(1S)-4alpha-Ethenyl-2alpha-hydroxy-3beta-[1-(hydroxymethyl)ethenyl]-6alpha-[[2-(hydroxymethyl)-1-oxo-2-propenyl]oxy

Details

• Internal ID: 92dfe905-963f-49ae-b4df-ea08f6e92de1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Elemane sesquiterpenoids
• IUPAC Name: [(1S,2S,3R,4R,5S)-5-ethenyl-3-hydroxy-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl] 2-(hydroxymethyl)prop-2-enoate
• SMILES (Canonical): CC1(CC(C(C(C1C(=C)CO)O)C(=C)C(=O)OC)OC(=O)C(=C)CO)C=C
• SMILES (Isomeric): C[C@]1(C[C@@H]([C@H]([C@@H]([C@H]1C(=C)CO)O)C(=C)C(=O)OC)OC(=O)C(=C)CO)C=C
• InChI: InChI=1S/C20H28O7/c1-7-20(5)8-14(27-18(24)12(3)10-22)15(13(4)19(25)26-6)17(23)16(20)11(2)9-21/h7,14-17,21-23H,1-4,8-10H2,5-6H3/t14-,15+,16+,17-,20+/m0/s1
• InChI Key: HHUHNVIGEYMOJY-HAJKQMQPSA-N
• Popularity: 9 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₇
• Molecular Weight: 380.40 g/mol
• Exact Mass: 380.18350323 g/mol
• Topological Polar Surface Area (TPSA): 113.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 0.91
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 8

Synonyms

• (1S)-4alpha-Ethenyl-2alpha-hydroxy-3beta-[1-(hydroxymethyl)ethenyl]-6alpha-[[2-(hydroxymethyl)-1-oxo-2-propenyl]oxy
• [(1S,2S,3R,4R,5S)-5-ethenyl-3-hydroxy-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl] 2-(hydroxymethyl)prop-2-enoate
• CHEMBL4572552

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8494	84.94%
Caco-2	-	0.7256	72.56%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8608	86.08%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9253	92.53%
OATP1B3 inhibitior	+	0.9171	91.71%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8226	82.26%
P-glycoprotein inhibitior	-	0.7238	72.38%
P-glycoprotein substrate	-	0.5572	55.72%
CYP3A4 substrate	+	0.6494	64.94%
CYP2C9 substrate	-	0.8190	81.90%
CYP2D6 substrate	-	0.8622	86.22%
CYP3A4 inhibition	-	0.8224	82.24%
CYP2C9 inhibition	-	0.8539	85.39%
CYP2C19 inhibition	-	0.7567	75.67%
CYP2D6 inhibition	-	0.9130	91.30%
CYP1A2 inhibition	-	0.8292	82.92%
CYP2C8 inhibition	-	0.7598	75.98%
CYP inhibitory promiscuity	-	0.9282	92.82%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7326	73.26%
Carcinogenicity (trinary)	Non-required	0.6738	67.38%
Eye corrosion	-	0.9767	97.67%
Eye irritation	-	0.9243	92.43%
Skin irritation	-	0.7621	76.21%
Skin corrosion	-	0.9718	97.18%
Ames mutagenesis	-	0.5744	57.44%
Human Ether-a-go-go-Related Gene inhibition	-	0.5169	51.69%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.5867	58.67%
skin sensitisation	-	0.6785	67.85%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	-	0.6375	63.75%
Nephrotoxicity	+	0.7547	75.47%
Acute Oral Toxicity (c)	III	0.6445	64.45%
Estrogen receptor binding	+	0.6462	64.62%
Androgen receptor binding	+	0.5655	56.55%
Thyroid receptor binding	+	0.6101	61.01%
Glucocorticoid receptor binding	+	0.6846	68.46%
Aromatase binding	-	0.5083	50.83%
PPAR gamma	-	0.4925	49.25%
Honey bee toxicity	-	0.5873	58.73%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9481	94.81%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.98%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.32%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	89.01%	90.17%
CHEMBL340	P08684	Cytochrome P450 3A4	88.86%	91.19%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	87.19%	94.33%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	87.00%	91.24%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.86%	94.45%
CHEMBL4040	P28482	MAP kinase ERK2	86.34%	83.82%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	83.54%	91.03%
CHEMBL3437	Q16853	Amine oxidase, copper containing	83.49%	94.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.70%	91.07%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.64%	99.17%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.08%	95.50%

Plants that contains it

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

Cross-Links

• PubChem: 13891365
• NPASS: NPC205355
• LOTUS: LTS0008678
• wikiData: Q104399241