Ophiocarpine

Details

• Internal ID: a6d672ba-198b-4eef-b7a1-eb0462fe49b1
• Taxonomy: Alkaloids and derivatives > Protoberberine alkaloids and derivatives
• IUPAC Name: (1R,21R)-16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-2,4(8),9,15(20),16,18-hexaen-21-ol
• SMILES (Canonical): COC1=C(C2=C(C=C1)C(C3C4=CC5=C(C=C4CCN3C2)OCO5)O)OC
• SMILES (Isomeric): COC1=C(C2=C(C=C1)[C@H]([C@H]3C4=CC5=C(C=C4CCN3C2)OCO5)O)OC
• InChI: InChI=1S/C20H21NO5/c1-23-15-4-3-12-14(20(15)24-2)9-21-6-5-11-7-16-17(26-10-25-16)8-13(11)18(21)19(12)22/h3-4,7-8,18-19,22H,5-6,9-10H2,1-2H3/t18-,19-/m1/s1
• InChI Key: FLSSXYPKPLFNLK-RTBURBONSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₁NO₅
• Molecular Weight: 355.40 g/mol
• Exact Mass: 355.14197277 g/mol
• Topological Polar Surface Area (TPSA): 60.40 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.58
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• MLS000574944
• SMR000156297
• SCHEMBL3132406
• CHEMBL1556795
• BDBM94121
• cid_12313750
• HMS2200F19
• AKOS040753381
• NCGC00247612-01
• (1R,21R)-16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-2,4(8),9,15(20),16,18-hexaen-21-ol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6659	66.59%
Caco-2	+	0.8331	83.31%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.5288	52.88%
OATP2B1 inhibitior	-	0.8664	86.64%
OATP1B1 inhibitior	+	0.9541	95.41%
OATP1B3 inhibitior	+	0.9377	93.77%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.5067	50.67%
BSEP inhibitior	+	0.7788	77.88%
P-glycoprotein inhibitior	-	0.4812	48.12%
P-glycoprotein substrate	-	0.7172	71.72%
CYP3A4 substrate	+	0.6133	61.33%
CYP2C9 substrate	-	0.6063	60.63%
CYP2D6 substrate	+	0.6929	69.29%
CYP3A4 inhibition	+	0.6099	60.99%
CYP2C9 inhibition	-	0.8670	86.70%
CYP2C19 inhibition	+	0.8029	80.29%
CYP2D6 inhibition	+	0.8195	81.95%
CYP1A2 inhibition	+	0.8310	83.10%
CYP2C8 inhibition	-	0.6404	64.04%
CYP inhibitory promiscuity	+	0.7737	77.37%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5699	56.99%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9709	97.09%
Skin irritation	-	0.7795	77.95%
Skin corrosion	-	0.9400	94.00%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3912	39.12%
Micronuclear	+	0.5400	54.00%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.8639	86.39%
Respiratory toxicity	+	0.9000	90.00%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.6559	65.59%
Acute Oral Toxicity (c)	III	0.5994	59.94%
Estrogen receptor binding	+	0.6422	64.22%
Androgen receptor binding	+	0.5477	54.77%
Thyroid receptor binding	+	0.5570	55.70%
Glucocorticoid receptor binding	+	0.6022	60.22%
Aromatase binding	-	0.7031	70.31%
PPAR gamma	+	0.6482	64.82%
Honey bee toxicity	-	0.8673	86.73%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	-	0.4401	44.01%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293235	P02545	Prelamin-A/C	3548.1 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.80%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.14%	94.45%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	95.34%	96.77%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.58%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.49%	95.89%
CHEMBL3192	Q9BY41	Histone deacetylase 8	91.01%	93.99%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.76%	89.62%
CHEMBL2535	P11166	Glucose transporter	88.53%	98.75%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.32%	92.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.05%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.86%	91.11%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	87.53%	82.67%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	86.70%	100.00%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	86.70%	82.38%
CHEMBL2581	P07339	Cathepsin D	86.10%	98.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.87%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.40%	85.14%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	85.04%	93.40%
CHEMBL2056	P21728	Dopamine D1 receptor	83.95%	91.00%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	83.68%	96.86%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	83.16%	90.95%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	82.70%	95.78%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.60%	100.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.01%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.11%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.98%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.65%	97.09%
CHEMBL261	P00915	Carbonic anhydrase I	80.42%	96.76%

Plants that contains it

• Angelica dahurica
• Artabotrys maingayi
• Corydalis caucasica
• Corydalis cheilanthifolia
• Corydalis ophiocarpa
• Corydalis ternata
• Diospyros ebenum
• Lappula squarrosa
• Ligularia sagitta
• Mezzettia parviflora
• Piper methysticum
• Psacalium peltatum
• Senna spectabilis
• Stachys plumosa
• Symphytum officinale
• Thuja plicata
• Ulex parviflorus subsp. airensis
• Vepris heterophylla

Cross-Links

• PubChem: 12313750
• NPASS: NPC2314
• ChEMBL: CHEMBL1556795
• LOTUS: LTS0181475
• wikiData: Q104396225