Desacylcynaropicrin

Details

• Internal ID: 6303066b-4a84-49b6-ba66-0b2ed8d4112b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3aR,4S,6aR,8S,9aR,9bR)-4,8-dihydroxy-3,6,9-trimethylidene-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one
• SMILES (Canonical): C=C1CC(C2C(C3C1CC(C3=C)O)OC(=O)C2=C)O
• SMILES (Isomeric): C=C1C[C@@H]([C@@H]2[C@@H]([C@@H]3[C@H]1C[C@@H](C3=C)O)OC(=O)C2=C)O
• InChI: InChI=1S/C15H18O4/c1-6-4-11(17)13-8(3)15(18)19-14(13)12-7(2)10(16)5-9(6)12/h9-14,16-17H,1-5H2/t9-,10-,11-,12-,13+,14+/m0/s1
• InChI Key: VPRPYNVJJXOFKZ-SNIKSBKOSA-N
• Popularity: 25 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₄
• Molecular Weight: 262.30 g/mol
• Exact Mass: 262.12050905 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): 0.96
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• CHEMBL464877

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9866	98.66%
Caco-2	-	0.5704	57.04%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.7286	72.86%
Subcellular localzation	Mitochondria	0.4789	47.89%
OATP2B1 inhibitior	-	0.8573	85.73%
OATP1B1 inhibitior	+	0.9019	90.19%
OATP1B3 inhibitior	+	0.9517	95.17%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9485	94.85%
P-glycoprotein inhibitior	-	0.9245	92.45%
P-glycoprotein substrate	-	0.8492	84.92%
CYP3A4 substrate	+	0.5267	52.67%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7973	79.73%
CYP3A4 inhibition	-	0.8361	83.61%
CYP2C9 inhibition	-	0.9320	93.20%
CYP2C19 inhibition	-	0.8428	84.28%
CYP2D6 inhibition	-	0.9357	93.57%
CYP1A2 inhibition	-	0.8231	82.31%
CYP2C8 inhibition	-	0.9350	93.50%
CYP inhibitory promiscuity	-	0.9097	90.97%
UGT catelyzed	+	0.6362	63.62%
Carcinogenicity (binary)	-	0.9325	93.25%
Carcinogenicity (trinary)	Non-required	0.5141	51.41%
Eye corrosion	-	0.8773	87.73%
Eye irritation	+	0.7602	76.02%
Skin irritation	-	0.5616	56.16%
Skin corrosion	-	0.8841	88.41%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7553	75.53%
Micronuclear	-	0.5200	52.00%
Hepatotoxicity	+	0.8172	81.72%
skin sensitisation	-	0.7351	73.51%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.6876	68.76%
Acute Oral Toxicity (c)	III	0.3534	35.34%
Estrogen receptor binding	+	0.5910	59.10%
Androgen receptor binding	+	0.5580	55.80%
Thyroid receptor binding	-	0.5449	54.49%
Glucocorticoid receptor binding	+	0.6748	67.48%
Aromatase binding	-	0.7293	72.93%
PPAR gamma	-	0.7227	72.27%
Honey bee toxicity	-	0.6206	62.06%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.8960	89.60%

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	91.54%	91.11%
CHEMBL308	P06493	Cyclin-dependent kinase 1	91.01%	91.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.71%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.42%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.21%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.99%	99.23%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	84.78%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.85%	89.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.18%	93.03%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.32%	95.89%

Plants that contains it

• Achillea arabica
• Acrisione denticulata
• Archidendron ellipticum
• Baccharis dracunculifolia
• Berberis orthobotrys
• Blumea eriantha
• Bulbinella floribunda
• Caryocar villosum
• Centaurea behen
• Centaurea collina
• Centaurea deflexa
• Centaurea kotschyi
• Centaurea scoparia
• Cephalotaxus harringtonii
• Ceriops decandra
• Cheirolophus canariensis
• Cipadessa baccifera
• Cousinia canescens
• 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
• Phlojodicarpus sibiricus
• Physalis sordida
• Pseudostifftia kingii
• Sanicula epipactis
• Saussurea pulchella
• Saussurea pulchella
• Senecio heliopsis
• Solidago petiolaris
• Tabernaemontana divaricata
• Vernonanthura montevidensis
• Volutaria tubuliflora
• Zaluzania grayana
• Zanthoxylum rhoifolium
• Zygia racemosa

Cross-Links

• PubChem: 13943205
• NPASS: NPC187661
• ChEMBL: CHEMBL464877
• LOTUS: LTS0037543
• wikiData: Q105290951