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10-hydroxy camptothecin
- Family: Plantae - Apocynaceae
- Kingdom: Plantae
- Class: Alkaloid
| Canonical Smiles | CC[C@@]1(O)C(=O)OCc2c1cc1c3nc4ccc(cc4cc3Cn1c2=O)O |
|---|---|
| InChI | InChI=1S/C20H16N2O5/c1-2-20(26)14-7-16-17-11(5-10-6-12(23)3-4-15(10)21-17)8-22(16)18(24)13(14)9-27-19(20)25/h3-7,23,26H,2,8-9H2,1H3/t20-/m0/s1 |
| InChIKey | HAWSQZCWOQZXHI-FQEVSTJZSA-N |
| Formula | C20H16N2O5 |
| HBA | 7 |
| HBD | 2 |
| MW | 364.36 |
| Rotatable Bonds | 1 |
| TPSA | 101.65 |
| LogP | 1.79 |
| Number Rings | 5 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 27 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.25 |
| Exact Mass | 364.11 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Pachypodium lamerei | Apocynaceae | Plantae | 69385 |
Showing of synonyms
10-hydroxy camptothecin
10-Hydroxycamptothecin
19685-09-7
(S)-10-Hydroxycamptothecin
Hydroxycamptothecin
Hydroxycamptothecine
Camptothecin, hydroxy-
Camptothecine, 10-hydroxy-
Camptothecin, 10-hydroxy-
NSC 107124
(S)-10-Hydroxycamptothecin hydrate
UNII-9Z01632KRV
9Z01632KRV
(+)-10-HYDROXYCAMPTOTHECIN
1H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione, 4-ethyl-4,9-dihydroxy-, hydrate, (S)-
10-HYDROXYCAMPTOTHECIN [WHO-DD]
1H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione-,4-ethyl-4,9-dihydroxy-, (S)-
1H-PYRANO(3',4':6,7)INDOLIZINO(1,2-B)QUINOLINE-3,14(4H,12H)-DIONE, 4-ETHYL-4,9-DIHYDROXY-, (4S)-
Camptothecine, 10-hydroxy-(8CI)
1H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione-,4-ethyl-4,9-dihydroxy-, (S)-(9CI)
613-598-9
(4s)-4-ethyl-4,10-dihydroxy-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-4,10-dihydroxy-, (s)-
Lczzwlidinbprc-uhfffaoysa-n
10-hydroxycamptothecine
(4S)-4-Ethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
(S)-4-Ethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
10-HCPT
10-Hydroxy-Camptothecin
MFCD02093100
NSC107124
NSC-107124
CHEMBL273862
CHEBI:81395
Hydroxy camptothecine
(S)-4-ethyl-4,9-dihydroxy-1,12-dihydro-14H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H)-dione
(19S)-19-ethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione
(20S)-4-Ethyl-4,9-dihydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione
(S)-4-Ethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione ((S)-10-Hydroxycamptothecin)
CAMPTOTHECIN, 10-HYDROXY
10-Hydroxy-CPT
Spectrum_001639
(+)-(S)-10-HYDROXYCAMPTOTHECIN
10-Hydroxycamp-totecin
SpecPlus_000763
Spectrum2_001660
Spectrum3_001621
Spectrum4_001815
Spectrum5_000549
Ethyl(dihydroxy)[?]dione
SCHEMBL25875
BSPBio_003281
KBioGR_002454
KBioSS_002119
DivK1c_006859
SPECTRUM1504123
SPBio_001819
HY-N0095R
KBio1_001803
KBio2_002119
KBio2_004687
KBio2_007255
KBio3_002501
DTXSID00941444
EX-A988
BCP01385
HY-N0095
BDBM50008922
CCG-38770
S2423
S3898
AKOS015919293
AC-5502
BCP9000058
CS-5193
DB12385
(S)-10-Hydroxycamptothecin (Standard)
NCGC00095986-01
NCGC00095986-02
NCGC00095986-03
NCGC00095986-04
NCGC00178165-01
AC-13221
AS-13196
NCI60_000173
SY010687
H1463
NS00018317
C17939
EN300-19810684
SR-05000002620
SR-05000002620-1
BRD-K63784565-001-02-1
BRD-K63784565-001-03-9
BRD-K63784565-001-05-4
BRD-K63784565-001-06-2
Q27155328
Z3093896188
4-Ethyl-4,9-dihydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione
(19S)-19-ethyl-7,19-dihydroxy-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-4,9-dihydroxy-1H-pyrano[3 inverted exclamation mark ,4 inverted exclamation mark :6,7]indolizino[1,2-b]quinoline-3,14-(4H,12H)-dione
(S)-4-Ethyl-4,9-dihydroxy-1H-pyrano[3',4':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-4,9-dihydroxy-, (S)-
4-Ethyl-4,10-dihydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione
4-Ethyl-4,9-dihydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione (10-hydroxycamptothecin)
Pubchem:
97226
Cas:
19685-09-7
Gnps:
CCMSLIB00004693781
Zinc:
ZINC000003979155
Kegg Ligand:
C17939
Chebi:
81395
Nmrshiftdb2:
70005121
Chembl:
CHEMBL273862
Drugbank:
DB12385
Bindingdb:
50008922
Selleck:
10-hydroxycamptothecin
CPRiL:
73456
SMILES: c1cccc(n2)c1cc(c23)Cn4c3cc5c(c4=O)COC(=O)C5
Level: 0
Mol. Weight: 364.36 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.02
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.9
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.41
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.09
- Plasma Protein Binding
- 63.93
- 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
- Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 5.56
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 0.17
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.14
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.65
- 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
- -10.11
- Rat (Acute)
- 2.75
- Rat (Chronic Oral)
- 1.72
- Fathead Minnow
- 4.82
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Toxic
General Properties
- Boiling Point
- 511.89
- Hydration Free Energy
- -7.43
- Log(D) at pH=7.4
- 1.43
- Log(P)
- 1.4
- Log S
- -3.94
- Log(Vapor Pressure)
- -10.63
- Melting Point
- 339.29
- pKa Acid
- 9.44
- pKa Basic
- 5.13
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.9538 |
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.9120 |
| CREB-binding protein | Q92793 | CBP_HUMAN | Homo sapiens | 3 | 0.8994 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.8823 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.8816 |
| Multidrug-efflux transporter 1 regulator | P39075 | BMRR_BACSU | Bacillus subtilis | 3 | 0.8771 |
| AGAP003309-PA | A0A1U7F4W2 | A0A1U7F4W2_ANOGA | Anopheles gambiae | 3 | 0.8697 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8640 |
| Retinol dehydratase | Q26490 | Q26490_SPOFR | Spodoptera frugiperda | 4 | 0.8585 |
| Phosphodiesterase | Q53I60 | Q53I60_TRYCR | Trypanosoma cruzi | 4 | 0.8582 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8564 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8525 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8522 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 4 | 0.8494 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8455 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8342 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.8310 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8267 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.8165 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.8165 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 3 | 0.8163 |
| Collagenase 3 | P45452 | MMP13_HUMAN | Homo sapiens | 4 | 0.8033 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.7943 |
| 17beta-hydroxysteroid dehydrogenase | O93874 | O93874_COCLU | Cochliobolus lunatus | 3 | 0.7819 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.7815 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | F6MZ55 | F6MZ55_9FIRM | Sporomusa ovata | 3 | 0.7755 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7695 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7678 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7545 |
| Biotin carboxylase | P24182 | ACCC_ECOLI | Escherichia coli | 3 | 0.7543 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.7515 |
| Jasmonoyl--L-amino acid synthetase JAR1 | Q9SKE2 | JAR1_ARATH | Arabidopsis thaliana | 3 | 0.7511 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7500 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7479 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7479 |
| Matrix metalloproteinase-9 | P14780 | MMP9_HUMAN | Homo sapiens | 3 | 0.7448 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7394 |
| cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B | Q13370 | PDE3B_HUMAN | Homo sapiens | 3 | 0.7392 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7332 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7326 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 4 | 0.7286 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.7270 |
| Aromatase | P11511 | CP19A_HUMAN | Homo sapiens | 3 | 0.7246 |
| Collagenase 3 | P45452 | MMP13_HUMAN | Homo sapiens | 4 | 0.7243 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 3 | 0.7232 |
| IOMT 3 | Q06YR3 | Q06YR3_MEDTR | Medicago truncatula | 3 | 0.7231 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 2 | 0.7226 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7206 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7184 |
| Transthyretin | P02766 | TTHY_HUMAN | Homo sapiens | 4 | 0.7127 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7083 |
| Gag-Pol polyprotein | P03367 | POL_HV1BR | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7082 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7077 |
| Cytochrome P450 3A4 | P08684 | CP3A4_HUMAN | Homo sapiens | 3 | 0.7042 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7021 |
| UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase | Q8DNV6 | Q8DNV6_STRR6 | Streptococcus pneumoniae | 2 | 0.7004 |