Tetrahydropapaveroline

Details

• Internal ID: 6c67cc64-3d2d-4ff1-a84e-ee878dd50e08
• Taxonomy: Organoheterocyclic compounds > Isoquinolines and derivatives > Benzylisoquinolines
• IUPAC Name: 1-[(3,4-dihydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol
• SMILES (Canonical): C1CNC(C2=CC(=C(C=C21)O)O)CC3=CC(=C(C=C3)O)O
• SMILES (Isomeric): C1CNC(C2=CC(=C(C=C21)O)O)CC3=CC(=C(C=C3)O)O
• InChI: InChI=1S/C16H17NO4/c18-13-2-1-9(6-14(13)19)5-12-11-8-16(21)15(20)7-10(11)3-4-17-12/h1-2,6-8,12,17-21H,3-5H2
• InChI Key: ABXZOXDTHTTZJW-UHFFFAOYSA-N
• Popularity: 156 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₇NO₄
• Molecular Weight: 287.31 g/mol
• Exact Mass: 287.11575802 g/mol
• Topological Polar Surface Area (TPSA): 93.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.94
• H-Bond Acceptor: 5
• H-Bond Donor: 5
• Rotatable Bonds: 2

Synonyms

• Norlaudanosoline
• 4747-99-3
• Tetrahydroxypapaveroline
• V1EWJ6B8KY
• DTXSID70963850
• 6,7-Isoquinolinediol, 1-((3,4-dihydroxyphenyl)methyl)-1,2,3,4-tetrahydro-
• CHEBI:28770
• RefChem:932811
• DTXCID801391579
• (R,S)-Norlaudanosoline
• 1-[(3,4-dihydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol
• 1-(3,4-dihydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol
• (RS)-NORLAUDANOSOLINE
• (+/-)-tetrahydropapaveroline
• CHEMBL19068
• (+/-)-NORLAUDANOSOLINE
• 1-[(3,4-Dihydroxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-isoquinolinediol
• UNII-V1EWJ6B8KY
• Norlaudanosolin
• 1-((3,4-DIHYDROXYPHENYL)METHYL)-1,2,3,4-TETRAHYDRO-6,7-ISOQUINOLINEDIOL
• ABXZOXDTHTTZJW-UHFFFAOYSA-N
• Oprea1_179526
• SCHEMBL221137
• SCHEMBL8818807
• SCHEMBL29375567
• Norlaudanosoline Hydrobromide Salt
• TETRAHYDROPAPAVEROLINE [MI]
• BDBM50027331
• STL565699
• Papaveroline, 1,2,3,4-tetrahydro-
• AKOS037623582
• EBC-145215
• TETRAHYDROPAPAVEROLINE, (+/-)-
• C06350
• Q27103884
• Z2752228094
• 1-(3,4-Dihydroxybenzyl)-1,2,3,4-tetrahydro-6,7-isoquinolinediol #
• 6,7-dihydroxy-1-(3',4'-dihydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline
• 1-[(3,4-dihydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol hydrobromide (JW8-5)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9248	92.48%
Caco-2	-	0.7411	74.11%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5352	53.52%
OATP2B1 inhibitior	-	0.5684	56.84%
OATP1B1 inhibitior	+	0.9522	95.22%
OATP1B3 inhibitior	+	0.9569	95.69%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.8464	84.64%
P-glycoprotein inhibitior	-	0.9582	95.82%
P-glycoprotein substrate	-	0.6988	69.88%
CYP3A4 substrate	-	0.5436	54.36%
CYP2C9 substrate	-	0.8209	82.09%
CYP2D6 substrate	+	0.6622	66.22%
CYP3A4 inhibition	-	0.9496	94.96%
CYP2C9 inhibition	-	0.9317	93.17%
CYP2C19 inhibition	-	0.9174	91.74%
CYP2D6 inhibition	+	0.6325	63.25%
CYP1A2 inhibition	+	0.7307	73.07%
CYP2C8 inhibition	-	0.6651	66.51%
CYP inhibitory promiscuity	-	0.9099	90.99%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.7610	76.10%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.4841	48.41%
Skin irritation	-	0.6603	66.03%
Skin corrosion	-	0.9184	91.84%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4127	41.27%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.7524	75.24%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.9273	92.73%
Acute Oral Toxicity (c)	III	0.5484	54.84%
Estrogen receptor binding	+	0.7462	74.62%
Androgen receptor binding	-	0.4873	48.73%
Thyroid receptor binding	+	0.7054	70.54%
Glucocorticoid receptor binding	+	0.5848	58.48%
Aromatase binding	+	0.6638	66.38%
PPAR gamma	+	0.8190	81.90%
Honey bee toxicity	-	0.8398	83.98%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	-	0.4532	45.32%

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	99.06%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.19%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.15%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.03%	97.09%
CHEMBL213	P08588	Beta-1 adrenergic receptor	89.82%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	89.43%	91.49%
CHEMBL3192	Q9BY41	Histone deacetylase 8	89.37%	93.99%
CHEMBL2581	P07339	Cathepsin D	88.83%	98.95%
CHEMBL226	P30542	Adenosine A1 receptor	85.91%	95.93%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.64%	96.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.20%	95.89%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	83.34%	93.40%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.81%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.51%	99.15%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 18519
• LOTUS: LTS0172452
• wikiData: Q27103884