Hernandezine (7CI, 8CI)

Details

• Internal ID: 613ef88d-31e4-40db-b705-27e5f60d625e
• Taxonomy: Phenylpropanoids and polyketides > Tannins
• IUPAC Name: (14S)-9,19,20,21,25-pentamethoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.23,6.18,12.114,18.027,31.022,33]hexatriaconta-3(36),4,6(35),8,10,12(34),18(33),19,21,24,26,31-dodecaene
• SMILES (Canonical): CN1CCC2=CC(=C3C=C2C1CC4=CC=C(C=C4)OC5=C(C=CC(=C5)CC6C7=C(CCN6C)C(=C(C(=C7O3)OC)OC)OC)OC)OC
• SMILES (Isomeric): CN1CCC2=C3[C@@H]1CC4=CC(=C(C=C4)OC)OC5=CC=C(CC6C7=CC(=C(C=C7CCN6C)OC)OC3=C(C(=C2OC)OC)OC)C=C5
• InChI: InChI=1S/C39H44N2O7/c1-40-16-14-25-21-32(43-4)34-22-28(25)29(40)18-23-8-11-26(12-9-23)47-33-20-24(10-13-31(33)42-3)19-30-35-27(15-17-41(30)2)36(44-5)38(45-6)39(46-7)37(35)48-34/h8-13,20-22,29-30H,14-19H2,1-7H3/t29?,30-/m0/s1
• InChI Key: FUZMQNZACIFDBL-ZSXSBBPPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₄₄N₂O₇
• Molecular Weight: 652.80 g/mol
• Exact Mass: 652.31485175 g/mol
• Topological Polar Surface Area (TPSA): 71.10 Ų
• XlogP: 6.40
• Atomic LogP (AlogP): 7.17
• H-Bond Acceptor: 9
• H-Bond Donor: 0
• Rotatable Bonds: 5

Synonyms

• AC1L2HVY
• Hernandezine (7CI, 8CI)
• NSC-626650
• (1|A)-5,6,6',7,12-pentamethoxy-2,2'-dimethylberbaman
• Berbaman,6,6',7,12-pentamethoxy-2,2'-dimethyl-, (1.beta.)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8746	87.46%
Caco-2	+	0.7289	72.89%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Lysosomes	0.4730	47.30%
OATP2B1 inhibitior	-	0.7134	71.34%
OATP1B1 inhibitior	+	0.9386	93.86%
OATP1B3 inhibitior	+	0.9426	94.26%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	1.0000	100.00%
P-glycoprotein inhibitior	+	0.9454	94.54%
P-glycoprotein substrate	+	0.6211	62.11%
CYP3A4 substrate	+	0.6783	67.83%
CYP2C9 substrate	+	0.7865	78.65%
CYP2D6 substrate	+	0.7650	76.50%
CYP3A4 inhibition	-	0.8442	84.42%
CYP2C9 inhibition	-	0.9631	96.31%
CYP2C19 inhibition	-	0.9340	93.40%
CYP2D6 inhibition	-	0.9054	90.54%
CYP1A2 inhibition	-	0.9136	91.36%
CYP2C8 inhibition	+	0.5776	57.76%
CYP inhibitory promiscuity	-	0.9489	94.89%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6145	61.45%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9395	93.95%
Skin irritation	-	0.7935	79.35%
Skin corrosion	-	0.9523	95.23%
Ames mutagenesis	+	0.8200	82.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9485	94.85%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.8923	89.23%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.8436	84.36%
Acute Oral Toxicity (c)	III	0.6973	69.73%
Estrogen receptor binding	+	0.6917	69.17%
Androgen receptor binding	+	0.7229	72.29%
Thyroid receptor binding	+	0.6606	66.06%
Glucocorticoid receptor binding	+	0.8525	85.25%
Aromatase binding	+	0.5853	58.53%
PPAR gamma	+	0.5567	55.67%
Honey bee toxicity	-	0.7171	71.71%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.6800	68.00%
Fish aquatic toxicity	+	0.8526	85.26%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4302	P08183	P-glycoprotein 1	1.59 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.06%	96.09%
CHEMBL2056	P21728	Dopamine D1 receptor	96.13%	91.00%
CHEMBL217	P14416	Dopamine D2 receptor	92.30%	95.62%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	91.89%	93.40%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	89.58%	82.38%
CHEMBL3192	Q9BY41	Histone deacetylase 8	89.22%	93.99%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.56%	86.33%
CHEMBL5747	Q92793	CREB-binding protein	88.10%	95.12%
CHEMBL2581	P07339	Cathepsin D	87.88%	98.95%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	87.35%	89.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.67%	94.45%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	86.03%	90.95%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	85.55%	95.53%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.25%	95.89%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	84.96%	95.78%
CHEMBL2535	P11166	Glucose transporter	84.34%	98.75%
CHEMBL2413	P32246	C-C chemokine receptor type 1	84.17%	89.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.15%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.76%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.10%	91.11%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.81%	100.00%
CHEMBL4835	P00338	L-lactate dehydrogenase A chain	82.33%	95.34%
CHEMBL4208	P20618	Proteasome component C5	81.19%	90.00%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	81.05%	93.65%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	80.95%	92.38%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.89%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.27%	94.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.09%	97.25%

Plants that contains it

• Thalictrum atriplex
• Thalictrum faberi
• Thalictrum foliolosum
• Thalictrum glandulosissimum
• Thalictrum microgynum
• Thalictrum petaloideum
• Thalictrum podocarpum
• Thalictrum simplex

Cross-Links

• PubChem: 362567
• NPASS: NPC150006