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Camptothecin
- Family: Plantae - Apocynaceae
- Kingdom: Plantae
- Class: Alkaloid
| Canonical Smiles | CC[C@@]1(O)C(=O)OCc2c1cc1c3nc4ccccc4cc3Cn1c2=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 |
| Formula | C20H16N2O4 |
| HBA | 6 |
| HBD | 1 |
| MW | 348.36 |
| Rotatable Bonds | 1 |
| TPSA | 81.42 |
| LogP | 2.08 |
| Number Rings | 5 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 26 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.25 |
| Exact Mass | 348.11 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Pachypodium lamerei | Apocynaceae | Plantae | 69385 |
Showing of synonyms
Camptothecin
Camptothecine
7689-03-4
(S)-(+)-Camptothecin
(+)-Camptothecin
D-Camptothecin
(+)-Camptothecine
20(S)-Camptothecine
21,22-Secocamptothecin-21-oic acid lactone
NSC94600
D-camptothecine
(s)-camptothecine
NSC-94600
XT3Z54Z28A
Camptothecine (8CI)
CHEBI:27656
(4S)-4-ethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
CAMPTOTHECIN [MI]
(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
CAMPTOTHECIN [WHO-DD]
CCRIS 8162
DTXSID0030956
NSC 94600
BRN 0631069
AI3-62475
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)-
(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)-4-ethyl-4-hydroxy-1H-pyrano-(3',4':6,7)indolozino(1,2-b)quinoline-3,14(4H,12H)-dione
(S)-4-ethyl-4-hydroxy-1H-pyrano-[3',4':6,7]indolozino[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)-
20-(S)-camptothecine
DTXCID8010956
21, 22-Secocamptothecin-21-oic acid lactone
1H-Pyrano(3',3'.6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione, 4-ethyl-4hydroxy-(S)-
1H-Pyrano[3',3'.6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 4-ethyl-4hydroxy-(S)-(9CI)
Vsjkwcgypahwds-fqevstjzsa-n
Campathecin
(S)-4-ethyl-4-hydroxy-1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
Camptothecine (S,+)
CHEMBL65
MFCD00081076
MLS000766223
NSC 100880
(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
(S)-Camptothecin
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
(S)-4-ethyl-4-hydroxy-1H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione
Prestwick_102
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
UNII-XT3Z54Z28A
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
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
BCP02857
MSK40312
Tox21_500341
AC-202
BBL033963
BDBM50008923
CCG-40255
GR-301
S1288
STK801886
AKOS004119861
CS-1049
DB04690
FC15450
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
NCGC00016994-19
NCGC00016994-23
NCGC00016994-29
NCGC00024997-01
NCGC00024997-02
NCGC00024997-03
NCGC00024997-04
NCGC00024997-05
NCGC00024997-06
NCGC00178592-01
NCGC00178592-02
NCGC00261026-01
1ST40312
HY-16560
NCI60_042105
SMR000445686
SY010324
EU-0100341
NS00011856
SW196414-3
C 9911
C01897
M01564
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
(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
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 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)
Pubchem:
24360
Cas:
7689-03-4
Gnps:
CCMSLIB00005772000
Zinc:
ZINC000000105309
Kegg Ligand:
C01897
Chebi:
27656
Nmrshiftdb2:
60020213
Metabolights:
MTBLC27656
Chembl:
CHEMBL65
Comptox:
DTXSID0030956
Drugbank:
DB04690
Pdb Ligand:
EHD
Bindingdb:
50008923
Selleck:
Camptothecine
CPRiL:
310
SMILES: c1cccc(n2)c1cc(c23)Cn4c3cc5c(c4=O)COC(=O)C5
Level: 0
Mol. Weight: 348.36 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.68
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.79
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.82
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.14
- Plasma Protein Binding
- 64.87
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 3.15
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 0.41
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.4
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.59
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Toxic
- T. Pyriformis
- -6.9
- Rat (Acute)
- 3.02
- Rat (Chronic Oral)
- 1.3
- Fathead Minnow
- 5.0
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 480.12
- Hydration Free Energy
- -7.14
- Log(D) at pH=7.4
- 1.78
- Log(P)
- 1.79
- Log S
- -3.86
- Log(Vapor Pressure)
- -9.9
- Melting Point
- 294.42
- pKa Acid
- 8.65
- pKa Basic
- 4.37
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.8965 |
| Multidrug-efflux transporter 1 regulator | P39075 | BMRR_BACSU | Bacillus subtilis | 3 | 0.8849 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.8794 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.8738 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8613 |
| Phosphodiesterase | Q53I60 | Q53I60_TRYCR | Trypanosoma cruzi | 4 | 0.8605 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.8529 |
| Carbonic anhydrase 12 | O43570 | CAH12_HUMAN | Homo sapiens | 3 | 0.8523 |
| Cell division cycle 7-related protein kinase | O00311 | CDC7_HUMAN | Homo sapiens | 4 | 0.8483 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.8413 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 4 | 0.8274 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.8246 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 3 | 0.8227 |
| Collagenase 3 | P45452 | MMP13_HUMAN | Homo sapiens | 4 | 0.8123 |
| Focal adhesion kinase 1 | Q05397 | FAK1_HUMAN | Homo sapiens | 3 | 0.8091 |
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.8041 |
| Aldo-keto reductase family 1 member B10 | O60218 | AK1BA_HUMAN | Homo sapiens | 3 | 0.7970 |
| Calmodulin-2 | P0DP24 | CALM2_HUMAN | Homo sapiens | 3 | 0.7929 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7851 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.7828 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7827 |
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 3 | 0.7774 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7698 |
| Protein S100-A13 | Q99584 | S10AD_HUMAN | Homo sapiens | 3 | 0.7619 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 3 | 0.7618 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 4 | 0.7593 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7505 |
| Riboflavin biosynthesis protein | Q9WZW1 | Q9WZW1_THEMA | Thermotoga maritima | 3 | 0.7473 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 2 | 0.7465 |
| Matrix metalloproteinase-9 | P14780 | MMP9_HUMAN | Homo sapiens | 3 | 0.7459 |
| Enoyl-[acyl-carrier-protein] reductase [NADH] | P9WGR1 | INHA_MYCTU | Mycobacterium tuberculosis | 3 | 0.7432 |
| Gag-Pol polyprotein | P04585 | POL_HV1H2 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7426 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 3 | 0.7406 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7376 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.7370 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.7368 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7354 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7333 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.7329 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 4 | 0.7307 |
| Collagenase 3 | P45452 | MMP13_HUMAN | Homo sapiens | 4 | 0.7301 |
| Estrogen receptor | P03372 | ESR1_HUMAN | Homo sapiens | 3 | 0.7289 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 4 | 0.7268 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.7265 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7253 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7154 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7152 |
| Metallo-beta-lactamase type 2 | P25910 | BLAB_BACFG | Bacteroides fragilis | 3 | 0.7144 |
| Prostaglandin E synthase 2 | Q9N0A4 | PGES2_MACFA | Macaca fascicularis | 3 | 0.7131 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 4 | 0.7117 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7112 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 3 | 0.7106 |
| Gag-Pol polyprotein | P03367 | POL_HV1BR | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7102 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7091 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 3 | 0.7058 |
| Apoptosis regulator Bcl-2 | P10415 | BCL2_HUMAN | Homo sapiens | 3 | 0.7048 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7019 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7012 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7011 |
| Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.7004 |