SN-38 (CHEBI:8988)

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CHEBI:8988 - SN-38

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ChEBI Name	SN-38

ChEBI ID	CHEBI:8988

Definition	A member of the class of pyranoindolizinoquinolines that is (4S)-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione bearing two additional ethyl substituents at positions 4 and 11 as well as two additional hydroxy substituents at positions 4 and 9. It is the active metabolite of irinotecan and is ~1000 times more active than irinotecan itself.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information	ChemicalBook:CB9431676, eMolecules:29547187, eMolecules:1935628, ZINC000003978987

Download	Molfile XML SDF

more structures >>

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The Resolver thinks Mol

RS4 - Ideal conformer

Mrv1927 05252115423D

starting HoverWatcher_5

Time for openFile(RS4 - Ideal conformer

Mrv1927 05252115423D

49 53 0 0 0 0 999 V2000

-1.8210 1.1160 0.1240 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.1310 -0.1070 0.1020 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.9320 2.4470 0.1690 C 0 0 1 0 0 0 0 0 0 0 0 0

-4.2000 2.9150 -1.2620 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.7790 2.2050 0.1330 C 0 0 1 0 0 0 0 0 0 0 0 0

0.3220 0.1820 0.0910 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.1200 -1.2960 0.1050 C 0 0 0 0 0 0 0 0 0 0 0 0

1.4020 -0.6750 0.0680 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.8680 -0.0900 0.1220 C 0 0 0 0 0 0 0 0 0 0 0 0

2.7070 -0.1660 0.0640 C 0 0 0 0 0 0 0 0 0 0 0 0

2.8990 1.1800 0.0910 C 0 0 0 0 0 0 0 0 0 0 0 0

1.7770 2.0340 0.1030 C 0 0 0 0 0 0 0 0 0 0 0 0

4.2710 1.7990 0.1150 C 0 0 1 0 0 0 0 0 0 0 0 0

3.8610 -1.1350 0.0100 C 0 0 2 0 0 0 0 0 0 0 0 0

5.1450 -0.3890 0.2920 C 0 0 0 0 0 0 0 0 0 0 0 0

-5.2690 -0.1420 0.1220 C 0 0 0 0 0 0 0 0 0 0 0 0

-5.9000 -1.3540 0.1040 C 0 0 0 0 0 0 0 0 0 0 0 0

-5.1650 -2.5430 0.0870 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.8060 -2.5270 0.0880 C 0 0 0 0 0 0 0 0 0 0 0 0

3.9320 -1.7700 -1.3800 C 0 0 1 0 0 0 0 0 0 0 0 0

5.1100 -2.7450 -1.4360 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.1810 1.1410 0.1380 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.7880 -1.2570 0.0940 N 0 0 0 0 0 0 0 0 0 0 0 0

0.5270 1.5320 0.1090 N 0 0 0 0 0 0 0 0 0 0 0 0

3.6750 -2.1540 0.9940 O 0 0 0 0 0 0 0 0 0 0 0 0

1.9400 3.2440 0.1100 O 0 0 0 0 0 0 0 0 0 0 0 0

5.2770 0.8300 -0.2790 O 0 0 0 0 0 0 0 0 0 0 0 0

6.0100 -0.8590 0.9910 O 0 0 0 0 0 0 0 0 0 0 0 0

-7.2580 -1.4040 0.1040 O 0 0 0 0 0 0 0 0 0 0 0 0

-3.3360 3.1960 0.6910 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.8790 2.3090 0.6900 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.2530 3.0530 -1.7830 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.7960 2.1660 -1.7840 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.7440 3.8600 -1.2400 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.8900 2.8360 -0.7480 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.8740 2.8060 1.0370 H 0 0 0 0 0 0 0 0 0 0 0 0

1.2410 -1.7430 0.0540 H 0 0 0 0 0 0 0 0 0 0 0 0

4.2960 2.6440 -0.5730 H 0 0 0 0 0 0 0 0 0 0 0 0

4.4880 2.1520 1.1230 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.8460 0.7710 0.1350 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.6850 -3.4900 0.0740 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.2530 -3.4550 0.0740 H 0 0 0 0 0 0 0 0 0 0 0 0

3.0060 -2.3070 -1.5820 H 0 0 0 0 0 0 0 0 0 0 0 0

4.0700 -0.9900 -2.1290 H 0 0 0 0 0 0 0 0 0 0 0 0

6.0360 -2.2070 -1.2340 H 0 0 0 0 0 0 0 0 0 0 0 0

4.9720 -3.5240 -0.6870 H 0 0 0 0 0 0 0 0 0 0 0 0

5.1610 -3.1970 -2.4260 H 0 0 0 0 0 0 0 0 0 0 0 0

4.3850 -2.8100 1.0200 H 0 0 0 0 0 0 0 0 0 0 0 0

-7.6510 -1.4050 -0.7790 H 0 0 0 0 0 0 0 0 0 0 0 0

21 20 1 0 0 0 0

20 14 1 0 0 0 0

19 18 2 0 0 0 0

19 7 1 0 0 0 0

18 17 1 0 0 0 0

14 25 1 1 0 0 0

28 15 2 0 0 0 0

14 15 1 0 0 0 0

14 10 1 0 0 0 0

23 7 2 0 0 0 0

23 2 1 0 0 0 0

7 9 1 0 0 0 0

29 17 1 0 0 0 0

17 16 2 0 0 0 0

15 27 1 0 0 0 0

8 10 1 0 0 0 0

8 6 2 0 0 0 0

10 11 2 0 0 0 0

2 6 1 0 0 0 0

2 1 2 0 0 0 0

6 24 1 0 0 0 0

16 9 1 0 0 0 0

9 22 2 0 0 0 0

27 13 1 0 0 0 0

11 13 1 0 0 0 0

11 12 1 0 0 0 0

1 22 1 0 0 0 0

1 5 1 0 0 0 0

22 3 1 0 0 0 0

24 12 1 0 0 0 0

24 5 1 0 0 0 0

12 26 2 0 0 0 0

3 4 1 0 0 0 0

3 30 1 0 0 0 0

3 31 1 0 0 0 0

4 32 1 0 0 0 0

4 33 1 0 0 0 0

4 34 1 0 0 0 0

5 35 1 0 0 0 0

5 36 1 0 0 0 0

8 37 1 0 0 0 0

13 38 1 0 0 0 0

13 39 1 0 0 0 0

16 40 1 0 0 0 0

18 41 1 0 0 0 0

19 42 1 0 0 0 0

20 43 1 0 0 0 0

20 44 1 0 0 0 0

21 45 1 0 0 0 0

21 46 1 0 0 0 0

21 47 1 0 0 0 0

25 48 1 0 0 0 0

29 49 1 0 0 0 0

M END): 26 ms

reading 49 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

49 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Wikipedia	License
Deguelin is a derivative of rotenone. Both are compounds classified as rotenoids of the flavonoid family and are naturally occurring insecticides. They can be produced by extraction from several plant species belonging to three genera of the legume family, Fabaceae: Lonchocarpus, Derris, or Tephrosia. Cubé resin, the root extract from cubé (Lonchocarpus utilis) and from barbasco (Lonchocarpus urucu), is used as a commercial insecticide and piscicide (fish poison). The major active ingredients are rotenone and deguelin. Although "organic" (produced by nature) cubé resin is no longer considered environmentally safe.
Read full article at Wikipedia

Formula

C22H20N2O5

Net Charge

Average Mass

392.411

Monoisotopic Mass

392.13722

InChI

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

InChIKey

FJHBVJOVLFPMQE-QFIPXVFZSA-N

SMILES

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

Roles Classification
Biological Role(s):	apoptosis inducer Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms. EC 5.99.1.2 (DNA topoisomerase) inhibitor A topoisomerase inhibitor that inhibits the bacterial enzymes of the DNA topoisomerases, Type I class (EC 5.99.1.2) that catalyze ATP-independent breakage of one of the two strands of DNA, passage of the unbroken strand through the break, and rejoining of the broken strand. These bacterial enzymes reduce the topological stress in the DNA structure by relaxing negatively, but not positively, supercoiled DNA. drug metabolite

Application(s):	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	SN-38 (CHEBI:8988) has role antineoplastic agent (CHEBI:35610) SN-38 (CHEBI:8988) has role apoptosis inducer (CHEBI:68495) SN-38 (CHEBI:8988) has role drug metabolite (CHEBI:49103) SN-38 (CHEBI:8988) has role EC 5.99.1.2 (DNA topoisomerase) inhibitor (CHEBI:50276) SN-38 (CHEBI:8988) is a δ-lactone (CHEBI:18946) SN-38 (CHEBI:8988) is a phenols (CHEBI:33853) SN-38 (CHEBI:8988) is a pyranoindolizinoquinoline (CHEBI:48626) SN-38 (CHEBI:8988) is a tertiary alcohol (CHEBI:26878)

Incoming	irinotecan (CHEBI:80630) has functional parent SN-38 (CHEBI:8988) SN-38 carboxylic acid (CHEBI:149481) has functional parent SN-38 (CHEBI:8988)

IUPAC Name

(4S)-4,11-diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione

Synonyms	Sources
10-Hydroxy-7-ethylcamptothecin	ChemIDplus
7-Ethyl-10-hydroxy-20(S)-camptothecin	ChemIDplus
7-Ethyl-10-hydroxycamptothecin	ChemIDplus
NK 012	ChemIDplus
NK-012	ChemIDplus
SN 38	ChemIDplus
SN 38 lactone	ChemIDplus
SN-38	UniProt

Manual Xrefs	Databases
C11173	KEGG COMPOUND
HMDB0060510	HMDB
RS4	PDBeChem
SN-38	Wikipedia
View more database links

Registry Numbers	Types	Sources
4829984	Reaxys Registry Number	Reaxys
86639-52-3	CAS Registry Number	KEGG COMPOUND
86639-52-3	CAS Registry Number	ChemIDplus

Citations

Lin ZY, Yun QZ, Wu L, Zhang TW, Yao TZ (2021)
Pharmacological basis and new insights of deguelin concerning its anticancer effects.
Pharmacological research 174, 105935 [PubMed:34644595]
[show Abstract]

Last Modified

25 May 2021

CHEBI:8988 - SN-38

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