(1S,4S,6R,8R,9R,12S,13S,14R,16S,17S)-6,9,14,17-tetrahydroxy-7,7,17-trimethyl-3,10-dioxapentacyclo[14.2.1.01,13.04,12.08,12]nonadecane-2,18-dione

Details

• Internal ID: cc28fd36-a333-4de5-b5ed-5e93ebbf29c9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: (1S,4S,6R,8R,9R,12S,13S,14R,16S,17S)-6,9,14,17-tetrahydroxy-7,7,17-trimethyl-3,10-dioxapentacyclo[14.2.1.01,13.04,12.08,12]nonadecane-2,18-dione
• SMILES (Canonical): CC1(C(CC2C3(C1C(OC3)O)C4C(CC5CC4(C(=O)C5(C)O)C(=O)O2)O)O)C
• SMILES (Isomeric): C[C@@]1([C@@H]2C[C@H]([C@@H]3[C@@](C2)(C1=O)C(=O)O[C@@H]4[C@@]35CO[C@H]([C@@H]5C([C@@H](C4)O)(C)C)O)O)O
• InChI: InChI=1S/C20H28O8/c1-17(2)10(22)5-11-20(7-27-14(23)13(17)20)12-9(21)4-8-6-19(12,16(25)28-11)15(24)18(8,3)26/h8-14,21-23,26H,4-7H2,1-3H3/t8-,9-,10-,11+,12-,13-,14-,18+,19+,20+/m1/s1
• InChI Key: FZFGOQVFSWJKRY-WPAHRGKHSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₈
• Molecular Weight: 396.40 g/mol
• Exact Mass: 396.17841785 g/mol
• Topological Polar Surface Area (TPSA): 134.00 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): -0.64
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9377	93.77%
Caco-2	-	0.6443	64.43%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7677	76.77%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8986	89.86%
OATP1B3 inhibitior	+	0.9088	90.88%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8864	88.64%
BSEP inhibitior	-	0.8355	83.55%
P-glycoprotein inhibitior	-	0.7977	79.77%
P-glycoprotein substrate	-	0.5410	54.10%
CYP3A4 substrate	+	0.6624	66.24%
CYP2C9 substrate	-	0.8070	80.70%
CYP2D6 substrate	-	0.8397	83.97%
CYP3A4 inhibition	-	0.9249	92.49%
CYP2C9 inhibition	-	0.9117	91.17%
CYP2C19 inhibition	-	0.9220	92.20%
CYP2D6 inhibition	-	0.9614	96.14%
CYP1A2 inhibition	-	0.9238	92.38%
CYP2C8 inhibition	-	0.7908	79.08%
CYP inhibitory promiscuity	-	0.9839	98.39%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5963	59.63%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.9659	96.59%
Skin irritation	-	0.7014	70.14%
Skin corrosion	-	0.9216	92.16%
Ames mutagenesis	+	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6154	61.54%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.8785	87.85%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.6281	62.81%
Acute Oral Toxicity (c)	I	0.4175	41.75%
Estrogen receptor binding	+	0.8817	88.17%
Androgen receptor binding	+	0.6252	62.52%
Thyroid receptor binding	+	0.6452	64.52%
Glucocorticoid receptor binding	+	0.7115	71.15%
Aromatase binding	+	0.6866	68.66%
PPAR gamma	+	0.6412	64.12%
Honey bee toxicity	-	0.7179	71.79%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9337	93.37%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.88%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.66%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.41%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.82%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.85%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.06%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.69%	97.09%
CHEMBL1937	Q92769	Histone deacetylase 2	84.79%	94.75%
CHEMBL226	P30542	Adenosine A1 receptor	84.61%	95.93%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	84.50%	89.34%
CHEMBL340	P08684	Cytochrome P450 3A4	83.31%	91.19%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.27%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.68%	89.00%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	80.71%	95.71%

Plants that contains it

• Arctotheca calendula
• Crotalaria laburnifolia
• Danae racemosa
• Daphniphyllum calycinum
• Elaeagnus angustifolia
• Isodon sculponeatus
• Melampodium argophyllum
• Ozothamnus obcordatus
• Quercus robur
• Salsola arbuscula

Cross-Links

• PubChem: 72947650
• NPASS: NPC88469
• LOTUS: LTS0217179
• wikiData: Q105004911