NP-MRD: Showing NP-Card for Œ≤-Amanitin (NP0137202)

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Record Information

Version

1.0

Created at

2022-05-30 16:44:58 UTC

Updated at

2022-05-30 16:44:58 UTC

NP-MRD ID

NP0137202

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Œ≤-Amanitin

Description

Beta-Amanitin, also known as β-amanitin, belongs to the class of organic compounds known as amatoxins. These are cyclic peptides containing eight amino acid residues arranged in a macrobicyclic motif. Treatment involves high dose penicillin as well as supportive care in cases of hepatic and renal injury. Beta-Amanitin is an extremely weak basic (essentially neutral) compound (based on its pKa). Beta-Amanitin is a potentially toxic compound. The most severe effects are toxic hepatitis with centrolobular necrosis and hepatic steatosis, as well as acute tubulointerstitial nephropathy, which altogether induce a severe hepatorenal syndrome. The major toxic mechanism of amatoxins is the inhibition of RNA polymerase II, a vital enzyme in the synthesis of messenger RNA (mRNA), microRNA, and small nuclear RNA (snRNA). Beta-Amanitin is one of a group of at least eight Amatoxins found in several genera of poisonous mushrooms, most notably Amanita phalloides and several other members of the genus Amanita, as well as some Conocybe, Galerina and Lepiota mushroom species. Without mRNA, essential protein synthesis, and hence cell metabolism, grind to a halt and the cell dies. Free toxin may be removed by opsonization via the reticuloendothelial system (primarily the liver and kidneys) or it may be degraded through cellular internalization via the lysosomes. Amatoxins cause liver damage. Œ≤-Amanitin is found in Amanita ocreata, Amanita phalloides and Amanita verna. Lysosomes are membrane-enclosed organelles that contain an array of digestive enzymes, including several proteases.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241205402D          

 64 68  0  0  0  0            999 V2000
    1.8998   -2.5699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2366   -1.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0384   -1.0278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2396   -1.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3384   -0.2255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5649    0.0852    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0012    0.6984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2382    0.3843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1059    1.5460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7189    2.2331    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5300    2.2926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2065    2.5648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5290    1.4843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7333    1.6837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2304    2.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5811    3.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0003    3.7639    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2905    3.3838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4668    3.6568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0820    3.1374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8676    3.3762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9398    2.3450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1824    2.0720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4327    2.5913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3492    3.5779    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.2043    4.3929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1304    3.2761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9259    2.9382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4539    2.0918    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6985    1.2529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5043    0.9020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6791    0.6142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9958   -0.1353    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1742   -0.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4306   -1.1485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1041    3.7698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4483    4.5133    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2543    4.3397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3188    5.1785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0356    5.9573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2291    6.1035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4918    6.6346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0040    3.9955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5647    4.6040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5255    3.3614    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3237    3.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6702    2.7394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4753    2.5942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0859    2.1854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3786    2.5698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.9917    1.8935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3687    0.2200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6478    1.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6779    0.7798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0974    0.9157    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  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
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 15 24  1  0  0  0  0
 18 24  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
  5 34  1  0  0  0  0
 34 35  2  0  0  0  0
 28 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
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 47 48  1  0  0  0  0
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 48 50  1  0  0  0  0
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 51 52  1  0  0  0  0
 52 53  2  0  0  0  0
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 55 56  1  0  0  0  0
 56 57  1  0  0  0  0
 56 58  1  0  0  0  0
 58 59  1  0  0  0  0
 58 60  1  0  0  0  0
 60 61  1  0  0  0  0
 55 62  1  0  0  0  0
 62 63  2  0  0  0  0
 62 64  1  0  0  0  0
 13 64  1  0  0  0  0
M  END

     RDKit          3D

117121  0  0  0  0  0  0  0  0999 V2000
    6.5253   -1.0685   -3.5225 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9080   -0.2606   -2.3194 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8596   -0.1855   -1.2680 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3876    0.6510   -0.1030 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5465    0.3927   -1.6633 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9150   -0.3638   -2.7137 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0461   -1.4829   -2.4439 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7214   -2.2551   -3.3817 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5536   -1.6911   -1.0409 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8541   -3.2160   -0.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4898   -1.3635    2.9703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0815   -0.3159    3.6561 C   0  0  0  0  0  0  0  0  0  0  0  0
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 64117  1  0
M  END


  Mrv0541 02241205402D          

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M  END
> <DATABASE_ID>
NP0137202

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C1NC(=O)CNC(=O)C2CC3=C(NC4=CC(O)=CC=C34)S(=O)CC(NC(=O)CNC1=O)C(=O)NC(CC(O)=O)C(=O)N1CC(O)CC1C(=O)NC(C(C)C(O)CO)C(=O)N2

> <INCHI_IDENTIFIER>
InChI=1S/C39H53N9O15S/c1-4-16(2)31-36(60)41-11-28(53)42-25-15-64(63)38-21(20-6-5-18(50)7-22(20)45-38)9-23(33(57)40-12-29(54)46-31)43-37(61)32(17(3)27(52)14-49)47-35(59)26-8-19(51)13-48(26)39(62)24(10-30(55)56)44-34(25)58/h5-7,16-17,19,23-27,31-32,45,49-52H,4,8-15H2,1-3H3,(H,40,57)(H,41,60)(H,42,53)(H,43,61)(H,44,58)(H,46,54)(H,47,59)(H,55,56)

> <INCHI_KEY>
IEQCUEXVAPAFMQ-UHFFFAOYSA-N

> <FORMULA>
C39H53N9O15S

> <MOLECULAR_WEIGHT>
919.954

> <EXACT_MASS>
919.338182761

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
89.25083159692818

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
13

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[34-(butan-2-yl)-13-(3,4-dihydroxybutan-2-yl)-8,22-dihydroxy-2,5,11,14,27,30,33,36,39-nonaoxo-27λ⁴-thia-3,6,12,15,25,29,32,35,38-nonaazapentacyclo[14.12.11.0⁶,¹⁰.0¹⁸,²⁶.0¹⁹,²⁴]nonatriaconta-18(26),19,21,23-tetraen-4-yl]acetic acid

> <ALOGPS_LOGP>
-1.31

> <JCHEM_LOGP>
-6.854337126999999

> <ALOGPS_LOGS>
-2.21

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.389656025452215

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6469860554766327

> <JCHEM_PKA_STRONGEST_BASIC>
-5.529577316852756

> <JCHEM_POLAR_SURFACE_AREA>
375.09

> <JCHEM_REFRACTIVITY>
219.48470000000015

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.70e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-amanitin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       3.546  -4.797   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.175  -3.421   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.805  -1.919   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.314  -2.328   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.365  -0.421   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       2.921   0.159   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       1.869   1.304   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.445   0.717   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.064   2.886   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       3.209   4.168   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       4.723   4.279   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.986   4.788   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.721   2.771   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.236   3.143   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.297   4.632   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.951   5.985   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       1.867   7.026   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       0.542   6.316   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.871   6.826   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.020   5.857   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -3.486   6.302   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.754   4.377   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.341   3.868   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.808   4.837   0.000  0.00  0.00           C+0
HETATM   25  S   UNK     0       4.385   6.679   0.000  0.00  0.00           S+0
HETATM   26  O   UNK     0       4.115   8.200   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.843   6.115   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.328   5.485   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0       8.314   3.905   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0       8.771   2.339   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      10.275   1.684   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       8.734   1.147   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0       7.459  -0.253   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0       5.925  -0.666   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       6.404  -2.144   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       7.661   7.037   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       6.632   8.195   0.000  0.00  0.00           O+0
HETATM   38  N   UNK     0       8.304   8.425   0.000  0.00  0.00           N+0
HETATM   39  C   UNK     0       9.808   8.101   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       9.928   9.667   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       9.400  11.120   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       7.894  11.393   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      10.251  12.385   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      11.208   7.458   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      12.254   8.594   0.000  0.00  0.00           O+0
HETATM   46  N   UNK     0      12.181   6.275   0.000  0.00  0.00           N+0
HETATM   47  C   UNK     0      13.671   6.470   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      14.318   5.114   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      15.821   4.842   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      13.227   4.079   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      11.907   4.797   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      10.365   4.880   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      11.185   3.535   0.000  0.00  0.00           O+0
HETATM   54  N   UNK     0       8.823   5.038   0.000  0.00  0.00           N+0
HETATM   55  C   UNK     0       7.321   4.262   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       7.900   2.667   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       9.462   3.286   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       7.816   0.853   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0       6.288   0.411   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0       8.905  -0.466   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0       9.145  -1.999   0.000  0.00  0.00           O+0
HETATM   62  C   UNK     0       6.809   2.812   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0       6.865   1.456   0.000  0.00  0.00           O+0
HETATM   64  N   UNK     0       5.782   1.709   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   34                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   64                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   24                                                  
CONECT   16   15   17   25                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   15   18                                                  
CONECT   25   16   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   36                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33    5   35                                                  
CONECT   35   34                                                            
CONECT   36   28   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   40   44                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41                                                            
CONECT   44   39   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47   51                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   51                                                       
CONECT   51   50   46   52                                                  
CONECT   52   51   53   54                                                  
CONECT   53   52                                                            
CONECT   54   52   55                                                       
CONECT   55   54   56   62                                                  
CONECT   56   55   57   58                                                  
CONECT   57   56                                                            
CONECT   58   56   59   60                                                  
CONECT   59   58                                                            
CONECT   60   58   61                                                       
CONECT   61   60                                                            
CONECT   62   55   63   64                                                  
CONECT   63   62                                                            
CONECT   64   62   13                                                       
MASTER        0    0    0    0    0    0    0    0   64    0  136    0
END

View in JSmol

Synonyms

Value	Source
b-Amanitin	Generator
Β-amanitin	Generator
1-Asp-alpha-amanitin	MeSH

Chemical Formula

C₃₉H₅₃N₉O₁₅S

Average Mass

919.9540 Da

Monoisotopic Mass

919.33818 Da

IUPAC Name

2-[34-(butan-2-yl)-13-(3,4-dihydroxybutan-2-yl)-8,22-dihydroxy-2,5,11,14,27,30,33,36,39-nonaoxo-27λ⁴-thia-3,6,12,15,25,29,32,35,38-nonaazapentacyclo[14.12.11.0⁶,¹⁰.0¹⁸,²⁶.0¹⁹,²⁴]nonatriaconta-18(26),19,21,23-tetraen-4-yl]acetic acid

Traditional Name

β-amanitin

CAS Registry Number

Not Available

SMILES

CCC(C)C1NC(=O)CNC(=O)C2CC3=C(NC4=CC(O)=CC=C34)S(=O)CC(NC(=O)CNC1=O)C(=O)NC(CC(O)=O)C(=O)N1CC(O)CC1C(=O)NC(C(C)C(O)CO)C(=O)N2

InChI Identifier

InChI=1S/C39H53N9O15S/c1-4-16(2)31-36(60)41-11-28(53)42-25-15-64(63)38-21(20-6-5-18(50)7-22(20)45-38)9-23(33(57)40-12-29(54)46-31)43-37(61)32(17(3)27(52)14-49)47-35(59)26-8-19(51)13-48(26)39(62)24(10-30(55)56)44-34(25)58/h5-7,16-17,19,23-27,31-32,45,49-52H,4,8-15H2,1-3H3,(H,40,57)(H,41,60)(H,42,53)(H,43,61)(H,44,58)(H,46,54)(H,47,59)(H,55,56)

InChI Key

IEQCUEXVAPAFMQ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Amanita ocreata	LOTUS Database	35616633
Amanita phalloides	LOTUS Database	35616633
Amanita verna	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as amatoxins. These are cyclic peptides containing eight amino acid residues arranged in a macrobicyclic motif.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Amatoxins

Alternative Parents

Substituents

Amatoxin skeleton
Alpha-oligopeptide
Alpha-amino acid or derivatives
Hydroxyindole
3-alkylindole
Indole
Indole or derivatives
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Pyrrole
Pyrrolidine
Heteroaromatic compound
Tertiary carboxylic acid amide
Carboxamide group
Lactam
Secondary alcohol
Secondary carboxylic acid amide
Sulfoxide
Monocarboxylic acid or derivatives
Carboxylic acid
Azacycle
Sulfinyl compound
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
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	-1.3	ALOGPS
logP	-6.9	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	3.65	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	375.09 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	219.48 m³·mol⁻¹	ChemAxon
Polarizability	89.25 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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Beta-Amanitin

METLIN ID

Not Available

PubChem Compound

2276

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Œ≤-Amanitin (NP0137202)

MOL for NP0137202 (Œ≤-Amanitin)

3D MOL for NP0137202 (Œ≤-Amanitin)

3D SDF for NP0137202 (Œ≤-Amanitin)

3D-SDF for NP0137202 (Œ≤-Amanitin)

PDB for NP0137202 (Œ≤-Amanitin)

3D PDB for NP0137202 (Œ≤-Amanitin)

SMILES for NP0137202 (Œ≤-Amanitin)

INCHI for NP0137202 (Œ≤-Amanitin)

Structure for NP0137202 (Œ≤-Amanitin)

3D Structure for NP0137202 (Œ≤-Amanitin)