Cynarinin B

Details

• Internal ID: bf44ec48-d9ae-49d9-9482-83763306e7b7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3S,3aR,4S,6aR,9aR,9bR)-3-(chloromethyl)-3,4,8-trihydroxy-9-methyl-6-methylidene-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2-one
• SMILES (Canonical): CC1=C(CC2C1C3C(C(CC2=C)O)C(C(=O)O3)(CCl)O)O
• SMILES (Isomeric): CC1=C(C[C@@H]2[C@H]1[C@@H]3[C@@H]([C@H](CC2=C)O)[C@](C(=O)O3)(CCl)O)O
• InChI: InChI=1S/C15H19ClO5/c1-6-3-10(18)12-13(21-14(19)15(12,20)5-16)11-7(2)9(17)4-8(6)11/h8,10-13,17-18,20H,1,3-5H2,2H3/t8-,10-,11-,12+,13+,15-/m0/s1
• InChI Key: PTDXNVRQLVXJTB-ALLIFDDBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₉ClO₅
• Molecular Weight: 314.76 g/mol
• Exact Mass: 314.0921014 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 1.29
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9640	96.40%
Caco-2	-	0.7641	76.41%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5177	51.77%
OATP2B1 inhibitior	-	0.8574	85.74%
OATP1B1 inhibitior	+	0.8764	87.64%
OATP1B3 inhibitior	+	0.9529	95.29%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9113	91.13%
P-glycoprotein inhibitior	-	0.9280	92.80%
P-glycoprotein substrate	-	0.6328	63.28%
CYP3A4 substrate	+	0.6257	62.57%
CYP2C9 substrate	-	0.8063	80.63%
CYP2D6 substrate	-	0.8536	85.36%
CYP3A4 inhibition	-	0.8797	87.97%
CYP2C9 inhibition	-	0.8552	85.52%
CYP2C19 inhibition	-	0.7790	77.90%
CYP2D6 inhibition	-	0.9164	91.64%
CYP1A2 inhibition	-	0.7251	72.51%
CYP2C8 inhibition	-	0.8658	86.58%
CYP inhibitory promiscuity	-	0.9111	91.11%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8444	84.44%
Carcinogenicity (trinary)	Non-required	0.4854	48.54%
Eye corrosion	-	0.9792	97.92%
Eye irritation	-	0.7686	76.86%
Skin irritation	-	0.5786	57.86%
Skin corrosion	-	0.8816	88.16%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7699	76.99%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	+	0.7236	72.36%
skin sensitisation	-	0.7803	78.03%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.8369	83.69%
Acute Oral Toxicity (c)	III	0.4409	44.09%
Estrogen receptor binding	+	0.5451	54.51%
Androgen receptor binding	+	0.5216	52.16%
Thyroid receptor binding	+	0.6930	69.30%
Glucocorticoid receptor binding	+	0.7931	79.31%
Aromatase binding	-	0.6234	62.34%
PPAR gamma	-	0.6476	64.76%
Honey bee toxicity	-	0.8068	80.68%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9739	97.39%

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	94.22%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.56%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.28%	96.09%
CHEMBL2581	P07339	Cathepsin D	87.12%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.27%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.66%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.59%	97.09%
CHEMBL5103	Q969S8	Histone deacetylase 10	82.28%	90.08%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.81%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.62%	95.89%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	81.24%	85.11%

Plants that contains it

• Carlina acaulis

Cross-Links

• PubChem: 101369114
• NPASS: NPC136983