(4R,9S)-12,19,21-trihydroxy-5,5,9-trimethyl-10,15,24-trioxahexacyclo[12.11.0.02,11.04,9.016,25.018,23]pentacosa-1(14),2(11),7,12,16(25),18,20,22-octaen-17-one

Details

• Internal ID: 08048809-2bb0-475d-a975-d2d06797f77b
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthenes
• IUPAC Name: (4R,9S)-12,19,21-trihydroxy-5,5,9-trimethyl-10,15,24-trioxahexacyclo[12.11.0.02,11.04,9.016,25.018,23]pentacosa-1(14),2(11),7,12,16(25),18,20,22-octaen-17-one
• SMILES (Canonical): CC1(CC=CC2(C1CC3=C(O2)C(=CC4=C3C5=C(O4)C(=O)C6=C(C=C(C=C6O5)O)O)O)C)C
• SMILES (Isomeric): C[C@]12C=CCC([C@H]1CC3=C(O2)C(=CC4=C3C5=C(O4)C(=O)C6=C(C=C(C=C6O5)O)O)O)(C)C
• InChI: InChI=1S/C25H22O7/c1-24(2)5-4-6-25(3)17(24)9-12-18-16(10-14(28)21(12)32-25)31-23-20(29)19-13(27)7-11(26)8-15(19)30-22(18)23/h4,6-8,10,17,26-28H,5,9H2,1-3H3/t17-,25+/m1/s1
• InChI Key: WYRBYPPKPYWQQK-NSYGIPOTSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₂O₇
• Molecular Weight: 434.40 g/mol
• Exact Mass: 434.13655304 g/mol
• Topological Polar Surface Area (TPSA): 109.00 Ų
• XlogP: 5.60
• Atomic LogP (AlogP): 5.11
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9737	97.37%
Caco-2	-	0.5751	57.51%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6285	62.85%
OATP2B1 inhibitior	-	0.7117	71.17%
OATP1B1 inhibitior	+	0.8607	86.07%
OATP1B3 inhibitior	+	0.9567	95.67%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8564	85.64%
BSEP inhibitior	+	0.5744	57.44%
P-glycoprotein inhibitior	+	0.6416	64.16%
P-glycoprotein substrate	-	0.5562	55.62%
CYP3A4 substrate	+	0.6382	63.82%
CYP2C9 substrate	-	0.5824	58.24%
CYP2D6 substrate	-	0.8243	82.43%
CYP3A4 inhibition	-	0.5182	51.82%
CYP2C9 inhibition	-	0.5258	52.58%
CYP2C19 inhibition	-	0.6095	60.95%
CYP2D6 inhibition	-	0.7201	72.01%
CYP1A2 inhibition	+	0.7449	74.49%
CYP2C8 inhibition	+	0.7281	72.81%
CYP inhibitory promiscuity	+	0.6615	66.15%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4736	47.36%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.7031	70.31%
Skin irritation	-	0.6996	69.96%
Skin corrosion	-	0.9232	92.32%
Ames mutagenesis	+	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4788	47.88%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.7559	75.59%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.5068	50.68%
Acute Oral Toxicity (c)	III	0.5588	55.88%
Estrogen receptor binding	+	0.8815	88.15%
Androgen receptor binding	+	0.6915	69.15%
Thyroid receptor binding	+	0.6684	66.84%
Glucocorticoid receptor binding	+	0.8697	86.97%
Aromatase binding	+	0.7247	72.47%
PPAR gamma	+	0.8103	81.03%
Honey bee toxicity	-	0.8303	83.03%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9953	99.53%

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	99.60%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.80%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.18%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.01%	95.56%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	91.55%	85.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.89%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.00%	99.23%
CHEMBL2581	P07339	Cathepsin D	89.54%	98.95%
CHEMBL3192	Q9BY41	Histone deacetylase 8	89.14%	93.99%
CHEMBL3038469	P24941	CDK2/Cyclin A	88.03%	91.38%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.75%	86.33%
CHEMBL4208	P20618	Proteasome component C5	84.64%	90.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.56%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.86%	95.89%
CHEMBL1929	P47989	Xanthine dehydrogenase	83.73%	96.12%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.61%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.11%	92.94%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.50%	90.71%
CHEMBL242	Q92731	Estrogen receptor beta	81.50%	98.35%
CHEMBL2535	P11166	Glucose transporter	81.16%	98.75%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.03%	95.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.99%	96.09%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	80.23%	94.42%
CHEMBL217	P14416	Dopamine D2 receptor	80.11%	95.62%

Plants that contains it

• Helminthostachys zeylanica

Cross-Links

• PubChem: 44233938
• LOTUS: LTS0030207
• wikiData: Q105322498