(1R,4R,4aS,10aS)-4,7,8-trihydroxy-1-(hydroxymethyl)-1,4a-dimethyl-3,4,10,10a-tetrahydro-2H-phenanthren-9-one

Details

• Internal ID: 880eafd3-fca3-413f-8599-470ff62e7b08
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (1R,4R,4aS,10aS)-4,7,8-trihydroxy-1-(hydroxymethyl)-1,4a-dimethyl-3,4,10,10a-tetrahydro-2H-phenanthren-9-one
• SMILES (Canonical): CC1(CCC(C2(C1CC(=O)C3=C2C=CC(=C3O)O)C)O)CO
• SMILES (Isomeric): C[C@]1(CC[C@H]([C@]2([C@H]1CC(=O)C3=C2C=CC(=C3O)O)C)O)CO
• InChI: InChI=1S/C17H22O5/c1-16(8-18)6-5-13(21)17(2)9-3-4-10(19)15(22)14(9)11(20)7-12(16)17/h3-4,12-13,18-19,21-22H,5-8H2,1-2H3/t12-,13+,16-,17+/m0/s1
• InChI Key: KVFFUBVUOKNGEJ-UWWPHRKUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₂O₅
• Molecular Weight: 306.40 g/mol
• Exact Mass: 306.14672380 g/mol
• Topological Polar Surface Area (TPSA): 98.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.71
• H-Bond Acceptor: 5
• H-Bond Donor: 4
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9904	99.04%
Caco-2	+	0.6812	68.12%
Blood Brain Barrier	-	0.6615	66.15%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8734	87.34%
OATP2B1 inhibitior	-	0.8592	85.92%
OATP1B1 inhibitior	+	0.8176	81.76%
OATP1B3 inhibitior	+	0.8976	89.76%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8643	86.43%
BSEP inhibitior	-	0.8448	84.48%
P-glycoprotein inhibitior	-	0.9361	93.61%
P-glycoprotein substrate	-	0.7662	76.62%
CYP3A4 substrate	+	0.6217	62.17%
CYP2C9 substrate	-	0.6087	60.87%
CYP2D6 substrate	-	0.8304	83.04%
CYP3A4 inhibition	-	0.6150	61.50%
CYP2C9 inhibition	-	0.8658	86.58%
CYP2C19 inhibition	-	0.8437	84.37%
CYP2D6 inhibition	-	0.9472	94.72%
CYP1A2 inhibition	+	0.7337	73.37%
CYP2C8 inhibition	-	0.7094	70.94%
CYP inhibitory promiscuity	-	0.9573	95.73%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8500	85.00%
Carcinogenicity (trinary)	Non-required	0.6810	68.10%
Eye corrosion	-	0.9952	99.52%
Eye irritation	-	0.8130	81.30%
Skin irritation	-	0.6286	62.86%
Skin corrosion	-	0.9537	95.37%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5385	53.85%
Micronuclear	-	0.9400	94.00%
Hepatotoxicity	-	0.5791	57.91%
skin sensitisation	-	0.8492	84.92%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.7132	71.32%
Acute Oral Toxicity (c)	III	0.6832	68.32%
Estrogen receptor binding	+	0.7326	73.26%
Androgen receptor binding	+	0.6332	63.32%
Thyroid receptor binding	+	0.5980	59.80%
Glucocorticoid receptor binding	+	0.8498	84.98%
Aromatase binding	+	0.6756	67.56%
PPAR gamma	+	0.7001	70.01%
Honey bee toxicity	-	0.8476	84.76%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9837	98.37%

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	99.34%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.06%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.09%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.63%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.59%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.46%	95.56%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	87.46%	93.04%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.73%	89.00%
CHEMBL1937	Q92769	Histone deacetylase 2	83.92%	94.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.58%	95.89%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.29%	96.09%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	81.99%	85.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.27%	99.23%

Plants that contains it

• Taiwania cryptomerioides

Cross-Links

• PubChem: 102478862
• LOTUS: LTS0101094
• wikiData: Q105146493