(3S)-5-[(1R,2S,3R,4aR,8aR)-5-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxymethyl]-3-hydroxy-1,2,4a-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpentanoic acid

Details

• Internal ID: c36702e3-834a-43f9-a2ee-4069b9ceb13c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Colensane and clerodane diterpenoids
• IUPAC Name: (3S)-5-[(1R,2S,3R,4aR,8aR)-5-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxymethyl]-3-hydroxy-1,2,4a-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpentanoic acid
• SMILES (Canonical): CC1C(CC2(C(C1(C)CCC(C)CC(=O)O)CCC=C2COC(=O)C=CC3=CC(=C(C=C3)O)O)C)O
• SMILES (Isomeric): C[C@@H]1[C@@H](C[C@@]2([C@@H]([C@@]1(C)CC[C@H](C)CC(=O)O)CCC=C2COC(=O)/C=C/C3=CC(=C(C=C3)O)O)C)O
• InChI: InChI=1S/C29H40O7/c1-18(14-26(33)34)12-13-28(3)19(2)24(32)16-29(4)21(6-5-7-25(28)29)17-36-27(35)11-9-20-8-10-22(30)23(31)15-20/h6,8-11,15,18-19,24-25,30-32H,5,7,12-14,16-17H2,1-4H3,(H,33,34)/b11-9+/t18-,19+,24+,25+,28-,29-/m0/s1
• InChI Key: WBXJTEOASUIUIA-QZEJUCPHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₀O₇
• Molecular Weight: 500.60 g/mol
• Exact Mass: 500.27740361 g/mol
• Topological Polar Surface Area (TPSA): 124.00 Ų
• XlogP: 5.50
• Atomic LogP (AlogP): 5.29
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9809	98.09%
Caco-2	-	0.8063	80.63%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8978	89.78%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9065	90.65%
OATP1B3 inhibitior	+	0.8965	89.65%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8292	82.92%
BSEP inhibitior	+	0.9474	94.74%
P-glycoprotein inhibitior	+	0.6723	67.23%
P-glycoprotein substrate	+	0.5074	50.74%
CYP3A4 substrate	+	0.6727	67.27%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8751	87.51%
CYP3A4 inhibition	-	0.7129	71.29%
CYP2C9 inhibition	-	0.8229	82.29%
CYP2C19 inhibition	-	0.7349	73.49%
CYP2D6 inhibition	-	0.8789	87.89%
CYP1A2 inhibition	+	0.5806	58.06%
CYP2C8 inhibition	+	0.6456	64.56%
CYP inhibitory promiscuity	-	0.8618	86.18%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.6821	68.21%
Eye corrosion	-	0.9951	99.51%
Eye irritation	-	0.9503	95.03%
Skin irritation	-	0.5703	57.03%
Skin corrosion	-	0.9658	96.58%
Ames mutagenesis	-	0.7478	74.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.8320	83.20%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.8379	83.79%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.8146	81.46%
Acute Oral Toxicity (c)	III	0.5791	57.91%
Estrogen receptor binding	+	0.8454	84.54%
Androgen receptor binding	+	0.7973	79.73%
Thyroid receptor binding	+	0.6254	62.54%
Glucocorticoid receptor binding	+	0.8250	82.50%
Aromatase binding	+	0.7680	76.80%
PPAR gamma	+	0.5984	59.84%
Honey bee toxicity	-	0.7364	73.64%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	99.78%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.78%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.20%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.07%	94.45%
CHEMBL2581	P07339	Cathepsin D	93.97%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.87%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	93.71%	90.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.39%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.84%	89.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	90.94%	94.62%
CHEMBL4208	P20618	Proteasome component C5	90.12%	90.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.56%	96.00%
CHEMBL1951	P21397	Monoamine oxidase A	89.55%	91.49%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.69%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.59%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.52%	99.17%
CHEMBL340	P08684	Cytochrome P450 3A4	86.45%	91.19%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.23%	93.56%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.55%	89.62%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.46%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.25%	95.89%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.77%	91.07%

Plants that contains it

• Nuxia sphaerocephala

Cross-Links

• PubChem: 11598539
• LOTUS: LTS0009958
• wikiData: Q105301140