Ancistrobrevine B

Details

• Internal ID: 5db74c21-04b7-4b45-aacc-421eb1078150
• Taxonomy: Organoheterocyclic compounds > Isoquinolines and derivatives > Naphthylisoquinolines
• IUPAC Name: (1S,3S)-5-(4,5-dimethoxy-7-methylnaphthalen-1-yl)-8-methoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-6-ol
• SMILES (Canonical): CC1CC2=C(C(=CC(=C2C(N1)C)OC)O)C3=C4C=C(C=C(C4=C(C=C3)OC)OC)C
• SMILES (Isomeric): C[C@H]1CC2=C(C(=CC(=C2[C@@H](N1)C)OC)O)C3=C4C=C(C=C(C4=C(C=C3)OC)OC)C
• InChI: InChI=1S/C25H29NO4/c1-13-9-17-16(7-8-20(28-4)25(17)21(10-13)29-5)24-18-11-14(2)26-15(3)23(18)22(30-6)12-19(24)27/h7-10,12,14-15,26-27H,11H2,1-6H3/t14-,15-/m0/s1
• InChI Key: XVHCBOXBWSMNHG-GJZGRUSLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₉NO₄
• Molecular Weight: 407.50 g/mol
• Exact Mass: 407.20965841 g/mol
• Topological Polar Surface Area (TPSA): 60.00 Ų
• XlogP: 5.00
• Atomic LogP (AlogP): 5.14
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• (-)-Ancistrobrevine B
• 146471-74-1
• 6-Isoquinolinol, 5-(4,5-dimethoxy-7-methyl-1-naphthalenyl)-1,2,3,4-tetrahydro-8-methoxy-1,3-dimethyl-, (1S,3S,5R)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9825	98.25%
Caco-2	+	0.7868	78.68%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5721	57.21%
OATP2B1 inhibitior	-	0.8665	86.65%
OATP1B1 inhibitior	+	0.8581	85.81%
OATP1B3 inhibitior	+	0.9550	95.50%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8111	81.11%
BSEP inhibitior	+	0.9358	93.58%
P-glycoprotein inhibitior	+	0.6624	66.24%
P-glycoprotein substrate	+	0.5432	54.32%
CYP3A4 substrate	+	0.6290	62.90%
CYP2C9 substrate	-	0.7713	77.13%
CYP2D6 substrate	+	0.7329	73.29%
CYP3A4 inhibition	-	0.6938	69.38%
CYP2C9 inhibition	-	0.5740	57.40%
CYP2C19 inhibition	-	0.5216	52.16%
CYP2D6 inhibition	+	0.5702	57.02%
CYP1A2 inhibition	-	0.6798	67.98%
CYP2C8 inhibition	+	0.7133	71.33%
CYP inhibitory promiscuity	+	0.5484	54.84%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.5439	54.39%
Eye corrosion	-	0.9934	99.34%
Eye irritation	-	0.8392	83.92%
Skin irritation	-	0.8319	83.19%
Skin corrosion	-	0.9251	92.51%
Ames mutagenesis	+	0.5963	59.63%
Human Ether-a-go-go-Related Gene inhibition	+	0.7850	78.50%
Micronuclear	+	0.6100	61.00%
Hepatotoxicity	-	0.5686	56.86%
skin sensitisation	-	0.9291	92.91%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.8123	81.23%
Acute Oral Toxicity (c)	III	0.4698	46.98%
Estrogen receptor binding	+	0.8016	80.16%
Androgen receptor binding	+	0.6464	64.64%
Thyroid receptor binding	+	0.7352	73.52%
Glucocorticoid receptor binding	+	0.7775	77.75%
Aromatase binding	-	0.4916	49.16%
PPAR gamma	+	0.6178	61.78%
Honey bee toxicity	-	0.7925	79.25%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	+	0.6835	68.35%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	98.73%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.56%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.80%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	94.71%	92.94%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	94.24%	91.79%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.48%	95.56%
CHEMBL2535	P11166	Glucose transporter	93.37%	98.75%
CHEMBL2581	P07339	Cathepsin D	93.28%	98.95%
CHEMBL4208	P20618	Proteasome component C5	89.93%	90.00%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	89.51%	97.31%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.35%	95.89%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	88.76%	89.62%
CHEMBL213	P08588	Beta-1 adrenergic receptor	88.35%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.31%	89.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	87.60%	96.21%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.25%	94.00%
CHEMBL5747	Q92793	CREB-binding protein	86.94%	95.12%
CHEMBL3492	P49721	Proteasome Macropain subunit	86.92%	90.24%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.38%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.60%	94.45%
CHEMBL3438	Q05513	Protein kinase C zeta	84.30%	88.48%
CHEMBL3192	Q9BY41	Histone deacetylase 8	83.51%	93.99%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.88%	93.03%
CHEMBL2243	O00519	Anandamide amidohydrolase	82.61%	97.53%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.35%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.77%	99.15%
CHEMBL1937	Q92769	Histone deacetylase 2	81.62%	94.75%
CHEMBL2056	P21728	Dopamine D1 receptor	81.57%	91.00%
CHEMBL4630	O14757	Serine/threonine-protein kinase Chk1	81.33%	97.03%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	80.51%	96.67%

Plants that contains it

• Ancistrocladus abbreviatus
• Ancistrocladus robertsoniorum

Cross-Links

• PubChem: 11015040
• LOTUS: LTS0028193
• wikiData: Q105342879