(1S,5S,5aS,8aR,9S)-1,5,9-trihydroxy-5,7,7-trimethyl-4,5a,6,8,8a,9-hexahydro-1H-azuleno[5,6-c]furan-3-one

Details

• Internal ID: 0f92bff5-4617-41bb-9007-c4be49d30ca3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (1S,5S,5aS,8aR,9S)-1,5,9-trihydroxy-5,7,7-trimethyl-4,5a,6,8,8a,9-hexahydro-1H-azuleno[5,6-c]furan-3-one
• SMILES (Canonical): CC1(CC2C(C1)C(CC3=C(C2O)C(OC3=O)O)(C)O)C
• SMILES (Isomeric): C[C@@]1(CC2=C([C@H]([C@H]3[C@@H]1CC(C3)(C)C)O)[C@H](OC2=O)O)O
• InChI: InChI=1S/C15H22O5/c1-14(2)4-7-9(6-14)15(3,19)5-8-10(11(7)16)13(18)20-12(8)17/h7,9,11,13,16,18-19H,4-6H2,1-3H3/t7-,9+,11+,13+,15+/m1/s1
• InChI Key: MWDNWQAVYQDZQI-WXOFPVIGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₅
• Molecular Weight: 282.33 g/mol
• Exact Mass: 282.14672380 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 0.73
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9846	98.46%
Caco-2	-	0.5717	57.17%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5706	57.06%
OATP2B1 inhibitior	-	0.8512	85.12%
OATP1B1 inhibitior	+	0.9260	92.60%
OATP1B3 inhibitior	+	0.9330	93.30%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.8754	87.54%
P-glycoprotein inhibitior	-	0.8946	89.46%
P-glycoprotein substrate	-	0.8768	87.68%
CYP3A4 substrate	+	0.5488	54.88%
CYP2C9 substrate	-	0.7948	79.48%
CYP2D6 substrate	-	0.8745	87.45%
CYP3A4 inhibition	-	0.8061	80.61%
CYP2C9 inhibition	-	0.7288	72.88%
CYP2C19 inhibition	-	0.7814	78.14%
CYP2D6 inhibition	-	0.9376	93.76%
CYP1A2 inhibition	-	0.5996	59.96%
CYP2C8 inhibition	-	0.9014	90.14%
CYP inhibitory promiscuity	-	0.9055	90.55%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5323	53.23%
Eye corrosion	-	0.9812	98.12%
Eye irritation	-	0.9511	95.11%
Skin irritation	-	0.5714	57.14%
Skin corrosion	-	0.9265	92.65%
Ames mutagenesis	+	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4611	46.11%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	+	0.5052	50.52%
skin sensitisation	-	0.7436	74.36%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.7947	79.47%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.7058	70.58%
Acute Oral Toxicity (c)	III	0.3167	31.67%
Estrogen receptor binding	+	0.5265	52.65%
Androgen receptor binding	-	0.5403	54.03%
Thyroid receptor binding	+	0.5959	59.59%
Glucocorticoid receptor binding	+	0.7673	76.73%
Aromatase binding	-	0.6705	67.05%
PPAR gamma	-	0.5468	54.68%
Honey bee toxicity	-	0.9078	90.78%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9739	97.39%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.05%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.39%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.64%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.96%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.55%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.28%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.55%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.09%	99.23%
CHEMBL2581	P07339	Cathepsin D	85.91%	98.95%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.58%	97.14%
CHEMBL221	P23219	Cyclooxygenase-1	81.15%	90.17%

Plants that contains it

• Anastatica hierochuntica
• Maclura cochinchinensis

Cross-Links

• PubChem: 95049893
• NPASS: NPC262486
• LOTUS: LTS0177804
• wikiData: Q105173520