Buergerinin B

Details

• Internal ID: 389d4a93-ae6c-4904-be4e-64bca48d7785
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (4aS,5R,7S,7aR)-4a,5,7-trihydroxy-7-methyl-4,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-3-one
• SMILES (Canonical): CC1(CC(C2(C1COC(=O)C2)O)O)O
• SMILES (Isomeric): C[C@@]1(C[C@H]([C@]2([C@@H]1COC(=O)C2)O)O)O
• InChI: InChI=1S/C9H14O5/c1-8(12)2-6(10)9(13)3-7(11)14-4-5(8)9/h5-6,10,12-13H,2-4H2,1H3/t5-,6-,8+,9+/m1/s1
• InChI Key: FQOXWSFMKSXFDD-YGBUUZGLSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₄O₅
• Molecular Weight: 202.20 g/mol
• Exact Mass: 202.08412354 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: -1.60
• Atomic LogP (AlogP): -1.20
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 0

Synonyms

• 919769-83-8
• (4aS,5R,7S,7aR)-4a,5,7-trihydroxy-7-methyl-4,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-3-one
• AKOS032961821
• (4aS,5R,7S,7aR)-4,4a,5,6,7,7a-Hexahydro-4a,5,7-trihydroxy-7-methylcyclopenta[c]pyran-3(1H)-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7734	77.34%
Caco-2	-	0.8033	80.33%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6368	63.68%
OATP2B1 inhibitior	-	0.8504	85.04%
OATP1B1 inhibitior	+	0.9405	94.05%
OATP1B3 inhibitior	+	0.9566	95.66%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9067	90.67%
P-glycoprotein inhibitior	-	0.9664	96.64%
P-glycoprotein substrate	-	0.8669	86.69%
CYP3A4 substrate	+	0.5125	51.25%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8420	84.20%
CYP3A4 inhibition	-	0.9446	94.46%
CYP2C9 inhibition	-	0.9528	95.28%
CYP2C19 inhibition	-	0.9259	92.59%
CYP2D6 inhibition	-	0.9591	95.91%
CYP1A2 inhibition	-	0.7876	78.76%
CYP2C8 inhibition	-	0.9816	98.16%
CYP inhibitory promiscuity	-	0.9924	99.24%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6493	64.93%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.7005	70.05%
Skin irritation	-	0.6535	65.35%
Skin corrosion	-	0.9267	92.67%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6578	65.78%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.9000	90.00%
skin sensitisation	-	0.8911	89.11%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.7049	70.49%
Acute Oral Toxicity (c)	III	0.4271	42.71%
Estrogen receptor binding	-	0.5367	53.67%
Androgen receptor binding	-	0.7596	75.96%
Thyroid receptor binding	-	0.7086	70.86%
Glucocorticoid receptor binding	-	0.7711	77.11%
Aromatase binding	-	0.8355	83.55%
PPAR gamma	-	0.7680	76.80%
Honey bee toxicity	-	0.8708	87.08%
Biodegradation	+	0.5500	55.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.8255	82.55%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.39%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.21%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.10%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.56%	96.77%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.89%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.98%	97.09%
CHEMBL2581	P07339	Cathepsin D	83.92%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.12%	94.45%

Plants that contains it

• Scrophularia buergeriana
• Scrophularia ningpoensis

Cross-Links

• PubChem: 91885076
• NPASS: NPC89121
• LOTUS: LTS0250308
• wikiData: Q104999765