1-[Hydroxy(4-hydroxyphenyl)methyl]-6-methoxyisoquinolin-7-ol

Details

• Internal ID: b91a76b2-56c9-4e04-abd9-ddff7a7bb6ed
• Taxonomy: Organoheterocyclic compounds > Isoquinolines and derivatives > Benzylisoquinolines
• IUPAC Name: 1-[(S)-hydroxy-(4-hydroxyphenyl)methyl]-6-methoxyisoquinolin-7-ol
• SMILES (Canonical): COC1=C(C=C2C(=C1)C=CN=C2C(C3=CC=C(C=C3)O)O)O
• SMILES (Isomeric): COC1=C(C=C2C(=C1)C=CN=C2[C@H](C3=CC=C(C=C3)O)O)O
• InChI: InChI=1S/C17H15NO4/c1-22-15-8-11-6-7-18-16(13(11)9-14(15)20)17(21)10-2-4-12(19)5-3-10/h2-9,17,19-21H,1H3/t17-/m0/s1
• InChI Key: XWZBLZPLPZOXQV-KRWDZBQOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₅NO₄
• Molecular Weight: 297.30 g/mol
• Exact Mass: 297.10010796 g/mol
• Topological Polar Surface Area (TPSA): 82.80 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.74
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• 1-[hydroxy(4-hydroxyphenyl)methyl]-6-methoxyisoquinolin-7-ol
• 1(S)-hydroxy-p-hydroxybenzyl-6-methoxy-7-hydroxyisoquinoline
• 1-[Hydroxy-(4-hydroxy-phenyl)-methyl]-6-methoxy-isoquinolin-7-ol
• 1-isoquinolinemethanol, 7-hydroxy-alpha-(4-hydroxyphenyl)-6-methoxy-, (alphaS)-
• InChI=1/C17H15NO4/c1-22-15-8-11-6-7-18-16(13(11)9-14(15)20)17(21)10-2-4-12(19)5-3-10/h2-9,17,19-21H,1H3/t17-/m0/s

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9797	97.97%
Caco-2	-	0.6402	64.02%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.4776	47.76%
OATP2B1 inhibitior	-	0.5733	57.33%
OATP1B1 inhibitior	+	0.9093	90.93%
OATP1B3 inhibitior	+	0.9768	97.68%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.6837	68.37%
P-glycoprotein inhibitior	-	0.8369	83.69%
P-glycoprotein substrate	-	0.5304	53.04%
CYP3A4 substrate	-	0.5176	51.76%
CYP2C9 substrate	-	0.8001	80.01%
CYP2D6 substrate	+	0.3908	39.08%
CYP3A4 inhibition	-	0.7219	72.19%
CYP2C9 inhibition	-	0.6995	69.95%
CYP2C19 inhibition	+	0.5148	51.48%
CYP2D6 inhibition	-	0.6133	61.33%
CYP1A2 inhibition	+	0.6861	68.61%
CYP2C8 inhibition	+	0.7447	74.47%
CYP inhibitory promiscuity	+	0.6188	61.88%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9510	95.10%
Carcinogenicity (trinary)	Non-required	0.6323	63.23%
Eye corrosion	-	0.9933	99.33%
Eye irritation	-	0.6906	69.06%
Skin irritation	-	0.7606	76.06%
Skin corrosion	-	0.9645	96.45%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6876	68.76%
Micronuclear	+	0.7300	73.00%
Hepatotoxicity	-	0.5646	56.46%
skin sensitisation	-	0.9245	92.45%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	-	0.7364	73.64%
Acute Oral Toxicity (c)	III	0.6857	68.57%
Estrogen receptor binding	+	0.6746	67.46%
Androgen receptor binding	+	0.6336	63.36%
Thyroid receptor binding	+	0.7512	75.12%
Glucocorticoid receptor binding	+	0.8141	81.41%
Aromatase binding	+	0.8675	86.75%
PPAR gamma	+	0.7194	71.94%
Honey bee toxicity	-	0.8779	87.79%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	-	0.7157	71.57%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.51%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.62%	91.11%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	96.87%	93.10%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.89%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.72%	99.15%
CHEMBL2535	P11166	Glucose transporter	93.33%	98.75%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	93.29%	89.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.92%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.63%	99.17%
CHEMBL5747	Q92793	CREB-binding protein	89.92%	95.12%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.18%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.74%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	88.63%	91.49%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	86.55%	100.00%
CHEMBL4208	P20618	Proteasome component C5	86.50%	90.00%
CHEMBL2581	P07339	Cathepsin D	85.67%	98.95%
CHEMBL5014	O43353	Serine/threonine-protein kinase RIPK2	83.02%	86.79%
CHEMBL1937	Q92769	Histone deacetylase 2	81.32%	94.75%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	81.32%	85.49%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	81.11%	94.03%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.10%	89.00%

Plants that contains it

• Alstonia angustiloba
• Amphiachyris dracunculoides
• Annona cherimola
• Baccharis grandicapitulata
• Beesia calthifolia
• Boschniakia rossica
• Botrychium ternatum
• Bursera kerberi
• Clerodendrum trichotomum
• Clinacanthus nutans
• Crotalaria stolzii
• Curcuma aeruginosa
• Delphinium giraldii
• Eucalyptus albens
• Euonymus fortunei
• Euploca racemosa
• Hedysarum gmelinii
• Helenium integrifolium
• Juniperus scopulorum
• Lasianthaea podocephala
• Lupinus cosentinii
• Melampodium leucanthum
• Myrica pensylvanica
• Neopallasia pectinata
• Papaver pseudocanescens
• Pellacalyx axillaris
• Peperomia filiformis
• Phlomis crinita
• Psidium acutangulum
• Pyrolirion flavum
• Renealmia alpinia
• Rhododendron mucronulatum
• Seseli libanotis
• Sideritis dasygnaphala
• Stellaria media
• Tephroseris kirilowii
• Tephroseris palustris

Cross-Links

• PubChem: 637078
• NPASS: NPC14818
• LOTUS: LTS0093016
• wikiData: Q105343885