NP-MRD: Showing NP-Card for (2s)-2-hydroxy-2-[8-(hydroxymethyl)-9-oxo-11h-indolizino[1,2-b]quinolin-7-yl]butanoic acid (NP0248528)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 10:49:17 UTC

Updated at

2022-09-07 10:49:17 UTC

NP-MRD ID

NP0248528

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

UNII-9EXB349FJ9, also known as na-CPT, 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). (2s)-2-hydroxy-2-[8-(hydroxymethyl)-9-oxo-11h-indolizino[1,2-b]quinolin-7-yl]butanoic acid is found in Camptotheca acuminata. UNII-9EXB349FJ9 is a moderately basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05041403232D          

 27 30  0  0  1  0            999 V2000
   -1.5395    2.3535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7181    2.4307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3198    0.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1571    0.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7006   -0.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3754    1.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2997   -0.6780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0583    1.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7990   -0.8190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9283    0.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9189   -0.1327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5180   -0.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1069    0.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2369    1.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7562    0.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5359    0.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3553    0.3944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3706   -0.3374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4321    2.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2406    1.7580    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9745    0.9396    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1920   -0.2602    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4058    0.9309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0268   -1.0874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3550    3.0569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1821    1.8917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9133    1.2805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
 11  5  2  0  0  0  0
 11  7  1  0  0  0  0
 12  7  2  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14  8  1  0  0  0  0
 14 13  2  0  0  0  0
 15  6  2  0  0  0  0
 15 11  1  0  0  0  0
 16  8  2  0  0  0  0
 17 12  1  0  0  0  0
 17 16  1  0  0  0  0
 18 13  1  0  0  0  0
 20  2  1  0  0  0  0
 20 14  1  0  0  0  0
 20 19  1  6  0  0  0
 21 15  1  0  0  0  0
 21 17  2  0  0  0  0
 22  9  1  0  0  0  0
 22 16  1  0  0  0  0
 22 18  1  0  0  0  0
 23 10  1  0  0  0  0
 24 18  2  0  0  0  0
 25 19  2  0  0  0  0
 26 19  1  0  0  0  0
 20 27  1  6  0  0  0
M  END

     RDKit          3D

 45 48  0  0  0  0  0  0  0  0999 V2000
   -4.8989    2.2753   -0.5383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9498    1.1111   -0.9162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9688    0.8686    0.1725 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2842    2.1473    0.2808 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5316    0.7477    1.5301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2491   -0.1838    1.8819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2597    1.7134    2.4850 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8663   -0.0689   -0.1331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5354    0.3648   -0.0641 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5394   -0.4782   -0.2406 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3239   -1.7593   -0.4875 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9285   -2.1968   -0.5602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0961   -3.4282   -0.7980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0558   -1.4037   -0.3948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3789   -2.0221   -0.6143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2350   -3.4218   -0.8258 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6076   -2.4354   -0.6320 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6004   -1.3867   -0.4413 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9833   -1.4455   -0.4698 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6810   -0.2866   -0.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0554   -0.3197   -0.2768 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7935    0.8193   -0.0647 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0984    1.9981    0.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7295    2.0500    0.1999 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0113    0.8910   -0.0162 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6684    0.9512    0.0120 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9880   -0.1873   -0.2008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8068    1.9031   -0.0489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3667    3.0239    0.0751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2295    2.7943   -1.4673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6593    0.2879   -1.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4080    1.4837   -1.8080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8840    2.1935    1.1627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9183    2.4036    2.7994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3348    1.4023    0.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6572   -1.7007   -1.6822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2053   -1.7749   -0.0168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4942   -3.8319    0.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6317   -3.2291    0.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6578   -2.8811   -1.6523 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4744   -2.3915   -0.6598 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5847   -1.2406   -0.4623 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8670    0.7718   -0.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6729    2.9018    0.3411 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2338    2.9706    0.3848 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  1
  3  5  1  0
  5  7  1  0
  5  6  2  0
  3  8  1  0
  8 14  2  0
 14 15  1  0
 15 16  1  0
 14 12  1  0
 12 13  2  0
 12 11  1  0
 11 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 10  1  0
 10  9  2  0
  9  8  1  0
 10 11  1  0
 27 18  1  0
 25 20  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  4 33  1  0
  7 34  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 19 41  1  0
 21 42  1  0
 22 43  1  0
 23 44  1  0
 24 45  1  0
  9 35  1  0
M  END


  Mrv0541 05041403232D          

 27 30  0  0  1  0            999 V2000
   -1.5395    2.3535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7181    2.4307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3198    0.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1571    0.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7006   -0.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3754    1.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2997   -0.6780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0583    1.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7990   -0.8190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9283    0.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9189   -0.1327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5180   -0.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1069    0.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2369    1.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7562    0.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5359    0.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3553    0.3944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3706   -0.3374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4321    2.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2406    1.7580    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9745    0.9396    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1920   -0.2602    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4058    0.9309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0268   -1.0874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3550    3.0569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1821    1.8917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9133    1.2805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
 11  5  2  0  0  0  0
 11  7  1  0  0  0  0
 12  7  2  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14  8  1  0  0  0  0
 14 13  2  0  0  0  0
 15  6  2  0  0  0  0
 15 11  1  0  0  0  0
 16  8  2  0  0  0  0
 17 12  1  0  0  0  0
 17 16  1  0  0  0  0
 18 13  1  0  0  0  0
 20  2  1  0  0  0  0
 20 14  1  0  0  0  0
 20 19  1  6  0  0  0
 21 15  1  0  0  0  0
 21 17  2  0  0  0  0
 22  9  1  0  0  0  0
 22 16  1  0  0  0  0
 22 18  1  0  0  0  0
 23 10  1  0  0  0  0
 24 18  2  0  0  0  0
 25 19  2  0  0  0  0
 26 19  1  0  0  0  0
 20 27  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0248528

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@](O)(C(O)=O)C1=C(CO)C(=O)N2CC3=CC4=CC=CC=C4N=C3C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H18N2O5/c1-2-20(27,19(25)26)14-8-16-17-12(9-22(16)18(24)13(14)10-23)7-11-5-3-4-6-15(11)21-17/h3-8,23,27H,2,9-10H2,1H3,(H,25,26)/t20-/m0/s1

> <INCHI_KEY>
SARNOWGPKQIWFT-FQEVSTJZSA-N

> <FORMULA>
C20H18N2O5

> <MOLECULAR_WEIGHT>
366.3673

> <EXACT_MASS>
366.121571696

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
38.2419198207844

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.31

> <JCHEM_LOGP>
0.0586598311451937

> <ALOGPS_LOGS>
-2.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.170260665930147

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7144841011965384

> <JCHEM_PKA_STRONGEST_BASIC>
2.8411576064531587

> <JCHEM_POLAR_SURFACE_AREA>
110.96000000000001

> <JCHEM_REFRACTIVITY>
97.98469999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.70e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   23  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1   20                                                       
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3   11                                                       
CONECT    6    4   15                                                       
CONECT    7   11   12                                                       
CONECT    8   14   16                                                       
CONECT    9   12   22                                                       
CONECT   10   13   23                                                       
CONECT   11    5    7   15                                                  
CONECT   12    7    9   17                                                  
CONECT   13   10   14   18                                                  
CONECT   14    8   13   20                                                  
CONECT   15    6   11   21                                                  
CONECT   16    8   17   22                                                  
CONECT   17   12   16   21                                                  
CONECT   18   13   22   24                                                  
CONECT   19   20   25   26                                                  
CONECT   20    2   14   19   27                                             
CONECT   21   15   17                                                       
CONECT   22    9   16   18                                                  
CONECT   23   10                                                            
CONECT   24   18                                                            
CONECT   25   19                                                            
CONECT   26   19                                                            
CONECT   27   20                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Value	Source
Na-CPT	MeSH
NSC 100880, Sodium salt, (S)-isomer	MeSH
(2S)-2-Hydroxy-2-[8-(hydroxymethyl)-9-oxo-9H,11H-indolizino[1,2-b]quinolin-7-yl]butanoate	Generator

Chemical Formula

C₂₀H₁₈N₂O₅

Average Mass

366.3673 Da

Monoisotopic Mass

366.12157 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC[C@@](O)(C(O)=O)C1=C(CO)C(=O)N2CC3=CC4=CC=CC=C4N=C3C2=C1

InChI Identifier

InChI=1S/C20H18N2O5/c1-2-20(27,19(25)26)14-8-16-17-12(9-22(16)18(24)13(14)10-23)7-11-5-3-4-6-15(11)21-17/h3-8,23,27H,2,9-10H2,1H3,(H,25,26)/t20-/m0/s1

InChI Key

SARNOWGPKQIWFT-FQEVSTJZSA-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
Camptotheca acuminata	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
Quinoline
Pyridinone
Alpha-hydroxy acid
Hydroxy acid
Pyridine
Benzenoid
Heteroaromatic compound
Tertiary alcohol
Lactam
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Alcohol
Primary alcohol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Aromatic alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.31	ALOGPS
logP	0.059	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	3.71	ChemAxon
pKa (Strongest Basic)	2.84	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	110.96 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	97.98 m³·mol⁻¹	ChemAxon
Polarizability	38.24 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

462146

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2-hydroxy-2-[8-(hydroxymethyl)-9-oxo-11h-indolizino[1,2-b]quinolin-7-yl]butanoic acid (NP0248528)

MOL for NP0248528 ((2s)-2-hydroxy-2-[8-(hydroxymethyl)-9-oxo-11h-indolizino[1,2-b]quinolin-7-yl]butanoic acid)

3D MOL for NP0248528 ((2s)-2-hydroxy-2-[8-(hydroxymethyl)-9-oxo-11h-indolizino[1,2-b]quinolin-7-yl]butanoic acid)

3D SDF for NP0248528 ((2s)-2-hydroxy-2-[8-(hydroxymethyl)-9-oxo-11h-indolizino[1,2-b]quinolin-7-yl]butanoic acid)

3D-SDF for NP0248528 ((2s)-2-hydroxy-2-[8-(hydroxymethyl)-9-oxo-11h-indolizino[1,2-b]quinolin-7-yl]butanoic acid)

PDB for NP0248528 ((2s)-2-hydroxy-2-[8-(hydroxymethyl)-9-oxo-11h-indolizino[1,2-b]quinolin-7-yl]butanoic acid)

3D PDB for NP0248528 ((2s)-2-hydroxy-2-[8-(hydroxymethyl)-9-oxo-11h-indolizino[1,2-b]quinolin-7-yl]butanoic acid)

SMILES for NP0248528 ((2s)-2-hydroxy-2-[8-(hydroxymethyl)-9-oxo-11h-indolizino[1,2-b]quinolin-7-yl]butanoic acid)

INCHI for NP0248528 ((2s)-2-hydroxy-2-[8-(hydroxymethyl)-9-oxo-11h-indolizino[1,2-b]quinolin-7-yl]butanoic acid)

Structure for NP0248528 ((2s)-2-hydroxy-2-[8-(hydroxymethyl)-9-oxo-11h-indolizino[1,2-b]quinolin-7-yl]butanoic acid)

3D Structure for NP0248528 ((2s)-2-hydroxy-2-[8-(hydroxymethyl)-9-oxo-11h-indolizino[1,2-b]quinolin-7-yl]butanoic acid)