Compound: camptothecin
SMILES: O=c1n2c(-c3nc4ccccc4cc3C2)cc5c1COC([C@]5(O)CC)=O
InChIKey: VSJKWCGYPAHWDS-FQEVSTJZSA-N
Synonyms: camptothecin, Camptothecine, 7689-03-4, (S)-(+)-Camptothecin, (+)-Camptothecin, d-Camptothecin, 20(S)-Camptothecine, (+)-Camptothecine, 21,22-Secocamptothecin-21-oic acid lactone, NSC94600, NSC-94600, (4S)-4-ethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, XT3Z54Z28A, DTXSID0030956, (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, CHEBI:27656, 1H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione, 4-ethyl-4-hydroxy-, (S)-, (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, 1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 4-ethyl-4-hydroxy-, (S)-, 20-(S)-camptothecine, RefChem:388854, DTXCID8010956, 21, 22-Secocamptothecin-21-oic acid lactone, (S)-4-ethyl-4-hydroxy-1H-pyrano-(3',4':6,7)indolozino(1,2-b)quinoline-3,14(4H,12H)-dione, 1H-Pyrano(3',3'.6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione, 4-ethyl-4hydroxy-(S)-, Campathecin, MFCD00081076, (S)-4-ethyl-4-hydroxy-1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, Camptothecine (S,+), CHEMBL65, MLS000766223, M01564, NSC 100880, (S)-4-ethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione, (s)-camptothecine, (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-, (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)-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, Prestwick_102, 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, 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, CCRIS 8162, orb1309690, orb3140737, SCHEMBL29351099, SCHEMBL29360250, 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, GLXC-10346, HMS1568H21, HMS1921N08, HMS2089F08, HMS2095H21, HMS3261E03, HMS3414J17, HMS3654D13, HMS3678J15, HMS3712H21, MSK40312, Tox21_500341, AC-202, BBL033963, BDBM50008923, CCG-40255, EBC-14151, GR-301, NSC 94600, s1288, STK801886, AKOS004119861, Camptothecin; Irinotecan EP Impurity D, DB04690, FC15450, KS-5235, LP00341, 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, NCGC00016994-19, NCGC00016994-23, 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, AI3-62475, EU-0100341, NS00011856, SW196414-3, C 9911, C01897, AB00052452-08, AB00052452-09, AB00052452_10, EN300-1725804, (S)-(+)-Camptothecin, >=90% (HPLC), powder, Q419964, SR-01000075798-1, SR-01000075798-4, SR-01000597379-1, SR-01000597379-3, BRD-K37890730-001-09-4, BRD-K37890730-001-10-2, BRD-K37890730-001-15-1, BRD-K37890730-001-16-9, BRD-K37890730-001-17-7, Z1741982070, (S)-4-ethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]florene-3,13-dione, 4-Ethyl-4-hydroxy-1H-pyrano-[3,4:6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-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-1,12-dihydro-14H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H)-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)
Theoretical properties:
molecular_formula: C20H16N2O4
molecular_weight: 348.4 g/mol
exact_mass: 348.11100700 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 1
heavy_atom_count: 26
topological_polar_surface_area: 79.7 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 275-277 °C
Descriptions:
pubchem: Camptothecin is a pyranoindolizinoquinoline that is pyrano[3',4':6,7]indolizino[1,2-b]quinoline which is substituted by oxo groups at positions 3 and 14, and by an ethyl group and a hydroxy group at position 4 (the S enantiomer). It has a role as an antineoplastic agent, an EC 5.99.1.2 (DNA topoisomerase) inhibitor, a genotoxin and a plant metabolite. It is a delta-lactone, a quinoline alkaloid, a tertiary alcohol and a pyranoindolizinoquinoline.
chebi: A pyranoindolizinoquinoline that is pyrano[3',4':6,7]indolizino[1,2-<em>b</em>]quinoline which is substituted by oxo groups at positions 3 and 14, and by an ethyl group and a hydroxy group at position 4 (the <i>S</i> enantiomer).
chembl: CAMPTOTHECIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase -1.0.
wikipedia: Camptothecin (CPT) is a topoisomerase inhibitor. It was discovered in 1966 by M. E. Wall and M. C. Wani in systematic screening of natural products for anticancer drugs. It was isolated from the bark of Camptotheca acuminata (喜树 "Happy tree"), a tree native to China used in traditional Chinese medicine. It has been used clinically in China for the treatment of gastrointestinal tumors.  CPT showed anticancer activity in preliminary clinical trials, especially against breast, ovarian, colon, lung, and stomach cancers. However, it has low solubility and adverse effects have been reported when used therapeutically, so synthetic and medicinal chemists have developed numerous syntheses of camptothecin and various derivatives to increase the benefits of the chemical, with good results.  Four CPT analogues have been approved and are used in cancer chemotherapy today: topotecan, irinotecan, belotecan, and trastuzumab deruxtecan. Camptothecin has also been found in other plants including Chonemorpha fragrans.