[(2R,3S,4S,5S)-4,5-diacetyloxy-3-hydroxyoxan-2-yl] (1R,2R,4aR,8aR)-1-[(E)-5-acetyloxy-3-methylpent-3-enyl]-1,4a,5-trimethyl-2,3,4,7,8,8a-hexahydronaphthalene-2-carboxylate

Details

• Internal ID: 416c90c0-574c-41fd-891e-c52280078e6c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Colensane and clerodane diterpenoids
• IUPAC Name: [(2R,3S,4S,5S)-4,5-diacetyloxy-3-hydroxyoxan-2-yl] (1R,2R,4aR,8aR)-1-[(E)-5-acetyloxy-3-methylpent-3-enyl]-1,4a,5-trimethyl-2,3,4,7,8,8a-hexahydronaphthalene-2-carboxylate
• SMILES (Canonical): CC1=CCCC2C1(CCC(C2(C)CCC(=CCOC(=O)C)C)C(=O)OC3C(C(C(CO3)OC(=O)C)OC(=O)C)O)C
• SMILES (Isomeric): CC1=CCC[C@H]2[C@]1(CC[C@H]([C@]2(C)CC/C(=C/COC(=O)C)/C)C(=O)O[C@@H]3[C@H]([C@@H]([C@H](CO3)OC(=O)C)OC(=O)C)O)C
• InChI: InChI=1S/C31H46O10/c1-18(13-16-37-20(3)32)11-14-31(7)23(12-15-30(6)19(2)9-8-10-25(30)31)28(36)41-29-26(35)27(40-22(5)34)24(17-38-29)39-21(4)33/h9,13,23-27,29,35H,8,10-12,14-17H2,1-7H3/b18-13+/t23-,24-,25-,26-,27+,29+,30-,31-/m0/s1
• InChI Key: IXDNKJKDUXFRCW-AZJHVEGPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₄₆O₁₀
• Molecular Weight: 578.70 g/mol
• Exact Mass: 578.30909766 g/mol
• Topological Polar Surface Area (TPSA): 135.00 Ų
• XlogP: 4.50
• Atomic LogP (AlogP): 4.18
• H-Bond Acceptor: 10
• H-Bond Donor: 1
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9012	90.12%
Caco-2	-	0.7780	77.80%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8139	81.39%
OATP2B1 inhibitior	-	0.7182	71.82%
OATP1B1 inhibitior	+	0.8658	86.58%
OATP1B3 inhibitior	+	0.9203	92.03%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6521	65.21%
BSEP inhibitior	+	0.9152	91.52%
P-glycoprotein inhibitior	+	0.8327	83.27%
P-glycoprotein substrate	-	0.5606	56.06%
CYP3A4 substrate	+	0.7153	71.53%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8615	86.15%
CYP3A4 inhibition	-	0.8876	88.76%
CYP2C9 inhibition	-	0.9341	93.41%
CYP2C19 inhibition	-	0.8790	87.90%
CYP2D6 inhibition	-	0.9560	95.60%
CYP1A2 inhibition	-	0.7028	70.28%
CYP2C8 inhibition	+	0.6465	64.65%
CYP inhibitory promiscuity	-	0.9154	91.54%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6494	64.94%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9206	92.06%
Skin irritation	-	0.5139	51.39%
Skin corrosion	-	0.9559	95.59%
Ames mutagenesis	-	0.5266	52.66%
Human Ether-a-go-go-Related Gene inhibition	-	0.5168	51.68%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.5226	52.26%
skin sensitisation	-	0.9003	90.03%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.6486	64.86%
Acute Oral Toxicity (c)	III	0.5762	57.62%
Estrogen receptor binding	+	0.7285	72.85%
Androgen receptor binding	+	0.6762	67.62%
Thyroid receptor binding	+	0.5442	54.42%
Glucocorticoid receptor binding	+	0.7815	78.15%
Aromatase binding	+	0.7017	70.17%
PPAR gamma	+	0.6993	69.93%
Honey bee toxicity	-	0.7303	73.03%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5255	52.55%
Fish aquatic toxicity	+	0.9780	97.80%

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	97.82%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.20%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.58%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.10%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.62%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.15%	89.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.52%	91.07%
CHEMBL2581	P07339	Cathepsin D	86.38%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.61%	97.09%
CHEMBL5028	O14672	ADAM10	85.52%	97.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.12%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.85%	96.77%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	84.25%	83.57%
CHEMBL5255	O00206	Toll-like receptor 4	82.24%	92.50%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	82.16%	89.67%
CHEMBL221	P23219	Cyclooxygenase-1	81.81%	90.17%
CHEMBL3922	P50579	Methionine aminopeptidase 2	81.73%	97.28%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.68%	92.62%

Plants that contains it

• Dryopteris crassirhizoma
• Dryopteris cristata
• Dryopteris dilatata
• Dryopteris fragrans
• Dryopteris gymnosora
• Phegopteris connectilis

Cross-Links

• PubChem: 163085540
• LOTUS: LTS0060150
• wikiData: Q27105862