2-Hydroxy-1,5-dimethoxydibenzo[cd,f]indol-4(5H)-one

Details

• Internal ID: 954ccf34-0cad-466c-b748-4e48e351bbef
• Taxonomy: Alkaloids and derivatives > Aristolactams
• IUPAC Name: 14-hydroxy-10,15-dimethoxy-10-azatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),2,4,6,8,12,14-heptaen-11-one
• SMILES (Canonical): COC1=C(C=C2C3=C1C4=CC=CC=C4C=C3N(C2=O)OC)O
• SMILES (Isomeric): COC1=C(C=C2C3=C1C4=CC=CC=C4C=C3N(C2=O)OC)O
• InChI: InChI=1S/C17H13NO4/c1-21-16-13(19)8-11-14-12(18(22-2)17(11)20)7-9-5-3-4-6-10(9)15(14)16/h3-8,19H,1-2H3
• InChI Key: LHSDJNRAZBFFLF-UHFFFAOYSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₃NO₄
• Molecular Weight: 295.29 g/mol
• Exact Mass: 295.08445790 g/mol
• Topological Polar Surface Area (TPSA): 59.00 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 3.23
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 2-Hydroxy-1,5-dimethoxydibenzo[cd,f]indol-4(5H)-one
• CHEMBL497039
• CHEBI:132657
• LHSDJNRAZBFFLF-UHFFFAOYSA-N
• DTXSID901189446
• HY-N10664
• CS-0633869
• 2-Hydroxy-1,5-dimethoxydibenzo[cd,f]indol-4(5H)-one #
• Dibenz[cd,f]indol-4(5H)-one, 2-hydroxy-1,5-dimethoxy-, (-)-
• Naphto[3,2,1-c,d]isoindol-4(5H)-one, 2-hydroxy-1,5-dimethoxy-
• 14-hydroxy-10,15-dimethoxy-10-azatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),2,4,6,8,12,14-heptaen-11-one
• 188546-49-8

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9837	98.37%
Caco-2	+	0.8203	82.03%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.5365	53.65%
OATP2B1 inhibitior	-	0.8558	85.58%
OATP1B1 inhibitior	+	0.8987	89.87%
OATP1B3 inhibitior	+	0.9441	94.41%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.5478	54.78%
P-glycoprotein inhibitior	-	0.7458	74.58%
P-glycoprotein substrate	-	0.9285	92.85%
CYP3A4 substrate	+	0.5705	57.05%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8171	81.71%
CYP3A4 inhibition	-	0.8372	83.72%
CYP2C9 inhibition	-	0.6959	69.59%
CYP2C19 inhibition	-	0.7558	75.58%
CYP2D6 inhibition	-	0.9078	90.78%
CYP1A2 inhibition	+	0.7176	71.76%
CYP2C8 inhibition	-	0.6508	65.08%
CYP inhibitory promiscuity	+	0.5635	56.35%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7715	77.15%
Carcinogenicity (trinary)	Non-required	0.4125	41.25%
Eye corrosion	-	0.9847	98.47%
Eye irritation	-	0.5058	50.58%
Skin irritation	-	0.8026	80.26%
Skin corrosion	-	0.9532	95.32%
Ames mutagenesis	+	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6071	60.71%
Micronuclear	+	0.8459	84.59%
Hepatotoxicity	+	0.5837	58.37%
skin sensitisation	-	0.8891	88.91%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	-	0.5299	52.99%
Nephrotoxicity	-	0.6262	62.62%
Acute Oral Toxicity (c)	III	0.5310	53.10%
Estrogen receptor binding	+	0.8001	80.01%
Androgen receptor binding	-	0.4841	48.41%
Thyroid receptor binding	+	0.5656	56.56%
Glucocorticoid receptor binding	+	0.8975	89.75%
Aromatase binding	+	0.8276	82.76%
PPAR gamma	+	0.7518	75.18%
Honey bee toxicity	-	0.9320	93.20%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6400	64.00%
Fish aquatic toxicity	+	0.9085	90.85%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.36%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.70%	95.56%
CHEMBL2581	P07339	Cathepsin D	93.87%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.15%	94.00%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	91.16%	80.78%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.74%	99.15%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.89%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.99%	86.33%
CHEMBL2535	P11166	Glucose transporter	88.92%	98.75%
CHEMBL3192	Q9BY41	Histone deacetylase 8	88.77%	93.99%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.98%	96.09%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	85.05%	92.67%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	83.99%	96.67%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.78%	99.17%
CHEMBL4208	P20618	Proteasome component C5	81.64%	90.00%
CHEMBL1907	P15144	Aminopeptidase N	81.23%	93.31%
CHEMBL240	Q12809	HERG	80.81%	89.76%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.12%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	80.04%	94.73%

Plants that contains it

• Castilleja sulphurea
• Dioscorea villosa
• Forsythia japonica
• Gymnosporia pyria
• Huperzia miyoshiana
• Lindera aggregata
• Piper kadsura
• Piper puberulum
• Pseudobrickellia brasiliensis
• Rhododendron latoucheae

Cross-Links

• PubChem: 622222
• NPASS: NPC90185
• ChEMBL: CHEMBL497039
• LOTUS: LTS0276372
• wikiData: Q105151918