Ancistrocladine

Details

• Internal ID: 421be59e-b22a-4010-ac97-82e1670d1eff
• Taxonomy: Organoheterocyclic compounds > Isoquinolines and derivatives > Naphthylisoquinolines
• IUPAC Name: (1S,3S)-5-(4,5-dimethoxy-2-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=CC=C(C4=C(C=C3C)OC)OC
• SMILES (Isomeric): C[C@H]1CC2=C(C(=CC(=C2[C@@H](N1)C)OC)O)C3=C4C=CC=C(C4=C(C=C3C)OC)OC
• InChI: InChI=1S/C25H29NO4/c1-13-10-20(29-5)25-16(8-7-9-19(25)28-4)22(13)24-17-11-14(2)26-15(3)23(17)21(30-6)12-18(24)27/h7-10,12,14-15,26-27H,11H2,1-6H3/t14-,15-/m0/s1
• InChI Key: XUFOYASAFNKRRE-GJZGRUSLSA-N
• Popularity: 3 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

• Hamatine
• Ancistrocladin
• (+)-Hamatine
• (-)-Ancistrocladine
• 32221-59-3
• 56688-90-5
• 5-(4,5-Dimethoxy-2-methyl-1-naphthalenyl)-1,2,3,4-tetrahydro-8-methoxy-1,3-dimethyl-6-isoquinolinol
• ( )-Hamatine
• (1s,3s)-5-(4,5-dimethoxy-2-methyl-1-naphthyl)-8-methoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-6-ol
• CHEBI:2707
• SCHEMBL3132504
• DTXSID60930490
• C09335
• Q27105775
• 1395-04-6
• 5-(4,5-dimethoxy-2-methylnaphthalen-1-yl)-8-methoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-6-ol
• 6-Isoquinolinol, 5-(4,5-dimethoxy-2-methyl-1-naphthalenyl)-1,2,3,4- tetrahydro-8-methoxy-1,3-dimethyl-, (1S,3S,5R)-
• 6-Isoquinolinol, 5-(4,5-dimethoxy-2-methyl-1-naphthalenyl)-1,2,3,4-tetrahydro-8-methoxy-1,3-dimethyl-, stereoisomer

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9825	98.25%
Caco-2	+	0.7392	73.92%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5721	57.21%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8869	88.69%
OATP1B3 inhibitior	+	0.9550	95.50%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8111	81.11%
BSEP inhibitior	+	0.8098	80.98%
P-glycoprotein inhibitior	+	0.6029	60.29%
P-glycoprotein substrate	+	0.5578	55.78%
CYP3A4 substrate	+	0.6525	65.25%
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	+	0.6695	66.95%
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	-	0.8368	83.68%
Skin irritation	-	0.8319	83.19%
Skin corrosion	-	0.9251	92.51%
Ames mutagenesis	+	0.6863	68.63%
Human Ether-a-go-go-Related Gene inhibition	+	0.7922	79.22%
Micronuclear	+	0.6100	61.00%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.9291	92.91%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.8337	83.37%
Acute Oral Toxicity (c)	III	0.4698	46.98%
Estrogen receptor binding	+	0.7254	72.54%
Androgen receptor binding	+	0.5294	52.94%
Thyroid receptor binding	+	0.7417	74.17%
Glucocorticoid receptor binding	+	0.7905	79.05%
Aromatase binding	-	0.5451	54.51%
PPAR gamma	+	0.6387	63.87%
Honey bee toxicity	-	0.8308	83.08%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.6500	65.00%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.05%	91.11%
CHEMBL2535	P11166	Glucose transporter	96.34%	98.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.09%	95.56%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	93.59%	91.79%
CHEMBL3192	Q9BY41	Histone deacetylase 8	93.51%	93.99%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.05%	96.09%
CHEMBL2581	P07339	Cathepsin D	92.31%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.19%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.44%	86.33%
CHEMBL1914	P06276	Butyrylcholinesterase	90.43%	95.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.11%	99.15%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.92%	95.89%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.89%	89.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.59%	94.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.22%	92.94%
CHEMBL4208	P20618	Proteasome component C5	87.56%	90.00%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	87.05%	94.03%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.21%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.77%	89.00%
CHEMBL1907	P15144	Aminopeptidase N	85.30%	93.31%
CHEMBL213	P08588	Beta-1 adrenergic receptor	84.09%	95.56%
CHEMBL4599	Q07912	Tyrosine kinase non-receptor protein 2	82.16%	94.29%
CHEMBL3492	P49721	Proteasome Macropain subunit	82.11%	90.24%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.74%	99.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.08%	99.17%
CHEMBL1937	Q92769	Histone deacetylase 2	81.02%	94.75%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.89%	97.14%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.86%	96.21%

Plants that contains it

• Ancistrocladus abbreviatus
• Ancistrocladus barteri
• Ancistrocladus benomensis
• Ancistrocladus congolensis
• Ancistrocladus griffithii
• Ancistrocladus heyneanus
• Ancistrocladus korupensis
• Ancistrocladus robertsoniorum
• Ancistrocladus tanzaniensis

Cross-Links

• PubChem: 161741
• NPASS: NPC141268
• LOTUS: LTS0196288
• wikiData: Q27105775