(2Z,4E)-5-[(1R,2S,3S,4R,4aS,8aS)-2,3,4-trihydroxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpenta-2,4-dienal

Details

• Internal ID: 757aae85-13f3-4ebc-ad97-b43b690b5af6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (2Z,4E)-5-[(1R,2S,3S,4R,4aS,8aS)-2,3,4-trihydroxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpenta-2,4-dienal
• SMILES (Canonical): CC(=CC=O)C=CC1C2(CCCC(C2C(C(C1(C)O)O)O)(C)C)C
• SMILES (Isomeric): C/C(=C/C=O)/C=C/[C@@H]1[C@]2(CCCC([C@@H]2[C@H]([C@@H]([C@@]1(C)O)O)O)(C)C)C
• InChI: InChI=1S/C20H32O4/c1-13(9-12-21)7-8-14-19(4)11-6-10-18(2,3)16(19)15(22)17(23)20(14,5)24/h7-9,12,14-17,22-24H,6,10-11H2,1-5H3/b8-7+,13-9-/t14-,15-,16+,17+,19-,20+/m1/s1
• InChI Key: XWVGZNYHKHGOKZ-FHELPVNXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₂O₄
• Molecular Weight: 336.50 g/mol
• Exact Mass: 336.23005950 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.62
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9743	97.43%
Caco-2	+	0.5192	51.92%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6488	64.88%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8352	83.52%
OATP1B3 inhibitior	+	0.9083	90.83%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.4731	47.31%
P-glycoprotein inhibitior	-	0.8255	82.55%
P-glycoprotein substrate	-	0.7286	72.86%
CYP3A4 substrate	+	0.6128	61.28%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8820	88.20%
CYP3A4 inhibition	-	0.8717	87.17%
CYP2C9 inhibition	-	0.7578	75.78%
CYP2C19 inhibition	-	0.8261	82.61%
CYP2D6 inhibition	-	0.9029	90.29%
CYP1A2 inhibition	-	0.6642	66.42%
CYP2C8 inhibition	-	0.8166	81.66%
CYP inhibitory promiscuity	-	0.7800	78.00%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6267	62.67%
Eye corrosion	-	0.9925	99.25%
Eye irritation	-	0.9846	98.46%
Skin irritation	+	0.5302	53.02%
Skin corrosion	-	0.9307	93.07%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4814	48.14%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.5176	51.76%
skin sensitisation	+	0.4753	47.53%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.6127	61.27%
Acute Oral Toxicity (c)	III	0.6017	60.17%
Estrogen receptor binding	+	0.7683	76.83%
Androgen receptor binding	-	0.6116	61.16%
Thyroid receptor binding	+	0.6466	64.66%
Glucocorticoid receptor binding	+	0.5817	58.17%
Aromatase binding	+	0.6639	66.39%
PPAR gamma	+	0.5261	52.61%
Honey bee toxicity	-	0.8603	86.03%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9895	98.95%

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	94.25%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.56%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.07%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.05%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.69%	97.25%
CHEMBL2581	P07339	Cathepsin D	82.19%	98.95%
CHEMBL325	Q13547	Histone deacetylase 1	81.62%	95.92%

Plants that contains it

• Stevia rebaudiana

Cross-Links

• PubChem: 101263052
• LOTUS: LTS0041295
• wikiData: Q105343794