Maximolide

Details

• Internal ID: 2aa24f86-f4b9-4ad5-9975-2e5e3d37c171
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3S,3aR,4S,6aR,9S,9aR,9bR)-4-hydroxy-3,9-dimethyl-6-methylidene-3a,4,5,6a,7,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2,8-dione
• SMILES (Canonical): CC1C2C(CC1=O)C(=C)CC(C3C2OC(=O)C3C)O
• SMILES (Isomeric): C[C@H]1[C@H]2[C@@H](CC1=O)C(=C)C[C@@H]([C@@H]3[C@@H]2OC(=O)[C@H]3C)O
• InChI: InChI=1S/C15H20O4/c1-6-4-11(17)13-8(3)15(18)19-14(13)12-7(2)10(16)5-9(6)12/h7-9,11-14,17H,1,4-5H2,2-3H3/t7-,8+,9+,11+,12+,13-,14-/m1/s1
• InChI Key: ZAPNUFCAIXITRW-LUQFHCQZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.32 g/mol
• Exact Mass: 264.13615911 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.33
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 30825-69-5
• DTXSID901109917
• (3S,3aR,4S,6aR,9S,9aR,9bR)-Octahydro-4-hydroxy-3,9-dimethyl-6-methyleneazuleno[4,5-b]furan-2,8(3H,4H)-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9879	98.79%
Caco-2	+	0.6368	63.68%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5326	53.26%
OATP2B1 inhibitior	-	0.8581	85.81%
OATP1B1 inhibitior	+	0.8675	86.75%
OATP1B3 inhibitior	+	0.9404	94.04%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9425	94.25%
P-glycoprotein inhibitior	-	0.8900	89.00%
P-glycoprotein substrate	-	0.8864	88.64%
CYP3A4 substrate	+	0.5418	54.18%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8352	83.52%
CYP3A4 inhibition	-	0.7204	72.04%
CYP2C9 inhibition	-	0.9237	92.37%
CYP2C19 inhibition	-	0.8937	89.37%
CYP2D6 inhibition	-	0.9506	95.06%
CYP1A2 inhibition	-	0.7368	73.68%
CYP2C8 inhibition	-	0.9547	95.47%
CYP inhibitory promiscuity	-	0.9658	96.58%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9425	94.25%
Carcinogenicity (trinary)	Non-required	0.5604	56.04%
Eye corrosion	-	0.9395	93.95%
Eye irritation	-	0.5899	58.99%
Skin irritation	-	0.5174	51.74%
Skin corrosion	-	0.8488	84.88%
Ames mutagenesis	-	0.6154	61.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6342	63.42%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	+	0.7587	75.87%
skin sensitisation	-	0.7173	71.73%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.6189	61.89%
Acute Oral Toxicity (c)	II	0.4600	46.00%
Estrogen receptor binding	-	0.6410	64.10%
Androgen receptor binding	-	0.5198	51.98%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.6353	63.53%
Aromatase binding	-	0.7865	78.65%
PPAR gamma	-	0.8931	89.31%
Honey bee toxicity	-	0.7640	76.40%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5150	51.50%
Fish aquatic toxicity	+	0.9701	97.01%

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	92.75%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	91.58%	91.49%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.83%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.82%	96.09%
CHEMBL2581	P07339	Cathepsin D	88.52%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.53%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.27%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.58%	99.23%

Plants that contains it

• Colchicum soboliferum
• Psorothamnus spinosus
• Trachelospermum asiaticum

Cross-Links

• PubChem: 12047616
• NPASS: NPC255250
• LOTUS: LTS0205563
• wikiData: Q105370009