Isolipidiol

Details

• Internal ID: fe75e697-5ae7-426f-a627-a6758aee3f7a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3S,3aR,4S,6aR,8S,9S,9aR,9bR)-4,8-dihydroxy-3,9-dimethyl-6-methylidene-3,3a,4,5,6a,7,8,9,9a,9b-decahydroazuleno[4,5-b]furan-2-one
• SMILES (Canonical): CC1C(CC2C1C3C(C(C(=O)O3)C)C(CC2=C)O)O
• SMILES (Isomeric): C[C@@H]1[C@H](C[C@@H]2[C@H]1[C@@H]3[C@H]([C@@H](C(=O)O3)C)[C@H](CC2=C)O)O
• InChI: InChI=1S/C15H22O4/c1-6-4-11(17)13-8(3)15(18)19-14(13)12-7(2)10(16)5-9(6)12/h7-14,16-17H,1,4-5H2,2-3H3/t7-,8+,9+,10+,11+,12+,13-,14-/m1/s1
• InChI Key: LWHRXFOPIDTJSG-PFKAGXPPSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33 g/mol
• Exact Mass: 266.15180918 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.12
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• RefChem:149488
• 30825-68-4
• MLS002473225
• CHEMBL1441727
• HMS2213F09
• SMR001397312

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9881	98.81%
Caco-2	-	0.5643	56.43%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.4832	48.32%
OATP2B1 inhibitior	-	0.8550	85.50%
OATP1B1 inhibitior	+	0.8294	82.94%
OATP1B3 inhibitior	+	0.9473	94.73%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9305	93.05%
P-glycoprotein inhibitior	-	0.9106	91.06%
P-glycoprotein substrate	-	0.7656	76.56%
CYP3A4 substrate	+	0.5541	55.41%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8313	83.13%
CYP3A4 inhibition	-	0.6890	68.90%
CYP2C9 inhibition	-	0.9163	91.63%
CYP2C19 inhibition	-	0.8492	84.92%
CYP2D6 inhibition	-	0.9393	93.93%
CYP1A2 inhibition	-	0.6633	66.33%
CYP2C8 inhibition	-	0.9517	95.17%
CYP inhibitory promiscuity	-	0.9152	91.52%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9425	94.25%
Carcinogenicity (trinary)	Non-required	0.5246	52.46%
Eye corrosion	-	0.9547	95.47%
Eye irritation	-	0.8717	87.17%
Skin irritation	-	0.5562	55.62%
Skin corrosion	-	0.8867	88.67%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6606	66.06%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	+	0.7375	73.75%
skin sensitisation	-	0.7147	71.47%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.5491	54.91%
Acute Oral Toxicity (c)	II	0.3494	34.94%
Estrogen receptor binding	-	0.5727	57.27%
Androgen receptor binding	-	0.5265	52.65%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.7611	76.11%
PPAR gamma	-	0.8774	87.74%
Honey bee toxicity	-	0.7228	72.28%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9590	95.90%

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	95.85%	85.14%
CHEMBL1951	P21397	Monoamine oxidase A	92.98%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.73%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.38%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.01%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.25%	89.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.89%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.28%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.98%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.86%	95.56%
CHEMBL2581	P07339	Cathepsin D	83.48%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.19%	100.00%

Plants that contains it

• Achillea arabica
• Acrisione denticulata
• Archidendron ellipticum
• Baccharis dracunculifolia
• Berberis orthobotrys
• Blumea eriantha
• Bulbinella floribunda
• Caryocar villosum
• Centaurea macrocephala
• Cephalotaxus harringtonii
• Ceriops decandra
• Cipadessa baccifera
• Crepis tectorum
• Cucurbita moschata
• Cyclolepis genistoides
• Dalbergia ecastaphyllum
• Diplazium esculentum
• Euonymus laxiflorus
• Euphorbia jolkinii
• Glochidion philippicum
• Himalaiella deltoidea
• Ilex brevicuspis
• Myoporum platycarpum
• Ocimum gratissimum
• Ongokea gore
• Palaquium canaliculatum
• Pertya triloba
• Phlojodicarpus sibiricus
• Physalis sordida
• Sanicula epipactis
• Senecio heliopsis
• Solidago petiolaris
• Tabernaemontana divaricata
• Zaluzania grayana
• Zanthoxylum rhoifolium
• Zygia racemosa

Cross-Links

• PubChem: 14589530
• NPASS: NPC111409
• ChEMBL: CHEMBL1441727
• LOTUS: LTS0037380
• wikiData: Q105158303