NP-MRD: Showing NP-Card for (2s)-5-carbamimidamido-2-[(8-{[(1r,2s,4r,6r,7r,10s,11s,14s,16r)-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]pentanoic acid (NP0221265)

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Record Information

Version

2.0

Created at

2022-09-05 22:47:25 UTC

Updated at

2022-09-05 22:47:25 UTC

NP-MRD ID

NP0221265

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-5-carbamimidamido-2-[(8-{[(1r,2s,4r,6r,7r,10s,11s,14s,16r)-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]pentanoic acid

Description

Resibufotoxin belongs to the class of organic compounds known as bufanolides and derivatives. These are steroid lactones containing a pyran-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative. (2s)-5-carbamimidamido-2-[(8-{[(1r,2s,4r,6r,7r,10s,11s,14s,16r)-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]pentanoic acid is found in Phrynoidis asper. Based on a literature review very few articles have been published on Resibufotoxin.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062200472D          

 50 55  0  0  1  0            999 V2000
    2.6201    0.3076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3345    0.7201    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3345   -0.1049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0490   -0.5174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7635   -0.1049    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4780   -0.5174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1924   -0.1049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1924    0.7201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9069   -0.5174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6214   -0.1049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3358   -0.5174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0503   -0.1049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7648   -0.5174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4793   -0.1049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1937   -0.5174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9082   -0.1049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1937   -1.3424    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9082   -1.7549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.9082   -2.5799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6227   -2.9924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6227   -3.8174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3371   -4.2299    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3371   -5.0549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0516   -5.4674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6227   -5.4674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6227   -1.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6227   -0.5174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3371   -1.7549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7635    0.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0490    1.1326    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0490    1.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3345    2.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6201    1.9576    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6201    1.1326    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9056    0.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1911    1.1326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1911    1.9576    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4375    1.6220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5780    2.5096    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2289    2.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4839    1.5535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2908    1.3819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8429    1.9950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6499    1.8235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5879    2.7797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7810    2.9512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9136    3.2633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7341    3.1771    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5187    2.9221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9056    2.3701    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  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  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  4  0  0  0
 15 17  2  0  0  0  0
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 18 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
  5 29  1  0  0  0  0
 30 29  1  6  0  0  0
  2 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 33 32  1  6  0  0  0
 33 34  1  0  0  0  0
  2 34  1  0  0  0  0
 34 35  1  1  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  1  0  0  0
 37 39  1  0  0  0  0
 39 40  1  1  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 43 45  1  0  0  0  0
 45 46  1  0  0  0  0
 40 46  2  0  0  0  0
 39 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  1  0  0  0
 50 49  1  1  0  0  0
 48 50  1  0  0  0  0
 33 50  1  0  0  0  0
 37 50  1  0  0  0  0
M  END


  Mrv1652309062200472D          

 50 55  0  0  1  0            999 V2000
    2.6201    0.3076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3345    0.7201    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3345   -0.1049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0490   -0.5174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7635   -0.1049    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4780   -0.5174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1924   -0.1049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1924    0.7201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9069   -0.5174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6214   -0.1049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3358   -0.5174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0503   -0.1049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7648   -0.5174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4793   -0.1049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1937   -0.5174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9082   -0.1049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1937   -1.3424    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9082   -1.7549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.9082   -2.5799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6227   -2.9924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6227   -3.8174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3371   -4.2299    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3371   -5.0549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0516   -5.4674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6227   -5.4674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6227   -1.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6227   -0.5174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3371   -1.7549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7635    0.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0490    1.1326    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0490    1.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3345    2.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6201    1.9576    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6201    1.1326    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9056    0.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1911    1.1326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1911    1.9576    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4375    1.6220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5780    2.5096    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2289    2.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4839    1.5535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2908    1.3819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8429    1.9950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6499    1.8235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5879    2.7797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7810    2.9512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9136    3.2633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7341    3.1771    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5187    2.9221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9056    2.3701    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  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  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  4  0  0  0
 15 17  2  0  0  0  0
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 18 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
  5 29  1  0  0  0  0
 30 29  1  6  0  0  0
  2 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 33 32  1  6  0  0  0
 33 34  1  0  0  0  0
  2 34  1  0  0  0  0
 34 35  1  1  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  1  0  0  0
 37 39  1  0  0  0  0
 39 40  1  1  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 43 45  1  0  0  0  0
 45 46  1  0  0  0  0
 40 46  2  0  0  0  0
 39 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  1  0  0  0
 50 49  1  1  0  0  0
 48 50  1  0  0  0  0
 33 50  1  0  0  0  0
 37 50  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0221265

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12CC[C@H]3[C@@H](CC[C@@H]4C[C@H](CC[C@]34C)OC(=O)CCCCCCC(O)=N[C@@H](CCCNC(N)=N)C(O)=O)[C@]11O[C@@H]1C[C@@H]2C1=COC(=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C38H56N4O8/c1-36-17-15-25(49-33(45)10-6-4-3-5-9-31(43)42-29(34(46)47)8-7-19-41-35(39)40)20-24(36)12-13-27-26(36)16-18-37(2)28(21-30-38(27,37)50-30)23-11-14-32(44)48-22-23/h11,14,22,24-30H,3-10,12-13,15-21H2,1-2H3,(H,42,43)(H,46,47)(H4,39,40,41)/t24-,25+,26+,27-,28-,29+,30-,36+,37-,38-/m1/s1

> <INCHI_KEY>
PRMSQJQRXAFMHG-JUFMYRFISA-N

> <FORMULA>
C38H56N4O8

> <MOLECULAR_WEIGHT>
696.886

> <EXACT_MASS>
696.409814779

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
106

> <JCHEM_AVERAGE_POLARIZABILITY>
77.59427527457694

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-5-carbamimidamido-2-[(8-{[(1R,2S,4R,6S,7R,10S,11S,14S,16R)-7,11-dimethyl-6-(2-oxo-2H-pyran-5-yl)-3-oxapentacyclo[8.8.0.0^{2,4}.0^{2,7}.0^{11,16}]octadecan-14-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]pentanoic acid

> <JCHEM_LOGP>
3.0571913092959213

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
5.82474643583695

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.755122361276705

> <JCHEM_PKA_STRONGEST_BASIC>
12.15267593345877

> <JCHEM_POLAR_SURFACE_AREA>
196.92

> <JCHEM_REFRACTIVITY>
196.03380000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-5-carbamimidamido-2-[(8-{[(1R,2S,4R,6S,7R,10S,11S,14S,16R)-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0^{2,4}.0^{2,7}.0^{11,16}]octadecan-14-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       4.891   0.574   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.224   1.344   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.224  -0.196   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.558  -0.966   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.892  -0.196   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      10.226  -0.966   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      11.559  -0.196   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      11.559   1.344   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      12.893  -0.966   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.227  -0.196   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.560  -0.966   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.894  -0.196   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.228  -0.966   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      19.561  -0.196   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.895  -0.966   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      22.229  -0.196   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0      20.895  -2.506   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      22.229  -3.276   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      22.229  -4.816   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      23.562  -5.586   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      23.562  -7.126   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      24.896  -7.896   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0      24.896  -9.436   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0      26.230 -10.206   0.000  0.00  0.00           N+0
HETATM   25  N   UNK     0      23.562 -10.206   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0      23.562  -2.506   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      23.562  -0.966   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      24.896  -3.276   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       8.892   1.344   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.558   2.114   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.558   3.654   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.224   4.424   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.891   3.654   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.891   2.114   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.557   1.344   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.223   2.114   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.223   3.654   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.817   3.028   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       1.079   4.685   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -0.427   4.364   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -0.903   2.900   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -2.410   2.580   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -3.440   3.724   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -4.946   3.404   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      -2.964   5.189   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      -1.458   5.509   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       1.705   6.091   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       3.237   5.931   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0       4.702   5.455   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0       3.557   4.424   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   30   34                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   29                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   26                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   18   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29    5   30                                                       
CONECT   30   29    2   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   50                                                  
CONECT   34   33    2   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38   39   50                                             
CONECT   38   37                                                            
CONECT   39   37   40   47                                                  
CONECT   40   39   41   46                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   46                                                       
CONECT   46   45   40                                                       
CONECT   47   39   48                                                       
CONECT   48   47   49   50                                                  
CONECT   49   48   50                                                       
CONECT   50   49   48   33   37                                             
MASTER        0    0    0    0    0    0    0    0   50    0  110    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₈H₅₆N₄O₈

Average Mass

696.8860 Da

Monoisotopic Mass

696.40981 Da

IUPAC Name

(2S)-5-carbamimidamido-2-[(8-{[(1R,2S,4R,6S,7R,10S,11S,14S,16R)-7,11-dimethyl-6-(2-oxo-2H-pyran-5-yl)-3-oxapentacyclo[8.8.0.0^{2,4}.0^{2,7}.0^{11,16}]octadecan-14-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]pentanoic acid

Traditional Name

(2S)-5-carbamimidamido-2-[(8-{[(1R,2S,4R,6S,7R,10S,11S,14S,16R)-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0^{2,4}.0^{2,7}.0^{11,16}]octadecan-14-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]pentanoic acid

CAS Registry Number

Not Available

SMILES

C[C@]12CC[C@H]3[C@@H](CC[C@@H]4C[C@H](CC[C@]34C)OC(=O)CCCCCCC(O)=N[C@@H](CCCNC(N)=N)C(O)=O)[C@]11O[C@@H]1C[C@@H]2C1=COC(=O)C=C1

InChI Identifier

InChI=1S/C38H56N4O8/c1-36-17-15-25(49-33(45)10-6-4-3-5-9-31(43)42-29(34(46)47)8-7-19-41-35(39)40)20-24(36)12-13-27-26(36)16-18-37(2)28(21-30-38(27,37)50-30)23-11-14-32(44)48-22-23/h11,14,22,24-30H,3-10,12-13,15-21H2,1-2H3,(H,42,43)(H,46,47)(H4,39,40,41)/t24-,25+,26+,27-,28-,29+,30-,36+,37-,38-/m1/s1

InChI Key

PRMSQJQRXAFMHG-JUFMYRFISA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Phrynoidis asper	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bufanolides and derivatives. These are steroid lactones containing a pyran-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Bufanolides and derivatives

Alternative Parents

Substituents

Bufanolide-skeleton
Steroid ester
Naphthopyran
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
N-acyl-alpha-amino acid
Alpha-amino acid or derivatives
Naphthalene
Fatty acid ester
Pyranone
Dicarboxylic acid or derivatives
Fatty acyl
Fatty amide
N-acyl-amine
Oxane
Pyran
Heteroaromatic compound
Lactone
Guanidine
Carboxamide group
Carboxylic acid ester
Secondary carboxylic acid amide
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Oxacycle
Oxirane
Ether
Organoheterocyclic compound
Organic 1,3-dipolar compound
Carboximidamide
Propargyl-type 1,3-dipolar organic compound
Organic oxide
Organic nitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organooxygen compound
Organonitrogen compound
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	3.06	ChemAxon
pKa (Strongest Acidic)	3.76	ChemAxon
pKa (Strongest Basic)	12.15	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	196.92 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	196.03 m³·mol⁻¹	ChemAxon
Polarizability	77.59 Å³	ChemAxon
Number of Rings	6	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

Not Available

METLIN ID

Not Available

PubChem Compound

101307888

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-5-carbamimidamido-2-[(8-{[(1r,2s,4r,6r,7r,10s,11s,14s,16r)-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]pentanoic acid (NP0221265)

MOL for NP0221265 ((2s)-5-carbamimidamido-2-[(8-{[(1r,2s,4r,6r,7r,10s,11s,14s,16r)-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]pentanoic acid)

3D MOL for NP0221265 ((2s)-5-carbamimidamido-2-[(8-{[(1r,2s,4r,6r,7r,10s,11s,14s,16r)-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]pentanoic acid)

3D SDF for NP0221265 ((2s)-5-carbamimidamido-2-[(8-{[(1r,2s,4r,6r,7r,10s,11s,14s,16r)-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]pentanoic acid)

3D-SDF for NP0221265 ((2s)-5-carbamimidamido-2-[(8-{[(1r,2s,4r,6r,7r,10s,11s,14s,16r)-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]pentanoic acid)

PDB for NP0221265 ((2s)-5-carbamimidamido-2-[(8-{[(1r,2s,4r,6r,7r,10s,11s,14s,16r)-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]pentanoic acid)

3D PDB for NP0221265 ((2s)-5-carbamimidamido-2-[(8-{[(1r,2s,4r,6r,7r,10s,11s,14s,16r)-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]pentanoic acid)

SMILES for NP0221265 ((2s)-5-carbamimidamido-2-[(8-{[(1r,2s,4r,6r,7r,10s,11s,14s,16r)-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]pentanoic acid)

INCHI for NP0221265 ((2s)-5-carbamimidamido-2-[(8-{[(1r,2s,4r,6r,7r,10s,11s,14s,16r)-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]pentanoic acid)

Structure for NP0221265 ((2s)-5-carbamimidamido-2-[(8-{[(1r,2s,4r,6r,7r,10s,11s,14s,16r)-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]pentanoic acid)

3D Structure for NP0221265 ((2s)-5-carbamimidamido-2-[(8-{[(1r,2s,4r,6r,7r,10s,11s,14s,16r)-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]pentanoic acid)