Hortiacine

Details

• Internal ID: 3a6d9c0e-3ea7-4143-a3ac-841a1b699d35
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Pyridoindoles > Beta carbolines
• IUPAC Name: 7-methoxy-3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-1(21),2(10),4(9),5,7,15,17,19-octaen-14-one
• SMILES (Canonical): COC1=CC2=C(C=C1)NC3=C2CCN4C3=NC5=CC=CC=C5C4=O
• SMILES (Isomeric): COC1=CC2=C(C=C1)NC3=C2CCN4C3=NC5=CC=CC=C5C4=O
• InChI: InChI=1S/C19H15N3O2/c1-24-11-6-7-16-14(10-11)12-8-9-22-18(17(12)20-16)21-15-5-3-2-4-13(15)19(22)23/h2-7,10,20H,8-9H2,1H3
• InChI Key: JNHSRGXMKPJTEV-UHFFFAOYSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₅N₃O₂
• Molecular Weight: 317.30 g/mol
• Exact Mass: 317.116426730 g/mol
• Topological Polar Surface Area (TPSA): 57.70 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 3.11
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 10-Methoxylrutaecarpine
• CHEMBL85826
• MLS000076384
• SMR000013006
• SR-01000366081
• NSC660030
• Opera_ID_833
• Oprea1_495321
• cid_378227
• HMS1691I06
• HMS2328H18
• BDBM50131053
• AKOS024284576
• NSC-660030
• 10-Methoxy-8,13-dihydro-7H-indolo[2',3':3,4]pyrido[2,1-b]quinazolin-5-one
• NCI60_021077
• SR-01000366081-1
• SR-01000366081-3
• 10-Methoxy-8,13-dihydro-7H-indolo[2'',3'':3,4]pyrido[2,1-b]quinazolin-5-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9972	99.72%
Caco-2	+	0.8677	86.77%
Blood Brain Barrier	+	0.8879	88.79%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7942	79.42%
OATP2B1 inhibitior	-	0.8594	85.94%
OATP1B1 inhibitior	+	0.9254	92.54%
OATP1B3 inhibitior	+	0.9465	94.65%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	+	0.6428	64.28%
BSEP inhibitior	+	0.9310	93.10%
P-glycoprotein inhibitior	-	0.4703	47.03%
P-glycoprotein substrate	-	0.7895	78.95%
CYP3A4 substrate	+	0.6149	61.49%
CYP2C9 substrate	-	0.7813	78.13%
CYP2D6 substrate	-	0.8230	82.30%
CYP3A4 inhibition	+	0.6217	62.17%
CYP2C9 inhibition	-	0.6155	61.55%
CYP2C19 inhibition	-	0.6141	61.41%
CYP2D6 inhibition	-	0.7773	77.73%
CYP1A2 inhibition	+	0.9339	93.39%
CYP2C8 inhibition	-	0.5844	58.44%
CYP inhibitory promiscuity	+	0.7242	72.42%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6377	63.77%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9230	92.30%
Skin irritation	-	0.8259	82.59%
Skin corrosion	-	0.9569	95.69%
Ames mutagenesis	+	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4794	47.94%
Micronuclear	+	0.8100	81.00%
Hepatotoxicity	+	0.6698	66.98%
skin sensitisation	-	0.9229	92.29%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.6779	67.79%
Acute Oral Toxicity (c)	II	0.5811	58.11%
Estrogen receptor binding	+	0.9068	90.68%
Androgen receptor binding	+	0.6880	68.80%
Thyroid receptor binding	+	0.7223	72.23%
Glucocorticoid receptor binding	+	0.8566	85.66%
Aromatase binding	+	0.5982	59.82%
PPAR gamma	+	0.8158	81.58%
Honey bee toxicity	-	0.8966	89.66%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6900	69.00%
Fish aquatic toxicity	-	0.8463	84.63%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	14125.4 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	25118.9 nM	Potency	via CMAUP
CHEMBL4096	P04637	Cellular tumor antigen p53	10000 nM	Potency	via CMAUP
CHEMBL2231	P04798	Cytochrome P450 1A1	1780 nM	IC50	PMID: 12852960
CHEMBL3356	P05177	Cytochrome P450 1A2	2920 nM	IC50	PMID: 12852960
CHEMBL4878	Q16678	Cytochrome P450 1B1	84 nM; 84 nM	IC50; IC50	PMID: 12852960; via Super-PRED
CHEMBL206	P03372	Estrogen receptor alpha	17183.79 nM	IC50	via CMAUP
CHEMBL1293299	Q03164	Histone-lysine N-methyltransferase MLL	794.3 nM; 794.3 nM	Potency; Potency	via Super-PRED; via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	3548.1 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	1778.3 nM	Potency	via CMAUP
CHEMBL1293277	O15118	Niemann-Pick C1 protein	199.5 nM; 199.5 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL1293294	P51151	Ras-related protein Rab-9A	251.2 nM; 251.2 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL6101	P42224	Signal transducer and activator of transcription 1-alpha/beta	< 2.83 nM; 2.83 nM	EC50; EC50	via CMAUP; via Super-PRED
CHEMBL1293232	Q16637	Survival motor neuron protein	1584.9 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.05%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	98.88%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.71%	91.11%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	95.65%	92.67%
CHEMBL2581	P07339	Cathepsin D	95.37%	98.95%
CHEMBL3192	Q9BY41	Histone deacetylase 8	94.61%	93.99%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.61%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.55%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	93.57%	99.23%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	92.29%	96.47%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	92.21%	93.40%
CHEMBL2535	P11166	Glucose transporter	91.60%	98.75%
CHEMBL1951	P21397	Monoamine oxidase A	91.40%	91.49%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	91.39%	91.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.29%	86.33%
CHEMBL1781	P11387	DNA topoisomerase I	89.76%	97.00%
CHEMBL4302	P08183	P-glycoprotein 1	89.31%	92.98%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	88.93%	85.49%
CHEMBL4208	P20618	Proteasome component C5	88.44%	90.00%
CHEMBL1913	P09619	Platelet-derived growth factor receptor beta	87.42%	95.70%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.09%	97.36%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	85.06%	96.39%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	84.69%	96.67%
CHEMBL2056	P21728	Dopamine D1 receptor	84.60%	91.00%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	84.39%	96.00%
CHEMBL1907	P15144	Aminopeptidase N	84.12%	93.31%
CHEMBL255	P29275	Adenosine A2b receptor	83.80%	98.59%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.80%	99.15%

Plants that contains it

• Aframomum daniellii
• Alchornea cordifolia
• Atalantia wightii
• Balanophora japonica
• Corydalis persica
• Corynanthe pachyceras
• Cota tinctoria
• Cynoglossum amabile
• Glycosmis pseudoracemosa
• Hortia brasiliana
• Hortia longifolia
• Iphiona grantioides
• Juniperus horizontalis
• Lathyrus tingitanus
• Plectranthus caninus
• Rauvolfia salicifolia
• Strychnos spinosa
• Tetradium glabrifolium

Cross-Links

• PubChem: 378227
• NPASS: NPC157931
• ChEMBL: CHEMBL85826
• LOTUS: LTS0253130
• wikiData: Q104403647