Dehydrocrebanine

Details

• Internal ID: a417263c-3ddf-40cf-962e-64b5e87c4009
• Taxonomy: Alkaloids and derivatives > Aporphines
• 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
• SMILES (Canonical): CN1CCC2=CC3=C(C4=C5C=CC(=C(C5=CC1=C24)OC)OC)OCO3
• SMILES (Isomeric): CN1CCC2=CC3=C(C4=C5C=CC(=C(C5=CC1=C24)OC)OC)OCO3
• InChI: InChI=1S/C20H19NO4/c1-21-7-6-11-8-16-20(25-10-24-16)18-12-4-5-15(22-2)19(23-3)13(12)9-14(21)17(11)18/h4-5,8-9H,6-7,10H2,1-3H3
• InChI Key: HCKFFNXOLCSPAI-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₉NO₄
• Molecular Weight: 337.40 g/mol
• Exact Mass: 337.13140809 g/mol
• Topological Polar Surface Area (TPSA): 40.20 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 3.73
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• 77784-22-6
• CCRIS 3812
• 6,7-Dihydro-9,10-dimethoxy-7-methyl-5H-benzo(g)-1,3-benzodioxolo(6,5,4-de)quinoline
• 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
• 5H-Benzo(g)-1,3-benzodioxolo(6,5,4-de)quinoline, 6,7-dihydro-9,10-dimethoxy-7-methyl-
• 6,7-Dihydro-9,10-dimethoxy-7-methyl-5H-benzo[g]-1,3-benzodioxolo[6,5,4-de]quinoline
• DTXSID60228400
• AKOS032948441
• LS-33657
• B2703-188596
• 15,16-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0^{2,6.0^{8,20.0^{14,19]icosa-1(19),2(6),7,12(20),13,15,17-heptaene

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9310	93.10%
Caco-2	+	0.9497	94.97%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Lysosomes	0.5126	51.26%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9518	95.18%
OATP1B3 inhibitior	+	0.9511	95.11%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.6370	63.70%
P-glycoprotein inhibitior	-	0.4915	49.15%
P-glycoprotein substrate	-	0.6160	61.60%
CYP3A4 substrate	+	0.5828	58.28%
CYP2C9 substrate	+	0.5824	58.24%
CYP2D6 substrate	+	0.5951	59.51%
CYP3A4 inhibition	+	0.7445	74.45%
CYP2C9 inhibition	+	0.5862	58.62%
CYP2C19 inhibition	+	0.8282	82.82%
CYP2D6 inhibition	+	0.7648	76.48%
CYP1A2 inhibition	-	0.5462	54.62%
CYP2C8 inhibition	-	0.6955	69.55%
CYP inhibitory promiscuity	+	0.5714	57.14%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5286	52.86%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.8867	88.67%
Skin irritation	-	0.7821	78.21%
Skin corrosion	-	0.9400	94.00%
Ames mutagenesis	+	0.9300	93.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7531	75.31%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.8629	86.29%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.8214	82.14%
Acute Oral Toxicity (c)	III	0.7455	74.55%
Estrogen receptor binding	+	0.8535	85.35%
Androgen receptor binding	+	0.6765	67.65%
Thyroid receptor binding	+	0.6319	63.19%
Glucocorticoid receptor binding	+	0.8674	86.74%
Aromatase binding	+	0.6429	64.29%
PPAR gamma	+	0.7523	75.23%
Honey bee toxicity	-	0.8400	84.00%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.7000	70.00%
Fish aquatic toxicity	+	0.8427	84.27%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	97.32%	83.82%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	96.64%	96.77%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.29%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.29%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.98%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.26%	94.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.06%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.76%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.72%	89.00%
CHEMBL2581	P07339	Cathepsin D	88.84%	98.95%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	87.94%	82.67%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	87.89%	89.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.36%	95.89%
CHEMBL4208	P20618	Proteasome component C5	87.31%	90.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.71%	92.62%
CHEMBL1951	P21397	Monoamine oxidase A	86.07%	91.49%
CHEMBL5747	Q92793	CREB-binding protein	85.88%	95.12%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	85.08%	93.65%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	83.91%	90.95%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	83.39%	82.38%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	83.16%	95.78%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	82.90%	80.96%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	82.61%	100.00%
CHEMBL2056	P21728	Dopamine D1 receptor	82.48%	91.00%
CHEMBL2535	P11166	Glucose transporter	82.03%	98.75%

Plants that contains it

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

Cross-Links

• PubChem: 149600
• NPASS: NPC255419
• LOTUS: LTS0042341
• wikiData: Q72461845