NPs Basic Information

Name
Camptothecin
Molecular Formula C20H16N2O4
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
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
InChIKey
VSJKWCGYPAHWDS-FQEVSTJZSA-N
Synonyms
camptothecin; Camptothecine; 7689-03-4; (S)-(+)-Camptothecin; Campathecin; (+)-Camptothecine; d-Camptothecin; (+)-Camptothecin; 20(S)-Camptothecine; 21,22-Secocamptothecin-21-oic acid lactone; NSC94600; Camptothecine (S,+); CHEMBL65; (4S)-4-ethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione; NSC-94600; (S)-4-ethyl-4-hydroxy-1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione; MLS000766223; XT3Z54Z28A; CHEBI:27656; MFCD00081076; (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; NSC 100880; 251316-95-7; (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); ( )-Camptothecin; (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; 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; 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; ACT02668; BCP02857; Tox21_500341; AC-202; BBL033963; BDBM50008923; CCG-40255; GR-301; NSC 94600; s1288; STK801886; AKOS004119861; CS-1049; DB04690; 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; NCGC00016994-29; 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; SW196414-3; C 9911; C01897; M01564; AB00052452-08; AB00052452-09; AB00052452_10; EN300-1725804; (S)-(+)-Camptothecin, >=90% (HPLC), powder; 689C034; 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)
CAS 7689-03-4
PubChem CID 24360
ChEMBL ID CHEMBL65
*Note: the IUPAC Name was collected from PubChem.
Chemical Classification:
  • Kingdom: Organic compounds
    • Superclass: Alkaloids and derivatives
      • Class: Camptothecins
        • Subclass: No Rank at Level Subclass
          • Direct Parent: Camptothecins

ClassyFire Version 1.0
PMID:27867422

NPs Species Source

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NPs Content

*Note: The vaules in Content Percentage are calculated by dividing the content value by the maximum content value in NP Content.
**Note: The units with different NP content, due to their incomparable values, are separated into different tables.

NPs Biological Activity

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NPs Physi-Chem Properties

Molecular Weight: 348.4 ALogp: 1.0
HBD: 1 HBA: 5
Rotatable Bonds: 1 Lipinski's rule of five: Accepted
Polar Surface Area: 79.7 Aromatic Rings: 5
Heavy Atoms: 26 QED Weighted: 0.535

NPs ADMET Properties*

ADMET: Absorption

Caco-2 Permeability: -4.958 MDCK Permeability: 0.00002840
Pgp-inhibitor: 0.011 Pgp-substrate: 0.034
Human Intestinal Absorption (HIA): 0.004 20% Bioavailability (F20%): 0.002
30% Bioavailability (F30%): 0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB): 0.586 Plasma Protein Binding (PPB): 88.65%
Volume Distribution (VD): 0.795 Fu: 4.73%

ADMET: Metabolism

CYP1A2-inhibitor: 0.962 CYP1A2-substrate: 0.765
CYP2C19-inhibitor: 0.635 CYP2C19-substrate: 0.26
CYP2C9-inhibitor: 0.574 CYP2C9-substrate: 0.324
CYP2D6-inhibitor: 0.045 CYP2D6-substrate: 0.365
CYP3A4-inhibitor: 0.374 CYP3A4-substrate: 0.357

ADMET: Excretion

Clearance (CL): 7.535 Half-life (T1/2): 0.239

ADMET: Toxicity

hERG Blockers: 0.221 Human Hepatotoxicity (H-HT): 0.788
Drug-inuced Liver Injury (DILI): 0.352 AMES Toxicity: 0.858
Rat Oral Acute Toxicity: 0.864 Maximum Recommended Daily Dose: 0.961
Skin Sensitization: 0.037 Carcinogencity: 0.779
Eye Corrosion: 0.003 Eye Irritation: 0.015
Respiratory Toxicity: 0.046
*Note: the ADMET properties was calculated by ADMETlab 2.0. Reference: PMID: 33893803.

Similar Compounds*

Compounds similar to EMNPD with top10 similarity:

*Note: the compound similarity was calculated by RDKIT.