(1S,2S,5S,6S,8R,11R,12S,13R)-5,6,13-trihydroxy-6-(hydroxymethyl)-2,12-dimethyl-16-oxapentacyclo[10.3.2.15,8.01,11.02,8]octadecane-7,17-dione

Details

• Internal ID: 8cdf0286-4af6-4b9e-8ff8-c94515fa4793
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: (1S,2S,5S,6S,8R,11R,12S,13R)-5,6,13-trihydroxy-6-(hydroxymethyl)-2,12-dimethyl-16-oxapentacyclo[10.3.2.15,8.01,11.02,8]octadecane-7,17-dione
• SMILES (Canonical): CC12CCC3(CC1(CCC4C25CCC(C4(C(=O)O5)C)O)C(=O)C3(CO)O)O
• SMILES (Isomeric): C[C@]12CC[C@@]3(C[C@@]1(CC[C@H]4[C@@]25CC[C@H]([C@]4(C(=O)O5)C)O)C(=O)[C@@]3(CO)O)O
• InChI: InChI=1S/C20H28O7/c1-15-7-8-18(25)9-17(15,13(23)19(18,26)10-21)5-3-11-16(2)12(22)4-6-20(11,15)27-14(16)24/h11-12,21-22,25-26H,3-10H2,1-2H3/t11-,12-,15+,16+,17+,18+,19-,20+/m1/s1
• InChI Key: CRUJJSCQVBIUDA-ZPXCCNANSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₇
• Molecular Weight: 380.40 g/mol
• Exact Mass: 380.18350323 g/mol
• Topological Polar Surface Area (TPSA): 124.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): 0.07
• H-Bond Acceptor: 7
• H-Bond Donor: 4
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8099	80.99%
Caco-2	+	0.6120	61.20%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7222	72.22%
OATP2B1 inhibitior	-	0.8594	85.94%
OATP1B1 inhibitior	+	0.9088	90.88%
OATP1B3 inhibitior	+	0.9612	96.12%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7609	76.09%
BSEP inhibitior	+	0.6471	64.71%
P-glycoprotein inhibitior	-	0.7941	79.41%
P-glycoprotein substrate	-	0.8074	80.74%
CYP3A4 substrate	+	0.6597	65.97%
CYP2C9 substrate	-	0.8038	80.38%
CYP2D6 substrate	-	0.8243	82.43%
CYP3A4 inhibition	-	0.7385	73.85%
CYP2C9 inhibition	-	0.8548	85.48%
CYP2C19 inhibition	-	0.8771	87.71%
CYP2D6 inhibition	-	0.9607	96.07%
CYP1A2 inhibition	-	0.8868	88.68%
CYP2C8 inhibition	-	0.7789	77.89%
CYP inhibitory promiscuity	-	0.9743	97.43%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6836	68.36%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.8994	89.94%
Skin irritation	-	0.5751	57.51%
Skin corrosion	-	0.9296	92.96%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5474	54.74%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.5199	51.99%
skin sensitisation	-	0.9345	93.45%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.6527	65.27%
Acute Oral Toxicity (c)	III	0.4536	45.36%
Estrogen receptor binding	+	0.9271	92.71%
Androgen receptor binding	+	0.7709	77.09%
Thyroid receptor binding	+	0.7171	71.71%
Glucocorticoid receptor binding	+	0.7680	76.80%
Aromatase binding	+	0.7853	78.53%
PPAR gamma	+	0.5479	54.79%
Honey bee toxicity	-	0.8401	84.01%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9474	94.74%

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	93.59%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.03%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.15%	96.09%
CHEMBL2581	P07339	Cathepsin D	90.23%	98.95%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	88.74%	96.38%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.40%	97.09%
CHEMBL1871	P10275	Androgen Receptor	87.83%	96.43%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.67%	100.00%
CHEMBL226	P30542	Adenosine A1 receptor	85.91%	95.93%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.60%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.21%	89.00%

Plants that contains it

• Parinari campestris
• Parinari sprucei

Cross-Links

• PubChem: 162848900
• LOTUS: LTS0178159
• wikiData: Q104968908