(3aR)-8-(hydroxymethyl)-1,5-dimethyl-3a,4-dihydroazuleno[6,5-b]furan-2,6-dione

Details

• Internal ID: e7cfa82b-bd14-4e9f-87fa-177cc50ea52f
• Taxonomy: Organoheterocyclic compounds > Dihydrofurans > Furanones > Butenolides
• IUPAC Name: (3aR)-8-(hydroxymethyl)-1,5-dimethyl-3a,4-dihydroazuleno[6,5-b]furan-2,6-dione
• SMILES (Canonical): CC1=C2C(=CC3=C(C(=O)OC3C1)C)C(=CC2=O)CO
• SMILES (Isomeric): CC1=C2C(=CC3=C(C(=O)O[C@@H]3C1)C)C(=CC2=O)CO
• InChI: InChI=1S/C15H14O4/c1-7-3-13-10(8(2)15(18)19-13)5-11-9(6-16)4-12(17)14(7)11/h4-5,13,16H,3,6H2,1-2H3/t13-/m1/s1
• InChI Key: GKSSCOBCDYINTF-CYBMUJFWSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₄O₄
• Molecular Weight: 258.27 g/mol
• Exact Mass: 258.08920892 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): 1.38
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9875	98.75%
Caco-2	+	0.8245	82.45%
Blood Brain Barrier	+	0.5839	58.39%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6493	64.93%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9234	92.34%
OATP1B3 inhibitior	+	0.9484	94.84%
MATE1 inhibitior	-	0.8212	82.12%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.7999	79.99%
P-glycoprotein inhibitior	-	0.9309	93.09%
P-glycoprotein substrate	-	0.7636	76.36%
CYP3A4 substrate	+	0.5066	50.66%
CYP2C9 substrate	-	0.8080	80.80%
CYP2D6 substrate	-	0.8974	89.74%
CYP3A4 inhibition	-	0.8786	87.86%
CYP2C9 inhibition	-	0.8379	83.79%
CYP2C19 inhibition	-	0.8915	89.15%
CYP2D6 inhibition	-	0.9286	92.86%
CYP1A2 inhibition	-	0.6136	61.36%
CYP2C8 inhibition	-	0.9223	92.23%
CYP inhibitory promiscuity	-	0.9015	90.15%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9160	91.60%
Carcinogenicity (trinary)	Non-required	0.5297	52.97%
Eye corrosion	-	0.9613	96.13%
Eye irritation	-	0.7142	71.42%
Skin irritation	-	0.6271	62.71%
Skin corrosion	-	0.8980	89.80%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8214	82.14%
Micronuclear	-	0.6141	61.41%
Hepatotoxicity	+	0.6000	60.00%
skin sensitisation	-	0.6999	69.99%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.5711	57.11%
Acute Oral Toxicity (c)	III	0.5145	51.45%
Estrogen receptor binding	+	0.6815	68.15%
Androgen receptor binding	+	0.5836	58.36%
Thyroid receptor binding	-	0.7061	70.61%
Glucocorticoid receptor binding	-	0.5217	52.17%
Aromatase binding	-	0.7445	74.45%
PPAR gamma	-	0.5660	56.60%
Honey bee toxicity	-	0.9211	92.11%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.8458	84.58%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	94.04%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.43%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.42%	85.14%
CHEMBL5103	Q969S8	Histone deacetylase 10	87.25%	90.08%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.68%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.39%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.55%	99.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.90%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.70%	96.09%

Plants that contains it

• Agathosma scaberula
• Balanophora harlandii
• Cichorium intybus
• Euphorbia nicaeensis
• Lupinus cosentinii
• Polemonium caeruleum
• Strychnos ledermannii
• Viburnum davidii

Cross-Links

• PubChem: 54576216
• NPASS: NPC47287
• LOTUS: LTS0171939
• wikiData: Q105010260