Tehranolide

Details

• Internal ID: 09b688a8-25c3-4231-a6d6-c4494f83c312
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (1R,4R,5S,12S,13S)-4,13-dihydroxy-5,9-dimethyl-11,14,15-trioxatetracyclo[11.2.1.01,5.08,12]hexadecan-10-one
• SMILES (Canonical): CC1C2CCC3(C(CCC34CC(C2OC1=O)(OO4)O)O)C
• SMILES (Isomeric): CC1C2CC[C@]3([C@@H](CC[C@@]34C[C@@]([C@H]2OC1=O)(OO4)O)O)C
• InChI: InChI=1S/C15H22O6/c1-8-9-3-5-13(2)10(16)4-6-14(13)7-15(18,21-20-14)11(9)19-12(8)17/h8-11,16,18H,3-7H2,1-2H3/t8?,9?,10-,11+,13+,14-,15+/m1/s1
• InChI Key: UKBRRPFBNDFXGR-PLTKTJNRSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₆
• Molecular Weight: 298.33 g/mol
• Exact Mass: 298.14163842 g/mol
• Topological Polar Surface Area (TPSA): 85.20 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 0.90
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• NSC647625
• NSC-647625
• NCI60_016578
• (1R,4R,5S,12S,13S)-4,13-dihydroxy-5,9-dimethyl-11,14,15-trioxatetracyclo[11.2.1.01,5.08,12]hexadecan-10-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9507	95.07%
Caco-2	+	0.5378	53.78%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6501	65.01%
OATP2B1 inhibitior	-	0.8547	85.47%
OATP1B1 inhibitior	+	0.9250	92.50%
OATP1B3 inhibitior	+	0.9171	91.71%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7821	78.21%
BSEP inhibitior	-	0.9379	93.79%
P-glycoprotein inhibitior	-	0.9066	90.66%
P-glycoprotein substrate	-	0.7806	78.06%
CYP3A4 substrate	+	0.5979	59.79%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8281	82.81%
CYP3A4 inhibition	-	0.8683	86.83%
CYP2C9 inhibition	-	0.9141	91.41%
CYP2C19 inhibition	-	0.8919	89.19%
CYP2D6 inhibition	-	0.9596	95.96%
CYP1A2 inhibition	-	0.5449	54.49%
CYP2C8 inhibition	-	0.8847	88.47%
CYP inhibitory promiscuity	-	0.9886	98.86%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5293	52.93%
Eye corrosion	-	0.9825	98.25%
Eye irritation	-	0.9534	95.34%
Skin irritation	-	0.5343	53.43%
Skin corrosion	-	0.8235	82.35%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7593	75.93%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	+	0.7283	72.83%
skin sensitisation	-	0.8546	85.46%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.7313	73.13%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.6843	68.43%
Acute Oral Toxicity (c)	III	0.3951	39.51%
Estrogen receptor binding	+	0.9292	92.92%
Androgen receptor binding	+	0.7019	70.19%
Thyroid receptor binding	+	0.5560	55.60%
Glucocorticoid receptor binding	+	0.6953	69.53%
Aromatase binding	+	0.7899	78.99%
PPAR gamma	+	0.5693	56.93%
Honey bee toxicity	-	0.8942	89.42%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5066	50.66%
Fish aquatic toxicity	+	0.8782	87.82%

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	90.97%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.73%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.22%	97.25%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.32%	99.23%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	86.23%	93.04%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.65%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	84.30%	94.75%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.27%	93.03%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.66%	89.00%

Plants that contains it

• Seriphidium diffusum

Cross-Links

• PubChem: 6711941
• LOTUS: LTS0207863
• wikiData: Q105274446