Rutaecarpine

Details

• Internal ID: 26135c5b-8a15-4a65-ab5c-9fb5a679f35b
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Pyridoindoles > Beta carbolines
• IUPAC Name: 3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-1(21),2(10),4,6,8,15,17,19-octaen-14-one
• SMILES (Canonical): C1CN2C(=NC3=CC=CC=C3C2=O)C4=C1C5=CC=CC=C5N4
• SMILES (Isomeric): C1CN2C(=NC3=CC=CC=C3C2=O)C4=C1C5=CC=CC=C5N4
• InChI: InChI=1S/C18H13N3O/c22-18-13-6-2-4-8-15(13)20-17-16-12(9-10-21(17)18)11-5-1-3-7-14(11)19-16/h1-8,19H,9-10H2
• InChI Key: ACVGWSKVRYFWRP-UHFFFAOYSA-N
• Popularity: 415 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₃N₃O
• Molecular Weight: 287.30 g/mol
• Exact Mass: 287.105862047 g/mol
• Topological Polar Surface Area (TPSA): 48.50 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 3.10
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 84-26-4
• Rutecarpine
• Rutacarpine
• Rhetine
• Rutaecarpin
• C18H13N3O
• 8,13-dihydroindolo[2',3':3,4]pyrido[2,1-b]quinazolin-5(7H)-one
• Indolo[2',3':3,4]pyrido[2,1-b]quinazolin-5(7H)-one, 8,13-dihydro-
• MFCD00210551
• UNII-8XZV289PRY
• NSC 258317
• 8XZV289PRY
• CHEMBL85139
• CHEBI:8922
• NSC-258317
• 7,8-dihydroindolo[2',3':3,4]pyrido[2,1-b]quinazolin-5(13H)-one
• 8,13-Dihydro-indolo[2',3':3,4]pyrido[2,1-b]quinazolin-5(7H)-one
• Indolo(2',3':3,4)pyrido(2,1-b)quinazolin-5(7H)-one, 8,13-dihydro-
• 8,13-DIHYDROINDOLO(2',3':3,4)PYRIDO(2,1-B)QUINAZOLIN-5(7H)-ONE
• 3,13,21-triazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-1(21),2(10),4,6,8,15,17,19-octaen-14-one
• 3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-1(21),2(10),4,6,8,15,17,19-octaen-14-one
• SMR001230721
• SR-01000076104
• 8,13-dihydro-Indolo(2',3':3,4)pyrido(2,1-b)quinazolin-5(7H)-one
• Rutaecarpine,(S)
• RUTECARPINE [MI]
• Lopac-R-3277
• Rutaecarpine (Rutecarpine)
• UPCMLD-DP040
• Lopac0_001091
• Oprea1_313284
• cid_65752
• MLS002153304
• MLS006011796
• SCHEMBL288507
• Rutaecarpine, >98% (HPLC)
• UPCMLD-DP040:001
• DTXSID00232884
• ACVGWSKVRYFWRP-UHFFFAOYSA-N
• HMS2233M24
• HMS3263K04
• HMS3374B10
• HMS3656C09
• HMS3884P13
• BCP21309
• HY-N0147
• Tox21_501091
• BBL028393
• BDBM50131046
• NSC258317
• s2349
• STL146385
• AKOS005720935
• CCG-205168
• CS-6160
• GS-3618
• LP01091
• SDCCGSBI-0051061.P002
• SMP2_000103
• NCGC00015892-01
• NCGC00015892-02
• NCGC00015892-03
• NCGC00015892-04
• NCGC00015892-05
• NCGC00015892-06
• NCGC00015892-07
• NCGC00015892-08
• NCGC00015892-13
• NCGC00094364-01
• NCGC00094364-03
• NCGC00094364-04
• NCGC00261776-01
• 3,13,21-triazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-1(21),2(10),4(9),5,7,15(20),16,18-octaen-14-one
• AC-34838
• LS-83901
• NCI60_002069
• EU-0101091
• FT-0653229
• R0102
• SW220226-1
• C09238
• EN300-302963
• H10091
• R 3277
• A864154
• Q-100850
• SR-01000076104-2
• SR-01000076104-6
• Q15424771
• Z2768165384
• Indolo[2',4]pyrido[2,1-b]quinazolin-5(7H)-one, 8,13-dihydro-
• 8,13-Dihydro-7H-indolo[2'',3'':3,4]pyrido[2,1-b]quinazolin-5-one
• 6,7-[Imino(1,2-phenylene)]-8,9-dihydro-11H-pyrido[2,1-b]quinazoline-11-one
• InChI=1/C18H13N3O/c22-18-13-6-2-4-8-15(13)20-17-16-12(9-10-21(17)18)11-5-1-3-7-14(11)19-16/h1-8,19H,9-10H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9967	99.67%
Caco-2	+	0.9313	93.13%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7793	77.93%
OATP2B1 inhibitior	-	0.8581	85.81%
OATP1B1 inhibitior	+	0.9382	93.82%
OATP1B3 inhibitior	+	0.9447	94.47%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	+	0.5612	56.12%
BSEP inhibitior	+	0.8075	80.75%
P-glycoprotein inhibitior	-	0.7270	72.70%
P-glycoprotein substrate	-	0.9281	92.81%
CYP3A4 substrate	+	0.5336	53.36%
CYP2C9 substrate	-	0.6079	60.79%
CYP2D6 substrate	-	0.8386	83.86%
CYP3A4 inhibition	-	0.6501	65.01%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	+	0.9238	92.38%
CYP2C8 inhibition	-	0.6807	68.07%
CYP inhibitory promiscuity	+	0.6023	60.23%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6830	68.30%
Eye corrosion	-	0.9878	98.78%
Eye irritation	-	0.9613	96.13%
Skin irritation	-	0.8147	81.47%
Skin corrosion	-	0.9588	95.88%
Ames mutagenesis	+	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6409	64.09%
Micronuclear	+	0.7900	79.00%
Hepatotoxicity	+	0.8500	85.00%
skin sensitisation	-	0.9181	91.81%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	+	0.4902	49.02%
Acute Oral Toxicity (c)	II	0.6671	66.71%
Estrogen receptor binding	+	0.9063	90.63%
Androgen receptor binding	-	0.5256	52.56%
Thyroid receptor binding	+	0.7607	76.07%
Glucocorticoid receptor binding	+	0.6279	62.79%
Aromatase binding	+	0.7738	77.38%
PPAR gamma	+	0.7859	78.59%
Honey bee toxicity	-	0.9234	92.34%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6400	64.00%
Fish aquatic toxicity	-	0.7465	74.65%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	35481.3 nM; 28183.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293237	P54132	Bloom syndrome protein	19952.6 nM; 19952.6 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4096	P04637	Cellular tumor antigen p53	12589.3 nM; 12589.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL221	P23219	Cyclooxygenase-1	8700 nM; 8700 nM	IC50; IC50	PMID: 23146282; PMID: 16038536
CHEMBL230	P35354	Cyclooxygenase-2	280 nM; 300 nM	IC50; IC50	PMID: 23146282; PMID: 16038536
CHEMBL2231	P04798	Cytochrome P450 1A1	260 nM	IC50	PMID: 12852960
CHEMBL3356	P05177	Cytochrome P450 1A2	22 nM	IC50	PMID: 12852960
CHEMBL4878	Q16678	Cytochrome P450 1B1	55 nM; 55 nM	IC50; IC50	via Super-PRED; PMID: 12852960
CHEMBL340	P08684	Cytochrome P450 3A4	3981.1 nM; 3981.1 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL2392	P06746	DNA polymerase beta	44668.4 nM	Potency	via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	25118.9 nM; 25118.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	15848.9 nM; 15848.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	28183.8 nM	Potency	via CMAUP
CHEMBL1293277	O15118	Niemann-Pick C1 protein	2909.3 nM; 5623.4 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	707.9 nM; 707.9 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL1075189	P14618	Pyruvate kinase isozymes M1/M2	3162.3 nM; 3162.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293294	P51151	Ras-related protein Rab-9A	1778.3 nM; 2909.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	18492.7 nM	Potency	via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	7943.3 nM	Potency	via CMAUP
CHEMBL1293256	P40225	Thrombopoietin	316.2 nM; 316.2 nM; 316.2 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via Super-PRED
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	12589.3 nM; 12589.3 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.65%	95.56%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	94.51%	93.40%
CHEMBL2581	P07339	Cathepsin D	94.49%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	94.34%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.14%	85.14%
CHEMBL1951	P21397	Monoamine oxidase A	91.92%	91.49%
CHEMBL1781	P11387	DNA topoisomerase I	91.91%	97.00%
CHEMBL3310	Q96DB2	Histone deacetylase 11	91.90%	88.56%
CHEMBL4302	P08183	P-glycoprotein 1	89.81%	92.98%
CHEMBL255	P29275	Adenosine A2b receptor	87.28%	98.59%
CHEMBL5805	Q9NR97	Toll-like receptor 8	87.15%	96.25%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	86.62%	91.71%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	86.30%	92.67%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	86.16%	96.39%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.06%	94.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	85.93%	93.99%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	85.15%	96.47%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	84.16%	96.67%
CHEMBL5103	Q969S8	Histone deacetylase 10	83.14%	90.08%
CHEMBL1913	P09619	Platelet-derived growth factor receptor beta	82.45%	95.70%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	82.19%	97.64%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.14%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.65%	86.33%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	81.59%	94.62%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.57%	96.09%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	81.34%	98.46%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	80.40%	91.11%
CHEMBL2094121	P14867	GABA-A receptor; alpha-1/beta-3/gamma-2	80.31%	95.50%

Plants that contains it

• Aframomum daniellii
• Alchornea cordifolia
• Atalantia wightii
• Balanophora japonica
• Bouchardatia neurococca
• Corydalis persica
• Corynanthe pachyceras
• Cota tinctoria
• Cynoglossum amabile
• Glycosmis pseudoracemosa
• Hesperocyparis abramsiana
• Hortia brasiliana
• Hortia oreadica
• Hortia regia
• Iphiona grantioides
• Juniperus horizontalis
• Lathyrus tingitanus
• Millettia pachycarpa
• Phellodendron amurense
• Phellodendron chinense
• Plectranthus caninus
• Rauvolfia salicifolia
• Spiranthera odoratissima
• Strychnos spinosa
• Tetradium glabrifolium
• Tetradium ruticarpum
• Vincetoxicum indicum var. indicum
• Zanthoxylum dimorphophyllum
• Zanthoxylum integrifoliolum
• Zanthoxylum rhetsa
• Zanthoxylum wutaiense

Cross-Links

• PubChem: 65752
• NPASS: NPC21429
• ChEMBL: CHEMBL85139
• LOTUS: LTS0179404
• wikiData: Q15424771