Camptothecin

Details

• Internal ID: 21f96ad9-171c-4dc1-bb17-5cfd7b7df006
• Taxonomy: Alkaloids and derivatives > Camptothecins
• IUPAC Name: (19S)-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione
• SMILES (Canonical): CCC1(C2=C(COC1=O)C(=O)N3CC4=CC5=CC=CC=C5N=C4C3=C2)O
• SMILES (Isomeric): CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=CC5=CC=CC=C5N=C4C3=C2)O
• InChI: InChI=1S/C20H16N2O4/c1-2-20(25)14-8-16-17-12(7-11-5-3-4-6-15(11)21-17)9-22(16)18(23)13(14)10-26-19(20)24/h3-8,25H,2,9-10H2,1H3/t20-/m0/s1
• InChI Key: VSJKWCGYPAHWDS-FQEVSTJZSA-N
• Popularity: 14,438 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₆N₂O₄
• Molecular Weight: 348.40 g/mol
• Exact Mass: 348.11100700 g/mol
• Topological Polar Surface Area (TPSA): 79.70 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 2.08
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 7689-03-4
• Camptothecine
• (S)-(+)-Camptothecin
• Campathecin
• (+)-Camptothecine
• d-Camptothecin
• (+)-Camptothecin
• 20(S)-Camptothecine
• 21,22-Secocamptothecin-21-oic acid lactone
• NSC94600
• Camptothecine (S,+)
• CHEMBL65
• (S)-4-ethyl-4-hydroxy-1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
• NSC-94600
• MLS000766223
• XT3Z54Z28A
• CHEBI:27656
• MFCD00081076
• (4S)-4-ethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
• (19S)-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione
• (S)-Camptothecin
• (19S)-19-ethyl-19-hydroxy-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
• 1H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione, 4-ethyl-4-hydroxy-, (4S)-
• 1H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione, 4-ethyl-4-hydroxy-, (S)-
• 1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 4-ethyl-4-hydroxy-, (4S)-
• 20(S)-Camptothecin
• 4-ETHYL-4-HYDROXY-1,12-DIHYDRO-4H-2-OXA-6,12A-DIAZA-DIBENZO[B,H]FLUORENE-3,13-DIONE
• SR-01000075798
• SR-01000597379
• d-camptothecine
• (s)-camptothecine
• Camptothecin,(S)
• (4S)-4-ETHYL-4-HYDROXY-1H-PYRANO(3',4':6,7)INDOLIZINO(1,2-B)QUINOLINE-3,14(4H,12H)-DIONE
• (S)-4-ethyl-4-hydroxy-1H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione
• (S)-4-Ethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-(4H,12H)-dione
• 1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 4-ethyl-4-hydroxy-, (S)-
• Prestwick_102
• (+)-Camptothecin;
• Camptothecine (8CI)
• Spectrum_000299
• Tocris-1100
• SpecPlus_000712
• Prestwick0_000200
• Prestwick1_000200
• Prestwick2_000200
• Prestwick3_000200
• Spectrum2_000903
• Spectrum3_001203
• Spectrum4_000738
• Spectrum5_001126
• CAMPTOTHECIN [MI]
• Lopac-C-9911
• D09YDM
• SCHEMBL6038
• UNII-XT3Z54Z28A
• Lopac0_000341
• BSPBio_000159
• BSPBio_002586
• KBioGR_001036
• KBioSS_000779
• KBioSS_002283
• cid_24360
• CAMPTOTHECIN [WHO-DD]
• DivK1c_000826
• DivK1c_006808
• SPECTRUM1502232
• SPBio_000746
• SPBio_002080
• BPBio1_000175
• DTXSID0030956
• HMS502J08
• KBio1_000826
• KBio1_001752
• KBio2_000779
• KBio2_003347
• KBio2_005915
• KBio3_002086
• 4-Ethyl-4-hydroxy-1H-pyrano-[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
• NINDS_000826
• Bio1_000400
• Bio1_000889
• Bio1_001378
• HMS1568H21
• HMS1921N08
• HMS2089F08
• HMS2095H21
• HMS3261E03
• HMS3414J17
• HMS3654D13
• HMS3678J15
• HMS3712H21
• BCP02857
• Tox21_500341
• AC-202
• BBL033963
• BDBM50008923
• CCG-40255
• GR-301
• s1288
• STK801886
• AKOS004119861
• CS-1049
• DB04690
• KS-5235
• LP00341
• SDCCGMLS-0066688.P001
• SDCCGSBI-0050329.P003
• CAS-2114454
• IDI1_000826
• NCGC00015290-01
• NCGC00016994-01
• NCGC00016994-02
• NCGC00016994-03
• NCGC00016994-04
• NCGC00016994-05
• NCGC00016994-06
• NCGC00016994-07
• NCGC00016994-08
• NCGC00016994-09
• NCGC00016994-10
• NCGC00016994-11
• NCGC00016994-12
• NCGC00016994-16
• NCGC00016994-29
• NCGC00024997-01
• NCGC00024997-02
• NCGC00024997-03
• NCGC00024997-04
• NCGC00024997-05
• NCGC00024997-06
• NCGC00178592-01
• NCGC00178592-02
• NCGC00261026-01
• HY-16560
• NCI60_042105
• SMR000445686
• SY010324
• EU-0100341
• SW196414-3
• C 9911
• C01897
• M01564
• AB00052452-08
• AB00052452-09
• AB00052452_10
• EN300-1725804
• (S)-(+)-Camptothecin, >=90% (HPLC), powder
• A838882
• Q419964
• Q-200785
• SR-01000075798-1
• SR-01000075798-4
• SR-01000597379-1
• SR-01000597379-3
• BRD-K37890730-001-09-4
• BRD-K37890730-001-10-2
• Z1741982070
• (S)-4-ethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]florene-3,13-dione
• (S)-4-ethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione
• 4-Ethyl-4-hydroxy-1H-pyrano-[3[,4[:6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
• (19S)-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione
• (S)-4-Ethyl-4-hydroxy-1H-pyrano-[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
• (S)-4-Ethyl-4-hydroxy-1H-pyrano-[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione;(S)-(+)-Camptothecin
• (S)-4-Ethyl-4-hydroxy-1H-pyrano[3 inverted exclamation mark ,4 inverted exclamation mark :6,7]indolizino[1,2-b]quinoline-3,14-(4H,12H)-dione
• 1H-Pyrano[3',7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 4-ethyl-4-hydroxy-, (S)-
• 4(S)-Ethyl-4-hydroxy-1H-pyrano-[3',4':6,7]indolizino[1,2-b]quinoline-3,14 (4H,12H)-dione
• 4-ethyl-4-hydroxy-(4S)-3,4,12,14-tetrahydro-1H-pyrano[3'',4'':6,7]indolizino[1,2-b]quinoline-3,14-dione
• 4-Ethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione (camptothecin or CPT)
• 4-Ethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione (Camptothecin)
• 4-Ethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione (CPT, Camptothecin)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9168	91.68%
Caco-2	-	0.7865	78.65%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Lysosomes	0.4965	49.65%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9392	93.92%
MATE1 inhibitior	-	0.6400	64.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.6326	63.26%
P-glycoprotein inhibitior	-	0.9166	91.66%
P-glycoprotein substrate	-	0.9362	93.62%
CYP3A4 substrate	+	0.6452	64.52%
CYP2C9 substrate	-	0.8162	81.62%
CYP2D6 substrate	-	0.8777	87.77%
CYP3A4 inhibition	+	0.7959	79.59%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9232	92.32%
CYP1A2 inhibition	+	0.9106	91.06%
CYP2C8 inhibition	-	0.7385	73.85%
CYP inhibitory promiscuity	-	0.5591	55.91%
UGT catelyzed	-	0.8000	80.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.4887	48.87%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9603	96.03%
Skin irritation	-	0.8236	82.36%
Skin corrosion	-	0.9463	94.63%
Ames mutagenesis	+	0.5446	54.46%
Human Ether-a-go-go-Related Gene inhibition	-	0.7314	73.14%
Micronuclear	+	0.8400	84.00%
Hepatotoxicity	+	0.8000	80.00%
skin sensitisation	-	0.8823	88.23%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.7838	78.38%
Acute Oral Toxicity (c)	II	0.7320	73.20%
Estrogen receptor binding	+	0.9322	93.22%
Androgen receptor binding	+	0.7855	78.55%
Thyroid receptor binding	+	0.6829	68.29%
Glucocorticoid receptor binding	+	0.9082	90.82%
Aromatase binding	+	0.6567	65.67%
PPAR gamma	+	0.6640	66.40%
Honey bee toxicity	-	0.9126	91.26%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.7332	73.32%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	2511.9 nM; 1995.3 nM; 12589.3 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	17782.8 nM; 22387.2 nM; 8912.5 nM; 11220.2 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL2524	P06280	Alpha-galactosidase A	4466.8 nM; 3548.1 nM; 2238.7 nM; 1995.3 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	39810.7 nM	Potency	via CMAUP
CHEMBL1293237	P54132	Bloom syndrome protein	35481.3 nM; 35481.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4096	P04637	Cellular tumor antigen p53	199.5 nM; 251.2 nM; 25.1 nM; 251.2 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via Super-PRED; via Super-PRED
CHEMBL3356	P05177	Cytochrome P450 1A2	1584.89 nM; 2511.89 nM	AC50; AC50	via CMAUP; via CMAUP
CHEMBL3622	P33261	Cytochrome P450 2C19	19952.6 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	6309.6 nM; 6309.6 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1781	P11387	DNA topoisomerase I	679 nM; 25 nM; 700 nM; 700 nM; 680 nM; 700 nM; 4000 nM; 9000 nM; 300 nM; 2200 nM; 3750 nM; 4950 nM; 4750 nM; 700 nM	IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50	PMID: 7853331; via Super-PRED; DOI: 10.1016/0960-894X(95)00360-6; PMID: 7707314; PMID: 8410981; PMID: 9003520; PMID: 11430001; PMID: 11430001; PMID: 15801827; PMID: 20662543; DOI: 10.1007/s00044-009-9233-5; DOI: 10.1007/s00044-009-9233-5; DOI: 10.1007/s00044-009-9233-5; DOI: 10.1016/S0960-894X(01)80589-8
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	3162.3 nM; 10000 nM; 3981.1 nM; 7943.3 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL1293278	O75496	Geminin	316.2 nM; 316.2 nM	Potency; Potency	via Super-PRED; via CMAUP
CHEMBL4331	P68871	Hemoglobin beta chain	5 nM; 5 nM; 1000 nM	Potency; Potency; Potency	via Super-PRED; via CMAUP; via CMAUP
CHEMBL5514	P42858	Huntingtin	5623.4 nM	Potency	via CMAUP
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	79.4 nM; 79.4 nM; 125.9 nM; 125.9 nM; 79.4 nM	Potency; Potency; Potency; Potency; Potency	via CMAUP; via Super-PRED; via CMAUP; via CMAUP; via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	10000 nM; 10000 nM; 3548.1 nM; 2511.9 nM; 4466.8 nM	Potency; Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL2608	P10253	Lysosomal alpha-glucosidase	31622.8 nM	Potency	via CMAUP
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	4466.8 nM; 4466.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293298	Q01453	Peripheral myelin protein 22	239.3 nM; 239.3 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	15.8 nM; 5.6 nM; 5.6 nM; 25.1 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via Super-PRED; via CMAUP
CHEMBL1293294	P51151	Ras-related protein Rab-9A	46109.1 nM; 398.1 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4630	O14757	Serine/threonine-protein kinase Chk1	2.1 nM; 2.1 nM	EC50; EC50	via Super-PRED; PMID: 17287122
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	46.5 nM; 104 nM; 46.5 nM	Potency; Potency; Potency	via Super-PRED; via CMAUP; via CMAUP
CHEMBL1833	P41595	Serotonin 2b (5-HT2b) receptor	970 nM	IC50	via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	28.2 nM; 35.5 nM; 31.6 nM; 28.2 nM	Potency; Potency; Potency; Potency	via Super-PRED; via CMAUP; via CMAUP; via CMAUP
CHEMBL1293256	P40225	Thrombopoietin	125.9 nM; 125.9 nM; 125.9 nM	Potency; Potency; Potency	via Super-PRED; via CMAUP; via CMAUP
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	39810.7 nM; 39810.7 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.99%	86.33%
CHEMBL2581	P07339	Cathepsin D	96.83%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.36%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.81%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.91%	94.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	88.87%	93.40%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.15%	95.56%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	85.11%	96.67%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.05%	99.23%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	84.91%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.63%	89.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.26%	97.25%
CHEMBL4208	P20618	Proteasome component C5	83.39%	90.00%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	82.87%	85.11%
CHEMBL220	P22303	Acetylcholinesterase	81.44%	94.45%
CHEMBL3192	Q9BY41	Histone deacetylase 8	81.08%	93.99%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	80.14%	98.00%

Plants that contains it

• Aristolochia triangularis
• Camptotheca acuminata
• Didymochlaena truncatula
• Hibiscus syriacus
• Idesia polycarpa
• Merrilliodendron megacarpum
• Ophiorrhiza kuroiwai
• Ophiorrhiza pumila
• Pyrenacantha klaineana
• Rinorea anguifera

Cross-Links

• PubChem: 24360
• NPASS: NPC129909
• ChEMBL: CHEMBL65
• LOTUS: LTS0270094
• wikiData: Q419964