Sclerotiorin

Details

• Internal ID: 6d853f37-9770-417e-9f95-3bc359d6f942
• Taxonomy: Organoheterocyclic compounds > Azaphilones
• IUPAC Name: [(7R)-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-7-methyl-6,8-dioxoisochromen-7-yl] acetate
• InChI: InChI=1S/C21H23ClO5/c1-6-12(2)9-13(3)7-8-15-10-16-17(11-26-15)19(24)21(5,27-14(4)23)20(25)18(16)22/h7-12H,6H2,1-5H3/b8-7+,13-9+/t12-,21+/m0/s1
• InChI Key: SWJLTKXURNHVHE-UPWXJBBJSA-N
• Popularity: 41 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₃ClO₅
• Molecular Weight: 390.90 g/mol
• Exact Mass: 390.1234015 g/mol
• Topological Polar Surface Area (TPSA): 69.70 Ų
• XlogP: 4.80
• Atomic LogP (AlogP): 4.30
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 5

Synonyms

• 549-23-5
• BA54VZ8Z50
• [(7R)-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-7-methyl-6,8-dioxoisochromen-7-yl] acetate
• DTXSID101043739
• 6H-2-BENZOPYRAN-6,8(7H)-DIONE, 7-(ACETYLOXY)-5-CHLORO-3-((1E,3E,5S)-3,5-DIMETHYL-1,3-HEPTADIEN-1-YL)-7-METHYL-, (7R)-
• ((7R)-5-chloro-3-((1E,3E,5S)-3,5-dimethylhepta-1,3-dienyl)-7-methyl-6,8-dioxoisochromen-7-yl) acetate
• RefChem:181918
• DTXCID901526161
• (S-(R*,R*-(E,E)))-Sclerotiorin
• (R)-5-chloro-3-((S,1E,3E)-3,5-dimethylhepta-1,3-dien-1-yl)-7-methyl-6,8-dioxo-7,8-dihydro-6H-isochromen-7-yl acetate
• [(7R)-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-7-methyl-6,8-dioxo-isochromen-7-yl] acetate
• (+)-SCLEROTIORIN
• C21H23ClO5
• UNII-BA54VZ8Z50
• MLS000563069
• orb1693368
• CHEMBL1095515
• SCHEMBL17241989
• CHEBI:186034
• SWJLTKXURNHVHE-UPWXJBBJSA-N
• HMS2267F03
• EX-A10617
• HB4080
• AKOS030213219
• (R-(R*,S*-(E,E)))-7-(Acetyloxy)-5-chloro-3-(3,5-dimethyl-1,3-heptadienyl)-7-methyl-6H-2-benzopyrane-6,8(7H)-dione
• SMR001215839
• HY-116866
• CS-0066712
• Q15424763
• (7R)-7-(ACETYLOXY)-5-CHLORO-3-((1E,3E,5S)-3,5-DIMETHYL-1,3-HEPTADIEN-1-YL)-7-METHYL-6H-2-BENZOPYRAN-6,8(7H)-DIONE
• 6H-2-Benzopyran-6,8(7H)-dione, 7-(acetyloxy)-5-chloro-3-[(1E,3E,5S)-3,5-dimethyl-1,3-heptadienyl]-7-methyl-, (7R)
• 6H-2-Benzopyrane-6,8(7H)-dione, 7-(acetyloxy)-5-chloro-3-(3,5-dimethyl-1,3-heptadienyl)-7-methyl-, (R-(R*,S*-(E,E)))-
• 7-(Acetyloxy)-5-chloro-3-[(1E,3E,5S)-3,5-dimethyl-1,3-heptadien-1-yl]-7-methyl-6H-2-benzopyran-6,8(7H)-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9911	99.11%
Caco-2	+	0.6514	65.14%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.4715	47.15%
OATP2B1 inhibitior	-	0.8594	85.94%
OATP1B1 inhibitior	+	0.7664	76.64%
OATP1B3 inhibitior	+	0.8985	89.85%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9291	92.91%
P-glycoprotein inhibitior	+	0.6058	60.58%
P-glycoprotein substrate	-	0.6416	64.16%
CYP3A4 substrate	+	0.6593	65.93%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8981	89.81%
CYP3A4 inhibition	-	0.6061	60.61%
CYP2C9 inhibition	-	0.7181	71.81%
CYP2C19 inhibition	-	0.6680	66.80%
CYP2D6 inhibition	-	0.9007	90.07%
CYP1A2 inhibition	-	0.7481	74.81%
CYP2C8 inhibition	+	0.4878	48.78%
CYP inhibitory promiscuity	+	0.5526	55.26%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8719	87.19%
Carcinogenicity (trinary)	Danger	0.4941	49.41%
Eye corrosion	-	0.9787	97.87%
Eye irritation	-	0.9591	95.91%
Skin irritation	-	0.6147	61.47%
Skin corrosion	-	0.9148	91.48%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8126	81.26%
Micronuclear	-	0.5600	56.00%
Hepatotoxicity	+	0.5708	57.08%
skin sensitisation	-	0.7178	71.78%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.6759	67.59%
Acute Oral Toxicity (c)	III	0.6390	63.90%
Estrogen receptor binding	+	0.8939	89.39%
Androgen receptor binding	+	0.7132	71.32%
Thyroid receptor binding	+	0.6312	63.12%
Glucocorticoid receptor binding	+	0.6896	68.96%
Aromatase binding	+	0.6168	61.68%
PPAR gamma	+	0.7885	78.85%
Honey bee toxicity	-	0.8303	83.03%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6352	63.52%
Fish aquatic toxicity	+	0.9932	99.32%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	800 nM	AC50	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.58%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.82%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.07%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	94.59%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.99%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	92.63%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.06%	96.09%
CHEMBL236	P41143	Delta opioid receptor	89.63%	99.35%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.39%	96.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	84.99%	89.34%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	83.91%	85.30%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	83.66%	92.29%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.51%	95.56%
CHEMBL1937	Q92769	Histone deacetylase 2	80.14%	94.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.06%	99.17%

Plants that contains it

• Isodon longitubus

Cross-Links

• PubChem: 6436015
• NPASS: NPC224270
• ChEMBL: CHEMBL1095515
• LOTUS: LTS0107242
• wikiData: Q15424763