NP-MRD: Showing NP-Card for (1ar,2s,7bs)-7-{[(2r)-2-carboxy-2-[(1-hydroxyethylidene)amino]ethyl]sulfanyl}-2-[(1e,3e,5e)-5-methylhepta-1,3,5-trien-1-yl]-1h,1ah,2h,7bh-3λ⁵-cyclopropa[a]indolizin-3-ylium (NP0236178)

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Record Information

Version

2.0

Created at

2022-09-06 19:00:31 UTC

Updated at

2022-09-06 19:00:31 UTC

NP-MRD ID

NP0236178

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1ar,2s,7bs)-7-{[(2r)-2-carboxy-2-[(1-hydroxyethylidene)amino]ethyl]sulfanyl}-2-[(1e,3e,5e)-5-methylhepta-1,3,5-trien-1-yl]-1h,1ah,2h,7bh-3λ⁵-cyclopropa[a]indolizin-3-ylium

Description

(1AR,2S,7bS)-7-{[(2R)-2-carboxy-2-[(1-hydroxyethylidene)amino]ethyl]sulfanyl}-2-[(1E,3E,5E)-5-methylhepta-1,3,5-trien-1-yl]-1H,1aH,2H,7bH-3λ⁵-cyclopropa[a]indolizin-3-ylium belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. (1ar,2s,7bs)-7-{[(2r)-2-carboxy-2-[(1-hydroxyethylidene)amino]ethyl]sulfanyl}-2-[(1e,3e,5e)-5-methylhepta-1,3,5-trien-1-yl]-1h,1ah,2h,7bh-3λ⁵-cyclopropa[a]indolizin-3-ylium is found in Streptomyces griseus. Based on a literature review very few articles have been published on (1aR,2S,7bS)-7-{[(2R)-2-carboxy-2-[(1-hydroxyethylidene)amino]ethyl]sulfanyl}-2-[(1E,3E,5E)-5-methylhepta-1,3,5-trien-1-yl]-1H,1aH,2H,7bH-3λ⁵-cyclopropa[a]indolizin-3-ylium.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062221002D          

 28 30  0  0  1  0            999 V2000
   -8.3550   -0.7698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5480   -0.5983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9960   -1.2114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2509   -1.9960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1890   -1.0398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6370   -1.6529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8300   -1.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2780   -2.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4710   -1.9230    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1354   -1.1693    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6505   -0.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3149   -1.2555    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 12 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  2  0  0  0  0
 19 20  1  4  0  0  0
 19 21  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 14 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 13 28  1  0  0  0  0
  9 28  1  0  0  0  0
M  CHG  1  28   1
M  END

     RDKit          3D

 55 57  0  0  0  0  0  0  0  0999 V2000
    8.8878   -1.0202    1.9729 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4653   -0.6289    2.2706 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6008   -0.4045    1.2761 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0594   -0.5454   -0.1237 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2272   -0.0272    1.5460 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3935    0.1890    0.5540 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0114    0.5684    0.8226 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1332    0.7973   -0.1309 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7502    1.1777    0.2200 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3014    2.4401   -0.3886 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0812    2.9866    0.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9251    2.1067   -1.1777 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1600    0.6633   -0.9380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2158   -0.0995   -1.4470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4386    0.6937   -2.4597 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8887   -0.2757   -2.7773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7433   -0.3420   -1.5384 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1466   -0.9069   -0.3850 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3993   -0.5905    0.8250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6822   -1.2825    1.9160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3301    0.3854    1.1159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0904   -0.9090   -1.8359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6515   -1.7834   -1.1636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7520   -0.4109   -2.9504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2599   -1.4319   -1.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2649   -1.9463   -0.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2474   -1.1633    0.1938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2133    0.1768   -0.1559 N   0  0  0  0  0  4  0  0  0  0  0  0
    9.3927   -0.1846    1.4376 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3526   -1.2360    2.9567 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8743   -1.9643    1.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0857   -0.5139    3.2667 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4726   -1.3647   -0.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8902    0.3645   -0.7249 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1483   -0.8228   -0.1469 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9135    0.0694    2.5702 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7552    0.0794   -0.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6741    0.6717    1.8592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4220    0.7076   -1.1469 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6323    1.2893    1.3390 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0216    3.1923   -0.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5649    2.5538    0.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2444    4.0650   -0.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9676    2.4915   -2.2073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5273    0.1942   -3.5631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6595   -1.3389   -3.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9548    0.7439   -1.2814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3247   -1.3175    2.8259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3960   -2.3115    1.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7966   -0.6746    2.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2477    1.0047    1.9229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5276    0.5169   -3.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0139   -2.0863   -1.4684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2924   -2.9880   -0.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5423   -1.5430    0.8395 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 17 22  1  0
 22 24  1  0
 22 23  2  0
 14 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28  9  1  0
 12 10  1  0
 28 13  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  4 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  6 37  1  0
  7 38  1  0
  8 39  1  0
  9 40  1  1
 10 41  1  6
 11 42  1  0
 11 43  1  0
 12 44  1  6
 16 45  1  0
 16 46  1  0
 17 47  1  1
 20 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  0
 24 52  1  0
 25 53  1  0
 26 54  1  0
 27 55  1  0
M  CHG  1  28   1
M  END


  Mrv1652309062221002D          

 28 30  0  0  1  0            999 V2000
   -8.3550   -0.7698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5480   -0.5983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9960   -1.2114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2509   -1.9960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1890   -1.0398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6370   -1.6529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8300   -1.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2780   -2.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4710   -1.9230    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1354   -1.1693    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6505   -0.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3149   -1.2555    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 12 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  2  0  0  0  0
 19 20  1  4  0  0  0
 19 21  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 14 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 13 28  1  0  0  0  0
  9 28  1  0  0  0  0
M  CHG  1  28   1
M  END
> <DATABASE_ID>
NP0236178

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(/C)\C=C\C=C\[C@H]1[C@@H]2C[C@@H]2C2=C(SC[C@H](N=C(C)O)C(O)=O)C=CC=[N+]12

> <INCHI_IDENTIFIER>
InChI=1S/C22H26N2O3S/c1-4-14(2)8-5-6-9-19-16-12-17(16)21-20(10-7-11-24(19)21)28-13-18(22(26)27)23-15(3)25/h4-11,16-19H,12-13H2,1-3H3,(H-,23,25,26,27)/p+1/b8-5+,9-6+,14-4+/t16-,17+,18+,19+/m1/s1

> <INCHI_KEY>
WAROMXVVDNYFEL-IKWXCPILSA-O

> <FORMULA>
C22H27N2O3S

> <MOLECULAR_WEIGHT>
399.53

> <EXACT_MASS>
399.173690332

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
44.38521177229411

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1aR,2S,7bS)-7-{[(2R)-2-carboxy-2-[(1-hydroxyethylidene)amino]ethyl]sulfanyl}-2-[(1E,3E,5E)-5-methylhepta-1,3,5-trien-1-yl]-1H,1aH,2H,7bH-3lambda5-cyclopropa[a]indolizin-3-ylium

> <JCHEM_LOGP>
-0.920223765138411

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
5.346040432030956

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1609486657996437

> <JCHEM_PKA_STRONGEST_BASIC>
0.4359982106200981

> <JCHEM_POLAR_SURFACE_AREA>
73.77

> <JCHEM_REFRACTIVITY>
116.5686

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1aR,2S,7bS)-7-{[(2R)-2-carboxy-2-[(1-hydroxyethylidene)amino]ethyl]sulfanyl}-2-[(1E,3E,5E)-5-methylhepta-1,3,5-trien-1-yl]-1H,1aH,2H,7bH-3lambda5-cyclopropa[a]indolizin-3-ylium

> <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     -15.596  -1.437   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -14.090  -1.117   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -13.059  -2.261   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -13.535  -3.726   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -11.553  -1.941   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -10.522  -3.085   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -9.016  -2.765   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -7.986  -3.910   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.479  -3.590   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.853  -2.183   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.948  -0.937   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.321  -2.344   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   15  S   UNK     0      -1.334  -3.850   0.000  0.00  0.00           S+0
HETATM   16  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      -0.000   0.000   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.667  -1.540   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       1.334  -3.850   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.667  -6.160   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0      -5.335  -4.620   0.000  0.00  0.00           N+1
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   28                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10   12                                                       
CONECT   12   11   10   13                                                  
CONECT   13   12   14   28                                                  
CONECT   14   13   15   25                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   17   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   14   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   13    9                                                  
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Value	Source
(1AR,2S,7BS)-7-{[(2R)-2-carboxy-2-[(1-hydroxyethylidene)amino]ethyl]sulphanyl}-2-[(1E,3E,5E)-5-methylhepta-1,3,5-trien-1-yl]-1H,1ah,2H,7BH-3-cyclopropa[a]indolizin-3-ylium	Generator

Chemical Formula

C₂₂H₂₇N₂O₃S

Average Mass

399.5300 Da

Monoisotopic Mass

399.17369 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C\C=C(/C)\C=C\C=C\[C@H]1[C@@H]2C[C@@H]2C2=C(SC[C@H](N=C(C)O)C(O)=O)C=CC=[N+]12

InChI Identifier

InChI=1S/C22H26N2O3S/c1-4-14(2)8-5-6-9-19-16-12-17(16)21-20(10-7-11-24(19)21)28-13-18(22(26)27)23-15(3)25/h4-11,16-19H,12-13H2,1-3H3,(H-,23,25,26,27)/p+1/b8-5+,9-6+,14-4+/t16-,17+,18+,19+/m1/s1

InChI Key

WAROMXVVDNYFEL-IKWXCPILSA-O

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
Streptomyces griseus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents

Substituents

N-acyl-alpha-amino acid
Cysteine or derivatives
Aryl thioether
Alkylarylthioether
Pyridinium
Pyridine
Heteroaromatic compound
Azacycle
Organoheterocyclic compound
Sulfenyl compound
Thioether
Monocarboxylic acid or derivatives
Carboxylic acid
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic cation
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

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

78443817

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139585262

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1ar,2s,7bs)-7-{[(2r)-2-carboxy-2-[(1-hydroxyethylidene)amino]ethyl]sulfanyl}-2-[(1e,3e,5e)-5-methylhepta-1,3,5-trien-1-yl]-1h,1ah,2h,7bh-3λ⁵-cyclopropa[a]indolizin-3-ylium (NP0236178)

MOL for NP0236178 ((1ar,2s,7bs)-7-{[(2r)-2-carboxy-2-[(1-hydroxyethylidene)amino]ethyl]sulfanyl}-2-[(1e,3e,5e)-5-methylhepta-1,3,5-trien-1-yl]-1h,1ah,2h,7bh-3λ⁵-cyclopropa[a]indolizin-3-ylium)

3D MOL for NP0236178 ((1ar,2s,7bs)-7-{[(2r)-2-carboxy-2-[(1-hydroxyethylidene)amino]ethyl]sulfanyl}-2-[(1e,3e,5e)-5-methylhepta-1,3,5-trien-1-yl]-1h,1ah,2h,7bh-3λ⁵-cyclopropa[a]indolizin-3-ylium)

3D SDF for NP0236178 ((1ar,2s,7bs)-7-{[(2r)-2-carboxy-2-[(1-hydroxyethylidene)amino]ethyl]sulfanyl}-2-[(1e,3e,5e)-5-methylhepta-1,3,5-trien-1-yl]-1h,1ah,2h,7bh-3λ⁵-cyclopropa[a]indolizin-3-ylium)

3D-SDF for NP0236178 ((1ar,2s,7bs)-7-{[(2r)-2-carboxy-2-[(1-hydroxyethylidene)amino]ethyl]sulfanyl}-2-[(1e,3e,5e)-5-methylhepta-1,3,5-trien-1-yl]-1h,1ah,2h,7bh-3λ⁵-cyclopropa[a]indolizin-3-ylium)

PDB for NP0236178 ((1ar,2s,7bs)-7-{[(2r)-2-carboxy-2-[(1-hydroxyethylidene)amino]ethyl]sulfanyl}-2-[(1e,3e,5e)-5-methylhepta-1,3,5-trien-1-yl]-1h,1ah,2h,7bh-3λ⁵-cyclopropa[a]indolizin-3-ylium)

3D PDB for NP0236178 ((1ar,2s,7bs)-7-{[(2r)-2-carboxy-2-[(1-hydroxyethylidene)amino]ethyl]sulfanyl}-2-[(1e,3e,5e)-5-methylhepta-1,3,5-trien-1-yl]-1h,1ah,2h,7bh-3λ⁵-cyclopropa[a]indolizin-3-ylium)

SMILES for NP0236178 ((1ar,2s,7bs)-7-{[(2r)-2-carboxy-2-[(1-hydroxyethylidene)amino]ethyl]sulfanyl}-2-[(1e,3e,5e)-5-methylhepta-1,3,5-trien-1-yl]-1h,1ah,2h,7bh-3λ⁵-cyclopropa[a]indolizin-3-ylium)

INCHI for NP0236178 ((1ar,2s,7bs)-7-{[(2r)-2-carboxy-2-[(1-hydroxyethylidene)amino]ethyl]sulfanyl}-2-[(1e,3e,5e)-5-methylhepta-1,3,5-trien-1-yl]-1h,1ah,2h,7bh-3λ⁵-cyclopropa[a]indolizin-3-ylium)

Structure for NP0236178 ((1ar,2s,7bs)-7-{[(2r)-2-carboxy-2-[(1-hydroxyethylidene)amino]ethyl]sulfanyl}-2-[(1e,3e,5e)-5-methylhepta-1,3,5-trien-1-yl]-1h,1ah,2h,7bh-3λ⁵-cyclopropa[a]indolizin-3-ylium)

3D Structure for NP0236178 ((1ar,2s,7bs)-7-{[(2r)-2-carboxy-2-[(1-hydroxyethylidene)amino]ethyl]sulfanyl}-2-[(1e,3e,5e)-5-methylhepta-1,3,5-trien-1-yl]-1h,1ah,2h,7bh-3λ⁵-cyclopropa[a]indolizin-3-ylium)