Chlorojanerin

Details

• Internal ID: ec052e6f-312a-4dc1-bffb-04722c1652b0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(3aR,4S,6aR,8S,9S,9aS,9bS)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoate
• InChI: InChI=1S/C19H23ClO7/c1-8-4-12(26-17(23)9(2)6-21)14-10(3)18(24)27-16(14)15-11(8)5-13(22)19(15,25)7-20/h11-16,21-22,25H,1-7H2/t11-,12-,13-,14+,15-,16-,19+/m0/s1
• InChI Key: UHEMKMBRGXUBMJ-URUZQALBSA-N
• Popularity: 19 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₃ClO₇
• Molecular Weight: 398.80 g/mol
• Exact Mass: 398.1132308 g/mol
• Topological Polar Surface Area (TPSA): 113.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): 0.47
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• 64205-85-2
• [(3aR,4S,6aR,8S,9S,9aS,9bS)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoate
• DTXSID60982752
• (1R,3S,4R,5S,6S,7R,8S)-4-chloromethyl-3,4-diyhdroxy- 8-(4-hydroxymethacrylate)-1H,5H,6H,7H-guaia-10(14),11(13)-dien-6,12-olide,
• [(3aR,4S,6aR,8S,9S,9aS,9bS)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoate
• 2-(Hydroxymethyl)propenoic acid 9-(chloromethyl)dodecahydro-8,9-dihydroxy-3,6-dimethylene-2-oxoazuleno[4,5-b]furan-4-yl ester
• 2-Propenoic acid, 2-(hydroxymethyl)-, 9-(chloromethyl)dodecahydro-8,9-dihydroxy-3,6-bis(methylene)-2-oxoazuleno(4,5-b)furan-4-yl ester, (3aR-(3aalpha,4alpha,6aalpha,8beta,9alpha,9aalpha,9bbeta))-
• 9-(Chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxododecahydroazuleno[4,5-b]furan-4-yl 2-(hydroxymethyl)prop-2-enoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8996	89.96%
Caco-2	-	0.7849	78.49%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6711	67.11%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8951	89.51%
OATP1B3 inhibitior	+	0.9523	95.23%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9227	92.27%
P-glycoprotein inhibitior	-	0.7383	73.83%
P-glycoprotein substrate	-	0.5356	53.56%
CYP3A4 substrate	+	0.6782	67.82%
CYP2C9 substrate	-	0.8167	81.67%
CYP2D6 substrate	-	0.8451	84.51%
CYP3A4 inhibition	-	0.7733	77.33%
CYP2C9 inhibition	-	0.8113	81.13%
CYP2C19 inhibition	-	0.7242	72.42%
CYP2D6 inhibition	-	0.8976	89.76%
CYP1A2 inhibition	-	0.7874	78.74%
CYP2C8 inhibition	-	0.6452	64.52%
CYP inhibitory promiscuity	-	0.9522	95.22%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8344	83.44%
Carcinogenicity (trinary)	Non-required	0.5633	56.33%
Eye corrosion	-	0.9767	97.67%
Eye irritation	-	0.8738	87.38%
Skin irritation	-	0.7273	72.73%
Skin corrosion	-	0.9144	91.44%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5816	58.16%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.8316	83.16%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.9042	90.42%
Acute Oral Toxicity (c)	III	0.4542	45.42%
Estrogen receptor binding	+	0.6797	67.97%
Androgen receptor binding	+	0.6480	64.80%
Thyroid receptor binding	+	0.5756	57.56%
Glucocorticoid receptor binding	+	0.6464	64.64%
Aromatase binding	+	0.5894	58.94%
PPAR gamma	+	0.6453	64.53%
Honey bee toxicity	-	0.5861	58.61%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9445	94.45%

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	97.66%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.25%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	92.08%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.54%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.89%	86.33%
CHEMBL2996	Q05655	Protein kinase C delta	86.31%	97.79%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.53%	96.09%
CHEMBL299	P17252	Protein kinase C alpha	82.83%	98.03%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	82.44%	89.34%
CHEMBL340	P08684	Cytochrome P450 3A4	81.64%	91.19%

Plants that contains it

• Centaurea aegyptiaca
• Centaurea hermannii
• Centaurea musimonum
• Centaurea scoparia
• Centaurea thracica
• Centaurothamnus maximus
• Cousinia adenosticta
• Cousinia piptocephala
• Psephellus bellus
• Psephellus marschallianus
• Rhaponticum carthamoides subsp. carthamoides
• Saussurea candicans
• Saussurea lipschitzii

Cross-Links

• PubChem: 182408
• LOTUS: LTS0194484
• wikiData: Q82969571