NP-MRD: Showing NP-Card for (2r)-2-[(1-hydroxyethylidene)amino]-3-({4,5,9-trihydroxy-2-methyl-10-oxobenzo[b]fluoren-11-yl}sulfanyl)propanoic acid (NP0188046)

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Record Information

Version

2.0

Created at

2022-09-04 04:18:30 UTC

Updated at

2022-09-04 04:18:30 UTC

NP-MRD ID

NP0188046

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r)-2-[(1-hydroxyethylidene)amino]-3-({4,5,9-trihydroxy-2-methyl-10-oxobenzo[b]fluoren-11-yl}sulfanyl)propanoic acid

Description

Seongomycin belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom. (2r)-2-[(1-hydroxyethylidene)amino]-3-({4,5,9-trihydroxy-2-methyl-10-oxobenzo[b]fluoren-11-yl}sulfanyl)propanoic acid is found in Streptomyces lividans. (2r)-2-[(1-hydroxyethylidene)amino]-3-({4,5,9-trihydroxy-2-methyl-10-oxobenzo[b]fluoren-11-yl}sulfanyl)propanoic acid was first documented in 2013 (PMID: 23803003). Based on a literature review very few articles have been published on Seongomycin (PMID: 28191843).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042206182D          

 32 35  0  0  1  0            999 V2000
   -0.7588    5.0841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0015    4.7569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6605    5.2492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0938    3.9374    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8511    3.6102    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9464    2.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7037    2.4635    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.7990    1.6440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5180    1.2394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2997    1.5030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4623    2.3118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9189    0.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7006    1.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8632    2.0301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3198    0.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1571   -0.1327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3754   -0.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7562    0.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9745   -0.1146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8119   -0.9235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3553    0.4306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5359    0.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0583   -0.3374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4022   -1.0874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2369   -0.2602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1069    0.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9283    0.5669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3706    1.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1920    1.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5131    4.1024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4179    4.9219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2705    3.7752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 22 29  1  0  0  0  0
  8 29  1  0  0  0  0
  5 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
M  END

     RDKit          3D

 51 54  0  0  0  0  0  0  0  0999 V2000
    6.2136   -0.0341   -0.4262 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6541   -1.2668   -1.0061 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4112   -2.0001   -1.8933 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4830   -1.6649   -0.7009 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6995   -0.9000    0.2214 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2831   -0.6656   -0.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4448    0.2962    0.9704 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2369    0.6587    0.5434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1973   -0.2212    0.3528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2465   -1.6753    0.4316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2638   -2.3946    0.7134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5294   -2.3362    0.1688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6175   -3.7228    0.2323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4708   -4.4561    0.5484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8084   -4.3291   -0.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9131   -3.5564   -0.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8101   -2.1740   -0.3811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6038   -1.5488   -0.1334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5697   -0.0935   -0.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7072    0.6283   -0.5239 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4222    0.5191    0.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0993    1.9401    0.0403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8438    3.0814   -0.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1786    3.0800   -0.5113 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1972    4.2946   -0.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8767    4.4057    0.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2083    5.7223    0.3418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1508    3.2510    0.4583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7606    2.0232    0.3614 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5844   -1.5287    1.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9275   -0.9650    2.4442 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2019   -2.7349    1.7880 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6846    0.8850   -0.7505 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2774    0.1155   -0.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1379   -0.0385    0.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2902   -2.4132   -1.6025 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1372    0.1274    0.3406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8084   -1.6099   -0.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3316   -0.1020   -1.2631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4708   -5.4576    0.6093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8623   -5.4024    0.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8409   -4.0506   -0.5111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6861   -1.6179   -0.6223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5252    0.6838    0.0775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7058    3.9143   -0.6737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7575    5.2072   -0.2550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9199    6.5085   -0.0440 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7335    5.7849   -0.2305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0176    6.0039    1.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9033    3.2781    0.7128 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2908   -3.4488    1.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
 21 19  2  0
 19 20  1  0
 19 18  1  0
 18 17  2  0
 17 16  1  0
 16 15  2  0
 15 13  1  0
 13 14  1  0
 13 12  2  0
 12 10  1  0
 10 11  2  0
  5 30  1  0
 30 32  1  0
 30 31  2  0
 29  8  1  0
 12 18  1  0
 10  9  1  0
 29 22  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  3 36  1  0
  5 37  1  1
  6 38  1  0
  6 39  1  0
 24 45  1  0
 25 46  1  0
 27 47  1  0
 27 48  1  0
 27 49  1  0
 28 50  1  0
 20 44  1  0
 17 43  1  0
 16 42  1  0
 15 41  1  0
 14 40  1  0
 32 51  1  0
M  END


  Mrv1652309042206182D          

 32 35  0  0  1  0            999 V2000
   -0.7588    5.0841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0015    4.7569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6605    5.2492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0938    3.9374    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8511    3.6102    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9464    2.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7037    2.4635    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.7990    1.6440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5180    1.2394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2997    1.5030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4623    2.3118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9189    0.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7006    1.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8632    2.0301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3198    0.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1571   -0.1327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3754   -0.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7562    0.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9745   -0.1146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8119   -0.9235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3553    0.4306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5359    0.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0583   -0.3374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4022   -1.0874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2369   -0.2602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1069    0.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9283    0.5669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3706    1.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1920    1.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5131    4.1024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4179    4.9219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2705    3.7752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 22 29  1  0  0  0  0
  8 29  1  0  0  0  0
  5 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0188046

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)=N[C@@H](CSC1=C2C(C3=C(O)C=C(C)C=C13)=C(O)C1=CC=CC(O)=C1C2=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H19NO7S/c1-9-6-12-16(15(27)7-9)18-19(22(12)32-8-13(23(30)31)24-10(2)25)21(29)17-11(20(18)28)4-3-5-14(17)26/h3-7,13,26-28H,8H2,1-2H3,(H,24,25)(H,30,31)/t13-/m0/s1

> <INCHI_KEY>
VINPUYZACTZLRR-ZDUSSCGKSA-N

> <FORMULA>
C23H19NO7S

> <MOLECULAR_WEIGHT>
453.47

> <EXACT_MASS>
453.08822313

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
46.25614966682616

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-2-[(1-hydroxyethylidene)amino]-3-({4,5,9-trihydroxy-2-methyl-10-oxo-10H-benzo[b]fluoren-11-yl}sulfanyl)propanoic acid

> <JCHEM_LOGP>
2.8204439939999997

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.23189175587911

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1519974242825497

> <JCHEM_PKA_STRONGEST_BASIC>
0.4579146259283066

> <JCHEM_POLAR_SURFACE_AREA>
147.65

> <JCHEM_REFRACTIVITY>
121.42269999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-[(1-hydroxyethylidene)amino]-3-({4,5,9-trihydroxy-2-methyl-10-oxobenzo[b]fluoren-11-yl}sulfanyl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.416   9.490   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.003   8.880   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.233   9.798   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       0.175   7.350   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       1.589   6.739   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.767   5.209   0.000  0.00  0.00           C+0
HETATM    7  S   UNK     0       3.180   4.599   0.000  0.00  0.00           S+0
HETATM    8  C   UNK     0       3.358   3.069   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.700   2.314   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.159   2.806   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.463   4.315   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.315   1.788   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.774   2.280   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.078   3.790   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.930   1.262   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.627  -0.248   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.167  -0.740   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.012   0.278   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.552  -0.214   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.249  -1.724   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.397   0.804   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.867   0.626   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.976  -0.630   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.617  -2.030   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.442  -0.486   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.200   0.914   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.733   1.058   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.692   2.170   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.225   2.026   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.825   7.658   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.647   9.188   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       4.238   7.047   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   30                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   29                                                  
CONECT    9    8   10   21                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   18                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   12   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    9   22                                                  
CONECT   22   21   23   29                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   22    8                                                  
CONECT   30    5   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₁₉NO₇S

Average Mass

453.4700 Da

Monoisotopic Mass

453.08822 Da

IUPAC Name

(2R)-2-[(1-hydroxyethylidene)amino]-3-({4,5,9-trihydroxy-2-methyl-10-oxo-10H-benzo[b]fluoren-11-yl}sulfanyl)propanoic acid

Traditional Name

(2R)-2-[(1-hydroxyethylidene)amino]-3-({4,5,9-trihydroxy-2-methyl-10-oxobenzo[b]fluoren-11-yl}sulfanyl)propanoic acid

CAS Registry Number

Not Available

SMILES

CC(O)=N[C@@H](CSC1=C2C(C3=C(O)C=C(C)C=C13)=C(O)C1=CC=CC(O)=C1C2=O)C(O)=O

InChI Identifier

InChI=1S/C23H19NO7S/c1-9-6-12-16(15(27)7-9)18-19(22(12)32-8-13(23(30)31)24-10(2)25)21(29)17-11(20(18)28)4-3-5-14(17)26/h3-7,13,26-28H,8H2,1-2H3,(H,24,25)(H,30,31)/t13-/m0/s1

InChI Key

VINPUYZACTZLRR-ZDUSSCGKSA-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
Streptomyces lividans	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon 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-L-alpha-amino acids

Alternative Parents

Substituents

N-acyl-l-alpha-amino acid
Cysteine or derivatives
1-naphthol
Naphthalene
Indene
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Vinylogous thioester
Acetamide
Vinylogous acid
Carboxamide group
Ketone
Secondary carboxylic acid amide
Thioenolether
Polyol
Monocarboxylic acid or derivatives
Enol
Carboxylic acid
Sulfenyl compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	2.82	ChemAxon
pKa (Strongest Acidic)	3.15	ChemAxon
pKa (Strongest Basic)	0.46	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	147.65 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	121.42 m³·mol⁻¹	ChemAxon
Polarizability	46.26 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

136734298

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Woo CM, Gholap SL, Herzon SB: Insights into lomaiviticin biosynthesis. Isolation and structure elucidation of (-)-homoseongomycin. J Nat Prod. 2013 Jul 26;76(7):1238-41. doi: 10.1021/np400355h. Epub 2013 Jun 26. [PubMed:23803003 ]
Wang P, Hong GJ, Wilson MR, Balskus EP: Production of Stealthin C Involves an S-N-Type Smiles Rearrangement. J Am Chem Soc. 2017 Mar 1;139(8):2864-2867. doi: 10.1021/jacs.6b10586. Epub 2017 Feb 16. [PubMed:28191843 ]
LOTUS database [Link]

Showing NP-Card for (2r)-2-[(1-hydroxyethylidene)amino]-3-({4,5,9-trihydroxy-2-methyl-10-oxobenzo[b]fluoren-11-yl}sulfanyl)propanoic acid (NP0188046)

MOL for NP0188046 ((2r)-2-[(1-hydroxyethylidene)amino]-3-({4,5,9-trihydroxy-2-methyl-10-oxobenzo[b]fluoren-11-yl}sulfanyl)propanoic acid)

3D MOL for NP0188046 ((2r)-2-[(1-hydroxyethylidene)amino]-3-({4,5,9-trihydroxy-2-methyl-10-oxobenzo[b]fluoren-11-yl}sulfanyl)propanoic acid)

3D SDF for NP0188046 ((2r)-2-[(1-hydroxyethylidene)amino]-3-({4,5,9-trihydroxy-2-methyl-10-oxobenzo[b]fluoren-11-yl}sulfanyl)propanoic acid)

3D-SDF for NP0188046 ((2r)-2-[(1-hydroxyethylidene)amino]-3-({4,5,9-trihydroxy-2-methyl-10-oxobenzo[b]fluoren-11-yl}sulfanyl)propanoic acid)

PDB for NP0188046 ((2r)-2-[(1-hydroxyethylidene)amino]-3-({4,5,9-trihydroxy-2-methyl-10-oxobenzo[b]fluoren-11-yl}sulfanyl)propanoic acid)

3D PDB for NP0188046 ((2r)-2-[(1-hydroxyethylidene)amino]-3-({4,5,9-trihydroxy-2-methyl-10-oxobenzo[b]fluoren-11-yl}sulfanyl)propanoic acid)

SMILES for NP0188046 ((2r)-2-[(1-hydroxyethylidene)amino]-3-({4,5,9-trihydroxy-2-methyl-10-oxobenzo[b]fluoren-11-yl}sulfanyl)propanoic acid)

INCHI for NP0188046 ((2r)-2-[(1-hydroxyethylidene)amino]-3-({4,5,9-trihydroxy-2-methyl-10-oxobenzo[b]fluoren-11-yl}sulfanyl)propanoic acid)

Structure for NP0188046 ((2r)-2-[(1-hydroxyethylidene)amino]-3-({4,5,9-trihydroxy-2-methyl-10-oxobenzo[b]fluoren-11-yl}sulfanyl)propanoic acid)

3D Structure for NP0188046 ((2r)-2-[(1-hydroxyethylidene)amino]-3-({4,5,9-trihydroxy-2-methyl-10-oxobenzo[b]fluoren-11-yl}sulfanyl)propanoic acid)