Higenamine

Details

• Internal ID: a23dcced-4664-4896-889d-2c379f57ca06
• Taxonomy: Organoheterocyclic compounds > Isoquinolines and derivatives > Benzylisoquinolines
• IUPAC Name: 1-[(4-hydroxyphenyl)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
• SMILES (Isomeric): C1CNC(C2=CC(=C(C=C21)O)O)CC3=CC=C(C=C3)O
• InChI: InChI=1S/C16H17NO3/c18-12-3-1-10(2-4-12)7-14-13-9-16(20)15(19)8-11(13)5-6-17-14/h1-4,8-9,14,17-20H,5-7H2
• InChI Key: WZRCQWQRFZITDX-UHFFFAOYSA-N
• Popularity: 161 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₇NO₃
• Molecular Weight: 271.31 g/mol
• Exact Mass: 271.12084340 g/mol
• Topological Polar Surface Area (TPSA): 72.70 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.23
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

• 5843-65-2
• Demethyl-Coclaurine
• Norcoclaurine
• (RS)-norcoclaurine
• (+-)-Norcoclaurine
• (+-)-Demethylcoclaurine
• (+-)-O-Demethylcoclaurine
• 1-(4-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol
• DL-DEMETHYLCOCLAURINE
• (+/-)-Higenamine - synthetic
• (R,S)-Norcoclaurine
• 6,7-dihydroxy-1-(4-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline
• 1-[(4-hydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol
• UNII-TBV5O16GAP
• TBV5O16GAP
• CHEBI:18418
• Coclaurine, O-demethyl-, (+-)-
• 6,7-Isoquinolinediol, 1,2,3,4-tetrahydro-1-((4-hydroxyphenyl)methyl)-, (+-)-
• 6,7-Dihydroxy-1-[(4-hydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline
• O-demethylcoclaurine
• (R)-Higenamine
• HIGENAMINE [WHO-DD]
• CHEMBL19344
• SCHEMBL636788
• DTXSID70973974
• (+/-)-DEMETHYLCOCLAURINE
• WZRCQWQRFZITDX-UHFFFAOYSA-N
• AMY36791
• HY-N2037
• 1-(p-hydroxybenzyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline
• MFCD01736979
• s3294
• AKOS023077522
• DB12779
• NCGC00408795-01
• AC-26394
• LS-54621
• XH164059
• CS-0018527
• C06346
• EN300-822192
• Q5754240
• 1,2,3,4-tetrahydro-1-(4-hydroxybenzyl)isoquinoline-6,7-diol
• 1-(4-Hydroxybenzyl)-1,2,3,4-tetrahydro-6,7-isoquinolinediol #
• Isoquinolin-6,7-diol, 1,2,3,4-tetrahydro-1-[4-hydroxybenzyl]-
• (+-)-1,2,3,4-Tetrahydro-1-((4-hydroxyphenyl)methyl)-6,7-isoquinolinediol
• 6,7-ISOQUINOLINEDIOL, 1,2,3,4-TETRAHYDRO-1-((4-HYDROXYPHENYL)METHYL)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9701	97.01%
Caco-2	-	0.7353	73.53%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6316	63.16%
OATP2B1 inhibitior	-	0.7107	71.07%
OATP1B1 inhibitior	+	0.9220	92.20%
OATP1B3 inhibitior	+	0.9576	95.76%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.7713	77.13%
P-glycoprotein inhibitior	-	0.9607	96.07%
P-glycoprotein substrate	-	0.5654	56.54%
CYP3A4 substrate	-	0.5084	50.84%
CYP2C9 substrate	-	0.8209	82.09%
CYP2D6 substrate	+	0.6622	66.22%
CYP3A4 inhibition	-	0.9583	95.83%
CYP2C9 inhibition	-	0.9398	93.98%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	+	0.6842	68.42%
CYP1A2 inhibition	+	0.7245	72.45%
CYP2C8 inhibition	+	0.6314	63.14%
CYP inhibitory promiscuity	-	0.8855	88.55%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.7481	74.81%
Eye corrosion	-	0.9914	99.14%
Eye irritation	-	0.7747	77.47%
Skin irritation	-	0.6416	64.16%
Skin corrosion	-	0.9120	91.20%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4117	41.17%
Micronuclear	+	0.5400	54.00%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.7427	74.27%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.9044	90.44%
Acute Oral Toxicity (c)	III	0.4836	48.36%
Estrogen receptor binding	+	0.6449	64.49%
Androgen receptor binding	-	0.4878	48.78%
Thyroid receptor binding	+	0.7108	71.08%
Glucocorticoid receptor binding	+	0.6175	61.75%
Aromatase binding	+	0.6187	61.87%
PPAR gamma	+	0.8596	85.96%
Honey bee toxicity	-	0.8288	82.88%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	-	0.5086	50.86%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL217	P14416	Dopamine D2 receptor	3900 nM	Ki	DOI: 10.1016/S0960-894X(97)00194-7
CHEMBL219	P21917	Dopamine D4 receptor	3100 nM	Ki	DOI: 10.1016/S0960-894X(97)00194-7

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.40%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.75%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.26%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.08%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.07%	97.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	89.51%	93.99%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.32%	95.89%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	88.15%	85.00%
CHEMBL226	P30542	Adenosine A1 receptor	87.26%	95.93%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	86.35%	91.71%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	86.12%	90.93%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.69%	95.89%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	85.22%	97.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.05%	99.17%
CHEMBL213	P08588	Beta-1 adrenergic receptor	83.03%	95.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.28%	96.95%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.15%	93.40%
CHEMBL1951	P21397	Monoamine oxidase A	81.15%	91.49%

Plants that contains it

• Aconitum carmichaelii
• Aconitum jaluense
• Aconitum japonicum
• Aconitum kusnezoffii
• Aconitum volubile var. pubescens
• Asarum sieboldii
• Gnetum parvifolium
• Macleaya cordata
• Nelumbo nucifera
• Phoebe chekiangensis

Cross-Links

• PubChem: 114840
• NPASS: NPC211468
• ChEMBL: CHEMBL19344
• LOTUS: LTS0113417
• wikiData: Q5754240