Hemistepsin

Details

• Internal ID: 4c2663b3-735b-4c61-af85-4f024c38b087
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones
• IUPAC Name: [(3aS,5aR,7S,8aR,9R,9aR)-7-hydroxy-1,5,8-trimethylidene-2-oxo-3a,4,5a,6,7,8a,9,9a-octahydroazuleno[6,5-b]furan-9-yl] 2-(hydroxymethyl)prop-2-enoate
• SMILES (Canonical): C=C1CC2C(C(C3C1CC(C3=C)O)OC(=O)C(=C)CO)C(=C)C(=O)O2
• SMILES (Isomeric): C=C1C[C@H]2[C@H]([C@@H]([C@@H]3[C@H]1C[C@@H](C3=C)O)OC(=O)C(=C)CO)C(=C)C(=O)O2
• InChI: InChI=1S/C19H22O6/c1-8-5-14-16(11(4)19(23)24-14)17(25-18(22)9(2)7-20)15-10(3)13(21)6-12(8)15/h12-17,20-21H,1-7H2/t12-,13-,14-,15-,16+,17+/m0/s1
• InChI Key: IPZJSGMDGJTDNK-NQLMQOPMSA-N
• Popularity: 10 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₂O₆
• Molecular Weight: 346.40 g/mol
• Exact Mass: 346.14163842 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 1.06
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• [(3aS,5aR,7S,8aR,9R,9aR)-7-hydroxy-1,5,8-trimethylidene-2-oxo-3a,4,5a,6,7,8a,9,9a-octahydroazuleno[6,5-b]furan-9-yl] 2-(hydroxymethyl)prop-2-enoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9776	97.76%
Caco-2	-	0.6335	63.35%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6079	60.79%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8929	89.29%
OATP1B3 inhibitior	+	0.9559	95.59%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8667	86.67%
P-glycoprotein inhibitior	-	0.7867	78.67%
P-glycoprotein substrate	-	0.6224	62.24%
CYP3A4 substrate	+	0.6190	61.90%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8228	82.28%
CYP3A4 inhibition	-	0.8308	83.08%
CYP2C9 inhibition	-	0.8816	88.16%
CYP2C19 inhibition	-	0.8290	82.90%
CYP2D6 inhibition	-	0.9145	91.45%
CYP1A2 inhibition	-	0.7904	79.04%
CYP2C8 inhibition	-	0.8101	81.01%
CYP inhibitory promiscuity	-	0.8741	87.41%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6613	66.13%
Eye corrosion	-	0.9416	94.16%
Eye irritation	-	0.5000	50.00%
Skin irritation	-	0.6794	67.94%
Skin corrosion	-	0.8874	88.74%
Ames mutagenesis	-	0.6054	60.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6840	68.40%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	+	0.7000	70.00%
skin sensitisation	-	0.8020	80.20%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.6683	66.83%
Acute Oral Toxicity (c)	III	0.4692	46.92%
Estrogen receptor binding	+	0.6016	60.16%
Androgen receptor binding	+	0.6228	62.28%
Thyroid receptor binding	-	0.5204	52.04%
Glucocorticoid receptor binding	+	0.5645	56.45%
Aromatase binding	-	0.5442	54.42%
PPAR gamma	+	0.5939	59.39%
Honey bee toxicity	-	0.6702	67.02%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.8791	87.91%

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	96.17%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.61%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.09%	96.09%
CHEMBL2996	Q05655	Protein kinase C delta	86.70%	97.79%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.71%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.56%	99.23%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	83.56%	96.37%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.48%	89.00%
CHEMBL221	P23219	Cyclooxygenase-1	83.17%	90.17%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.15%	99.17%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	82.63%	89.34%
CHEMBL299	P17252	Protein kinase C alpha	81.72%	98.03%
CHEMBL340	P08684	Cytochrome P450 3A4	81.49%	91.19%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.30%	93.04%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.24%	93.03%

Plants that contains it

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

Cross-Links

• PubChem: 10043230
• NPASS: NPC200254
• LOTUS: LTS0257026
• wikiData: Q103816419