Cryptopine

Details

• Internal ID: 8cc09e1f-051e-4579-9561-91dc8e9ecce6
• Taxonomy: Alkaloids and derivatives > Protopine alkaloids
• IUPAC Name: 6,7-dimethoxy-12-methyl-16,18-dioxa-12-azatetracyclo[12.7.0.04,9.015,19]henicosa-1(14),4,6,8,15(19),20-hexaen-3-one
• SMILES (Canonical): CN1CCC2=CC(=C(C=C2C(=O)CC3=C(C1)C4=C(C=C3)OCO4)OC)OC
• SMILES (Isomeric): CN1CCC2=CC(=C(C=C2C(=O)CC3=C(C1)C4=C(C=C3)OCO4)OC)OC
• InChI: InChI=1S/C21H23NO5/c1-22-7-6-14-9-19(24-2)20(25-3)10-15(14)17(23)8-13-4-5-18-21(16(13)11-22)27-12-26-18/h4-5,9-10H,6-8,11-12H2,1-3H3
• InChI Key: XPOJSWHIKCNLEQ-UHFFFAOYSA-N
• Popularity: 167 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₃NO₅
• Molecular Weight: 369.40 g/mol
• Exact Mass: 369.15762283 g/mol
• Topological Polar Surface Area (TPSA): 57.20 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 2.85
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• 482-74-6
• Cryptopin
• Cryptocavine
• Kryptocavin
• Kryptopine
• EINECS 207-584-8
• NSC 32984
• NSC-32984
• UNII-MW13X5YK4A
• BRN 0354948
• MW13X5YK4A
• MLS000737655
• 482-74-6 (free base)
• NSC32984
• 4-27-00-06652 (Beilstein Handbook Reference)
• 11,12-dimethoxy-7-methyl-6,8,9,15-tetrahydro-[1,3]dioxolo[4',5':5,6]benzo[1,2-c]benzo[g]azecin-14(7H)-one
• 12,13,14,15,-Tetrahydro-9,10-dimethoxy-14-methylbenzo(e)-1,3-dioxolo(4,5-1)(2)benzazecin-7(6H)-one
• 6,7-dimethoxy-12-methyl-16,18-dioxa-12-azatetracyclo[12.7.0.04,9.015,19]henicosa-1(14),4,6,8,15(19),20-hexaen-3-one
• Benzo(e)-1,3-dioxolo(4,5-l)(2)benzazecin-12(5H)-one, 4,6,7,13-tetrahydro-9,10-dimethoxy-5-methyl-
• SMR000386998
• 4,6,7,13-TETRAHYDRO-9,10-DIMETHOXY-5-METHYLBENZO(G)-1,3-BENZODIOXOLO(4,5-C)AZECIN-12(5H)-ONE
• 4,6,7,13-Tetrahydro-9,10-dimethoxy-5-methylbenzo[g]-1,3-benzodioxolo[4,5-c]azecin-12(5H)-one
• CRYPTOPINE [MI]
• Oprea1_763951
• 2,3-dimethoxy-13-methyl-12,13,14,15-tetrahydro[1,3]benzodioxolo[4,5-c]benzo[g]azecin-5(6h)-one
• MLS001048981
• SCHEMBL178039
• CHEMBL1339015
• DTXSID40197463
• HMS2268G15
• TNP00336
• STL561433
• AKOS002141588
• NCGC00017386-01
• NCGC00017386-02
• NCGC00017386-03
• NCGC00142563-01
• NCGC00142563-02
• LS-34768
• FT-0701441
• Q1142307
• W-202849
• Benzo[e]-1,5-l][2]benzazecin-12(5H)-one, 4,6,7,13-tetrahydro-9,10-dimethoxy-5-methyl-
• 11,12-dimethoxy-7-methyl-6,8,9,15-tetrahydro[1,3]benzodioxolo[4,5-c]benzo[g]azecin-14(7H)-one
• 2,3-dimethoxy-13-methyl-12,13,14,15-tetrahydrobenzo[g][1,3]benzodioxolo[4,5-c]azecin-5(6H)-one
• 4,6,7,13-tetrahydro-9,10-dimethoxy-5-methylbenzo[e]-1,3-dioxolo[4,5-l][2]benzazecin-12(5H)-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9729	97.29%
Caco-2	+	0.8871	88.71%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Lysosomes	0.4975	49.75%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9235	92.35%
OATP1B3 inhibitior	+	0.9422	94.22%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	+	0.7967	79.67%
P-glycoprotein inhibitior	+	0.8216	82.16%
P-glycoprotein substrate	-	0.5845	58.45%
CYP3A4 substrate	+	0.5928	59.28%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4730	47.30%
CYP3A4 inhibition	+	0.5509	55.09%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	+	0.8994	89.94%
CYP2D6 inhibition	+	0.8931	89.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.8907	89.07%
CYP inhibitory promiscuity	-	0.7296	72.96%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.5380	53.80%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.9391	93.91%
Skin irritation	-	0.8240	82.40%
Skin corrosion	-	0.9512	95.12%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7339	73.39%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.8555	85.55%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.6240	62.40%
Acute Oral Toxicity (c)	III	0.6981	69.81%
Estrogen receptor binding	+	0.6970	69.70%
Androgen receptor binding	-	0.5126	51.26%
Thyroid receptor binding	-	0.6210	62.10%
Glucocorticoid receptor binding	+	0.5782	57.82%
Aromatase binding	-	0.6862	68.62%
PPAR gamma	+	0.5710	57.10%
Honey bee toxicity	-	0.7888	78.88%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9467	94.67%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3622	P33261	Cytochrome P450 2C19	10000 nM	Potency	via CMAUP
CHEMBL289	P10635	Cytochrome P450 2D6	25.1 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	39810.7 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	99.41%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.09%	95.56%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	97.05%	93.40%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.96%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.69%	98.95%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	92.99%	90.95%
CHEMBL4208	P20618	Proteasome component C5	92.43%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.29%	86.33%
CHEMBL2535	P11166	Glucose transporter	91.37%	98.75%
CHEMBL2056	P21728	Dopamine D1 receptor	91.36%	91.00%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	90.36%	82.67%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.82%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.13%	95.89%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	88.45%	96.86%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	87.94%	82.38%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.31%	94.00%
CHEMBL5747	Q92793	CREB-binding protein	85.98%	95.12%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	83.97%	92.38%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.78%	92.94%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	82.81%	95.53%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.76%	89.50%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.38%	91.11%

Plants that contains it

• Aloe microstigma
• Argemone mexicana
• Chelidonium majus
• Chrozophora plicata
• Corydalis nobilis
• Corydalis ochotensis
• Corydalis pallida
• Corydalis rutifolia
• Corydalis sewerzowi
• Fumaria capreolata
• Fumaria densiflora
• Fumaria indica
• Fumaria kralikii
• Fumaria officinalis
• Fumaria parviflora
• Fumaria rostellata
• Hylomecon japonica
• Hypecoum leptocarpum
• Hypecoum procumbens
• Ichtyoselmis macrantha
• Lamprocapnos spectabilis
• Meconopsis napaulensis
• Meconopsis robusta
• Papaver atlanticum
• Papaver canescens
• Papaver heterophyllum
• Papaver lateritium
• Papaver pygmaeum
• Papaver rhoeas
• Papaver somniferum
• Papaver somniferum subsp. setigerum
• Stylophorum diphyllum
• Stylophorum lasiocarpum
• Thalictrum delavayi
• Thalictrum foliolosum
• Thalictrum minus subsp. thunbergii

Cross-Links

• PubChem: 72616
• NPASS: NPC303581
• ChEMBL: CHEMBL1339015
• LOTUS: LTS0256990
• wikiData: Q1142307