Allocryptopine

Details

• Internal ID: 36a22800-a1c6-4c32-b001-f377cd5dc794
• Taxonomy: Alkaloids and derivatives > Protopine alkaloids
• IUPAC Name: 7,8-dimethoxy-11-methyl-17,19-dioxa-11-azatetracyclo[12.7.0.04,9.016,20]henicosa-1(21),4(9),5,7,14,16(20)-hexaen-2-one
• SMILES (Canonical): CN1CCC2=CC3=C(C=C2C(=O)CC4=C(C1)C(=C(C=C4)OC)OC)OCO3
• SMILES (Isomeric): CN1CCC2=CC3=C(C=C2C(=O)CC4=C(C1)C(=C(C=C4)OC)OC)OCO3
• InChI: InChI=1S/C21H23NO5/c1-22-7-6-14-9-19-20(27-12-26-19)10-15(14)17(23)8-13-4-5-18(24-2)21(25-3)16(13)11-22/h4-5,9-10H,6-8,11-12H2,1-3H3
• InChI Key: HYBRYAPKQCZIAE-UHFFFAOYSA-N
• Popularity: 206 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

• 485-91-6
• Thalictrimine
• 24240-04-8
• alpha-Allocryptopine
• Allocrytopine
• alpha-Fagarine
• Fagarine I
• beta-Homochelidonine
• .alpha.-Fagarine
• beta-Allocryptopine
• gamma-Homochelidonine
• .beta.-Homochelidonine
• CHEBI:17390
• UNII-EK27J8ROYB
• EK27J8ROYB
• .alpha.-Allocryptopine
• 5,7,8,15-Tetrahydro-3,4-dimethoxy-6-methyl(1,3)benzodioxolo(5,6-e)(2)benzazecin-14(6H)-one
• EINECS 207-626-5
• allo-cryptopine
• NSC 404531
• NSC-404531
• 3,4-Dimethoxy-6-methyl-5,7,8,15-tetrahydrobenzo[c][1,3]benzodioxolo[5,6-g]azecin-14(6H)-one
• DTXSID60871677
• NSC645286
• 5,7,8,15-Tetrahydro-3,4-dimethoxy-6-methylbenzo(e)(1,3)dioxolo(4,5-k)(3)benzazecin-14(6H)-one
• NSC 148824
• 7,8-dimethoxy-11-methyl-17,19-dioxa-11-azatetracyclo[12.7.0.04,9.016,20]henicosa-1(21),4(9),5,7,14,16(20)-hexaen-2-one
• Benzo(e)(1,3)dioxolo(4,5-k)(3)benzazecin-14(6H)-one, 5,7,8,15-tetrahydro-3,4-dimethoxy-6-methyl-
• Benzo(e)(1,3)dioxolo(4,5-k)(3)benzazecin-14(6H)-one, 5,7,8,15-tetrahydro-3,4-dimethoxy-6-methyl- (VAN)
• Allocryptopin
• Taliktrimin
• |A-Homochelidonine
• 3,4-dimethoxy-6-methyl-5,7,8,15-tetrahydrobenzo(c)(1,3)benzodioxolo(5,6-g)azecin-14(6H)-one
• 5,7,8,15-tetrahydro-3,4-dimethoxy-6-methyl[1,3]benzodioxolo[5,6-e][2]benzazecin-14(6H)-one
• Benzo[e][1,5-k][3]benzazecin-14(6H)-one, 5,7,8,15-tetrahydro-3,4-dimethoxy-6-methyl- (VAN8C
• .beta.-Allocryptopine
• .gamma.-Homochelidonine
• ALLOCRYPTOPINE [MI]
• Taliktrimin (thalictrimine)
• Oprea1_535693
• Oprea1_700961
• MLS000765018
• SCHEMBL673252
• CHEMBL520043
• MEGxp0_001784
• ACon1_000293
• DTXCID40203972
• HYBRYAPKQCZIAE-UHFFFAOYSA-N
• HMS2735D09
• Allocryptopine; Alpha-Allocryptopine
• BCP24946
• HY-N1933
• ZAA24004
• BBL027872
• BDBM50130203
• NSC148824
• NSC404531
• STL372863
• AKOS000730626
• CCG-104087
• NSC-148824
• NSC-645286
• 3,4-dimethoxy-6-methyl-5,7,8,15-tetrahydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-g]benzo[c]azecin-14(6H)-one
• AC-31294
• SMR000283023
• VS-08608
• CS-0018245
• FT-0632205
• FT-0701356
• C02134
• A827567
• Q-100541
• BRD-K86670801-001-01-1
• BRD-K86670801-001-09-4
• Q15410229
• [1,3]Benzodioxolo[5,6-e][2]benzazecin-14(6H)-one, 5,7,8,15-tetrahydro-3,4-dimethoxy-6-methyl-
• 3,4-dimethoxy-6-methyl-5,6,7,8,14,15-hexahydrobenzo[c][1,3]dioxolo[4',5':4, 5]benzo[g]azecin-14-one
• 3,4-Dimethoxy-6-methyl-5,7,8,15-tetrahydrobenzo[c][1,3]benzodioxolo[5,6-g]azecin-14(6H)-one #
• 5,7,8,15-tetrahydro-3,4-dimethoxy-6-methylbenzo-[e][1,3]dioxolo[4,5-k][3]benzazecin-14(6H)-one
• 7,8-dimethoxy-11-methyl-17,19-dioxa-11-azatetracyclo[12.7.0.0 , .0 , ]henicosa-1(14),4(9),5,7,15,20-hexaen-2-one
• 7,8-DIMETHOXY-11-METHYL-17,19-DIOXA-11-AZATETRACYCLO[12.7.0.0?,?.0(1)?,(2)?]HENICOSA-1(14),4(9),5,7,15,20-HEXAEN-2-ONE
• Benzo(e)(1,3)dioxolo(4,5-k)(3)benzazecin-14(6H)-one, 5,7,8,15-tetrahydro-3,4-dimethoxy-6-methyl-(VAN) (8CI)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9583	95.83%
Caco-2	+	0.8949	89.49%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Lysosomes	0.5210	52.10%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9421	94.21%
OATP1B3 inhibitior	+	0.9371	93.71%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	+	0.7645	76.45%
P-glycoprotein inhibitior	+	0.7275	72.75%
P-glycoprotein substrate	-	0.7199	71.99%
CYP3A4 substrate	+	0.5994	59.94%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4730	47.30%
CYP3A4 inhibition	+	0.6522	65.22%
CYP2C9 inhibition	-	0.9308	93.08%
CYP2C19 inhibition	+	0.8272	82.72%
CYP2D6 inhibition	+	0.8798	87.98%
CYP1A2 inhibition	-	0.8788	87.88%
CYP2C8 inhibition	-	0.8658	86.58%
CYP inhibitory promiscuity	-	0.7281	72.81%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.5425	54.25%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9419	94.19%
Skin irritation	-	0.8223	82.23%
Skin corrosion	-	0.9490	94.90%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3833	38.33%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.8605	86.05%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.6612	66.12%
Acute Oral Toxicity (c)	III	0.6425	64.25%
Estrogen receptor binding	+	0.6491	64.91%
Androgen receptor binding	-	0.4842	48.42%
Thyroid receptor binding	-	0.6051	60.51%
Glucocorticoid receptor binding	+	0.6285	62.85%
Aromatase binding	-	0.6206	62.06%
PPAR gamma	+	0.6067	60.67%
Honey bee toxicity	-	0.8486	84.86%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9499	94.99%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL289	P10635	Cytochrome P450 2D6	122 nM	Ki	PMID: 26125082
CHEMBL1293299	Q03164	Histone-lysine N-methyltransferase MLL	14125.4 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	99.63%	96.77%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	97.80%	93.40%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.03%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.64%	95.56%
CHEMBL2581	P07339	Cathepsin D	95.56%	98.95%
CHEMBL4208	P20618	Proteasome component C5	93.38%	90.00%
CHEMBL2056	P21728	Dopamine D1 receptor	92.16%	91.00%
CHEMBL2535	P11166	Glucose transporter	92.06%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.87%	86.33%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	91.64%	90.95%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	90.41%	82.38%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.60%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.33%	94.00%
CHEMBL5747	Q92793	CREB-binding protein	88.05%	95.12%
CHEMBL3192	Q9BY41	Histone deacetylase 8	87.24%	93.99%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.14%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.33%	99.17%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	86.03%	80.78%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	85.55%	96.86%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	84.35%	82.67%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.29%	94.45%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	82.82%	92.38%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.60%	91.11%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.81%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.52%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.29%	99.23%

Plants that contains it

• Aegle marmelos
• Angelica dahurica
• Arctomecon merriamii
• Argemone grandiflora
• Argemone mexicana
• Argemone munita
• Artabotrys maingayi
• Bocconia frutescens
• Caltha palustris
• Chelidonium majus
• Corydalis bulleyana
• Corydalis campulicarpa
• Corydalis caseana
• Corydalis decumbens
• Corydalis ledebouriana
• Corydalis nobilis
• Corydalis ophiocarpa
• Corydalis orthopoda
• Corydalis rutifolia
• Corydalis sewerzowi
• Corydalis solida
• Corydalis ternata
• Corydalis turtschaninovii
• Corydalis yanhusuo
• Cyperus nipponicus
• Dalbergia spruceana
• Dendrobium amplum
• Diospyros ebenum
• Erythrophleum suaveolens
• Eschscholzia californica
• Garcinia xanthochymus
• Glaucium fimbrilligerum
• Glaucium flavum
• Glaucium grandiflorum
• Glaucium leiocarpum
• Glaucium squamigerum
• Horsfieldia glabra
• Hunnemannia fumariifolia
• Hylomecon japonica
• Hypecoum lactiflorum
• Hypecoum leptocarpum
• Hypecoum procumbens
• Lappula squarrosa
• Larix decidua
• Ligularia sagitta
• Macleaya cordata
• Macleaya microcarpa
• Meconopsis robusta
• Mezzettia parviflora
• Nuxia sphaerocephala
• Papaver albiflorum
• Papaver curviscapum
• Papaver dubium
• Papaver glaucum
• Papaver lapponicum
• Papaver orientale
• Papaver pavoninum
• Papaver pinnatifidum
• Papaver pygmaeum
• Papaver rhoeas
• Piper methysticum
• Prunus humilis
• Psacalium peltatum
• Ruta corsica
• Sanguinaria canadensis
• Senna spectabilis
• Stachys plumosa
• Stylophorum diphyllum
• Stylophorum lasiocarpum
• Swertia mussotii
• Symphytum officinale
• Thalictrum atriplex
• Thalictrum faberi
• Thalictrum foliolosum
• Thalictrum glandulosissimum
• Thalictrum microgynum
• Thalictrum minus subsp. thunbergii
• Thalictrum petaloideum
• Thalictrum revolutum
• Thalictrum simplex
• Thuja plicata
• Ulex parviflorus subsp. airensis
• Vepris heterophylla
• Zanthoxylum avicennae
• Zanthoxylum beecheyanum
• Zanthoxylum integrifoliolum
• Zanthoxylum nitidum

Cross-Links

• PubChem: 98570
• NPASS: NPC67978
• ChEMBL: CHEMBL520043
• LOTUS: LTS0174113
• wikiData: Q15410229