1.4917    3.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0382   -0.2615    3.6645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7761    1.8981    0.4269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8314    1.2847    2.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0831   -0.6189    1.4759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9352   -1.2688    2.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1925   -1.9557    1.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3655   -1.1873   -1.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2115    1.4801   -1.5666 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 13  2  0
 13 14  1  0
 13  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  2  0
  3 29  1  0
 28 29  1  6
 28 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 24  1  0
 21 22  2  0
 21 23  2  0
 19 25  1  0
 25 26  1  0
 25 27  1  0
 17 15  1  0
 28  5  1  0
 25 28  1  0
 16 36  1  0
 16 37  1  0
  6 32  1  6
  7 33  1  0
  7 34  1  0
 10 35  1  0
 11 12  1  0
  5 31  1  1
  4 30  1  0
  2  1  1  0
 29 44  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  1
 24 41  1  0
 26 42  1  0
 27 43  1  0
M  CHG  2  13   1  14  -1
M  END


  Mrv1652309072216462D          

 27 29  0  0  1  0            999 V2000
   -0.1712   -0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    2.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.6021    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4663   -2.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6458   -2.4162    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2333   -3.1306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6458   -3.8451    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0583   -4.5596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9313   -4.2576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3603   -3.4326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3102   -1.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5958   -2.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8253   -0.9950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 N   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
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  2  0  0  0  0
 19 22  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
  4 26  1  0  0  0  0
 26 15  1  1  0  0  0
 26 27  1  0  0  0  0
  2 27  1  0  0  0  0
M  CHG  2  11   1  12  -1
M  END
> <DATABASE_ID>
NP0251554

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=[N+]([O-])[C@@H](COC(O)=N)[C@@H]2NC(=N)N[C@]22N1C[C@@H](OS(O)(=O)=O)C2(O)O

> <INCHI_IDENTIFIER>
InChI=1S/C10H17N7O9S/c11-6-14-5-3(2-25-8(13)18)17(21)7(12)16-1-4(26-27(22,23)24)10(19,20)9(5,16)15-6/h3-5,19-20H,1-2,12H2,(H2,13,18)(H3,11,14,15)(H,22,23,24)/t3-,4+,5-,9-/m0/s1

> <INCHI_KEY>
MVZZBUBVEGHJKI-XXKOCQOQSA-N

> <FORMULA>
C10H17N7O9S

> <MOLECULAR_WEIGHT>
411.35

> <EXACT_MASS>
411.080846329

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
35.277141538521434

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4R,9R,10aS,10bS)-6-amino-10,10-dihydroxy-4-[(C-hydroxycarbonimidoyloxy)methyl]-2-imino-9-(sulfooxy)-1H,2H,3H,4H,8H,9H,10H,10bH-pyrrolo[1,2-c]purin-5-ium-5-olate

> <JCHEM_LOGP>
-13.196355504620126

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
-1.7950133202658636

> <JCHEM_PKA_STRONGEST_ACIDIC>
-4.62563450097718

> <JCHEM_PKA_STRONGEST_BASIC>
10.231040557172525

> <JCHEM_POLAR_SURFACE_AREA>
260.60999999999996

> <JCHEM_REFRACTIVITY>
104.29469999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(4R,9R,10aS,10bS)-6-amino-10,10-dihydroxy-4-[(C-hydroxycarbonimidoyloxy)methyl]-2-imino-9-(sulfooxy)-1H,3H,4H,8H,9H,10bH-pyrrolo[1,2-c]purin-5-ium-5-olate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  N   UNK     0      -0.320  -1.303   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   1.777   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.258   2.547   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.258   4.087   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       7.591   4.857   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0       4.924   4.857   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       6.258  -0.533   0.000  0.00  0.00           N+1
HETATM   12  O   UNK     0       7.591   0.237   0.000  0.00  0.00           O-1
HETATM   13  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       7.591  -2.843   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       4.924  -2.843   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       4.604  -4.349   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.072  -4.510   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.302  -5.844   0.000  0.00  0.00           O+0
HETATM   19  S   UNK     0       3.072  -7.178   0.000  0.00  0.00           S+0
HETATM   20  O   UNK     0       3.842  -8.511   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.738  -7.948   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.406  -6.408   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.446  -3.103   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.112  -3.873   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       1.541  -1.857   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0       2.126  -2.549   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   27                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   26                                                  
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    5   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   26                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19                                                            
CONECT   23   17   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23    4   15   27                                             
CONECT   27   26    2                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Value	Source
Gonyautoxin-I	MeSH
Gonyautoxin I	MeSH
Gonyautoxin IV	MeSH
Gonyautoxin-IV	MeSH

Chemical Formula

C₁₀H₁₇N₇O₉S

Average Mass

411.3500 Da

Monoisotopic Mass

411.08085 Da

IUPAC Name

(4R,9R,10aS,10bS)-6-amino-10,10-dihydroxy-4-[(C-hydroxycarbonimidoyloxy)methyl]-2-imino-9-(sulfooxy)-1H,2H,3H,4H,8H,9H,10H,10bH-pyrrolo[1,2-c]purin-5-ium-5-olate

Traditional Name

(4R,9R,10aS,10bS)-6-amino-10,10-dihydroxy-4-[(C-hydroxycarbonimidoyloxy)methyl]-2-imino-9-(sulfooxy)-1H,3H,4H,8H,9H,10bH-pyrrolo[1,2-c]purin-5-ium-5-olate

CAS Registry Number

Not Available

SMILES

NC1=[N+]([O-])[C@@H](COC(O)=N)[C@@H]2NC(=N)N[C@]22N1C[C@@H](OS(O)(=O)=O)C2(O)O

InChI Identifier

InChI=1S/C10H17N7O9S/c11-6-14-5-3(2-25-8(13)18)17(21)7(12)16-1-4(26-27(22,23)24)10(19,20)9(5,16)15-6/h3-5,19-20H,1-2,12H2,(H2,13,18)(H3,11,14,15)(H,22,23,24)/t3-,4+,5-,9-/m0/s1

InChI Key

MVZZBUBVEGHJKI-XXKOCQOQSA-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 saxitoxins, gonyautoxins, and derivatives. Saxitoxins, gonyautoxins, and derivatives are compounds with a structure based on a 2,6-diamino-4-methyl-pyrrolo[1,2-c]purin-10-ol skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Saxitoxins, gonyautoxins, and derivatives

Sub Class

Not Available

Direct Parent

Saxitoxins, gonyautoxins, and derivatives

Alternative Parents

Substituents

Saxitoxin-gonyautoxin skeleton
Alkaloid or derivatives
Imidazopyrimidine
Sulfuric acid ester
Alkyl sulfate
Sulfate-ester
Sulfuric acid monoester
1,4,5,6-tetrahydropyrimidine
Hydropyrimidine
Carbamic acid ester
Pyrrolidine
Organic sulfuric acid or derivatives
2-imidazoline
Carbonic acid derivative
Nitrone
Guanidine
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Carboximidamide
Carbonyl hydrate
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic zwitterion
Organooxygen compound
Organonitrogen compound
Carbonyl group
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	-13	ChemAxon
pKa (Strongest Acidic)	-4.6	ChemAxon
pKa (Strongest Basic)	10.23	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	260.61 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	104.29 m³·mol⁻¹	ChemAxon
Polarizability	35.28 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	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

Not Available

Chemspider ID

78431281

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

135871116

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ramos PB, Colombo GM, Schmitz MJ, Simiao CS, Machado KDS, Werhli AV, Costa LDF, Yunes JS, Prentice C, Wasielesky W, Monserrat JM: Chemoprotection mediated by acai berry (Euterpe oleracea) in white shrimp Litopenaeus vannamei exposed to the cyanotoxin saxitoxin analyzed by in vivo assays and docking modeling. Aquat Toxicol. 2022 May;246:106148. doi: 10.1016/j.aquatox.2022.106148. Epub 2022 Mar 22. [PubMed:35364510 ]
LOTUS database [Link]

Showing NP-Card for (3as,4r,9r,10as)-6-amino-10,10-dihydroxy-4-[(c-hydroxycarbonimidoyloxy)methyl]-2-imino-9-(sulfooxy)-1h,3h,3ah,4h,8h,9h-pyrrolo[1,2-c]purin-5-ium-5-olate (NP0251554)

MOL for NP0251554 ((3as,4r,9r,10as)-6-amino-10,10-dihydroxy-4-[(c-hydroxycarbonimidoyloxy)methyl]-2-imino-9-(sulfooxy)-1h,3h,3ah,4h,8h,9h-pyrrolo[1,2-c]purin-5-ium-5-olate)

3D MOL for NP0251554 ((3as,4r,9r,10as)-6-amino-10,10-dihydroxy-4-[(c-hydroxycarbonimidoyloxy)methyl]-2-imino-9-(sulfooxy)-1h,3h,3ah,4h,8h,9h-pyrrolo[1,2-c]purin-5-ium-5-olate)

3D SDF for NP0251554 ((3as,4r,9r,10as)-6-amino-10,10-dihydroxy-4-[(c-hydroxycarbonimidoyloxy)methyl]-2-imino-9-(sulfooxy)-1h,3h,3ah,4h,8h,9h-pyrrolo[1,2-c]purin-5-ium-5-olate)

3D-SDF for NP0251554 ((3as,4r,9r,10as)-6-amino-10,10-dihydroxy-4-[(c-hydroxycarbonimidoyloxy)methyl]-2-imino-9-(sulfooxy)-1h,3h,3ah,4h,8h,9h-pyrrolo[1,2-c]purin-5-ium-5-olate)

PDB for NP0251554 ((3as,4r,9r,10as)-6-amino-10,10-dihydroxy-4-[(c-hydroxycarbonimidoyloxy)methyl]-2-imino-9-(sulfooxy)-1h,3h,3ah,4h,8h,9h-pyrrolo[1,2-c]purin-5-ium-5-olate)

3D PDB for NP0251554 ((3as,4r,9r,10as)-6-amino-10,10-dihydroxy-4-[(c-hydroxycarbonimidoyloxy)methyl]-2-imino-9-(sulfooxy)-1h,3h,3ah,4h,8h,9h-pyrrolo[1,2-c]purin-5-ium-5-olate)

SMILES for NP0251554 ((3as,4r,9r,10as)-6-amino-10,10-dihydroxy-4-[(c-hydroxycarbonimidoyloxy)methyl]-2-imino-9-(sulfooxy)-1h,3h,3ah,4h,8h,9h-pyrrolo[1,2-c]purin-5-ium-5-olate)

INCHI for NP0251554 ((3as,4r,9r,10as)-6-amino-10,10-dihydroxy-4-[(c-hydroxycarbonimidoyloxy)methyl]-2-imino-9-(sulfooxy)-1h,3h,3ah,4h,8h,9h-pyrrolo[1,2-c]purin-5-ium-5-olate)

Structure for NP0251554 ((3as,4r,9r,10as)-6-amino-10,10-dihydroxy-4-[(c-hydroxycarbonimidoyloxy)methyl]-2-imino-9-(sulfooxy)-1h,3h,3ah,4h,8h,9h-pyrrolo[1,2-c]purin-5-ium-5-olate)

3D Structure for NP0251554 ((3as,4r,9r,10as)-6-amino-10,10-dihydroxy-4-[(c-hydroxycarbonimidoyloxy)methyl]-2-imino-9-(sulfooxy)-1h,3h,3ah,4h,8h,9h-pyrrolo[1,2-c]purin-5-ium-5-olate)