NP-MRD: Showing NP-Card for 11-Hydroxycamptothecin (NP0083417)

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Record Information

Version

2.0

Created at

2022-04-29 04:28:22 UTC

Updated at

2022-04-29 04:28:22 UTC

NP-MRD ID

NP0083417

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11-Hydroxycamptothecin

Description

11-Hydroxycamptothecin 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). 11-Hydroxycamptothecin is found in Camptotheca acuminata and Camptotheca acuminata Decaisne (Texas, USA). 11-Hydroxycamptothecin was first documented in 1986 (PMID: 3735324). Based on a literature review very few articles have been published on 11-Hydroxycamptothecin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292206282D          

 27 31  0  0  1  0            999 V2000
    6.9755    1.6387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4235    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6784    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1264   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6165    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0645    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3194   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7674   -0.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604   -0.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054    0.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8804    0.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3284    0.7556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.2410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694    1.1971    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8262    2.0096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5629    1.7702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3559    1.5428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896    1.6387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2575    0.7556    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2929   -1.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6255   -0.6422    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8185   -0.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5636   -1.5983    0.0000 O   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  2  0  0  0  0
  2  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  4  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  1  0  0  0  0
 11 12  2  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  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  6  0  0  0
 20 21  1  0  0  0  0
 17 22  2  0  0  0  0
 10 23  2  0  0  0  0
  6 23  1  0  0  0  0
  9 24  1  0  0  0  0
 24 25  1  0  0  0  0
 11 25  1  0  0  0  0
 25 26  1  0  0  0  0
 14 26  1  0  0  0  0
 26 27  2  0  0  0  0
M  END

     RDKit          3D

 43 47  0  0  0  0  0  0  0  0999 V2000
   -4.6361    2.2094   -1.2418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4569    1.2698   -1.1190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5411    0.4465    0.1515 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5470    1.3619    1.2262 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8137   -0.2672    0.1592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8919    0.3392    0.0348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8433   -1.6526    0.3078 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7821   -2.3197    0.9635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4614   -1.7051    0.7171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3647   -0.4024    0.3391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1133    0.1149    0.1294 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0048   -0.6841    0.3030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0762   -1.9517    0.6699 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3109   -2.4919    0.8855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4095   -3.6835    1.2316 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2531   -2.5605    0.7785 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1839   -1.4697    0.4203 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5584   -1.4053    0.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1913   -0.2295   -0.0337 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5644   -0.1351   -0.1285 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1918    1.0552   -0.5003 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4150    2.1632   -0.7791 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0462    3.3632   -1.1538 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0488    2.0508   -0.6796 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4063    0.8856   -0.3143 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0678    0.7869   -0.2200 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4382   -0.3496    0.1365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9924    2.4707   -0.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3037    3.1409   -1.7520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4449    1.7149   -1.7892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5353    1.8451   -1.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5396    0.5264   -1.9595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6426    1.7957    1.2415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7337   -3.3554    0.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9923   -2.4041    2.0461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9665    1.1285   -0.1663 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3034   -3.4207    0.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4283   -2.9091    1.8170 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1326   -2.2931    0.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1712   -1.0028    0.0900 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2695    1.1257   -0.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2843    3.9821   -0.4066 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4393    2.9168   -0.8974 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  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 25  2  0
 25 24  1  0
 24 22  2  0
 22 23  1  0
 22 21  1  0
 21 20  2  0
 25 26  1  0
 26 27  2  0
 13 14  1  0
 14 15  2  0
 10  3  1  0
 27 12  1  0
 14  9  1  0
 27 17  1  0
 20 19  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
  8 34  1  0
  8 35  1  0
 11 36  1  0
 16 37  1  0
 16 38  1  0
 18 39  1  0
 24 43  1  0
 23 42  1  0
 21 41  1  0
 20 40  1  0
M  END


  Mrv1652304292206282D          

 27 31  0  0  1  0            999 V2000
    6.9755    1.6387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4235    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6784    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1264   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6165    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0645    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3194   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7674   -0.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604   -0.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054    0.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8804    0.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3284    0.7556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.2410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694    1.1971    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8262    2.0096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5629    1.7702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3559    1.5428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896    1.6387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2575    0.7556    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2929   -1.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6255   -0.6422    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8185   -0.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5636   -1.5983    0.0000 O   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  2  0  0  0  0
  2  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  4  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  1  0  0  0  0
 11 12  2  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  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  6  0  0  0
 20 21  1  0  0  0  0
 17 22  2  0  0  0  0
 10 23  2  0  0  0  0
  6 23  1  0  0  0  0
  9 24  1  0  0  0  0
 24 25  1  0  0  0  0
 11 25  1  0  0  0  0
 25 26  1  0  0  0  0
 14 26  1  0  0  0  0
 26 27  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0083417

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@]1(O)C(=O)OCC2=C1C=C1N(CC3=CC4=C(C=C(O)C=C4)N=C13)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H16N2O5/c1-2-20(26)14-7-16-17-11(5-10-3-4-12(23)6-15(10)21-17)8-22(16)18(24)13(14)9-27-19(20)25/h3-7,23,26H,2,8-9H2,1H3/t20-/m0/s1

> <INCHI_KEY>
KXJNTORVTHBKGW-FQEVSTJZSA-N

> <FORMULA>
C20H16N2O5

> <MOLECULAR_WEIGHT>
364.357

> <EXACT_MASS>
364.105921623

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
37.69464829850402

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(19S)-19-ethyl-6,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione

> <ALOGPS_LOGP>
1.70

> <JCHEM_LOGP>
0.9166779163333334

> <ALOGPS_LOGS>
-3.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.70022292701509

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.725489746927515

> <JCHEM_PKA_STRONGEST_BASIC>
3.5028388232893968

> <JCHEM_POLAR_SURFACE_AREA>
99.95999999999998

> <JCHEM_REFRACTIVITY>
96.47339999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.48e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(19S)-19-ethyl-6,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0      13.021   3.059   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      11.990   1.914   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.466   0.450   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.436  -0.695   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.484   2.235   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.454   1.090   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.930  -0.374   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.899  -1.519   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.393  -1.199   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.917   0.266   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.377   0.266   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.346   1.410   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.840   1.090   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.364  -0.374   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.858  -0.695   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.173   0.450   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.303   1.914   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.810   2.235   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.542   3.751   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.917   3.304   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.398   2.880   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.727   3.059   0.000  0.00  0.00           O+0
HETATM   23  N   UNK     0       7.947   1.410   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       6.147  -2.104   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0       4.901  -1.199   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       3.395  -1.519   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.919  -2.984   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3    7                                                       
CONECT    5    2    6                                                       
CONECT    6    5    7   23                                                  
CONECT    7    6    4    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   24                                                  
CONECT   10    9   11   23                                                  
CONECT   11   10   12   25                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   26                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   13   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20                                                            
CONECT   22   17                                                            
CONECT   23   10    6                                                       
CONECT   24    9   25                                                       
CONECT   25   24   11   26                                                  
CONECT   26   25   14   27                                                  
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₁₆N₂O₅

Average Mass

364.3570 Da

Monoisotopic Mass

364.10592 Da

IUPAC Name

(19S)-19-ethyl-6,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione

Traditional Name

(19S)-19-ethyl-6,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione

CAS Registry Number

Not Available

SMILES

CC[C@@]1(O)C(=O)OCC2=C1C=C1N(CC3=CC4=C(C=C(O)C=C4)N=C13)C2=O

InChI Identifier

InChI=1S/C20H16N2O5/c1-2-20(26)14-7-16-17-11(5-10-3-4-12(23)6-15(10)21-17)8-22(16)18(24)13(14)9-27-19(20)25/h3-7,23,26H,2,8-9H2,1H3/t20-/m0/s1

InChI Key

KXJNTORVTHBKGW-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Camptotheca acuminata Decaisne (Texas, USA)	Plant	KNApSAcK

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
Pyranopyridine
Quinoline
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyridinone
Pyridine
Benzenoid
Heteroaromatic compound
Tertiary alcohol
Carboxylic acid ester
Lactam
Lactone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Alcohol
Carbonyl group
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	1.7	ALOGPS
logP	0.92	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	8.73	ChemAxon
pKa (Strongest Basic)	3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	99.96 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	96.47 m³·mol⁻¹	ChemAxon
Polarizability	37.69 Å³	ChemAxon
Number of Rings	5	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

C00052100

Chemspider ID

19980488

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

135515469

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wall ME, Wani MC, Natschke SM, Nicholas AW: Plant antitumor agents. 22. Isolation of 11-hydroxycamptothecin from Camptotheca acuminata Decne: total synthesis and biological activity. J Med Chem. 1986 Aug;29(8):1553-5. doi: 10.1021/jm00158a044. [PubMed:3735324 ]

Showing NP-Card for 11-Hydroxycamptothecin (NP0083417)

MOL for NP0083417 (11-Hydroxycamptothecin)

3D MOL for NP0083417 (11-Hydroxycamptothecin)

3D SDF for NP0083417 (11-Hydroxycamptothecin)

3D-SDF for NP0083417 (11-Hydroxycamptothecin)

PDB for NP0083417 (11-Hydroxycamptothecin)

3D PDB for NP0083417 (11-Hydroxycamptothecin)

SMILES for NP0083417 (11-Hydroxycamptothecin)

INCHI for NP0083417 (11-Hydroxycamptothecin)

Structure for NP0083417 (11-Hydroxycamptothecin)

3D Structure for NP0083417 (11-Hydroxycamptothecin)