4,5-Dioxodehydrocrebanine

Details

• Internal ID: ab647b3d-244e-49a2-b164-1f3adf294e35
• Taxonomy: Alkaloids and derivatives > Aporphines > 4,5-dioxoaporphines
• IUPAC Name: 15,16-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(19),2(6),7,12(20),13,15,17-heptaene-9,10-dione
• SMILES (Canonical): CN1C2=C3C(=CC4=C(C3=C5C=CC(=C(C5=C2)OC)OC)OCO4)C(=O)C1=O
• SMILES (Isomeric): CN1C2=C3C(=CC4=C(C3=C5C=CC(=C(C5=C2)OC)OC)OCO4)C(=O)C1=O
• InChI: InChI=1S/C20H15NO6/c1-21-12-6-10-9(4-5-13(24-2)18(10)25-3)16-15(12)11(17(22)20(21)23)7-14-19(16)27-8-26-14/h4-7H,8H2,1-3H3
• InChI Key: TVMABCBARSLKAA-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₅NO₆
• Molecular Weight: 365.30 g/mol
• Exact Mass: 365.08993720 g/mol
• Topological Polar Surface Area (TPSA): 74.30 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 2.90
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• CCRIS 3816
• 5H-Benzo(g)-1,3-benzodioxolo(6,5,4-de)quinoline-5,6(7H)-dione, 9,10-dimethoxy-7-methyl-
• 77784-21-5
• 9,10-Dimethoxy-7-methyl-5H-benzo(g)-1,3-benzodioxolo(6,5,4-de)quinoline-5,6(7H)-dione
• DTXSID10228399
• LS-33658

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8597	85.97%
Caco-2	+	0.8759	87.59%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.3397	33.97%
OATP2B1 inhibitior	-	0.8650	86.50%
OATP1B1 inhibitior	+	0.9501	95.01%
OATP1B3 inhibitior	+	0.9429	94.29%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9848	98.48%
BSEP inhibitior	+	0.6576	65.76%
P-glycoprotein inhibitior	+	0.5771	57.71%
P-glycoprotein substrate	-	0.7203	72.03%
CYP3A4 substrate	+	0.5973	59.73%
CYP2C9 substrate	-	0.7980	79.80%
CYP2D6 substrate	-	0.8632	86.32%
CYP3A4 inhibition	+	0.5300	53.00%
CYP2C9 inhibition	+	0.6112	61.12%
CYP2C19 inhibition	+	0.5824	58.24%
CYP2D6 inhibition	-	0.8975	89.75%
CYP1A2 inhibition	+	0.7519	75.19%
CYP2C8 inhibition	-	0.7050	70.50%
CYP inhibitory promiscuity	+	0.7711	77.11%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5089	50.89%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.8295	82.95%
Skin irritation	-	0.8246	82.46%
Skin corrosion	-	0.9509	95.09%
Ames mutagenesis	+	0.9000	90.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4029	40.29%
Micronuclear	+	0.7700	77.00%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.8911	89.11%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.5914	59.14%
Acute Oral Toxicity (c)	III	0.7425	74.25%
Estrogen receptor binding	+	0.8926	89.26%
Androgen receptor binding	+	0.6273	62.73%
Thyroid receptor binding	+	0.5706	57.06%
Glucocorticoid receptor binding	+	0.8606	86.06%
Aromatase binding	+	0.5414	54.14%
PPAR gamma	+	0.6908	69.08%
Honey bee toxicity	-	0.7909	79.09%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.8842	88.42%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	99.36%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.75%	95.56%
CHEMBL2581	P07339	Cathepsin D	95.80%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.90%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.43%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.78%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.28%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.01%	96.09%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	87.61%	95.53%
CHEMBL3192	Q9BY41	Histone deacetylase 8	87.25%	93.99%
CHEMBL214	P08908	Serotonin 1a (5-HT1a) receptor	86.94%	92.83%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	86.23%	96.67%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.21%	96.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	86.20%	93.40%
CHEMBL1951	P21397	Monoamine oxidase A	86.00%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.77%	91.11%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	85.46%	82.67%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	85.33%	89.62%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	84.01%	80.78%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.15%	95.89%
CHEMBL4208	P20618	Proteasome component C5	82.93%	90.00%
CHEMBL2535	P11166	Glucose transporter	82.92%	98.75%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.71%	92.62%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	82.57%	92.38%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	82.40%	97.31%
CHEMBL4040	P28482	MAP kinase ERK2	82.19%	83.82%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	81.92%	90.95%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	81.61%	80.96%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.61%	97.14%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	80.21%	100.00%

Plants that contains it

• Ardisia crispa
• Doronicum grandiflorum
• Leibnitzia anandria
• Lithocarpus haipinii
• Oxytropis lanata
• Populus balsamifera
• Sphaerophysa salsula
• Strychnos gossweileri

Cross-Links

• PubChem: 149599
• NPASS: NPC217280
• LOTUS: LTS0119145
• wikiData: Q83108390