(3S)-2-Oxo-3beta,6,9-trimethyl-2,3,3abeta,5,6,9balpha-hexahydro-4H-cyclohepta[2,1-b:3,4-c']difuran-4beta,6alpha-diol 4-acetate

Details

• Internal ID: 97cf6221-7c25-4097-8372-cca4046dfcd6
• Taxonomy: Organoheterocyclic compounds > Cycloheptafurans
• IUPAC Name: [(2S,5S,6R,7S,9S)-9-hydroxy-5,9,13-trimethyl-4-oxo-3,12-dioxatricyclo[8.3.0.02,6]trideca-1(13),10-dien-7-yl] acetate
• SMILES (Canonical): CC1C2C(CC(C3=COC(=C3C2OC1=O)C)(C)O)OC(=O)C
• SMILES (Isomeric): C[C@H]1[C@@H]2[C@H](C[C@](C3=COC(=C3[C@H]2OC1=O)C)(C)O)OC(=O)C
• InChI: InChI=1S/C16H20O6/c1-7-12-11(21-9(3)17)5-16(4,19)10-6-20-8(2)13(10)14(12)22-15(7)18/h6-7,11-12,14,19H,5H2,1-4H3/t7-,11-,12+,14-,16-/m0/s1
• InChI Key: KOUVNGDGNNAPQW-LWFZOEDRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₀O₆
• Molecular Weight: 308.33 g/mol
• Exact Mass: 308.12598835 g/mol
• Topological Polar Surface Area (TPSA): 86.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.98
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• (3S)-2-Oxo-3beta,6,9-trimethyl-2,3,3abeta,5,6,9balpha-hexahydro-4H-cyclohepta[2,1-b:3,4-c']difuran-4beta,6alpha-diol 4-acetate
• (3S,3aR,4S,6S,9bS)-4-(Acetyloxy)-3a,5,6,9b-tetrahydro-6-hydroxy-3,6,9-trimethyl-4H-cyclohepta[2,1-b:3,4-c']difuran-2(3H)-one
• 142449-62-5

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9731	97.31%
Caco-2	-	0.5408	54.08%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5186	51.86%
OATP2B1 inhibitior	-	0.8581	85.81%
OATP1B1 inhibitior	+	0.9157	91.57%
OATP1B3 inhibitior	+	0.8833	88.33%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7657	76.57%
P-glycoprotein inhibitior	-	0.7204	72.04%
P-glycoprotein substrate	-	0.7775	77.75%
CYP3A4 substrate	+	0.6443	64.43%
CYP2C9 substrate	-	0.7953	79.53%
CYP2D6 substrate	-	0.8344	83.44%
CYP3A4 inhibition	-	0.8770	87.70%
CYP2C9 inhibition	-	0.8696	86.96%
CYP2C19 inhibition	-	0.9219	92.19%
CYP2D6 inhibition	-	0.9570	95.70%
CYP1A2 inhibition	-	0.7951	79.51%
CYP2C8 inhibition	-	0.8364	83.64%
CYP inhibitory promiscuity	-	0.9767	97.67%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.4517	45.17%
Eye corrosion	-	0.9733	97.33%
Eye irritation	-	0.7686	76.86%
Skin irritation	-	0.7440	74.40%
Skin corrosion	-	0.8719	87.19%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	+	0.5534	55.34%
skin sensitisation	-	0.7581	75.81%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.4523	45.23%
Acute Oral Toxicity (c)	II	0.3714	37.14%
Estrogen receptor binding	+	0.5769	57.69%
Androgen receptor binding	+	0.6171	61.71%
Thyroid receptor binding	+	0.6384	63.84%
Glucocorticoid receptor binding	+	0.5887	58.87%
Aromatase binding	-	0.6682	66.82%
PPAR gamma	-	0.5277	52.77%
Honey bee toxicity	-	0.8267	82.67%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.8566	85.66%

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	97.04%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.52%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.44%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.80%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.16%	97.25%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.85%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.77%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.77%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.59%	89.00%

Plants that contains it

• Achillea collina
• Achillea millefolium
• Annona rensoniana
• Archidendron clypearia
• Aristolochia maxima
• Bergenia purpurascens
• Betula pendula subsp. mandshurica
• Bischofia javanica
• Caragana tibetica
• Crataegus sinaica
• Discaria chacaye
• Euphorbia ferganensis
• Gardenia jasminoides
• Isodon rubescens
• Jasminum officinale
• Lasiocephalus ovatus
• Ligularia platyglossa
• Macrotyloma axillare
• Malus asiatica
• Mikania obtusata
• Montrouziera sphaeroidea
• Pimpinella saxifraga
• Polygala myrtifolia
• Polystichum deltodon
• Rhodiola stephani
• Sarcomelicope argyrophylla
• Scrophularia wattii
• Seriphidium vachanicum
• Solanum bahamense
• Tinospora smilacina
• Trigonostemon reidioides
• Tropaeolum speciosum
• Vatica diospyroides

Cross-Links

• PubChem: 15127111
• NPASS: NPC255497
• LOTUS: LTS0145410
• wikiData: Q105143997