(+)-Camptothecin

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	db2bbe61-dcf2-434b-8988-38af3a93fceb
Taxonomy	Alkaloids and derivatives > Camptothecins
IUPAC Name	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 (Canonical)	CCC1(C2=C(COC1=O)C(=O)N3CC4=CC5=CC=CC=C5N=C4C3=C2)O
SMILES (Isomeric)	CCC1(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
InChI Key	VSJKWCGYPAHWDS-UHFFFAOYSA-N
Popularity	12 references in papers

Physical and Chemical Properties

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Molecular Formula	C₂₀H₁₆N₂O₄
Molecular Weight	348.40 g/mol
Exact Mass	348.11100700 g/mol
Topological Polar Surface Area (TPSA)	79.70 Å²
XlogP	1.00
Atomic LogP (AlogP)	2.08
H-Bond Acceptor	6
H-Bond Donor	1
Rotatable Bonds	1

Synonyms

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(+)-Camptothecin

CHEMBL276820

(+/-)Campathecin

NSC302991

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

4-ETHYL-4-HYDROXY-3,4,12,14-TETRAHYDRO-1H-PYRANO[3'4':6,7]INDOLIZINO[1,2-B]QUINOLINE-3,14-DIONE

4-ETHYL-4-HYDROXY-3,4,12,14-TETRAHYDRO-1H-PYRANO[3'4'

(+/-)-Camptothecine;20(RS)-Camptothecin;dl-Camptothecin

TNP00113

()Campathecin

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9168	91.68%
Caco-2	-	0.7865	78.65%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Lysosomes	0.4965	49.65%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9392	93.92%
MATE1 inhibitior	-	0.6400	64.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.6326	63.26%
P-glycoprotein inhibitior	-	0.9166	91.66%
P-glycoprotein substrate	-	0.9362	93.62%
CYP3A4 substrate	+	0.6452	64.52%
CYP2C9 substrate	-	0.8162	81.62%
CYP2D6 substrate	-	0.8777	87.77%
CYP3A4 inhibition	+	0.7959	79.59%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9232	92.32%
CYP1A2 inhibition	+	0.9106	91.06%
CYP2C8 inhibition	-	0.7385	73.85%
CYP inhibitory promiscuity	-	0.5591	55.91%
UGT catelyzed	-	0.8000	80.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.4887	48.87%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9603	96.03%
Skin irritation	-	0.8236	82.36%
Skin corrosion	-	0.9463	94.63%
Ames mutagenesis	+	0.5446	54.46%
Human Ether-a-go-go-Related Gene inhibition	-	0.7314	73.14%
Micronuclear	+	0.8400	84.00%
Hepatotoxicity	+	0.8000	80.00%
skin sensitisation	-	0.8823	88.23%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.7838	78.38%
Acute Oral Toxicity (c)	II	0.7320	73.20%
Estrogen receptor binding	+	0.9322	93.22%
Androgen receptor binding	+	0.7855	78.55%
Thyroid receptor binding	+	0.6829	68.29%
Glucocorticoid receptor binding	+	0.9082	90.82%
Aromatase binding	+	0.6567	65.67%
PPAR gamma	+	0.6640	66.40%
Honey bee toxicity	-	0.9126	91.26%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.7332	73.32%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4096	P04637	Cellular tumor antigen p53	25.1 nM 251.2 nM	Potency Potency	via Super-PRED via Super-PRED
CHEMBL1781	P11387	DNA topoisomerase I	25 nM	IC50	via Super-PRED
CHEMBL1293278	O75496	Geminin	316.2 nM	Potency	via Super-PRED
CHEMBL4331	P68871	Hemoglobin beta chain	5 nM	Potency	via Super-PRED
CHEMBL1955709	P09651	Heterogeneous nuclear ribonucleoprotein A1	82.7 nM	Kd	via Super-PRED
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	79.4 nM	Potency	via Super-PRED
CHEMBL1293298	Q01453	Peripheral myelin protein 22	239.3 nM	Potency	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	5.6 nM	Potency	via Super-PRED
CHEMBL4630	O14757	Serine/threonine-protein kinase Chk1	2.1 nM	EC50	via Super-PRED
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	46.5 nM	Potency	via Super-PRED
CHEMBL1293232	Q16637	Survival motor neuron protein	28.2 nM	Potency	via Super-PRED
CHEMBL1293256	P40225	Thrombopoietin	125.9 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.99%	86.33%
CHEMBL2581	P07339	Cathepsin D	96.83%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.36%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.81%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.91%	94.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	88.87%	93.40%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.15%	95.56%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	85.11%	96.67%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.05%	99.23%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	84.91%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.63%	89.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.26%	97.25%
CHEMBL4208	P20618	Proteasome component C5	83.39%	90.00%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	82.87%	85.11%
CHEMBL220	P22303	Acetylcholinesterase	81.44%	94.45%
CHEMBL3192	Q9BY41	Histone deacetylase 8	81.08%	93.99%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	80.14%	98.00%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Camptotheca acuminata

Didymochlaena truncatula

Ophiorrhiza kuroiwai

Ophiorrhiza pumila

Rinorea anguifera