Sanguinarium

Details

• Internal ID: 5aa2154d-62f5-44f5-8642-1c89d0e7f15f
• Taxonomy: Alkaloids and derivatives > Benzophenanthridine alkaloids > Quaternary benzophenanthridine alkaloids
• IUPAC Name: 24-methyl-5,7,18,20-tetraoxa-24-azoniahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-1(24),2,4(8),9,11,13,15,17(21),22-nonaene
• SMILES (Canonical): C[N+]1=C2C(=C3C=CC4=C(C3=C1)OCO4)C=CC5=CC6=C(C=C52)OCO6
• SMILES (Isomeric): C[N+]1=C2C(=C3C=CC4=C(C3=C1)OCO4)C=CC5=CC6=C(C=C52)OCO6
• InChI: InChI=1S/C20H14NO4/c1-21-8-15-12(4-5-16-20(15)25-10-22-16)13-3-2-11-6-17-18(24-9-23-17)7-14(11)19(13)21/h2-8H,9-10H2,1H3/q+1
• InChI Key: INVGWHRKADIJHF-UHFFFAOYSA-N
• Popularity: 805 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₄NO₄+
• Molecular Weight: 332.30 g/mol
• Exact Mass: 332.09228293 g/mol
• Topological Polar Surface Area (TPSA): 40.80 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 3.43
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• 2447-54-3
• Pseudochelerythrine
• Sanguinarin
• sangvinarin
• SANGUINARIUM
• Veadent
• Sanguiritrin
• Sangrovit
• Dimethylenedioxy benzphenanthridine
• UNII-AV9VK043SS
• EINECS 219-503-3
• AV9VK043SS
• Pseudochelerythrine;Sanguinarin
• BRN 3915507
• DTXSID0045204
• CHEBI:17183
• C20H14NO4
• [1,3]Benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium, 13-methyl-
• Benzophenanthridine alkaloid
• DTXCID8025204
• (1,3)-Benzodioxolo(5,6-c)-1,3-dioxolo(4,5-i)phenanthridinium, 13-methyl-
• 24-methyl-5,7,18,20-tetraoxa-24-azoniahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-1(24),2,4(8),9,11,13,15,17(21),22-nonaene
• NCGC00015959-03
• CAS-2447-54-3
• 13-Methyl[1,3]benzodioxolo[5,6-C][1,3]dioxolo[4,5-I]phenanthridin-13-Ium
• (1,3)BENZODIOXOLO(5,6-C)-1,3-DIOXOLO(4,5-I)PHENANTHRIDINIUM, 13-METHYL-
• 13-Methyl-[1,3]dioxolo[4',5':4,5]benzo[1,2-c][1,3]dioxolo[4,5-i]phenanthridin-13-ium
• pseudo-chelerythrine
• UI5
• y-Chelerythrine
• SR-01000075650
• |x-Chelerythrine
• 13-methyl(1,3)benzodioxolo(5,6-c)-1,3-dioxolo(4,5-i)phenanthridinium
• 13-methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium
• pseudocheleryth-rine
• 13-methyl-2H,10H-(1,3)dioxolo(4,5-i)(1,3)dioxolo(4',5':4,5)benzo(1,2-c)phenanthridinium
• 13-methyl-2H,10H-[1,3]dioxolo[4,5-i][1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridinium
• sanguinarium-chloride
• Spectrum_000259
• Prestwick0_000987
• Prestwick1_000987
• Prestwick2_000987
• Prestwick3_000987
• Spectrum2_000724
• Spectrum3_001148
• Spectrum4_001838
• Spectrum5_000635
• Lopac-S-5890
• SANGUINARINE [MI]
• D0T3NB
• cid_5154
• Lopac0_001108
• BSPBio_001053
• BSPBio_002675
• KBioGR_002542
• KBioSS_000739
• MLS002154085
• DivK1c_000495
• SANGUINARINE [WHO-DD]
• SCHEMBL123241
• SPBio_000648
• SPBio_002954
• BPBio1_001159
• CHEMBL417799
• SCHEMBL17131945
• BDBM25525
• GTPL11563
• KBio1_000495
• KBio2_000739
• KBio2_003307
• KBio2_005875
• KBio3_002175
• INVGWHRKADIJHF-UHFFFAOYSA-N
• NINDS_000495
• HMS1571E15
• HMS2098E15
• BCP13614
• EX-A5014
• HY-N0052
• Tox21_110268
• C20-H14-N-O4
• NSC765394
• s9032
• AKOS025311557
• Tox21_110268_1
• CCG-205184
• compound 1 [PMID: 28621943]
• CS-3818
• NSC-765394
• SDCCGMLS-0066612.P001
• IDI1_000495
• NCGC00015959-01
• NCGC00015959-02
• NCGC00015959-04
• NCGC00015959-05
• NCGC00015959-09
• NCGC00015959-16
• NCGC00160289-01
• NCGC00160289-02
• AC-34836
• SMR001233394
• SBI-0051077.P003
• LS-144493
• AB00053789
• FT-0634289
• C06162
• E80766
• AB00053789_04
• Q347392
• Q-100313
• SR-01000075650-7
• BRD-K66898851-001-03-7
• 5-Methyl-2,3:7,8-bis(methylenedioxy)benzo[c]phenanthridinium(1+)
• 13-Methyl[1,3]benzodi-oxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium
• 13-Methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium nitrate
• 13-Methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium(1+), 9CI
• 24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0^{2,10}.0^{4,8}.0^{14,22}.0^{17,21}]tetracosa-1(13),2,4(8),9,11,14(22),15,17(21),23-nonaen-24-ium
• 24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0^{2,10}.0^{4,8}.0^{14,22}.0^{17,21}]tetracosa-1(13),2,4(8),9,11,14,16,21,23-nonaen-24-ium
• 24-methyl-5,7,18,20-tetraoxa-24-azoniahexacyclo[11.11.0.0^{2,10.0^{4,8.0^{14,22.0^{17,21]tetracosa-1(24),2,4(8),9,11,13,15,17(21),22-nonaene

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7780	77.80%
Caco-2	+	0.9024	90.24%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.4697	46.97%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9483	94.83%
OATP1B3 inhibitior	+	0.9527	95.27%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7848	78.48%
BSEP inhibitior	+	0.8643	86.43%
P-glycoprotein inhibitior	+	0.5790	57.90%
P-glycoprotein substrate	-	0.8155	81.55%
CYP3A4 substrate	-	0.5483	54.83%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8031	80.31%
CYP3A4 inhibition	+	0.6244	62.44%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	+	0.8994	89.94%
CYP2D6 inhibition	+	0.8933	89.33%
CYP1A2 inhibition	+	0.9378	93.78%
CYP2C8 inhibition	-	0.6966	69.66%
CYP inhibitory promiscuity	+	0.8559	85.59%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Warning	0.4166	41.66%
Eye corrosion	-	0.9848	98.48%
Eye irritation	-	0.8491	84.91%
Skin irritation	-	0.7282	72.82%
Skin corrosion	-	0.9391	93.91%
Ames mutagenesis	+	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4200	42.00%
Micronuclear	+	0.7400	74.00%
Hepatotoxicity	+	0.7177	71.77%
skin sensitisation	-	0.8414	84.14%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.5836	58.36%
Acute Oral Toxicity (c)	III	0.7774	77.74%
Estrogen receptor binding	+	0.8962	89.62%
Androgen receptor binding	+	0.8466	84.66%
Thyroid receptor binding	+	0.6951	69.51%
Glucocorticoid receptor binding	+	0.8970	89.70%
Aromatase binding	+	0.5301	53.01%
PPAR gamma	+	0.8272	82.72%
Honey bee toxicity	-	0.8483	84.83%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.7300	73.00%
Fish aquatic toxicity	-	0.4924	49.24%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	14125.4 nM; 28183.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	22387.2 nM	Potency	via CMAUP
CHEMBL3687	P18054	Arachidonate 12-lipoxygenase	12589.3 nM; 10000 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	7943.3 nM; 3162.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4096	P04637	Cellular tumor antigen p53	3162.3 nM; 6309.6 nM; 2511.9 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL3356	P05177	Cytochrome P450 1A2	3981.07 nM; 10000 nM	AC50; AC50	via CMAUP; via CMAUP
CHEMBL3622	P33261	Cytochrome P450 2C19	3162.28 nM; 6309.57 nM	AC50; AC50	via CMAUP; via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	15848.9 nM	Potency	via CMAUP
CHEMBL289	P10635	Cytochrome P450 2D6	31622.78 nM; 7943.28 nM	AC50; AC50	via CMAUP; via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	3162.3 nM; 12589.3 nM; 3162.3 nM; 12589.3 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	12589.3 nM; 31622.8 nM; 3981.1 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL5514	P42858	Huntingtin	6309.6 nM	Potency	via CMAUP
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	10000 nM; 7943.3 nM; 10000 nM; 7943.3 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	25118.9 nM; 7079.5 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	25118.9 nM; 25118.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	17782.8 nM; 28183.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	10000 nM; 10000 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	398.1 nM; 398.1 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL1075189	P14618	Pyruvate kinase isozymes M1/M2	10000 nM; 10000 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293294	P51151	Ras-related protein Rab-9A	46109.1 nM	Potency	via CMAUP
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	3288.5 nM	Potency	via CMAUP
CHEMBL5401	P42226	Signal transducer and activator of transcription 6	7943.3 nM; 7943.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	11220.2 nM; 22387.2 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293256	P40225	Thrombopoietin	1000 nM; 1000 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	25118.9 nM; 12589.3 nM; 12589.3 nM; 25118.9 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL1293227	O75604	Ubiquitin carboxyl-terminal hydrolase 2	25118.9 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	97.32%	96.77%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	94.44%	94.80%
CHEMBL2039	P27338	Monoamine oxidase B	92.13%	92.51%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.76%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.62%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.45%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	88.72%	91.49%
CHEMBL3401	O75469	Pregnane X receptor	84.40%	94.73%
CHEMBL2581	P07339	Cathepsin D	84.20%	98.95%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	83.94%	85.30%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.73%	92.62%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.25%	89.62%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.82%	93.40%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.65%	86.33%
CHEMBL240	Q12809	HERG	80.61%	89.76%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.23%	100.00%

Plants that contains it

• Aloe microstigma
• Angelica dahurica
• Argemone mexicana
• Argemone ochroleuca
• Argemone polyanthemos
• Argemone subfusiformis
• Artabotrys maingayi
• Bocconia arborea
• Bocconia latisepala
• Chelidonium majus
• Chrozophora plicata
• Coptis japonica
• Corydalis caucasica
• Corydalis cheilanthifolia
• Corydalis ledebouriana
• Corydalis ophiocarpa
• Corydalis paniculigera
• Corydalis pseudoadunca
• Corydalis sewerzowi
• Corydalis stricta
• Corydalis ternata
• Corydalis vaginans
• Diospyros ebenum
• Eschscholzia californica
• Fumaria capreolata
• Fumaria parviflora
• Garcinia xanthochymus
• Glaucium fimbrilligerum
• Glaucium flavum
• Glaucium grandiflorum
• Glaucium squamigerum
• Hylomecon japonica
• Hypecoum procumbens
• Lappula squarrosa
• Ligularia sagitta
• Macleaya cordata
• Mezzettia parviflora
• Papaver bracteatum
• Papaver cambricum
• Papaver glaucum
• Papaver somniferum
• Piper methysticum
• Psacalium peltatum
• Sanguinaria canadensis
• Senna spectabilis
• Stachys plumosa
• Stylophorum diphyllum
• Stylophorum lasiocarpum
• Symphytum officinale
• Thuja plicata
• Ulex parviflorus subsp. airensis
• Vepris heterophylla
• Zanthoxylum nitidum

Cross-Links

• PubChem: 5154
• NPASS: NPC46451
• ChEMBL: CHEMBL417799
• LOTUS: LTS0149026
• wikiData: Q347392