(1S)-1-[(2R,4aR,4bS,8aR)-4a-hydroxy-2,4b,8,8-tetramethyl-1,3,4,5,6,7,8a,9-octahydrophenanthren-2-yl]ethane-1,2-diol

Details

• Internal ID: 904dfc57-86d8-410f-b8fd-afd007e9fb71
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (1S)-1-[(2R,4aR,4bS,8aR)-4a-hydroxy-2,4b,8,8-tetramethyl-1,3,4,5,6,7,8a,9-octahydrophenanthren-2-yl]ethane-1,2-diol
• SMILES (Canonical): CC1(CCCC2(C1CC=C3C2(CCC(C3)(C)C(CO)O)O)C)C
• SMILES (Isomeric): C[C@]1(CC[C@]2(C(=CC[C@H]3[C@@]2(CCCC3(C)C)C)C1)O)[C@@H](CO)O
• InChI: InChI=1S/C20H34O3/c1-17(2)8-5-9-19(4)15(17)7-6-14-12-18(3,16(22)13-21)10-11-20(14,19)23/h6,15-16,21-23H,5,7-13H2,1-4H3/t15-,16-,18-,19+,20-/m1/s1
• InChI Key: SXVNRZCECDALIM-CVYSASLGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₄O₃
• Molecular Weight: 322.50 g/mol
• Exact Mass: 322.25079494 g/mol
• Topological Polar Surface Area (TPSA): 60.70 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.42
• H-Bond Acceptor: 3
• 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	+	0.9923	99.23%
Caco-2	+	0.7643	76.43%
Blood Brain Barrier	+	0.6885	68.85%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7818	78.18%
OATP2B1 inhibitior	-	0.8549	85.49%
OATP1B1 inhibitior	+	0.8767	87.67%
OATP1B3 inhibitior	+	0.9525	95.25%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6083	60.83%
BSEP inhibitior	-	0.4540	45.40%
P-glycoprotein inhibitior	-	0.9057	90.57%
P-glycoprotein substrate	-	0.7646	76.46%
CYP3A4 substrate	+	0.5773	57.73%
CYP2C9 substrate	-	0.7657	76.57%
CYP2D6 substrate	-	0.7779	77.79%
CYP3A4 inhibition	-	0.7785	77.85%
CYP2C9 inhibition	-	0.8538	85.38%
CYP2C19 inhibition	-	0.8556	85.56%
CYP2D6 inhibition	-	0.9316	93.16%
CYP1A2 inhibition	-	0.9009	90.09%
CYP2C8 inhibition	-	0.7214	72.14%
CYP inhibitory promiscuity	-	0.8579	85.79%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.7041	70.41%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9322	93.22%
Skin irritation	-	0.6197	61.97%
Skin corrosion	-	0.9609	96.09%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5069	50.69%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.7071	70.71%
skin sensitisation	-	0.7317	73.17%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.7232	72.32%
Acute Oral Toxicity (c)	III	0.6985	69.85%
Estrogen receptor binding	+	0.6496	64.96%
Androgen receptor binding	+	0.6113	61.13%
Thyroid receptor binding	+	0.6788	67.88%
Glucocorticoid receptor binding	+	0.7868	78.68%
Aromatase binding	+	0.6169	61.69%
PPAR gamma	-	0.5412	54.12%
Honey bee toxicity	-	0.8879	88.79%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	+	0.9725	97.25%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.04%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.08%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.15%	91.11%
CHEMBL2581	P07339	Cathepsin D	91.85%	98.95%
CHEMBL1937	Q92769	Histone deacetylase 2	89.78%	94.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.47%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.44%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.18%	93.56%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.67%	95.56%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.20%	82.69%

Plants that contains it

• Palafoxia rosea

Cross-Links

• PubChem: 162966302
• LOTUS: LTS0049949
• wikiData: Q105263358