Buphanidrine

Details

• Internal ID: 0a8a9d60-1cfe-428a-9e9d-ec6bc7438c1c
• Taxonomy: Alkaloids and derivatives > Amaryllidaceae alkaloids > Crinine- and Haemanthamine-type amaryllidaceae alkaloids
• IUPAC Name: (1S,13R,15R)-9,15-dimethoxy-5,7-dioxa-12-azapentacyclo[10.5.2.01,13.02,10.04,8]nonadeca-2,4(8),9,16-tetraene
• SMILES (Canonical): COC1CC2C3(CCN2CC4=C(C5=C(C=C43)OCO5)OC)C=C1
• SMILES (Isomeric): CO[C@@H]1C[C@@H]2[C@@]3(CCN2CC4=C(C5=C(C=C43)OCO5)OC)C=C1
• InChI: InChI=1S/C18H21NO4/c1-20-11-3-4-18-5-6-19(15(18)7-11)9-12-13(18)8-14-17(16(12)21-2)23-10-22-14/h3-4,8,11,15H,5-7,9-10H2,1-2H3/t11-,15+,18+/m0/s1
• InChI Key: RNEXSBPDDRJJIY-BKGUAONASA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₁NO₄
• Molecular Weight: 315.40 g/mol
• Exact Mass: 315.14705815 g/mol
• Topological Polar Surface Area (TPSA): 40.20 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.22
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• Buphanidrin
• Buphandrin
• Buphanidrine
• 1162-10-3
• NSC 358661
• NSC-358661
• Crinan, 1,2-didehydro-3alpha,7-dimethoxy-
• BUPHANIDRIN B678018K239
• (1S,13R,15R)-9,15-dimethoxy-5,7-dioxa-12-azapentacyclo[10.5.2.01,13.02,10.04,8]nonadeca-2,4(8),9,16-tetraene
• (-)-Buphanidrine
• 6CAV9T8L8Q
• CHEMBL2146603
• NSC358661
• 1,2-Didehydro-3alpha,7-dimethoxycrinan
• Crinan, 1,2-didehydro-3,7-dimethoxy-, (3alpha)-
• (3R,4aR,5S,11bS)-4,4a-Dihydro-3,7-dimethoxy-3H,6H-5,11b-ethano[1,3]dioxolo[4,5-j]phenanthridine
• 3H,6H-5,11b-Ethano[1,3]dioxolo[4,5-j]phenanthridine, 4,4a-dihydro-3,7-dimethoxy-, (3R,4aR,5S,11bS)-
• 3H,6H-5,11b-Ethano[1,3]dioxolo[4,5-j]phenanthridine, 4,4a-dihydro-3,7-dimethoxy-, [3R-(3alpha,4aalpha,5beta,11bbeta)]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9670	96.70%
Caco-2	+	0.8656	86.56%
Blood Brain Barrier	+	0.9500	95.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Lysosomes	0.5684	56.84%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9418	94.18%
OATP1B3 inhibitior	+	0.9419	94.19%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.6601	66.01%
P-glycoprotein inhibitior	-	0.7662	76.62%
P-glycoprotein substrate	-	0.5167	51.67%
CYP3A4 substrate	+	0.6110	61.10%
CYP2C9 substrate	-	0.8076	80.76%
CYP2D6 substrate	+	0.5125	51.25%
CYP3A4 inhibition	-	0.6636	66.36%
CYP2C9 inhibition	-	0.9337	93.37%
CYP2C19 inhibition	-	0.7524	75.24%
CYP2D6 inhibition	+	0.5651	56.51%
CYP1A2 inhibition	-	0.6912	69.12%
CYP2C8 inhibition	-	0.7076	70.76%
CYP inhibitory promiscuity	-	0.6781	67.81%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5543	55.43%
Eye corrosion	-	0.9880	98.80%
Eye irritation	-	0.9873	98.73%
Skin irritation	-	0.8124	81.24%
Skin corrosion	-	0.9435	94.35%
Ames mutagenesis	+	0.5446	54.46%
Human Ether-a-go-go-Related Gene inhibition	+	0.6519	65.19%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	+	0.5627	56.27%
skin sensitisation	-	0.8077	80.77%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.4932	49.32%
Acute Oral Toxicity (c)	III	0.6511	65.11%
Estrogen receptor binding	+	0.7704	77.04%
Androgen receptor binding	+	0.5314	53.14%
Thyroid receptor binding	+	0.6835	68.35%
Glucocorticoid receptor binding	+	0.7346	73.46%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	-	0.5516	55.16%
Honey bee toxicity	-	0.6514	65.14%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.7690	76.90%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	98.74%	96.77%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.47%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.85%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.70%	91.11%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	91.56%	80.96%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.88%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.84%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.48%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.97%	97.25%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	86.41%	82.67%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	86.40%	93.40%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	86.17%	94.80%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	85.32%	82.38%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.82%	95.56%
CHEMBL4208	P20618	Proteasome component C5	84.73%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.17%	95.89%
CHEMBL5747	Q92793	CREB-binding protein	83.49%	95.12%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.35%	94.00%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	82.58%	91.03%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.43%	92.62%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	81.82%	90.24%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.49%	100.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.47%	89.62%

Plants that contains it

• Amaryllidaceae
• Ammocharis tinneana
• Boophone disticha
• Brunsvigia josephinae
• Crinum macowanii
• Psorothamnus arborescens
• Tanacetum cinerariifolium

Cross-Links

• PubChem: 338023
• NPASS: NPC75958
• ChEMBL: CHEMBL2146603
• LOTUS: LTS0207793
• wikiData: Q105241301