NP-MRD: Showing NP-Card for saxitoxin (NP0039462)

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Record Information

Version

2.0

Created at

2021-06-20 21:53:12 UTC

Updated at

2021-06-30 00:12:48 UTC

NP-MRD ID

NP0039462

Secondary Accession Numbers

None

Natural Product Identification

Common Name

saxitoxin

Provided By

JEOL Database JEOL Logo

Description

Saxitoxin, also known as saxitoxin (8ci) or gonyaulax toxin, 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. Saxitoxin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. saxitoxin is found in Aphanizomenon flos-aquae, Atelopus zeteki, Carcinoscorpius rotundicauda, Cylindrospermopsis raciborskii, Gonyaulax catenella, Lingulodinium polyedra, Mytilus californianus , Protogonyaulax tamarensis, Pyrodinium bahamense, Saxidomus gigantea, Saxidomus giganteus, Saxidomus nuttalli and Zosimus aeneus. saxitoxin was first documented in 2013 (PMID: 22628533). Based on a literature review a small amount of articles have been published on Saxitoxin (PMID: 23966031) (PMID: 24184516) (PMID: 24460188) (PMID: 32323358).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123533D          

 38 40  0  0  0  0            999 V2000
    0.5939    5.8879   -0.9171 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5658    4.6637   -0.5666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5557    3.9473   -0.3461 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3099    2.5320   -0.0403 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9253    1.6088   -1.0965 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1580    0.1960   -0.5162 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9159   -0.6261   -1.4282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2468   -0.3965   -1.4310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8584   -1.2355   -2.2927 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8307    0.4455   -0.7693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0796    1.5129   -2.2889 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2484    1.2711   -2.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8992    0.7320   -3.1940 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8209    1.5792   -1.0415 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9975    0.8991   -0.5235 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2524    1.5180    0.8503 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8718    1.9926    1.2959 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1397    0.9317    1.8915 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9992    3.0074    2.2779 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2394    2.4631   -0.0592 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6186    3.8449   -0.3516 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5659    6.1835   -1.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4682    4.3448   -0.5187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7328    2.3446    0.9522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8866    2.0229   -1.4211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2106   -0.3260   -0.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6730    0.2394    0.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3182   -1.9163   -2.8041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8600   -1.1863   -2.4027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5644    1.3380   -3.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2637    0.5783   -3.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8664    1.0287   -1.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7914   -0.1727   -0.4221 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7028    0.7938    1.5367 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9429    2.3657    0.7605 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6364    0.7230    2.7033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5405    3.7945    1.9220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5435    4.0419   -0.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
  4 20  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  0  0  0  0
 11 12  1  0  0  0  0
 17 18  1  1  0  0  0
 11  5  1  0  0  0  0
 17 19  1  0  0  0  0
 12 14  1  0  0  0  0
  2  1  2  3  0  0  0
 14 20  1  0  0  0  0
  5  6  1  0  0  0  0
 20 21  1  6  0  0  0
  4 24  1  1  0  0  0
 21  2  1  0  0  0  0
  6  7  1  0  0  0  0
  2  3  1  0  0  0  0
  7  8  1  0  0  0  0
  3  4  1  0  0  0  0
  8  9  1  0  0  0  0
  4  5  1  0  0  0  0
  8 10  2  0  0  0  0
 20 17  1  0  0  0  0
 12 13  2  3  0  0  0
 11 30  1  0  0  0  0
  5 25  1  6  0  0  0
 21 38  1  0  0  0  0
  3 23  1  0  0  0  0
 15 32  1  0  0  0  0
 15 33  1  0  0  0  0
 16 34  1  0  0  0  0
 16 35  1  0  0  0  0
 18 36  1  0  0  0  0
 19 37  1  0  0  0  0
  1 22  1  0  0  0  0
  6 26  1  0  0  0  0
  6 27  1  0  0  0  0
  9 28  1  0  0  0  0
  9 29  1  0  0  0  0
 13 31  1  0  0  0  0
M  END

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
    0.5939    5.8879   -0.9171 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5658    4.6637   -0.5666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5557    3.9473   -0.3461 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3099    2.5320   -0.0403 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9253    1.6088   -1.0965 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1580    0.1960   -0.5162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9159   -0.6261   -1.4282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2468   -0.3965   -1.4310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8584   -1.2355   -2.2927 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8307    0.4455   -0.7693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0796    1.5129   -2.2889 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2484    1.2711   -2.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8992    0.7320   -3.1940 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8209    1.5792   -1.0415 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9975    0.8991   -0.5235 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2524    1.5180    0.8503 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8718    1.9926    1.2959 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1397    0.9317    1.8915 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9992    3.0074    2.2779 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2394    2.4631   -0.0592 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6186    3.8449   -0.3516 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5659    6.1835   -1.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4682    4.3448   -0.5187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7328    2.3446    0.9522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8866    2.0229   -1.4211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2106   -0.3260   -0.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6730    0.2394    0.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3182   -1.9163   -2.8041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8600   -1.1863   -2.4027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5644    1.3380   -3.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2637    0.5783   -3.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8664    1.0287   -1.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7914   -0.1727   -0.4221 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7028    0.7938    1.5367 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9429    2.3657    0.7605 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6364    0.7230    2.7033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5405    3.7945    1.9220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5435    4.0419   -0.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
  4 20  1  0
 14 15  1  0
 15 16  1  0
 17 16  1  0
 11 12  1  0
 17 18  1  1
 11  5  1  0
 17 19  1  0
 12 14  1  0
  2  1  2  3
 14 20  1  0
  5  6  1  0
 20 21  1  6
  4 24  1  1
 21  2  1  0
  6  7  1  0
  2  3  1  0
  7  8  1  0
  3  4  1  0
  8  9  1  0
  4  5  1  0
  8 10  2  0
 20 17  1  0
 12 13  2  3
 11 30  1  0
  5 25  1  6
 21 38  1  0
  3 23  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 18 36  1  0
 19 37  1  0
  1 22  1  0
  6 26  1  0
  6 27  1  0
  9 28  1  0
  9 29  1  0
 13 31  1  0
M  END


  Mrv1652306202123533D          

 38 40  0  0  0  0            999 V2000
    0.5939    5.8879   -0.9171 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5658    4.6637   -0.5666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5557    3.9473   -0.3461 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3099    2.5320   -0.0403 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9253    1.6088   -1.0965 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1580    0.1960   -0.5162 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9159   -0.6261   -1.4282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2468   -0.3965   -1.4310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8584   -1.2355   -2.2927 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8307    0.4455   -0.7693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0796    1.5129   -2.2889 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2484    1.2711   -2.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8992    0.7320   -3.1940 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8209    1.5792   -1.0415 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9975    0.8991   -0.5235 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2524    1.5180    0.8503 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8718    1.9926    1.2959 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1397    0.9317    1.8915 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9992    3.0074    2.2779 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2394    2.4631   -0.0592 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6186    3.8449   -0.3516 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5659    6.1835   -1.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4682    4.3448   -0.5187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7328    2.3446    0.9522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8866    2.0229   -1.4211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2106   -0.3260   -0.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6730    0.2394    0.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3182   -1.9163   -2.8041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8600   -1.1863   -2.4027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5644    1.3380   -3.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2637    0.5783   -3.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8664    1.0287   -1.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7914   -0.1727   -0.4221 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7028    0.7938    1.5367 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9429    2.3657    0.7605 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6364    0.7230    2.7033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5405    3.7945    1.9220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5435    4.0419   -0.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
  4 20  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  0  0  0  0
 11 12  1  0  0  0  0
 17 18  1  1  0  0  0
 11  5  1  0  0  0  0
 17 19  1  0  0  0  0
 12 14  1  0  0  0  0
  2  1  2  3  0  0  0
 14 20  1  0  0  0  0
  5  6  1  0  0  0  0
 20 21  1  6  0  0  0
  4 24  1  1  0  0  0
 21  2  1  0  0  0  0
  6  7  1  0  0  0  0
  2  3  1  0  0  0  0
  7  8  1  0  0  0  0
  3  4  1  0  0  0  0
  8  9  1  0  0  0  0
  4  5  1  0  0  0  0
  8 10  2  0  0  0  0
 20 17  1  0  0  0  0
 12 13  2  3  0  0  0
 11 30  1  0  0  0  0
  5 25  1  6  0  0  0
 21 38  1  0  0  0  0
  3 23  1  0  0  0  0
 15 32  1  0  0  0  0
 15 33  1  0  0  0  0
 16 34  1  0  0  0  0
 16 35  1  0  0  0  0
 18 36  1  0  0  0  0
 19 37  1  0  0  0  0
  1 22  1  0  0  0  0
  6 26  1  0  0  0  0
  6 27  1  0  0  0  0
  9 28  1  0  0  0  0
  9 29  1  0  0  0  0
 13 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0039462

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1(O[H])C([H])([H])C([H])([H])N2C(=N[H])N([H])[C@@]([H])(C([H])([H])OC(=O)N([H])[H])[C@]3([H])N([H])C(=N[H])N([H])[C@]123

> <INCHI_IDENTIFIER>
InChI=1S/C10H17N7O4/c11-6-15-5-4(3-21-8(13)18)14-7(12)17-2-1-9(19,20)10(5,17)16-6/h4-5,19-20H,1-3H2,(H2,12,14)(H2,13,18)(H3,11,15,16)/t4-,5-,10-/m0/s1

> <INCHI_KEY>
RPQXVSUAYFXFJA-HGRQIUPRSA-N

> <FORMULA>
C10H17N7O4

> <MOLECULAR_WEIGHT>
299.2865

> <EXACT_MASS>
299.134202067

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
27.63375430942351

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(4R,10aS,10bS)-10,10-dihydroxy-2,6-diimino-decahydropyrrolo[1,2-c]purin-4-yl]methyl carbamate

> <ALOGPS_LOGP>
-2.70

> <JCHEM_LOGP>
-2.4072090809613855

> <ALOGPS_LOGS>
-2.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
12.667118728423866

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.780342980662928

> <JCHEM_PKA_STRONGEST_BASIC>
9.374772952915185

> <JCHEM_POLAR_SURFACE_AREA>
179.80999999999997

> <JCHEM_REFRACTIVITY>
88.4224

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.92e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(4R,10aS,10bS)-10,10-dihydroxy-2,6-diimino-hexahydro-1H-pyrrolo[1,2-c]purin-4-yl]methyl carbamate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
    0.5939    5.8879   -0.9171 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5658    4.6637   -0.5666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5557    3.9473   -0.3461 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3099    2.5320   -0.0403 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9253    1.6088   -1.0965 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1580    0.1960   -0.5162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9159   -0.6261   -1.4282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2468   -0.3965   -1.4310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8584   -1.2355   -2.2927 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8307    0.4455   -0.7693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0796    1.5129   -2.2889 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2484    1.2711   -2.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8992    0.7320   -3.1940 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8209    1.5792   -1.0415 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9975    0.8991   -0.5235 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2524    1.5180    0.8503 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8718    1.9926    1.2959 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1397    0.9317    1.8915 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9992    3.0074    2.2779 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2394    2.4631   -0.0592 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6186    3.8449   -0.3516 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5659    6.1835   -1.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4682    4.3448   -0.5187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7328    2.3446    0.9522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8866    2.0229   -1.4211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2106   -0.3260   -0.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6730    0.2394    0.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3182   -1.9163   -2.8041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8600   -1.1863   -2.4027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5644    1.3380   -3.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2637    0.5783   -3.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8664    1.0287   -1.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7914   -0.1727   -0.4221 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7028    0.7938    1.5367 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9429    2.3657    0.7605 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6364    0.7230    2.7033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5405    3.7945    1.9220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5435    4.0419   -0.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
  4 20  1  0
 14 15  1  0
 15 16  1  0
 17 16  1  0
 11 12  1  0
 17 18  1  1
 11  5  1  0
 17 19  1  0
 12 14  1  0
  2  1  2  3
 14 20  1  0
  5  6  1  0
 20 21  1  6
  4 24  1  1
 21  2  1  0
  6  7  1  0
  2  3  1  0
  7  8  1  0
  3  4  1  0
  8  9  1  0
  4  5  1  0
  8 10  2  0
 20 17  1  0
 12 13  2  3
 11 30  1  0
  5 25  1  6
 21 38  1  0
  3 23  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 18 36  1  0
 19 37  1  0
  1 22  1  0
  6 26  1  0
  6 27  1  0
  9 28  1  0
  9 29  1  0
 13 31  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  N   UNK     0       0.594   5.888  -0.917  0.00  0.00           N+0
HETATM    2  C   UNK     0       0.566   4.664  -0.567  0.00  0.00           C+0
HETATM    3  N   UNK     0      -0.556   3.947  -0.346  0.00  0.00           N+0
HETATM    4  C   UNK     0      -0.310   2.532  -0.040  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.925   1.609  -1.097  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.158   0.196  -0.516  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.916  -0.626  -1.428  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.247  -0.397  -1.431  0.00  0.00           C+0
HETATM    9  N   UNK     0      -3.858  -1.236  -2.293  0.00  0.00           N+0
HETATM   10  O   UNK     0      -3.831   0.446  -0.769  0.00  0.00           O+0
HETATM   11  N   UNK     0      -0.080   1.513  -2.289  0.00  0.00           N+0
HETATM   12  C   UNK     0       1.248   1.271  -2.225  0.00  0.00           C+0
HETATM   13  N   UNK     0       1.899   0.732  -3.194  0.00  0.00           N+0
HETATM   14  N   UNK     0       1.821   1.579  -1.042  0.00  0.00           N+0
HETATM   15  C   UNK     0       2.998   0.899  -0.524  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.252   1.518   0.850  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.872   1.993   1.296  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.140   0.932   1.892  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.999   3.007   2.278  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.239   2.463  -0.059  0.00  0.00           C+0
HETATM   21  N   UNK     0       1.619   3.845  -0.352  0.00  0.00           N+0
HETATM   22  H   UNK     0       1.566   6.184  -1.025  0.00  0.00           H+0
HETATM   23  H   UNK     0      -1.468   4.345  -0.519  0.00  0.00           H+0
HETATM   24  H   UNK     0      -0.733   2.345   0.952  0.00  0.00           H+0
HETATM   25  H   UNK     0      -1.887   2.023  -1.421  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.211  -0.326  -0.344  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.673   0.239   0.452  0.00  0.00           H+0
HETATM   28  H   UNK     0      -3.318  -1.916  -2.804  0.00  0.00           H+0
HETATM   29  H   UNK     0      -4.860  -1.186  -2.403  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.564   1.338  -3.159  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.264   0.578  -3.977  0.00  0.00           H+0
HETATM   32  H   UNK     0       3.866   1.029  -1.177  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.791  -0.173  -0.422  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.703   0.794   1.537  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.943   2.366   0.761  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.636   0.723   2.703  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.541   3.795   1.922  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.543   4.042  -0.697  0.00  0.00           H+0
CONECT    1    2   22                                                       
CONECT    2    1   21    3                                                  
CONECT    3    2    4   23                                                  
CONECT    4   20   24    3    5                                             
CONECT    5   11    6    4   25                                             
CONECT    6    5    7   26   27                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8   28   29                                                  
CONECT   10    8                                                            
CONECT   11   12    5   30                                                  
CONECT   12   11   14   13                                                  
CONECT   13   12   31                                                       
CONECT   14   15   12   20                                                  
CONECT   15   14   16   32   33                                             
CONECT   16   15   17   34   35                                             
CONECT   17   16   18   19   20                                             
CONECT   18   17   36                                                       
CONECT   19   17   37                                                       
CONECT   20    4   14   21   17                                             
CONECT   21   20    2   38                                                  
CONECT   22    1                                                            
CONECT   23    3                                                            
CONECT   24    4                                                            
CONECT   25    5                                                            
CONECT   26    6                                                            
CONECT   27    6                                                            
CONECT   28    9                                                            
CONECT   29    9                                                            
CONECT   30   11                                                            
CONECT   31   13                                                            
CONECT   32   15                                                            
CONECT   33   15                                                            
CONECT   34   16                                                            
CONECT   35   16                                                            
CONECT   36   18                                                            
CONECT   37   19                                                            
CONECT   38   21                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   80    0
END

RDKit          3D

38 40  0  0  0  0  0  0  0  0999 V2000
    0.5939    5.8879   -0.9171 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5658    4.6637   -0.5666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5557    3.9473   -0.3461 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3099    2.5320   -0.0403 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9253    1.6088   -1.0965 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1580    0.1960   -0.5162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9159   -0.6261   -1.4282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2468   -0.3965   -1.4310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8584   -1.2355   -2.2927 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8307    0.4455   -0.7693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0796    1.5129   -2.2889 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2484    1.2711   -2.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8992    0.7320   -3.1940 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8209    1.5792   -1.0415 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9975    0.8991   -0.5235 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2524    1.5180    0.8503 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8718    1.9926    1.2959 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1397    0.9317    1.8915 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9992    3.0074    2.2779 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2394    2.4631   -0.0592 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6186    3.8449   -0.3516 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5659    6.1835   -1.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4682    4.3448   -0.5187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7328    2.3446    0.9522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8866    2.0229   -1.4211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2106   -0.3260   -0.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6730    0.2394    0.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3182   -1.9163   -2.8041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8600   -1.1863   -2.4027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5644    1.3380   -3.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2637    0.5783   -3.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8664    1.0287   -1.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7914   -0.1727   -0.4221 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7028    0.7938    1.5367 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9429    2.3657    0.7605 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6364    0.7230    2.7033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5405    3.7945    1.9220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5435    4.0419   -0.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
  4 20  1  0
 14 15  1  0
 15 16  1  0
 17 16  1  0
 11 12  1  0
 17 18  1  1
 11  5  1  0
 17 19  1  0
 12 14  1  0
  2  1  2  3
 14 20  1  0
  5  6  1  0
 20 21  1  6
  4 24  1  1
 21  2  1  0
  6  7  1  0
  2  3  1  0
  7  8  1  0
  3  4  1  0
  8  9  1  0
  4  5  1  0
  8 10  2  0
 20 17  1  0
 12 13  2  3
 11 30  1  0
  5 25  1  6
 21 38  1  0
  3 23  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 18 36  1  0
 19 37  1  0
  1 22  1  0
  6 26  1  0
  6 27  1  0
  9 28  1  0
  9 29  1  0
 13 31  1  0
M  END

View in JSmol

Synonyms

Value	Source
Gonyaulax catenella poison	HMDB
Mytilus californianus poison	HMDB
Saxidomus giganteus poison	HMDB
Saxitoxin (8ci)	HMDB
Gonyaulax toxin	HMDB
Mitilotoxin	HMDB
Toxin, gonyaulax	HMDB
Saxitonin	HMDB

Chemical Formula

C₁₀H₁₇N₇O₄

Average Mass

299.2865 Da

Monoisotopic Mass

299.13420 Da

IUPAC Name

[(4R,10aS,10bS)-10,10-dihydroxy-2,6-diimino-decahydropyrrolo[1,2-c]purin-4-yl]methyl carbamate

Traditional Name

[(4R,10aS,10bS)-10,10-dihydroxy-2,6-diimino-hexahydro-1H-pyrrolo[1,2-c]purin-4-yl]methyl carbamate

CAS Registry Number

Not Available

SMILES

[H]OC1(O[H])C([H])([H])C([H])([H])N2C(=N[H])N([H])[C@@]([H])(C([H])([H])OC(=O)N([H])[H])[C@]3([H])N([H])C(=N[H])N([H])[C@]123

InChI Identifier

InChI=1S/C10H17N7O4/c11-6-15-5-4(3-21-8(13)18)14-7(12)17-2-1-9(19,20)10(5,17)16-6/h4-5,19-20H,1-3H2,(H2,12,14)(H2,13,18)(H3,11,15,16)/t4-,5-,10-/m0/s1

InChI Key

RPQXVSUAYFXFJA-HGRQIUPRSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃COOD/D₂O (4 : 96), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃COOD/D₂O (4 : 96), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃COOD/D₂O (4 : 96), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃COOD/D₂O (4 : 96), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃COOD/D₂O (4 : 96), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃COOD/D₂O (4 : 96), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃COOD/D₂O (4 : 96), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃COOD/D₂O (4 : 96), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃COOD/D₂O (4 : 96), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃COOD/D₂O (4 : 96), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃COOD/D₂O (4 : 96), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃COOD/D₂O (4 : 96), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃COOD/D₂O (4 : 96), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃COOD/D₂O (4 : 96), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃COOD/D₂O (4 : 96), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃COOD/D₂O (4 : 96), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃COOD/D₂O (4 : 96), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃COOD/D₂O (4 : 96), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃COOD/D₂O (4 : 96), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃COOD/D₂O (4 : 96), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aphanizomenon flos-aquae	LOTUS Database	35616633
Atelopus zeteki	JEOL database	Yotsu-Yamashita, M. Heterocycl Chem, 5, 53 (2006)
Carcinoscorpius rotundicauda	LOTUS Database	35616633
Cylindrospermopsis raciborskii	-	KNApSAcK
Gonyaulax catenella	-	KNApSAcK
Gonyaulax polyedra	LOTUS Database	35616633
Mytilus californianus	-	KNApSAcK
Protogonyaulax tamarensis	-	KNApSAcK
Pyrodinium bahamense	LOTUS Database	35616633
Saxidomus gigantea	LOTUS Database	35616633
Saxidomus giganteus	-	KNApSAcK
Saxidomus nuttalli	LOTUS Database	35616633
Zosimus aeneus	LOTUS Database	35616633

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
Imidazopyrimidine
Alkaloid or derivatives
1,3-diazinane
Imidazolidine
Pyrrolidine
Guanidine
Organoheterocyclic compound
Carboximidamide
Carbonyl hydrate
Carboximidic acid derivative
Azacycle
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Imine
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

carbamate ester (CHEBI:34970 )
organic heterotricyclic compound (CHEBI:34970 )
guanidines (CHEBI:34970 )
alkaloid (CHEBI:34970 )
Alkaloids (C13757 )
Carbamate derivatives (C13757 )

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	-2.7	ALOGPS
logP	-2.4	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	10.78	ChemAxon
pKa (Strongest Basic)	9.37	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	179.81 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	88.42 m³·mol⁻¹	ChemAxon
Polarizability	27.63 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0029368

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Saxitoxin

METLIN ID

Not Available

PubChem Compound

37165

PDB ID

Not Available

ChEBI ID

34970

Good Scents ID

Not Available

References

General References

Hackett JD, Wisecaver JH, Brosnahan ML, Kulis DM, Anderson DM, Bhattacharya D, Plumley FG, Erdner DL: Evolution of saxitoxin synthesis in cyanobacteria and dinoflagellates. Mol Biol Evol. 2013 Jan;30(1):70-8. doi: 10.1093/molbev/mss142. Epub 2012 May 23. [PubMed:22628533 ]
Orr RJ, Stuken A, Murray SA, Jakobsen KS: Evolution and distribution of saxitoxin biosynthesis in dinoflagellates. Mar Drugs. 2013 Aug 8;11(8):2814-28. doi: 10.3390/md11082814. [PubMed:23966031 ]
Tian L, Cheng J, Chen X, Cheng SH, Mak YL, Lam PK, Chan LL, Wang M: Early developmental toxicity of saxitoxin on medaka (Oryzias melastigma) embryos. Toxicon. 2014 Jan;77:16-25. doi: 10.1016/j.toxicon.2013.10.022. Epub 2013 Oct 30. [PubMed:24184516 ]
D'Agostino PM, Song X, Neilan BA, Moffitt MC: Comparative proteomics reveals that a saxitoxin-producing and a nontoxic strain of Anabaena circinalis are two different ecotypes. J Proteome Res. 2014 Mar 7;13(3):1474-84. doi: 10.1021/pr401007k. Epub 2014 Feb 3. [PubMed:24460188 ]
De Bock MFS, Moraes GSO, Almeida RGDS, Vieira KDDS, Santoro KR, Bicudo AJA, Molica RJR: Exposure of Nile Tilapia (Oreochromis niloticus) Fingerlings to a Saxitoxin-Producing Strain of Raphidiopsis (Cylindrospermopsis) raciborskii (Cyanobacterium) Reduces Growth Performance and Increases Mortality Rate. Environ Toxicol Chem. 2020 Jul;39(7):1409-1420. doi: 10.1002/etc.4728. Epub 2020 Jun 3. [PubMed:32323358 ]
Yotsu-Yamashita, M. (2010). Yotsu-Yamashita, M. Heterocycl Chem, 5, 53 (2006). Heterocycl Chem..

Showing NP-Card for saxitoxin (NP0039462)

MOL for NP0039462 (saxitoxin)

3D MOL for NP0039462 (saxitoxin)

3D SDF for NP0039462 (saxitoxin)

3D-SDF for NP0039462 (saxitoxin)

PDB for NP0039462 (saxitoxin)

3D PDB for NP0039462 (saxitoxin)

SMILES for NP0039462 (saxitoxin)

INCHI for NP0039462 (saxitoxin)

Structure for NP0039462 (saxitoxin)

3D Structure for NP0039462 (saxitoxin)