Smardaesidin E, (rel)-

Details

• Internal ID: a63cac94-78cc-4fae-a671-4c493df01dc9
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (1R,2R,4S,5R,8S,9S,10S)-5-ethenyl-2,4,8-trihydroxy-5,11,11-trimethyl-16-oxatetracyclo[7.5.2.01,10.02,7]hexadec-6-en-15-one
• SMILES (Canonical): CC1(CCCC23C1C(C(C4=CC(C(CC42O)O)(C)C=C)O)OC3=O)C
• SMILES (Isomeric): C[C@]1(C=C2[C@@H]([C@@H]3[C@@H]4[C@@]([C@]2(C[C@@H]1O)O)(CCCC4(C)C)C(=O)O3)O)C=C
• InChI: InChI=1S/C20H28O5/c1-5-18(4)9-11-13(22)14-15-17(2,3)7-6-8-19(15,16(23)25-14)20(11,24)10-12(18)21/h5,9,12-15,21-22,24H,1,6-8,10H2,2-4H3/t12-,13-,14+,15-,18+,19-,20+/m0/s1
• InChI Key: GMBCLCQVLOXAGM-JFNPQPDZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₅
• Molecular Weight: 348.40 g/mol
• Exact Mass: 348.19367399 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.71
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

• Smardaesidin E
• CHEBI:69491
• Q27137829

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9819	98.19%
Caco-2	-	0.5436	54.36%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6784	67.84%
OATP2B1 inhibitior	-	0.8602	86.02%
OATP1B1 inhibitior	+	0.8841	88.41%
OATP1B3 inhibitior	+	0.8450	84.50%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.5821	58.21%
BSEP inhibitior	-	0.8556	85.56%
P-glycoprotein inhibitior	-	0.8128	81.28%
P-glycoprotein substrate	-	0.7948	79.48%
CYP3A4 substrate	+	0.5945	59.45%
CYP2C9 substrate	-	0.7853	78.53%
CYP2D6 substrate	-	0.8023	80.23%
CYP3A4 inhibition	-	0.6650	66.50%
CYP2C9 inhibition	-	0.7312	73.12%
CYP2C19 inhibition	-	0.7633	76.33%
CYP2D6 inhibition	-	0.9379	93.79%
CYP1A2 inhibition	-	0.7107	71.07%
CYP2C8 inhibition	-	0.7692	76.92%
CYP inhibitory promiscuity	-	0.8896	88.96%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5328	53.28%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.9732	97.32%
Skin irritation	+	0.5753	57.53%
Skin corrosion	-	0.9129	91.29%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7461	74.61%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	+	0.6585	65.85%
skin sensitisation	-	0.7922	79.22%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.5745	57.45%
Acute Oral Toxicity (c)	I	0.3741	37.41%
Estrogen receptor binding	+	0.7248	72.48%
Androgen receptor binding	+	0.6642	66.42%
Thyroid receptor binding	+	0.7030	70.30%
Glucocorticoid receptor binding	+	0.7525	75.25%
Aromatase binding	+	0.6243	62.43%
PPAR gamma	-	0.4936	49.36%
Honey bee toxicity	-	0.8534	85.34%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9951	99.51%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.10%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.93%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.89%	85.14%
CHEMBL4040	P28482	MAP kinase ERK2	88.61%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.79%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.52%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.75%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.96%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.36%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.92%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.81%	99.23%
CHEMBL1902	P62942	FK506-binding protein 1A	81.30%	97.05%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.10%	93.00%

Plants that contains it

• Ceratodon purpureus

Cross-Links

• PubChem: 56599464
• LOTUS: LTS0004232
• wikiData: Q27137829