6-Hydroxysugiol

Details

• Internal ID: 9bfe67ef-a709-4871-8726-1878d2d287a6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (4aS,10R,10aS)-6,10-dihydroxy-1,1,4a-trimethyl-7-propan-2-yl-3,4,10,10a-tetrahydro-2H-phenanthren-9-one
• SMILES (Canonical): CC(C)C1=C(C=C2C(=C1)C(=O)C(C3C2(CCCC3(C)C)C)O)O
• SMILES (Isomeric): CC(C)C1=C(C=C2C(=C1)C(=O)[C@@H]([C@@H]3[C@@]2(CCCC3(C)C)C)O)O
• InChI: InChI=1S/C20H28O3/c1-11(2)12-9-13-14(10-15(12)21)20(5)8-6-7-19(3,4)18(20)17(23)16(13)22/h9-11,17-18,21,23H,6-8H2,1-5H3/t17-,18-,20+/m0/s1
• InChI Key: VQGOEQIXFUUUQP-CMKODMSKSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₃
• Molecular Weight: 316.40 g/mol
• Exact Mass: 316.20384475 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 5.10
• Atomic LogP (AlogP): 4.16
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• (4aS,10R,10aS)-6,10-dihydroxy-1,1,4a-trimethyl-7-propan-2-yl-3,4,10,10a-tetrahydro-2H-phenanthren-9-one
• 6alpha-Hydroxysugiol
• CHEMBL3814903
• AKOS040734739

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9962	99.62%
Caco-2	+	0.6867	68.67%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8596	85.96%
OATP2B1 inhibitior	-	0.8601	86.01%
OATP1B1 inhibitior	+	0.8713	87.13%
OATP1B3 inhibitior	+	0.9675	96.75%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.7444	74.44%
P-glycoprotein inhibitior	-	0.8484	84.84%
P-glycoprotein substrate	-	0.8003	80.03%
CYP3A4 substrate	+	0.6012	60.12%
CYP2C9 substrate	-	0.5764	57.64%
CYP2D6 substrate	-	0.7392	73.92%
CYP3A4 inhibition	-	0.8804	88.04%
CYP2C9 inhibition	-	0.7484	74.84%
CYP2C19 inhibition	-	0.8248	82.48%
CYP2D6 inhibition	-	0.9023	90.23%
CYP1A2 inhibition	+	0.8405	84.05%
CYP2C8 inhibition	-	0.8350	83.50%
CYP inhibitory promiscuity	-	0.7270	72.70%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8500	85.00%
Carcinogenicity (trinary)	Non-required	0.5910	59.10%
Eye corrosion	-	0.9868	98.68%
Eye irritation	-	0.8485	84.85%
Skin irritation	-	0.5112	51.12%
Skin corrosion	-	0.9167	91.67%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7133	71.33%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.5029	50.29%
skin sensitisation	-	0.7372	73.72%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.6245	62.45%
Acute Oral Toxicity (c)	III	0.8207	82.07%
Estrogen receptor binding	+	0.7269	72.69%
Androgen receptor binding	-	0.5415	54.15%
Thyroid receptor binding	+	0.7174	71.74%
Glucocorticoid receptor binding	+	0.8152	81.52%
Aromatase binding	+	0.7038	70.38%
PPAR gamma	+	0.7852	78.52%
Honey bee toxicity	-	0.8317	83.17%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9943	99.43%

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	98.09%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.74%	98.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	96.12%	96.77%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	95.52%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.97%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.86%	99.15%
CHEMBL1937	Q92769	Histone deacetylase 2	91.58%	94.75%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	88.76%	93.40%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.53%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.22%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.53%	100.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	85.79%	93.03%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.45%	82.69%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.30%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.58%	89.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.63%	91.07%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.21%	97.25%

Plants that contains it

• Breonia chinensis
• Campylotropis hirtella
• Ceropegia dichotoma
• Crinum moorei
• Crotalaria candicans
• Cryptomeria japonica
• Dendrobium loddigesii
• Distephanus angulifolius
• Eucalyptus apodophylla
• Glycosmis macrophylla
• Gypsophila perfoliata
• Hypericum polyanthemum
• Juniperus chinensis
• Juniperus drupacea
• Lophostemon confertus
• Mentha × gentilis
• Ononis spinosa
• Orbivestus karaguensis
• Pentaclethra macrophylla
• Periploca sepium
• Pinalia japonica
• Plectranthus hereroensis
• Pterocaulon virgatum
• Rhodiola semenovii
• Salvia sessei
• Salvia yunnanensis
• Sequoia sempervirens
• Sonneratia caseolaris
• Stephania zippeliana
• Taiwania cryptomerioides
• Veronica polita

Cross-Links

• PubChem: 12114761
• NPASS: NPC78307
• ChEMBL: CHEMBL3814903
• LOTUS: LTS0254189
• wikiData: Q105291238