NP-MRD: Showing NP-Card for sucurchalasin B (NP0333617)

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Record Information

Version

2.0

Created at

2024-07-16 10:14:58 UTC

Updated at

2024-11-01 00:36:18 UTC

NP-MRD ID

NP0333617

Natural Product DOI

https://doi.org/10.57994/3096

Secondary Accession Numbers

None

Natural Product Identification

Common Name

sucurchalasin B

Description

Sucurchalasin B belongs to the class of organic compounds known as aspochalasins. These are cytochalasans with a structure in which the hydrogenated isoindole bears a 2-methylpropyl group. Based on a literature review very few articles have been published on sucurchalasin B.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 03302312492D          

 53 57  0  0  1  0            999 V2000
   -0.8284   -2.7268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0476   -2.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0598   -1.5605    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6800   -1.1338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8219   -1.2445    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0970   -0.4668    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9218   -0.4881    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0485   -1.2344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9347   -1.6706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5382    0.2158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4605    1.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2887    1.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1343    1.5388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6070   -2.8805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3691   -2.5645    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4766   -1.7465    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2947   -1.3649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6497   -0.6202    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1314    0.2061    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.6866    0.8083    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4409    1.5959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6360    1.7768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0768    1.1702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4915    0.6273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0507    1.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8050    2.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3641    2.6281    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1184    3.4156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3135    3.5966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7543    2.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9494    3.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7037    3.9585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8988    4.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6530    4.9270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3396    3.5329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5853    2.7453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0262    2.1388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3902    2.5644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0678    4.3841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1690    2.4471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4676   -0.7276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5407   -2.3181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2617   -3.3825    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0238   -3.0665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7859   -2.7506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3801   -1.8870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4406   -3.2526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2027   -2.9366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3101   -2.1187    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1079   -1.8048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6182   -1.5387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1010   -2.2773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  0  0  0  0
  3  4  1  1  0  0  0
  5  3  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  7 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  2 15  2  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
  5 17  1  0  0  0  0
 17  9  1  1  0  0  0
 17 18  1  0  0  0  0
 19 18  1  0  0  0  0
 19 20  1  6  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 21 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 28 27  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 23 39  1  0  0  0  0
 32 39  1  0  0  0  0
 30 40  2  0  0  0  0
 28 41  1  1  0  0  0
 19 42  1  0  0  0  0
 18 43  2  0  0  0  0
 16 44  1  6  0  0  0
 16 45  1  0  0  0  0
 45 46  2  0  0  0  0
 46 47  1  0  0  0  0
 46 48  1  0  0  0  0
 48 49  1  0  0  0  0
 50 49  1  0  0  0  0
 50 51  1  6  0  0  0
 50 52  1  0  0  0  0
 42 52  1  0  0  0  0
 52 53  2  0  0  0  0
M  END


  Mrv2104 03302312492D          

 53 57  0  0  1  0            999 V2000
   -0.8284   -2.7268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0476   -2.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0598   -1.5605    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6800   -1.1338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8219   -1.2445    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0970   -0.4668    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9218   -0.4881    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0485   -1.2344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9347   -1.6706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5382    0.2158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4605    1.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2887    1.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1343    1.5388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6070   -2.8805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3691   -2.5645    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4766   -1.7465    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2947   -1.3649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6497   -0.6202    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1314    0.2061    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.6866    0.8083    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4409    1.5959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6360    1.7768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0768    1.1702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4915    0.6273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0507    1.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8050    2.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3641    2.6281    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1184    3.4156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3135    3.5966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7543    2.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9494    3.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7037    3.9585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8988    4.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6530    4.9270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3396    3.5329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5853    2.7453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0262    2.1388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3902    2.5644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0678    4.3841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1690    2.4471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4676   -0.7276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5407   -2.3181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2617   -3.3825    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0238   -3.0665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7859   -2.7506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3801   -1.8870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4406   -3.2526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2027   -2.9366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3101   -2.1187    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1079   -1.8048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6182   -1.5387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1010   -2.2773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  0  0  0  0
  3  4  1  1  0  0  0
  5  3  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  7 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  2 15  2  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
  5 17  1  0  0  0  0
 17  9  1  1  0  0  0
 17 18  1  0  0  0  0
 19 18  1  0  0  0  0
 19 20  1  6  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 21 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 28 27  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 23 39  1  0  0  0  0
 32 39  1  0  0  0  0
 30 40  2  0  0  0  0
 28 41  1  1  0  0  0
 19 42  1  0  0  0  0
 18 43  2  0  0  0  0
 16 44  1  6  0  0  0
 16 45  1  0  0  0  0
 45 46  2  0  0  0  0
 46 47  1  0  0  0  0
 46 48  1  0  0  0  0
 48 49  1  0  0  0  0
 50 49  1  0  0  0  0
 50 51  1  6  0  0  0
 50 52  1  0  0  0  0
 42 52  1  0  0  0  0
 52 53  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0333617

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12[C@H](CC(C)C)NC(=O)[C@]11C(=O)[C@@H](CC(=O)[C@H](O)CC\C(C)=C\[C@@]1([H])C=C(C)[C@H]2C)S[C@H]1CCC[C@H](C)OC(=O)CC2=CC(O)=CC(O)=C2C(=O)C1

> <INCHI_IDENTIFIER>
InChI=1S/C40H53NO9S/c1-20(2)12-29-37-24(6)22(4)14-26-13-21(3)10-11-30(43)31(44)19-34(38(48)40(26,37)39(49)41-29)51-28-9-7-8-23(5)50-35(47)16-25-15-27(42)17-32(45)36(25)33(46)18-28/h13-15,17,20,23-24,26,28-30,34,37,42-43,45H,7-12,16,18-19H2,1-6H3,(H,41,49)/b21-13+/t23-,24+,26-,28-,29-,30+,34+,37-,40-/m0/s1

> <INCHI_KEY>
XZBGYPKLRSRPJQ-IANCEBCKSA-N

> <FORMULA>
C40H53NO9S

> <MOLECULAR_WEIGHT>
723.92

> <EXACT_MASS>
723.344103465

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
104

> <JCHEM_AVERAGE_POLARIZABILITY>
77.89477786710792

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,3aR,4S,6aS,11R,14R,15aS)-14-{[(4S,8S)-11,13-dihydroxy-4-methyl-2,10-dioxo-2,4,5,6,7,8,9,10-octahydro-1H-3-benzoxacyclododecin-8-yl]sulfanyl}-11-hydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-1H,2H,3H,3aH,4H,6aH,9H,10H,11H,12H,13H,14H,15H-cycloundeca[d]isoindole-1,12,15-trione

> <JCHEM_LOGP>
6.3786291943333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.660129948729093

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.776684271320482

> <JCHEM_PKA_STRONGEST_BASIC>
-2.1773799190450474

> <JCHEM_POLAR_SURFACE_AREA>
167.29999999999998

> <JCHEM_REFRACTIVITY>
197.50840000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3S,3aR,4S,6aS,11R,14R,15aS)-14-{[(4S,8S)-11,13-dihydroxy-4-methyl-2,10-dioxo-4,5,6,7,8,9-hexahydro-1H-3-benzoxacyclododecin-8-yl]sulfanyl}-11-hydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-2H,3H,3aH,4H,6aH,9H,10H,11H,13H,14H-cycloundeca[d]isoindole-1,12,15-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 30-MAR-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-MAR-23         0                                  
HETATM    1  C   UNK     0      -1.546  -5.090   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.089  -4.440   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.112  -2.913   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.269  -2.116   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.534  -2.323   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0       1.334  -3.850   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0       2.048  -0.871   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       3.587  -0.911   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       3.824  -2.304   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.478  -3.118   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.005   0.403   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.860   1.984   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.539   2.629   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.117   2.872   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.133  -5.377   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.556  -4.787   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.756  -3.260   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.284  -2.548   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.946  -1.158   0.000  0.00  0.00           C+0
HETATM   20  S   UNK     0       3.979   0.385   0.000  0.00  0.00           S+0
HETATM   21  C   UNK     0       5.015   1.509   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.556   2.979   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.054   3.317   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.010   2.184   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.517   1.171   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.561   2.303   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.103   3.773   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.146   4.906   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       7.688   6.376   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.185   6.714   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.141   5.581   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.639   5.919   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.180   7.389   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.678   7.727   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       1.219   9.197   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       0.634   6.595   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.093   5.125   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       0.049   3.992   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       2.595   4.787   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       5.726   8.184   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       9.649   4.568   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       6.473  -1.358   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       4.743  -4.327   0.000  0.00  0.00           O+0
HETATM   44  H   UNK     0       2.355  -6.314   0.000  0.00  0.00           H+0
HETATM   45  C   UNK     0       3.778  -5.724   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       5.200  -5.134   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       4.443  -3.522   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       6.422  -6.072   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       7.845  -5.482   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       8.046  -3.955   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       9.535  -3.369   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0       6.754  -2.872   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0       5.789  -4.251   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7   17                                             
CONECT    6    5                                                            
CONECT    7    5    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   17                                                  
CONECT   10    9                                                            
CONECT   11    7   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    2   16                                                       
CONECT   16   15   17   44   45                                             
CONECT   17   16    5    9   18                                             
CONECT   18   17   19   43                                                  
CONECT   19   18   20   42                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   39                                                  
CONECT   24   23                                                            
CONECT   25   21   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   41                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   40                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   39                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   23   32                                                  
CONECT   40   30                                                            
CONECT   41   28                                                            
CONECT   42   19   52                                                       
CONECT   43   18                                                            
CONECT   44   16                                                            
CONECT   45   16   46                                                       
CONECT   46   45   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   42   53                                                  
CONECT   53   52                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  114    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₀H₅₃NO₉S

Average Mass

723.9200 Da

Monoisotopic Mass

723.34410 Da

IUPAC Name

(3S,3aR,4S,6aS,11R,14R,15aS)-14-{[(4S,8S)-11,13-dihydroxy-4-methyl-2,10-dioxo-2,4,5,6,7,8,9,10-octahydro-1H-3-benzoxacyclododecin-8-yl]sulfanyl}-11-hydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-1H,2H,3H,3aH,4H,6aH,9H,10H,11H,12H,13H,14H,15H-cycloundeca[d]isoindole-1,12,15-trione

Traditional Name

(3S,3aR,4S,6aS,11R,14R,15aS)-14-{[(4S,8S)-11,13-dihydroxy-4-methyl-2,10-dioxo-4,5,6,7,8,9-hexahydro-1H-3-benzoxacyclododecin-8-yl]sulfanyl}-11-hydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-2H,3H,3aH,4H,6aH,9H,10H,11H,13H,14H-cycloundeca[d]isoindole-1,12,15-trione

CAS Registry Number

Not Available

SMILES

[H][C@]12[C@H](CC(C)C)NC(=O)[C@]11C(=O)[C@@H](CC(=O)[C@H](O)CC\C(C)=C\[C@@]1([H])C=C(C)[C@H]2C)S[C@H]1CCC[C@H](C)OC(=O)CC2=CC(O)=CC(O)=C2C(=O)C1

InChI Identifier

InChI=1S/C40H53NO9S/c1-20(2)12-29-37-24(6)22(4)14-26-13-21(3)10-11-30(43)31(44)19-34(38(48)40(26,37)39(49)41-29)51-28-9-7-8-23(5)50-35(47)16-25-15-27(42)17-32(45)36(25)33(46)18-28/h13-15,17,20,23-24,26,28-30,34,37,42-43,45H,7-12,16,18-19H2,1-6H3,(H,41,49)/b21-13+/t23-,24+,26-,28-,29-,30+,34+,37-,40-/m0/s1

InChI Key

XZBGYPKLRSRPJQ-IANCEBCKSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	xuweifeng_u@163.com	Guangxi Normal University	Wei-Feng Xu	2024-07-16	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	xuweifeng_u@163.com	Guangxi Normal University	Wei-Feng Xu	2024-07-16	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	xuweifeng_u@163.com	Guangxi Normal University	Wei-Feng Xu	2024-07-16	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	xuweifeng_u@163.com	Guangxi Normal University	Wei-Feng Xu	2024-07-16	View Spectrum
1D_DEPT NMR	¹³C NMR Spectrum (1D, 151 MHz, C2D6OS, experimental)	xuweifeng_u@163.com	Guangxi Normal University	Wei-Feng Xu	2024-07-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	xuweifeng_u@163.com	Guangxi Normal University	Wei-Feng Xu	2024-07-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C2D6OS, experimental)	xuweifeng_u@163.com	Guangxi Normal University	Wei-Feng Xu	2024-07-16	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
spelaeus		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as aspochalasins. These are cytochalasans with a structure in which the hydrogenated isoindole bears a 2-methylpropyl group.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Cytochalasans

Sub Class

Aspochalasins

Direct Parent

Aspochalasins

Alternative Parents

Substituents

Carbocyclic aspochalasin skeleton
Aspochalasin skeleton
Diterpenoid
Diterpene lactone
Isoindolone
Isoindole or derivatives
Isoindoline
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Fatty acyl
Alpha-branched alpha,beta-unsaturated-ketone
Benzenoid
2-pyrrolidone
Pyrrolidone
N-acyl-amine
Monosaccharide
Fatty amide
Acyloin
Vinylogous acid
Alpha,beta-unsaturated ketone
Pyrrolidine
Enone
Alpha-hydroxy ketone
Acryloyl-group
Cyclic ketone
Secondary alcohol
Lactone
Lactam
Ketone
Carboxylic acid ester
Carboxamide group
Oxacycle
Azacycle
Organoheterocyclic compound
Dialkylthioether
Sulfenyl compound
Thioether
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
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	6.38	ChemAxon
pKa (Strongest Acidic)	7.78	ChemAxon
pKa (Strongest Basic)	-2.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	167.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	197.51 m³·mol⁻¹	ChemAxon
Polarizability	77.89 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	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for sucurchalasin B (NP0333617)

MOL for NP0333617 (sucurchalasin B)

3D MOL for NP0333617 (sucurchalasin B)

3D SDF for NP0333617 (sucurchalasin B)

3D-SDF for NP0333617 (sucurchalasin B)

PDB for NP0333617 (sucurchalasin B)

3D PDB for NP0333617 (sucurchalasin B)

SMILES for NP0333617 (sucurchalasin B)

INCHI for NP0333617 (sucurchalasin B)

Structure for NP0333617 (sucurchalasin B)

3D Structure for NP0333617 (sucurchalasin B)