Hydrastinine

Details

• Internal ID: 12e49bc5-0463-4178-871d-ad7b4ef65d95
• Taxonomy: Organoheterocyclic compounds > Tetrahydroisoquinolines
• IUPAC Name: 6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-ol
• SMILES (Canonical): CN1CCC2=CC3=C(C=C2C1O)OCO3
• SMILES (Isomeric): CN1CCC2=CC3=C(C=C2C1O)OCO3
• InChI: InChI=1S/C11H13NO3/c1-12-3-2-7-4-9-10(15-6-14-9)5-8(7)11(12)13/h4-5,11,13H,2-3,6H2,1H3
• InChI Key: YOJQZPVUNUQTDF-UHFFFAOYSA-N
• Popularity: 262 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₃NO₃
• Molecular Weight: 207.23 g/mol
• Exact Mass: 207.08954328 g/mol
• Topological Polar Surface Area (TPSA): 41.90 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 0.89
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 6592-85-4
• 6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-ol
• V1I0L48X6E
• NSC-755892
• DTXSID3048073
• 1,3-Dioxolo(4,5-g)isoquinolin-5-ol, 5,6,7,8-tetrahyro-6-methyl-
• 6-methyl-7,8-dihydro-5H-(1,3)dioxolo(4,5-g)isoquinolin-5-ol
• RefChem:414949
• DTXCID4028044
• 229-533-9
• Hydraztinine
• 5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-ol
• 5,6,7,8-Tetrahydro-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-ol
• 1,3-Dioxolo[4,5-g]isoquinolin-5-ol, 5,6,7,8-tetrahydro-6-methyl-
• 1,3-DIOXOLO(4,5-g)ISOQUINOLIN-5-OL, 5,6,7,8-TETRAHYDRO-6-METHYL-
• EINECS 229-533-9
• BRN 0014208
• UNII-V1I0L48X6E
• Hydrastinin
• Spectrum_000377
• 6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-ol
• Prestwick0_000195
• Prestwick1_000195
• Prestwick2_000195
• Spectrum2_000742
• Spectrum3_001149
• Spectrum4_001762
• Spectrum5_000343
• HYDRASTININE [MI]
• NCIOpen2_005877
• Oprea1_843481
• BSPBio_002677
• KBioGR_002243
• KBioSS_000857
• 4-27-00-06396 (Beilstein Handbook Reference)
• DivK1c_000897
• HYDRASTININE [WHO-DD]
• SCHEMBL308521
• SPBio_000724
• SPBio_002070
• orb1690372
• CHEMBL1623232
• HY-B1181A
• KBio1_000897
• KBio2_000857
• KBio2_003425
• KBio2_005993
• KBio3_002177
• YOJQZPVUNUQTDF-UHFFFAOYSA-
• CHEBI:233287
• NINDS_000897
• BDBM729096
• 1-hydroxy-6,7-methylenedioxy-2-methyl-1,2,3,4-tetrahydroisoquinoline
• MFCD00179051
• MSK181209
• AKOS040758263
• US12257253, Compound Hydrastinine
• NSC 755892
• IDI1_000897
• NCGC00178535-02
• DA-64312
• MS-23130
• SBI-0051895.P003
• SBI-0051895.P004
• CS-0108783
• NS00005375
• 1,3-DIOXOLO(4,5-G)ISOQUINOLIN-5-OL
• F82493
• AB00053699_03
• AB00053699_04
• Q905844
• BRD-A57900429-003-05-8
• BRD-A57900429-003-06-6
• 6-Methyl-5,6,7,8-tetrahydro-2H-[1,3]dioxolo[4,5-g]isoquinolin-5-ol
• 6-Methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-ol #
• InChI=1/C11H13NO3/c1-12-3-2-7-4-9-10(15-6-14-9)5-8(7)11(12)13/h4-5,11,13H,2-3,6H2,1H3

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9625	96.25%
Caco-2	+	0.8429	84.29%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.4014	40.14%
OATP2B1 inhibitior	-	0.8577	85.77%
OATP1B1 inhibitior	+	0.9507	95.07%
OATP1B3 inhibitior	+	0.9485	94.85%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.8169	81.69%
P-glycoprotein inhibitior	-	0.9774	97.74%
P-glycoprotein substrate	-	0.8773	87.73%
CYP3A4 substrate	-	0.5469	54.69%
CYP2C9 substrate	-	0.7907	79.07%
CYP2D6 substrate	+	0.3502	35.02%
CYP3A4 inhibition	-	0.7790	77.90%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	+	0.8933	89.33%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.9846	98.46%
CYP inhibitory promiscuity	-	0.8445	84.45%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6100	61.00%
Eye corrosion	-	0.9858	98.58%
Eye irritation	-	0.7029	70.29%
Skin irritation	-	0.7319	73.19%
Skin corrosion	-	0.9058	90.58%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7656	76.56%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.8513	85.13%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.7579	75.79%
Acute Oral Toxicity (c)	III	0.5660	56.60%
Estrogen receptor binding	-	0.8035	80.35%
Androgen receptor binding	-	0.6875	68.75%
Thyroid receptor binding	+	0.5279	52.79%
Glucocorticoid receptor binding	+	0.6612	66.12%
Aromatase binding	-	0.8582	85.82%
PPAR gamma	-	0.6395	63.95%
Honey bee toxicity	-	0.9277	92.77%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	-	0.5219	52.19%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	97.80%	96.77%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.65%	96.09%
CHEMBL2581	P07339	Cathepsin D	91.55%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	90.59%	83.82%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	88.55%	93.40%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.47%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.72%	85.14%
CHEMBL4208	P20618	Proteasome component C5	85.43%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.18%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.90%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.60%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.52%	89.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.51%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.24%	95.89%
CHEMBL2056	P21728	Dopamine D1 receptor	81.64%	91.00%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	81.45%	90.24%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.11%	92.62%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.17%	97.25%
CHEMBL261	P00915	Carbonic anhydrase I	80.13%	96.76%

Plants that contains it

• Chelidonium majus
• Dactylicapnos torulosa
• Hydrastis canadensis

Cross-Links

• PubChem: 3638
• LOTUS: LTS0215897
• wikiData: Q905844