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Natural Product (NP) Details

General Information of the NP (ID: NP9436)
Name
Camptothecin
Synonyms
camptothecin; Camptothecine; (S)-(+)-Camptothecin; 7689-03-4; Campathecin; (+)-Camptothecine; d-Camptothecin; (+)-Camptothecin; 20(S)-Camptothecine; 21,22-Secocamptothecin-21-oic acid lactone; NSC94600; Camptothecine (8CI); Camptothecine (S,+); CHEMBL65; (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; UNII-XT3Z54Z28A; MLS000766223; XT3Z54Z28A; CHEBI:27656; MFCD00081076; NSC-94600; (+)-Camptothecin, 98%; (S)-Camptothecin; 1H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione, 4-ethyl-4-hydroxy-, (S)-; 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, Camptotheca acuminata; Camptothecin,(S); ( )-Camptothecin; (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-, (4S)-; 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)-; Prestwick_102; (+)-Camptothecin;; PubChem10183; Spectrum_000299; Tocris-1100; SpecPlus_000712; Prestwick0_000200; Prestwick1_000200; Prestwick2_000200; Prestwick3_000200; Spectrum2_000903; Spectrum3_001203; Spectrum4_000738; Spectrum5_001126; Lopac-C-9911; SCHEMBL6038; Lopac0_000341; BSPBio_000159; BSPBio_002586; KBioGR_001036; KBioSS_000779; KBioSS_002283; cid_24360; DivK1c_000826; DivK1c_006808; SPECTRUM1502232; SPBio_000746; SPBio_002080; BPBio1_000175; CCRIS 8162; 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; ZINC105309; (S)-4-Ethyl-4-hydroxy-1H-pyrano-[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione; ACT02668; BCP02857; Tox21_500341; AC-202; BBL033963; BDBM50008923; CCG-40255; GR-301; NSC 94600; s1288; STK801886; AKOS004119861; CS-1049; DB04690; KS-5235; LP00341; MCULE-1654983682; SDCCGMLS-0066688.P001; SDCCGSBI-0050329.P003; BRN 0631069; 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; AK-39842; HY-16560; K332; NCI60_042105; SMR000445686; SY010324; AI3-62475; EU-0100341; N1868; SW196414-3; C 9911; C01897; J10012; M01564; S-2515; 32320-EP2270008A1; 32320-EP2272827A1; 32320-EP2275420A1; 32320-EP2277507A1; 32320-EP2277865A1; 32320-EP2280013A1; 32320-EP2281815A1; 32320-EP2286795A1; 32320-EP2286812A1; 32320-EP2289892A1; 32320-EP2292615A1; 32320-EP2292617A1; 32320-EP2295055A2; 32320-EP2295416A2; 32320-EP2298748A2; 32320-EP2298764A1; 32320-EP2298765A1; 32320-EP2298778A1; 32320-EP2301933A1; 32320-EP2305640A2; 32320-EP2305642A2; 32320-EP2305671A1; 32320-EP2308855A1; 32320-EP2311453A1; 32320-EP2311827A1; 32320-EP2311840A1; AB00052452-08; AB00052452-09; AB00052452_10; (S)-(+)-Camptothecin, >=90% (HPLC), powder; 157594-EP2277507A1; 157594-EP2286795A1; 179002-EP2280013A1; 689C034; 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; (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; Topotecan Related Compound C, United States Pharmacopeia (USP) Reference Standard; (19S)-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0(2),(1)(1).0?,?.0(1)?,(2)?]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione; (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)
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Species Origin Camptotheca acuminata ...     Click to Show/Hide
Camptotheca acuminata
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Cornales
Family: Nyssaceae
Genus: Camptotheca
Species: Camptotheca acuminata
Disease Solid tumour/cancer [ICD-11: 2A00-2F9Z] Phase 3 [1]
Structure
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2D MOL

3D MOL

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Formula
C20H16N2O4
PubChem CID
24360
Canonical SMILES
CCC1(C2=C(COC1=O)C(=O)N3CC4=CC5=CC=CC=C5N=C4C3=C2)O
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
InChIKey
VSJKWCGYPAHWDS-FQEVSTJZSA-N
CAS Number
CAS 7689-03-4
ChEBI ID
CHEBI:27656
Herb ID
HBIN019519
SymMap ID
SMIT14558
TTD Drug ID
D09YDM
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Doxorubicin      Solid tumour/cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation
Up-regulation Expression CTNNB1  Molecule Info 
Pathway MAP
                    In-vitro Model 4T1 CVCL_0125 Malignant neoplasms Mus musculus
BT-474 CVCL_0179 Invasive breast carcinoma Homo sapiens
                    In-vivo Model Tumor inoculation was achieved by subcutaneously injecting 5*104 4T1 cells in the abdominal mammary gland of female BALB/c mice in order to prevent interference with normal bodily functions
                    Experimental
                    Result(s)
Camptothecin-doxorubicin combinations showed synergistic antitumor acitivity.
Target and Pathway
Target(s) DNA topoisomerase I (TOP1)  Molecule Info  [1]
NetPath Pathway IL2 Signaling Pathway Click to Show/Hide
Panther Pathway DNA replication Click to Show/Hide
Pathway Interaction Database Caspase Cascade in Apoptosis Click to Show/Hide
WikiPathways Integrated Pancreatic Cancer Pathway Click to Show/Hide
References
Reference 1 Topoisomerase I inhibitors: camptothecins and beyond. Nat Rev Cancer. 2006 Oct;6(10):789-802.
Reference 2 Synergistic antitumor activity of camptothecin-doxorubicin combinations and their conjugates with hyaluronic acid. J Control Release. 2015 Jul 28;210:198-207.
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Cite NPCDR
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Correspondence

X. N. Sun, Y. T. Zhang, Y. Zhou, X. C. Lian, L. L. Yan, T. Pan, T. Jin, H. Xie, Z. M. Liang, W. Q. Qiu, J. X. Wang, Z. R. Li, F. Zhu*, X. B. Sui*. NPCDR: natural product-based drug combination and its disease-specific molecular regulation. Nucleic Acids Research. 50(D1): 1324-1333 (2020). PMID: 34664659

Prof. Feng ZHU  (zhufeng@zju.edu.cn)

College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, China


Prof. Xinbing SUI  (hzzju@hznu.edu.cn)

School of Pharmacy and Department of Medical Oncology, the Affiliated Hospital of Hangzhou Normal University, Hangzhou Normal University, Hangzhou, China