Hydrocotarnine

Details

• Internal ID: e2f1b71e-f3da-419e-a76d-f6cfa8b3ae6f
• Taxonomy: Organoheterocyclic compounds > Tetrahydroisoquinolines
• IUPAC Name: 4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline
• SMILES (Canonical): CN1CCC2=CC3=C(C(=C2C1)OC)OCO3
• SMILES (Isomeric): CN1CCC2=CC3=C(C(=C2C1)OC)OCO3
• InChI: InChI=1S/C12H15NO3/c1-13-4-3-8-5-10-12(16-7-15-10)11(14-2)9(8)6-13/h5H,3-4,6-7H2,1-2H3
• InChI Key: XXANNZJIZQTCBP-UHFFFAOYSA-N
• Popularity: 46 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₅NO₃
• Molecular Weight: 221.25 g/mol
• Exact Mass: 221.10519334 g/mol
• Topological Polar Surface Area (TPSA): 30.90 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.41
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• 550-10-7
• Hydrocotarnin
• 4-methoxy-6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinoline
• 4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline
• 4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline
• UNII-G22L6JNE61
• 4-Methoxy-6-methyl-5,6,7,8-tetrahydro-1,3-dioxolo(4,5-g)isoquinoline
• G22L6JNE61
• hydrocotarnine hydrochloride
• EINECS 208-978-2
• 1,3-DIOXOLO(4,5-g)ISOQUINOLINE, 5,6,7,8-TETRAHYDRO-4-METHOXY-6-METHYL-
• MFCD00868501
• BRN 0017283
• 5,6,7,8-Tetrahydro-4-methoxy-6-methyl-1,3-dioxolo(4,5-g)isoquinoline
• 4-27-00-06395 (Beilstein Handbook Reference)
• 8-methoxy-5,6-methylenedioxy-2-methyl-1,2,3,4-tetrahydroisoquinoline
• 1,3-Dioxolo[4,5-g]isoquinoline, 5,6,7,8-tetrahydro-4-methoxy-6-methyl-
• NCGC00016666-01
• CAS-5985-00-2
• 4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinoline
• 5,6,7,8-Tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinoline
• Spectrum_000366
• SpecPlus_000929
• Prestwick0_000605
• Prestwick1_000605
• Prestwick2_000605
• Prestwick3_000605
• Spectrum2_001393
• Spectrum3_001433
• Spectrum4_001851
• Spectrum5_000382
• HYDROCOTARNINE [MI]
• BSPBio_000510
• BSPBio_002504
• BSPBio_003166
• KBioGR_002283
• KBioSS_000846
• DivK1c_007025
• SCHEMBL680035
• SPBio_001406
• SPBio_002729
• BPBio1_000562
• HYDROCOTARNINE [WHO-DD]
• CHEMBL1606295
• CHEBI:92664
• KBio1_001969
• KBio2_000846
• KBio2_003414
• KBio2_005982
• KBio3_002386
• DTXSID60203535
• Hydrocotarnine hydrochloride (JP15)
• BBL029075
• STK802005
• AKOS005068108
• HY-W176629
• SDCCGMLS-0066725.P001
• NCGC00016666-02
• NCGC00016666-03
• NCGC00016666-04
• VS-09097
• AB00053339
• CS-0237743
• EN300-186673
• BRD-K37447567-001-01-8
• BRD-K37447567-004-05-3
• Q27164371
• Z1824565757
• 1,2,3,4-Tetrahydro-8-methoxy-2-methyl-6,7-methylenedioxyisoquinoline
• 8-methoxy-2-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline
• 1,2,3,4-Tetrahydro-8-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinoline, 9CI

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9628	96.28%
Caco-2	+	0.9184	91.84%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Lysosomes	0.6124	61.24%
OATP2B1 inhibitior	-	0.8511	85.11%
OATP1B1 inhibitior	+	0.9619	96.19%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	-	0.8477	84.77%
P-glycoprotein inhibitior	-	0.9670	96.70%
P-glycoprotein substrate	-	0.8480	84.80%
CYP3A4 substrate	-	0.5296	52.96%
CYP2C9 substrate	-	0.6129	61.29%
CYP2D6 substrate	+	0.7342	73.42%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9298	92.98%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	+	0.8932	89.32%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	-	0.9468	94.68%
CYP inhibitory promiscuity	-	0.6263	62.63%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6152	61.52%
Eye corrosion	-	0.9848	98.48%
Eye irritation	-	0.7104	71.04%
Skin irritation	-	0.7915	79.15%
Skin corrosion	-	0.9350	93.50%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5530	55.30%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	-	0.5466	54.66%
skin sensitisation	-	0.8307	83.07%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.7737	77.37%
Acute Oral Toxicity (c)	III	0.6330	63.30%
Estrogen receptor binding	-	0.8682	86.82%
Androgen receptor binding	-	0.6209	62.09%
Thyroid receptor binding	-	0.5896	58.96%
Glucocorticoid receptor binding	-	0.6547	65.47%
Aromatase binding	-	0.7649	76.49%
PPAR gamma	-	0.7785	77.85%
Honey bee toxicity	-	0.9016	90.16%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.7875	78.75%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3356	P05177	Cytochrome P450 1A2	1995.26 nM	AC50	via CMAUP
CHEMBL289	P10635	Cytochrome P450 2D6	3981.07 nM	AC50	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	98.73%	96.77%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	98.16%	93.40%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.60%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.41%	91.11%
CHEMBL2056	P21728	Dopamine D1 receptor	90.89%	91.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.84%	94.45%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	89.82%	80.96%
CHEMBL4208	P20618	Proteasome component C5	89.13%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.27%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.86%	95.56%
CHEMBL3192	Q9BY41	Histone deacetylase 8	87.59%	93.99%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	85.61%	82.38%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.36%	85.14%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	84.62%	93.65%
CHEMBL2581	P07339	Cathepsin D	84.42%	98.95%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	83.91%	82.67%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.79%	94.00%
CHEMBL2535	P11166	Glucose transporter	83.37%	98.75%
CHEMBL1841	P06241	Tyrosine-protein kinase FYN	83.07%	81.29%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	81.47%	90.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.42%	95.89%
CHEMBL5747	Q92793	CREB-binding protein	80.10%	95.12%

Plants that contains it

• Aloe microstigma
• Aquilaria malaccensis
• Chrozophora plicata
• Corydalis ophiocarpa
• Papaver somniferum

Cross-Links

• PubChem: 3646
• NPASS: NPC59907
• ChEMBL: CHEMBL1606295
• LOTUS: LTS0039161
• wikiData: Q27164371