(1S,8S,9R)-2,8-dihydroxy-7-methyl-12-prop-1-en-2-ylspiro[4,10-dioxatetracyclo[7.2.1.02,7.03,5]dodecane-6,2'-oxirane]-11-one

Details

• Internal ID: 6bf52bee-2918-4c1a-863c-8bfb367937af
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (1S,8S,9R)-2,8-dihydroxy-7-methyl-12-prop-1-en-2-ylspiro[4,10-dioxatetracyclo[7.2.1.02,7.03,5]dodecane-6,2'-oxirane]-11-one
• SMILES (Canonical): CC(=C)C1C2C(C3(C4(CO4)C5C(C3(C1C(=O)O2)O)O5)C)O
• SMILES (Isomeric): CC(=C)C1[C@@H]2[C@H](C3(C4(CO4)C5C(C3([C@H]1C(=O)O2)O)O5)C)O
• InChI: InChI=1S/C15H18O6/c1-5(2)6-7-12(17)20-8(6)9(16)13(3)14(4-19-14)10-11(21-10)15(7,13)18/h6-11,16,18H,1,4H2,2-3H3/t6?,7-,8-,9-,10?,11?,13?,14?,15?/m1/s1
• InChI Key: CCAZWUJBLXKBAY-QSJQHWBNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₆
• Molecular Weight: 294.30 g/mol
• Exact Mass: 294.11033829 g/mol
• Topological Polar Surface Area (TPSA): 91.80 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -0.62
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9210	92.10%
Caco-2	-	0.7764	77.64%
Blood Brain Barrier	-	0.5973	59.73%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6116	61.16%
OATP2B1 inhibitior	-	0.8540	85.40%
OATP1B1 inhibitior	+	0.9067	90.67%
OATP1B3 inhibitior	+	0.9612	96.12%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9078	90.78%
P-glycoprotein inhibitior	-	0.8577	85.77%
P-glycoprotein substrate	-	0.6869	68.69%
CYP3A4 substrate	+	0.5936	59.36%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8612	86.12%
CYP3A4 inhibition	-	0.7029	70.29%
CYP2C9 inhibition	-	0.8534	85.34%
CYP2C19 inhibition	-	0.7948	79.48%
CYP2D6 inhibition	-	0.8974	89.74%
CYP1A2 inhibition	-	0.8026	80.26%
CYP2C8 inhibition	-	0.9372	93.72%
CYP inhibitory promiscuity	-	0.6464	64.64%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6547	65.47%
Eye corrosion	-	0.9819	98.19%
Eye irritation	-	0.9233	92.33%
Skin irritation	-	0.6262	62.62%
Skin corrosion	-	0.9051	90.51%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8136	81.36%
Micronuclear	-	0.5300	53.00%
Hepatotoxicity	+	0.7282	72.82%
skin sensitisation	-	0.7456	74.56%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.9178	91.78%
Acute Oral Toxicity (c)	I	0.4498	44.98%
Estrogen receptor binding	+	0.7104	71.04%
Androgen receptor binding	+	0.6413	64.13%
Thyroid receptor binding	+	0.5765	57.65%
Glucocorticoid receptor binding	-	0.4819	48.19%
Aromatase binding	-	0.5396	53.96%
PPAR gamma	+	0.6998	69.98%
Honey bee toxicity	-	0.8182	81.82%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9576	95.76%

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	94.91%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	93.98%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.21%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.40%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.28%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.62%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.34%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.94%	100.00%
CHEMBL2581	P07339	Cathepsin D	83.89%	98.95%

Plants that contains it

• Tussilago farfara

Cross-Links

• PubChem: 5322181
• NPASS: NPC53872