NP-MRD: Showing NP-Card for (2s)-2-[12-ethyl-2-hydroxy-8-(hydroxymethyl)-9-oxo-11h-indolizino[1,2-b]quinolin-7-yl]-2-hydroxybutanoic acid (NP0206887)

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Record Information

Version

2.0

Created at

2022-09-05 03:17:52 UTC

Updated at

2022-09-05 03:17:52 UTC

NP-MRD ID

NP0206887

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-[12-ethyl-2-hydroxy-8-(hydroxymethyl)-9-oxo-11h-indolizino[1,2-b]quinolin-7-yl]-2-hydroxybutanoic acid

Description

SN-38 carboxylic acid, also known as sn-38 carboxylate form or sn-38C, belongs to the class of organic compounds known as camptothecins. These are heterocyclic compounds comprising a planar pentacyclic ring structure, that includes a pyrrolo[3,4-beta]-quinoline moiety (rings A, B and C), conjugated pyridone moiety (ring D) and one chiral center at position 20 within the alpha-hydroxy lactone ring with (S) configuration (the E-ring). SN-38 carboxylic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (2s)-2-[12-ethyl-2-hydroxy-8-(hydroxymethyl)-9-oxo-11h-indolizino[1,2-b]quinolin-7-yl]-2-hydroxybutanoic acid is found in Apis cerana. Based on a literature review very few articles have been published on SN-38 carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052205172D          

 30 33  0  0  1  0            999 V2000
    4.2441    2.5754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4623    2.3118    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
    2.5180    1.2394    0.0000 C   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
    2.9745   -0.1146    0.0000 N   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
    4.3754   -0.3963    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
    5.3198    0.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1015    0.9396    0.0000 O   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
    3.9189    0.9577    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
    0.2369   -0.2602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2406   -0.9330    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9133   -0.4555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7181   -1.6057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3743   -2.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4321   -1.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3550   -2.2319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1821   -1.0667    0.0000 O   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
   -1.2721    1.3168    0.0000 O   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
    0.0268    1.9124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1920    1.0852    0.0000 N   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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  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  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
  3 13  2  0  0  0  0
  7 13  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  6  0  0  0
 19 20  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 16 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 14 29  1  0  0  0  0
 29 30  1  0  0  0  0
  4 30  1  0  0  0  0
M  END

     RDKit          3D

 52 55  0  0  0  0  0  0  0  0999 V2000
    4.8176   -1.9141    0.9060 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1164   -1.5766   -0.3897 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1847   -0.4250   -0.2455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8055   -0.6322   -0.1801 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9238    0.4032   -0.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3627    1.6721    0.0258 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7003    1.9210   -0.0339 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1942    3.2071    0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5458    3.4551   -0.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4327    2.3970   -0.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8050    2.6412   -0.2205 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9778    1.0995   -0.2326 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6141    0.8799   -0.1691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4260   -0.1739   -0.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6890    0.4214    0.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8460   -0.3199    0.1209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1437    0.3099    0.2956 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7157   -0.1478    1.4861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1234    1.8229    0.4198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6059    2.5744   -0.7359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1246   -0.0761   -0.7748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8884    0.0930   -1.9927 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3426   -0.6387   -0.4336 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6832   -1.6797    0.0045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8392   -2.5715   -0.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4753   -3.9241   -0.1136 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4183   -2.2463   -0.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2999   -3.5166   -0.2210 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3133   -1.4874   -0.1215 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0792   -1.9033   -0.2367 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6998   -1.0534    1.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8761   -2.1600    0.6898 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3415   -2.8368    1.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8594   -1.4110   -1.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5135   -2.4697   -0.7216 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5288    4.0467    0.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9647    4.4678    0.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4556    1.8805   -0.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6657    0.2567   -0.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7080    1.4803    0.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2531    0.3139    2.2208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4708    2.0460    1.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1159    2.2181    0.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1667    2.0100   -1.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4583    3.1456   -1.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8914    3.4030   -0.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6443   -0.7106    0.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4154   -2.4151   -0.9839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5641   -2.4748    0.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5094   -4.3862    0.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2674   -2.4631   -1.1809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3994   -2.5527    0.5963 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 13  2  0
 13 12  1  0
 12 10  2  0
 10 11  1  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  4 30  1  0
 30 29  1  0
 29 14  1  0
 14 15  2  0
 15 16  1  0
 16 24  2  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  2  0
 16 17  1  0
 17 18  1  1
 17 19  1  0
 19 20  1  0
 17 21  1  0
 21 23  1  0
 21 22  2  0
  4  3  1  0
 27 29  1  0
  7 13  1  0
 14  5  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
 12 39  1  0
 11 38  1  0
  9 37  1  0
  8 36  1  0
 30 51  1  0
 30 52  1  0
 15 40  1  0
 25 48  1  0
 25 49  1  0
 26 50  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 20 46  1  0
 23 47  1  0
M  END


  Mrv1652309052205172D          

 30 33  0  0  1  0            999 V2000
    4.2441    2.5754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4623    2.3118    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
    2.5180    1.2394    0.0000 C   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
    2.9745   -0.1146    0.0000 N   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
    4.3754   -0.3963    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
    5.3198    0.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1015    0.9396    0.0000 O   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
    3.9189    0.9577    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
    0.2369   -0.2602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2406   -0.9330    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9133   -0.4555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7181   -1.6057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3743   -2.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4321   -1.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3550   -2.2319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1821   -1.0667    0.0000 O   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
   -1.2721    1.3168    0.0000 O   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
    0.0268    1.9124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1920    1.0852    0.0000 N   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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  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  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
  3 13  2  0  0  0  0
  7 13  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  6  0  0  0
 19 20  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 16 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 14 29  1  0  0  0  0
 29 30  1  0  0  0  0
  4 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0206887

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1=C2C=C(O)C=CC2=NC2=C1CN1C2=CC(=C(CO)C1=O)[C@@](O)(CC)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H22N2O6/c1-3-12-13-7-11(26)5-6-17(13)23-19-14(12)9-24-18(19)8-16(15(10-25)20(24)27)22(30,4-2)21(28)29/h5-8,25-26,30H,3-4,9-10H2,1-2H3,(H,28,29)/t22-/m0/s1

> <INCHI_KEY>
IRKZFHZUIBLGKU-QFIPXVFZSA-N

> <FORMULA>
C22H22N2O6

> <MOLECULAR_WEIGHT>
410.426

> <EXACT_MASS>
410.147786436

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
43.222505653343106

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-[12-ethyl-2-hydroxy-8-(hydroxymethyl)-9-oxo-9H,11H-indolizino[1,2-b]quinolin-7-yl]-2-hydroxybutanoic acid

> <JCHEM_LOGP>
0.2749473544480399

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.662865185091313

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2911635848794827

> <JCHEM_PKA_STRONGEST_BASIC>
4.041596844315594

> <JCHEM_POLAR_SURFACE_AREA>
131.19000000000003

> <JCHEM_REFRACTIVITY>
109.60779999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[12-ethyl-2-hydroxy-8-(hydroxymethyl)-9-oxo-11H-indolizino[1,2-b]quinolin-7-yl]-2-hydroxybutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       7.922   4.807   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.463   4.315   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.159   2.806   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.700   2.314   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.397   0.804   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       5.552  -0.214   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       7.012   0.278   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.167  -0.740   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.627  -0.248   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.930   1.262   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      11.390   1.754   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.774   2.280   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.315   1.788   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.867   0.626   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.976  -0.630   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.442  -0.486   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.449  -1.742   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.705  -0.850   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.341  -2.997   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.699  -4.397   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.807  -2.633   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.663  -4.166   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.207  -1.991   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.200   0.914   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.733   1.058   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.375   2.458   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.692   2.170   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.050   3.570   0.000  0.00  0.00           O+0
HETATM   29  N   UNK     0       2.225   2.026   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0       3.358   3.069   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5   30                                                  
CONECT    5    4    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    3    7                                                  
CONECT   14    5   15   29                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   24                                                  
CONECT   17   16   18   19   21                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19                                                            
CONECT   21   17   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   16   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   14   30                                                  
CONECT   30   29    4                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
sn-38 Carboxylic acid form	ChEBI
sn-38C	ChEBI
sn-38 Carboxylate form	Generator
sn-38 Carboxylate	Generator

Chemical Formula

C₂₂H₂₂N₂O₆

Average Mass

410.4260 Da

Monoisotopic Mass

410.14779 Da

IUPAC Name

(2S)-2-[12-ethyl-2-hydroxy-8-(hydroxymethyl)-9-oxo-9H,11H-indolizino[1,2-b]quinolin-7-yl]-2-hydroxybutanoic acid

Traditional Name

(2S)-2-[12-ethyl-2-hydroxy-8-(hydroxymethyl)-9-oxo-11H-indolizino[1,2-b]quinolin-7-yl]-2-hydroxybutanoic acid

CAS Registry Number

Not Available

SMILES

CCC1=C2C=C(O)C=CC2=NC2=C1CN1C2=CC(=C(CO)C1=O)[C@@](O)(CC)C(O)=O

InChI Identifier

InChI=1S/C22H22N2O6/c1-3-12-13-7-11(26)5-6-17(13)23-19-14(12)9-24-18(19)8-16(15(10-25)20(24)27)22(30,4-2)21(28)29/h5-8,25-26,30H,3-4,9-10H2,1-2H3,(H,28,29)/t22-/m0/s1

InChI Key

IRKZFHZUIBLGKU-QFIPXVFZSA-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
Apis cerana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as camptothecins. These are heterocyclic compounds comprising a planar pentacyclic ring structure, that includes a pyrrolo[3,4-beta]-quinoline moiety (rings A, B and C), conjugated pyridone moiety (ring D) and one chiral center at position 20 within the alpha-hydroxy lactone ring with (S) configuration (the E-ring).

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Camptothecins

Sub Class

Not Available

Direct Parent

Camptothecins

Alternative Parents

Substituents

Camptothecin
Hydroxyquinoline
Quinoline
1-hydroxy-2-unsubstituted benzenoid
Pyridinone
Alpha-hydroxy acid
Hydroxy acid
Pyridine
Benzenoid
Heteroaromatic compound
Tertiary alcohol
Lactam
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organonitrogen compound
Carbonyl group
Aromatic alcohol
Organic oxygen compound
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Primary alcohol
Organopnictogen compound
Organic oxide
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	0.27	ChemAxon
pKa (Strongest Acidic)	3.29	ChemAxon
pKa (Strongest Basic)	4.04	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	131.19 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	109.61 m³·mol⁻¹	ChemAxon
Polarizability	43.22 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

391421

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

443149

PDB ID

Not Available

ChEBI ID

149481

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2-[12-ethyl-2-hydroxy-8-(hydroxymethyl)-9-oxo-11h-indolizino[1,2-b]quinolin-7-yl]-2-hydroxybutanoic acid (NP0206887)

MOL for NP0206887 ((2s)-2-[12-ethyl-2-hydroxy-8-(hydroxymethyl)-9-oxo-11h-indolizino[1,2-b]quinolin-7-yl]-2-hydroxybutanoic acid)

3D MOL for NP0206887 ((2s)-2-[12-ethyl-2-hydroxy-8-(hydroxymethyl)-9-oxo-11h-indolizino[1,2-b]quinolin-7-yl]-2-hydroxybutanoic acid)

3D SDF for NP0206887 ((2s)-2-[12-ethyl-2-hydroxy-8-(hydroxymethyl)-9-oxo-11h-indolizino[1,2-b]quinolin-7-yl]-2-hydroxybutanoic acid)

3D-SDF for NP0206887 ((2s)-2-[12-ethyl-2-hydroxy-8-(hydroxymethyl)-9-oxo-11h-indolizino[1,2-b]quinolin-7-yl]-2-hydroxybutanoic acid)

PDB for NP0206887 ((2s)-2-[12-ethyl-2-hydroxy-8-(hydroxymethyl)-9-oxo-11h-indolizino[1,2-b]quinolin-7-yl]-2-hydroxybutanoic acid)

3D PDB for NP0206887 ((2s)-2-[12-ethyl-2-hydroxy-8-(hydroxymethyl)-9-oxo-11h-indolizino[1,2-b]quinolin-7-yl]-2-hydroxybutanoic acid)

SMILES for NP0206887 ((2s)-2-[12-ethyl-2-hydroxy-8-(hydroxymethyl)-9-oxo-11h-indolizino[1,2-b]quinolin-7-yl]-2-hydroxybutanoic acid)

INCHI for NP0206887 ((2s)-2-[12-ethyl-2-hydroxy-8-(hydroxymethyl)-9-oxo-11h-indolizino[1,2-b]quinolin-7-yl]-2-hydroxybutanoic acid)

Structure for NP0206887 ((2s)-2-[12-ethyl-2-hydroxy-8-(hydroxymethyl)-9-oxo-11h-indolizino[1,2-b]quinolin-7-yl]-2-hydroxybutanoic acid)

3D Structure for NP0206887 ((2s)-2-[12-ethyl-2-hydroxy-8-(hydroxymethyl)-9-oxo-11h-indolizino[1,2-b]quinolin-7-yl]-2-hydroxybutanoic acid)