(4aS)-5,8-dihydroxy-7-[(2S)-2-hydroxypropyl]-1,2,4a-trimethyl-4H-phenanthrene-3,6-dione

Details

• Internal ID: 41b6c44c-6841-44f8-ae89-c5858d4cb779
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (4aS)-5,8-dihydroxy-7-[(2S)-2-hydroxypropyl]-1,2,4a-trimethyl-4H-phenanthrene-3,6-dione
• InChI: InChI=1S/C20H22O5/c1-9(21)7-13-17(23)12-5-6-14-10(2)11(3)15(22)8-20(14,4)16(12)19(25)18(13)24/h5-6,9,21,23,25H,7-8H2,1-4H3/t9-,20-/m0/s1
• InChI Key: ZPXWCKGSWWRWCO-LXGOIASLSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₂O₅
• Molecular Weight: 342.40 g/mol
• Exact Mass: 342.14672380 g/mol
• Topological Polar Surface Area (TPSA): 94.80 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 3.15
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9938	99.38%
Caco-2	+	0.5888	58.88%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6916	69.16%
OATP2B1 inhibitior	-	0.5678	56.78%
OATP1B1 inhibitior	+	0.8915	89.15%
OATP1B3 inhibitior	+	0.9332	93.32%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.4903	49.03%
P-glycoprotein inhibitior	-	0.9323	93.23%
P-glycoprotein substrate	-	0.6994	69.94%
CYP3A4 substrate	+	0.5779	57.79%
CYP2C9 substrate	-	0.7828	78.28%
CYP2D6 substrate	-	0.8630	86.30%
CYP3A4 inhibition	-	0.6668	66.68%
CYP2C9 inhibition	-	0.9053	90.53%
CYP2C19 inhibition	-	0.8456	84.56%
CYP2D6 inhibition	-	0.9151	91.51%
CYP1A2 inhibition	-	0.9025	90.25%
CYP2C8 inhibition	-	0.8650	86.50%
CYP inhibitory promiscuity	-	0.8506	85.06%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5811	58.11%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.8343	83.43%
Skin irritation	+	0.5553	55.53%
Skin corrosion	-	0.9246	92.46%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5744	57.44%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	+	0.6084	60.84%
skin sensitisation	-	0.6707	67.07%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.5168	51.68%
Acute Oral Toxicity (c)	III	0.4949	49.49%
Estrogen receptor binding	-	0.5491	54.91%
Androgen receptor binding	+	0.5569	55.69%
Thyroid receptor binding	-	0.6331	63.31%
Glucocorticoid receptor binding	+	0.6719	67.19%
Aromatase binding	-	0.5459	54.59%
PPAR gamma	+	0.6198	61.98%
Honey bee toxicity	-	0.8715	87.15%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.9741	97.41%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.67%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.83%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.51%	95.56%
CHEMBL230	P35354	Cyclooxygenase-2	90.37%	89.63%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.99%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.84%	96.09%
CHEMBL1937	Q92769	Histone deacetylase 2	87.54%	94.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.26%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.82%	99.23%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.80%	96.77%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	82.56%	92.68%
CHEMBL221	P23219	Cyclooxygenase-1	81.71%	90.17%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.35%	93.40%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.72%	94.45%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.41%	90.71%

Plants that contains it

• Coleus barbatus var. barbatus

Cross-Links

• PubChem: 95240134
• LOTUS: LTS0132818
• wikiData: Q105381306