(1R,2R,3R,4aR,5S,6R,8aR)-5-[(Z)-5-hydroxy-3-(hydroxymethyl)pent-3-enyl]-1,5,6,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-2H-naphthalene-1,2,3-triol

Details

• Internal ID: 1fe37d24-8677-476c-87c7-aad4f6419f85
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Colensane and clerodane diterpenoids
• IUPAC Name: (1R,2R,3R,4aR,5S,6R,8aR)-5-[(Z)-5-hydroxy-3-(hydroxymethyl)pent-3-enyl]-1,5,6,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-2H-naphthalene-1,2,3-triol
• SMILES (Canonical): CC1CCC2(C(C1(C)CCC(=CCO)CO)CC(C(C2(C)O)O)O)C
• SMILES (Isomeric): C[C@@H]1CC[C@@]2([C@@H]([C@@]1(C)CC/C(=C/CO)/CO)C[C@H]([C@H]([C@]2(C)O)O)O)C
• InChI: InChI=1S/C20H36O5/c1-13-5-9-19(3)16(11-15(23)17(24)20(19,4)25)18(13,2)8-6-14(12-22)7-10-21/h7,13,15-17,21-25H,5-6,8-12H2,1-4H3/b14-7-/t13-,15-,16-,17-,18+,19-,20+/m1/s1
• InChI Key: YSUHEZZGWKTCBQ-CDFMJAMYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₆O₅
• Molecular Weight: 356.50 g/mol
• Exact Mass: 356.25627424 g/mol
• Topological Polar Surface Area (TPSA): 101.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.61
• H-Bond Acceptor: 5
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9311	93.11%
Caco-2	-	0.5291	52.91%
Blood Brain Barrier	+	0.7035	70.35%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.5904	59.04%
OATP2B1 inhibitior	-	0.8634	86.34%
OATP1B1 inhibitior	+	0.8841	88.41%
OATP1B3 inhibitior	+	0.8461	84.61%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5675	56.75%
BSEP inhibitior	-	0.4725	47.25%
P-glycoprotein inhibitior	-	0.8633	86.33%
P-glycoprotein substrate	-	0.6057	60.57%
CYP3A4 substrate	+	0.6231	62.31%
CYP2C9 substrate	-	0.7657	76.57%
CYP2D6 substrate	-	0.7779	77.79%
CYP3A4 inhibition	-	0.8714	87.14%
CYP2C9 inhibition	-	0.8959	89.59%
CYP2C19 inhibition	-	0.8474	84.74%
CYP2D6 inhibition	-	0.9361	93.61%
CYP1A2 inhibition	-	0.9005	90.05%
CYP2C8 inhibition	-	0.7192	71.92%
CYP inhibitory promiscuity	-	0.9522	95.22%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.7130	71.30%
Eye corrosion	-	0.9924	99.24%
Eye irritation	-	0.9617	96.17%
Skin irritation	-	0.6095	60.95%
Skin corrosion	-	0.9616	96.16%
Ames mutagenesis	-	0.7370	73.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4418	44.18%
Micronuclear	-	0.9500	95.00%
Hepatotoxicity	-	0.6075	60.75%
skin sensitisation	-	0.8570	85.70%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.7832	78.32%
Acute Oral Toxicity (c)	III	0.6792	67.92%
Estrogen receptor binding	+	0.8419	84.19%
Androgen receptor binding	+	0.6107	61.07%
Thyroid receptor binding	+	0.6812	68.12%
Glucocorticoid receptor binding	+	0.8227	82.27%
Aromatase binding	+	0.7685	76.85%
PPAR gamma	-	0.5914	59.14%
Honey bee toxicity	-	0.8559	85.59%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9374	93.74%

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	95.61%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.52%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.57%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.88%	100.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	89.77%	82.69%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.86%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.64%	96.09%
CHEMBL2996	Q05655	Protein kinase C delta	84.26%	97.79%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.07%	95.50%
CHEMBL226	P30542	Adenosine A1 receptor	82.56%	95.93%

Plants that contains it

• Baccharis boliviensis

Cross-Links

• PubChem: 14262604
• LOTUS: LTS0133325
• wikiData: Q105360823