(3R)-5-[(1R,2S,4aS,5S,6S,7S,8aS)-5,6-dihydroxy-1,2,4a,5-tetramethyl-7-[(Z)-2-methylbut-2-enoyl]oxy-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]-3-methylpentanoic acid

Details

• Internal ID: 38d49ea6-bc88-4ce7-99b5-9963ad4a1d2e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Colensane and clerodane diterpenoids
• IUPAC Name: (3R)-5-[(1R,2S,4aS,5S,6S,7S,8aS)-5,6-dihydroxy-1,2,4a,5-tetramethyl-7-[(Z)-2-methylbut-2-enoyl]oxy-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]-3-methylpentanoic acid
• SMILES (Canonical): CC=C(C)C(=O)OC1CC2C(CCC(C2(C)CCC(C)CC(=O)O)C)(C(C1O)(C)O)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@H]1C[C@@H]2[C@](CC[C@@H]([C@@]2(C)CC[C@@H](C)CC(=O)O)C)([C@]([C@H]1O)(C)O)C
• InChI: InChI=1S/C25H42O6/c1-8-16(3)22(29)31-18-14-19-23(5,11-9-15(2)13-20(26)27)17(4)10-12-24(19,6)25(7,30)21(18)28/h8,15,17-19,21,28,30H,9-14H2,1-7H3,(H,26,27)/b16-8-/t15-,17+,18+,19+,21+,23-,24+,25-/m1/s1
• InChI Key: OTXKTQXPSVVIOE-OQUGQKHVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₄₂O₆
• Molecular Weight: 438.60 g/mol
• Exact Mass: 438.29813906 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 4.90
• Atomic LogP (AlogP): 4.33
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9718	97.18%
Caco-2	-	0.5537	55.37%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8306	83.06%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8732	87.32%
OATP1B3 inhibitior	-	0.2131	21.31%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7021	70.21%
BSEP inhibitior	+	0.8112	81.12%
P-glycoprotein inhibitior	-	0.5843	58.43%
P-glycoprotein substrate	-	0.5474	54.74%
CYP3A4 substrate	+	0.6680	66.80%
CYP2C9 substrate	-	0.8027	80.27%
CYP2D6 substrate	-	0.9092	90.92%
CYP3A4 inhibition	-	0.6643	66.43%
CYP2C9 inhibition	-	0.8919	89.19%
CYP2C19 inhibition	-	0.7956	79.56%
CYP2D6 inhibition	-	0.9544	95.44%
CYP1A2 inhibition	-	0.8285	82.85%
CYP2C8 inhibition	-	0.7731	77.31%
CYP inhibitory promiscuity	-	0.9653	96.53%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9843	98.43%
Carcinogenicity (trinary)	Non-required	0.6766	67.66%
Eye corrosion	-	0.9940	99.40%
Eye irritation	-	0.9398	93.98%
Skin irritation	+	0.6371	63.71%
Skin corrosion	-	0.9504	95.04%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5651	56.51%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.5459	54.59%
skin sensitisation	-	0.8081	80.81%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.5732	57.32%
Acute Oral Toxicity (c)	IV	0.3809	38.09%
Estrogen receptor binding	+	0.8072	80.72%
Androgen receptor binding	+	0.5921	59.21%
Thyroid receptor binding	+	0.6465	64.65%
Glucocorticoid receptor binding	+	0.7685	76.85%
Aromatase binding	+	0.7784	77.84%
PPAR gamma	+	0.5863	58.63%
Honey bee toxicity	-	0.6314	63.14%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5655	56.55%
Fish aquatic toxicity	+	0.9954	99.54%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	98.76%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.24%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.18%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.44%	94.45%
CHEMBL2581	P07339	Cathepsin D	90.75%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.17%	97.25%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	88.56%	94.62%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	87.80%	93.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.43%	97.09%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	85.62%	94.23%
CHEMBL340	P08684	Cytochrome P450 3A4	85.57%	91.19%
CHEMBL284	P27487	Dipeptidyl peptidase IV	85.57%	95.69%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.31%	82.69%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	84.95%	96.47%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.94%	100.00%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	84.15%	94.08%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	81.99%	97.53%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.14%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.29%	95.56%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.03%	91.07%

Plants that contains it

• Gymnosperma glutinosum

Cross-Links

• PubChem: 101663393
• LOTUS: LTS0195322
• wikiData: Q105199913