NP-MRD: Showing NP-Card for 7-ethyl-10-hydroxycamptothecin (NP0276993)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-09 01:24:01 UTC

Updated at

2022-09-09 01:24:01 UTC

NP-MRD ID

NP0276993

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-ethyl-10-hydroxycamptothecin

Description

SN-38, also known as sn 38 or irrinotecan, 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 is a strong basic compound (based on its pKa). Click on genes, proteins and metabolites below to link to respective articles. SN-38 exists in all living organisms, ranging from bacteria to humans. In vitro cytotoxicity assays show that the potency of SN-38 relative to irinotecan varies from 2- to 2000-fold. Within humans, SN-38 participates in a number of enzymatic reactions. In particular, SN-38 can be biosynthesized from irinotecan; which is mediated by the enzymes liver carboxylesterase 1 and cocaine esterase. In addition, SN-38 and uridine diphosphate glucuronic acid can be converted into sn-38 glucuronide and uridine 5'-diphosphate; which is catalyzed by the enzymes UDP-glucuronosyltransferase 1-10 and UDP-glucuronosyltransferase 1-1. SN38 is formed via hydrolysis of irinotecan by carboxylesterases and metabolized via glucuronidation by UGT1A1. In humans, SN-38 is involved in irinotecan action pathway. The variant of UGT1A1 in ~10% of Caucasians which leads to poor metabolism of SN-38 predicts irinotecan toxicity, as it is then less easily excreted from the body in its SN-38 glucuronide form. SN-38 and its glucuronide are lost into the bile and intestines. It can cause the symptoms of diarrhoea and myelosuppression experienced by ~25% of the patients administered irinotecan. It is the active metabolite of irinotecan (an analog of camptothecin - a topoisomerase I inhibitor) but has 1000 times more activity than irinotecan itself. 7-ethyl-10-hydroxycamptothecin is found in Apis cerana. 7-ethyl-10-hydroxycamptothecin was first documented in 2013 (PMID: 23233044). SN-38 is an antineoplastic drug (PMID: 23384250) (PMID: 22882086) (PMID: 22454224).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231218122D          

 29 33  0  0  1  0            999 V2000
    4.8919    3.9995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4542    2.7012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7356    2.7051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3519    3.9796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1148   -3.5844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4499    1.4677    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5038   -0.4301    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1643    1.0552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8788    2.2926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6294    2.7108    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8419    0.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1761    0.1685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9917    0.2536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1643    2.7051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8788    1.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4499    2.2926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8160   -0.6059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0336    1.9916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1511    3.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6360    3.5700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3122   -1.3013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9947   -0.6820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1617   -1.2128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6128    1.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9371   -2.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6499   -1.4314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6951   -1.9248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4539   -2.8324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3388   -2.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
 10  2  1  1  0  0  0
  3 16  2  0  0  0  0
  4 20  2  0  0  0  0
  5 28  1  0  0  0  0
  6  8  1  0  0  0  0
  6 11  1  0  0  0  0
  6 16  1  0  0  0  0
  7 13  1  0  0  0  0
  7 23  2  0  0  0  0
  8 13  1  0  0  0  0
  8 15  2  0  0  0  0
  9 10  1  0  0  0  0
  9 14  2  0  0  0  0
  9 15  1  0  0  0  0
 10 18  1  0  0  0  0
 10 20  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 17  1  0  0  0  0
 14 16  1  0  0  0  0
 14 19  1  0  0  0  0
 17 21  2  0  0  0  0
 17 22  1  0  0  0  0
 18 24  1  0  0  0  0
 21 23  1  0  0  0  0
 21 25  1  0  0  0  0
 22 26  1  0  0  0  0
 23 27  1  0  0  0  0
 25 28  2  0  0  0  0
 27 29  2  0  0  0  0
 28 29  1  0  0  0  0
M  END

     RDKit          3D

 49 53  0  0  0  0  0  0  0  0999 V2000
   -4.5869   -1.8752   -1.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0545   -0.4910   -1.5995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1180   -0.1037   -0.5457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7453   -0.1535   -0.8171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8418    0.2059    0.1495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2241    0.6188    1.3907 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5518    0.6623    1.6401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0288    1.0706    2.8827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3728    1.1246    3.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2772    0.7601    2.1889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6495    0.8030    2.4465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8586    0.3546    0.9603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5040    0.3101    0.6991 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5220    0.0670   -0.3711 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7745    0.2970    0.1977 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9429    0.0903   -0.4944 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8338   -0.3583   -1.7883 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5774   -0.5750   -2.3182 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4724   -0.9856   -3.5015 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4253   -0.3709   -1.6349 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9681   -0.5355   -2.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0651   -0.6019   -2.5898 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1160   -1.0415   -1.7498 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1483   -0.7615   -0.3931 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8781   -1.4060    0.3835 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2839    0.3268    0.0809 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7173    1.5670   -0.3859 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2489    0.4177    1.5870 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6533    0.6641    2.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2799   -2.2098   -0.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7033   -1.9035   -1.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2909   -2.6351   -2.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4666   -0.6129   -2.5581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9249    0.1519   -1.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2795    1.3504    3.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7402    1.4487    4.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1312    1.6784    2.2384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5541    0.0575    0.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8346    0.6431    1.1980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1179   -1.6366   -2.1500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2205    0.0416   -2.9107 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9038   -1.3879   -3.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3581    0.3634   -3.0458 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2838    1.5354   -1.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6478    1.3063    1.8562 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7863   -0.4864    2.0458 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4183    0.6639    1.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8570   -0.1060    2.8705 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7418    1.6575    2.5992 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 21  1  0
 21 20  1  0
 20 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  6
 26 28  1  0
 28 29  1  0
 17 18  1  0
 18 19  2  0
  4  3  1  0
 18 20  1  0
  7 13  1  0
 14  5  1  0
 26 16  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
 12 38  1  0
 11 37  1  0
  9 36  1  0
  8 35  1  0
 21 40  1  0
 21 41  1  0
 15 39  1  0
 22 42  1  0
 22 43  1  0
 27 44  1  0
 28 45  1  0
 28 46  1  0
 29 47  1  0
 29 48  1  0
 29 49  1  0
M  END


  Mrv0541 02231218122D          

 29 33  0  0  1  0            999 V2000
    4.8919    3.9995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4542    2.7012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7356    2.7051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3519    3.9796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1148   -3.5844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4499    1.4677    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5038   -0.4301    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1643    1.0552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8788    2.2926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6294    2.7108    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8419    0.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1761    0.1685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9917    0.2536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1643    2.7051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8788    1.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4499    2.2926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8160   -0.6059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0336    1.9916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1511    3.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6360    3.5700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3122   -1.3013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9947   -0.6820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1617   -1.2128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6128    1.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9371   -2.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6499   -1.4314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6951   -1.9248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4539   -2.8324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3388   -2.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
 10  2  1  1  0  0  0
  3 16  2  0  0  0  0
  4 20  2  0  0  0  0
  5 28  1  0  0  0  0
  6  8  1  0  0  0  0
  6 11  1  0  0  0  0
  6 16  1  0  0  0  0
  7 13  1  0  0  0  0
  7 23  2  0  0  0  0
  8 13  1  0  0  0  0
  8 15  2  0  0  0  0
  9 10  1  0  0  0  0
  9 14  2  0  0  0  0
  9 15  1  0  0  0  0
 10 18  1  0  0  0  0
 10 20  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 17  1  0  0  0  0
 14 16  1  0  0  0  0
 14 19  1  0  0  0  0
 17 21  2  0  0  0  0
 17 22  1  0  0  0  0
 18 24  1  0  0  0  0
 21 23  1  0  0  0  0
 21 25  1  0  0  0  0
 22 26  1  0  0  0  0
 23 27  1  0  0  0  0
 25 28  2  0  0  0  0
 27 29  2  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0276993

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1=C2C=C(O)C=CC2=NC2=C1CN1C2=CC2=C(COC(=O)[C@]2(O)CC)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H20N2O5/c1-3-12-13-7-11(25)5-6-17(13)23-19-14(12)9-24-18(19)8-16-15(20(24)26)10-29-21(27)22(16,28)4-2/h5-8,25,28H,3-4,9-10H2,1-2H3/t22-/m0/s1

> <INCHI_KEY>
FJHBVJOVLFPMQE-QFIPXVFZSA-N

> <FORMULA>
C22H20N2O5

> <MOLECULAR_WEIGHT>
392.4046

> <EXACT_MASS>
392.13722176

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
41.42873410088942

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(19S)-10,19-diethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione

> <ALOGPS_LOGP>
2.73

> <JCHEM_LOGP>
1.8746679706666658

> <ALOGPS_LOGS>
-3.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.714422630150532

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.675196104856266

> <JCHEM_PKA_STRONGEST_BASIC>
3.9059124952786752

> <JCHEM_POLAR_SURFACE_AREA>
99.96

> <JCHEM_REFRACTIVITY>
106.11560000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.90e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-ethyl-10-hydroxycamptothecin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       9.131   7.466   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      12.048   5.042   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       5.106   5.049   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      11.857   7.429   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       5.814  -6.691   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       6.440   2.740   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       8.407  -0.803   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       7.773   1.970   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.107   4.280   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.508   5.060   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.305   1.713   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.929   0.315   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.451   0.473   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.773   5.049   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.107   2.740   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.440   4.280   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.257  -1.131   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.263   3.718   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.749   6.653   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.521   6.664   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.183  -2.429   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.723  -1.273   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.769  -2.264   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.477   2.393   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.483  -3.935   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.080  -2.672   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.764  -3.593   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.447  -5.287   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.099  -5.115   0.000  0.00  0.00           C+0
CONECT    1   19   20                                                       
CONECT    2   10                                                            
CONECT    3   16                                                            
CONECT    4   20                                                            
CONECT    5   28                                                            
CONECT    6    8   11   16                                                  
CONECT    7   13   23                                                       
CONECT    8    6   13   15                                                  
CONECT    9   10   14   15                                                  
CONECT   10    2    9   18   20                                             
CONECT   11    6   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13    7    8   12                                                  
CONECT   14    9   16   19                                                  
CONECT   15    8    9                                                       
CONECT   16    3    6   14                                                  
CONECT   17   12   21   22                                                  
CONECT   18   10   24                                                       
CONECT   19    1   14                                                       
CONECT   20    1    4   10                                                  
CONECT   21   17   23   25                                                  
CONECT   22   17   26                                                       
CONECT   23    7   21   27                                                  
CONECT   24   18                                                            
CONECT   25   21   28                                                       
CONECT   26   22                                                            
CONECT   27   23   29                                                       
CONECT   28    5   25   29                                                  
CONECT   29   27   28                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Value	Source
10-Hydroxy-7-ethylcamptothecin	ChEBI
7-Ethyl-10-hydroxy-20(S)-camptothecin	ChEBI
7-Ethyl-10-hydroxycamptothecin	ChEBI
sn 38	ChEBI
sn 38 Lactone	ChEBI
CPT 11	HMDB
Camptosar	HMDB
Irrinotecan	HMDB
Camptothecin-11	HMDB
Irinotecan hydrochloride	HMDB
CPT-11	HMDB
sn38 CPD	HMDB
Irinotecan	HMDB
NK012 Compound	HMDB
CPT11	MeSH
7 Ethyl 10 hydroxycamptothecin	MeSH
Camptothecin 11	MeSH

Chemical Formula

C₂₂H₂₀N₂O₅

Average Mass

392.4046 Da

Monoisotopic Mass

392.13722 Da

IUPAC Name

(19S)-10,19-diethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione

Traditional Name

7-ethyl-10-hydroxycamptothecin

CAS Registry Number

Not Available

SMILES

CCC1=C2C=C(O)C=CC2=NC2=C1CN1C2=CC2=C(COC(=O)[C@]2(O)CC)C1=O

InChI Identifier

InChI=1S/C22H20N2O5/c1-3-12-13-7-11(25)5-6-17(13)23-19-14(12)9-24-18(19)8-16-15(20(24)26)10-29-21(27)22(16,28)4-2/h5-8,25,28H,3-4,9-10H2,1-2H3/t22-/m0/s1

InChI Key

FJHBVJOVLFPMQE-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
Pyranopyridine
Quinoline
1-hydroxy-2-unsubstituted benzenoid
Pyridinone
Pyridine
Benzenoid
Heteroaromatic compound
Tertiary alcohol
Carboxylic acid ester
Lactam
Lactone
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Organic nitrogen compound
Alcohol
Organic oxygen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

pyranoindolizinoquinoline (CHEBI:8988 )

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	2.73	ALOGPS
logP	1.87	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	9.68	ChemAxon
pKa (Strongest Basic)	3.91	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	2	ChemAxon
Refractivity	106.12 m³·mol⁻¹	ChemAxon
Polarizability	41.43 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

HMDB0060510

DrugBank ID

DB05482

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

94634

KEGG Compound ID

C11173

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

SN-38

METLIN ID

Not Available

PubChem Compound

104842

PDB ID

Not Available

ChEBI ID

8988

Good Scents ID

Not Available

References

General References

Sostelly A, Payen L, Guitton J, Di Pietro A, Falson P, Honorat M, Boumendjel A, Geze A, Freyer G, Tod M: Quantitative evaluation of the combination between cytotoxic drug and efflux transporter inhibitors based on a tumour growth inhibition model. Fundam Clin Pharmacol. 2014 Apr;28(2):161-9. doi: 10.1111/fcp.12005. Epub 2013 Feb 6. [PubMed:23384250 ]
Yao Y, Su X, Xie Y, Wang Y, Kang T, Gou L, Yi C, Yang J: Synthesis, characterization, and antitumor evaluation of the albumin-SN38 conjugate. Anticancer Drugs. 2013 Mar;24(3):270-7. doi: 10.1097/CAD.0b013e32835c3543. [PubMed:23233044 ]
Sostelly A, Payen L, Guitton J, Di Pietro A, Falson P, Honorat M, Valdameri G, Geze A, Boumendjel A, Freyer G, Tod M: A template model for studying anticancer drug efflux transporter inhibitors in vitro. Fundam Clin Pharmacol. 2013 Oct;27(5):544-56. doi: 10.1111/j.1472-8206.2012.01054.x. Epub 2012 Aug 8. [PubMed:22882086 ]
Shimo T, Kurebayashi J, Kanomata N, Yamashita T, Kozuka Y, Moriya T, Sonoo H: Antitumor and anticancer stem cell activity of a poly ADP-ribose polymerase inhibitor olaparib in breast cancer cells. Breast Cancer. 2014 Jan;21(1):75-85. doi: 10.1007/s12282-012-0356-z. Epub 2012 Mar 28. [PubMed:22454224 ]
LOTUS database [Link]

Showing NP-Card for 7-ethyl-10-hydroxycamptothecin (NP0276993)

MOL for NP0276993 (7-ethyl-10-hydroxycamptothecin)

3D MOL for NP0276993 (7-ethyl-10-hydroxycamptothecin)

3D SDF for NP0276993 (7-ethyl-10-hydroxycamptothecin)

3D-SDF for NP0276993 (7-ethyl-10-hydroxycamptothecin)

PDB for NP0276993 (7-ethyl-10-hydroxycamptothecin)

3D PDB for NP0276993 (7-ethyl-10-hydroxycamptothecin)

SMILES for NP0276993 (7-ethyl-10-hydroxycamptothecin)

INCHI for NP0276993 (7-ethyl-10-hydroxycamptothecin)

Structure for NP0276993 (7-ethyl-10-hydroxycamptothecin)

3D Structure for NP0276993 (7-ethyl-10-hydroxycamptothecin)