(4S)-6beta-Hydroxy-4beta,9aalpha-dimethoxy-3,4abeta,5beta-trimethyl-4a,5,6,7,8,8abeta,9,9a-octahydronaphtho[2,3-b]furan-2(4H)-one

Details

• Internal ID: c07b1093-56c1-402e-b1dd-c302874a7c5c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (4S,4aS,5R,6S,8aR,9aR)-6-hydroxy-4,9a-dimethoxy-3,4a,5-trimethyl-5,6,7,8,8a,9-hexahydro-4H-benzo[f][1]benzofuran-2-one
• SMILES (Canonical): CC1C(CCC2C1(C(C3=C(C(=O)OC3(C2)OC)C)OC)C)O
• SMILES (Isomeric): C[C@H]1[C@H](CC[C@H]2[C@@]1([C@@H](C3=C(C(=O)O[C@@]3(C2)OC)C)OC)C)O
• InChI: InChI=1S/C17H26O5/c1-9-13-14(20-4)16(3)10(2)12(18)7-6-11(16)8-17(13,21-5)22-15(9)19/h10-12,14,18H,6-8H2,1-5H3/t10-,11+,12-,14+,16+,17+/m0/s1
• InChI Key: JCGMJARSAZGXHM-LYPRXNHISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₆O₅
• Molecular Weight: 310.40 g/mol
• Exact Mass: 310.17802393 g/mol
• Topological Polar Surface Area (TPSA): 65.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 2.03
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• (4S)-6beta-Hydroxy-4beta,9aalpha-dimethoxy-3,4abeta,5beta-trimethyl-4a,5,6,7,8,8abeta,9,9a-octahydronaphtho[2,3-b]furan-2(4H)-one
• (4S,4aS,5R,6S,8aR,9aR)-4a,5,6,7,8,8a,9,9a-Octahydro-6-hydroxy-4,9a-dimethoxy-3,4a,5-trimethylnaphtho[2,3-b]furan-2(4H)-one
• 162613-65-2

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9950	99.50%
Caco-2	+	0.8110	81.10%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7290	72.90%
OATP2B1 inhibitior	-	0.8567	85.67%
OATP1B1 inhibitior	+	0.8802	88.02%
OATP1B3 inhibitior	+	0.9499	94.99%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.7439	74.39%
P-glycoprotein inhibitior	-	0.7812	78.12%
P-glycoprotein substrate	-	0.7234	72.34%
CYP3A4 substrate	+	0.6583	65.83%
CYP2C9 substrate	-	0.8019	80.19%
CYP2D6 substrate	-	0.8729	87.29%
CYP3A4 inhibition	-	0.6675	66.75%
CYP2C9 inhibition	-	0.8551	85.51%
CYP2C19 inhibition	-	0.8972	89.72%
CYP2D6 inhibition	-	0.9486	94.86%
CYP1A2 inhibition	-	0.6831	68.31%
CYP2C8 inhibition	-	0.6671	66.71%
CYP inhibitory promiscuity	-	0.8836	88.36%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4810	48.10%
Eye corrosion	-	0.9861	98.61%
Eye irritation	-	0.9452	94.52%
Skin irritation	-	0.5205	52.05%
Skin corrosion	-	0.9104	91.04%
Ames mutagenesis	-	0.5964	59.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.6393	63.93%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	+	0.5435	54.35%
skin sensitisation	-	0.8086	80.86%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.5897	58.97%
Acute Oral Toxicity (c)	III	0.3236	32.36%
Estrogen receptor binding	+	0.8299	82.99%
Androgen receptor binding	+	0.6078	60.78%
Thyroid receptor binding	+	0.7218	72.18%
Glucocorticoid receptor binding	+	0.7024	70.24%
Aromatase binding	+	0.5214	52.14%
PPAR gamma	+	0.6191	61.91%
Honey bee toxicity	-	0.7880	78.80%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9340	93.40%

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	97.51%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.95%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.23%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.00%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.13%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.52%	92.94%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.69%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.50%	97.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.70%	95.89%
CHEMBL1937	Q92769	Histone deacetylase 2	82.22%	94.75%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.16%	93.03%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.63%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.23%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.80%	89.00%
CHEMBL1871	P10275	Androgen Receptor	80.53%	96.43%

Plants that contains it

• Acacia paradoxa
• Adonis sutchuenensis
• Astragalus ernestii
• Berneuxia thibetica
• Bongardia chrysogonum
• Eragrostis curvula
• Fritillaria meleagris
• Isophysis tasmanica
• Matricaria discoidea
• Metasequoia glyptostroboides
• Petasites japonicus
• Philenoptera laxiflora
• Plantago lundborgii
• Sideritis arborescens
• Solanum pseudoquina
• Triadica sebifera

Cross-Links

• PubChem: 10018278
• NPASS: NPC17985
• LOTUS: LTS0110454
• wikiData: Q105124803