(Z)-2-[(E)-2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethenyl]but-2-enedioic acid

Details

• Internal ID: 0be7ada2-3778-427f-8b55-aed346c1cba5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (Z)-2-[(E)-2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethenyl]but-2-enedioic acid
• SMILES (Canonical): CC12CCC(C(C1CCC(=C)C2C=CC(=CC(=O)O)C(=O)O)(C)CO)O
• SMILES (Isomeric): C[C@]12CC[C@H]([C@@]([C@H]1CCC(=C)[C@H]2/C=C/C(=C/C(=O)O)/C(=O)O)(C)CO)O
• InChI: InChI=1S/C20H28O6/c1-12-4-7-15-19(2,9-8-16(22)20(15,3)11-21)14(12)6-5-13(18(25)26)10-17(23)24/h5-6,10,14-16,21-22H,1,4,7-9,11H2,2-3H3,(H,23,24)(H,25,26)/b6-5+,13-10-/t14-,15+,16-,19-,20+/m1/s1
• InChI Key: IMDVHFGRDJPERC-NSTPHGKVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₆
• Molecular Weight: 364.40 g/mol
• Exact Mass: 364.18858861 g/mol
• Topological Polar Surface Area (TPSA): 115.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.38
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9639	96.39%
Caco-2	-	0.6188	61.88%
Blood Brain Barrier	+	0.5777	57.77%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.8069	80.69%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8933	89.33%
OATP1B3 inhibitior	+	0.8364	83.64%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	+	0.5088	50.88%
BSEP inhibitior	-	0.7685	76.85%
P-glycoprotein inhibitior	-	0.8699	86.99%
P-glycoprotein substrate	-	0.7280	72.80%
CYP3A4 substrate	+	0.6526	65.26%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9071	90.71%
CYP3A4 inhibition	-	0.6901	69.01%
CYP2C9 inhibition	-	0.8814	88.14%
CYP2C19 inhibition	-	0.9285	92.85%
CYP2D6 inhibition	-	0.9304	93.04%
CYP1A2 inhibition	-	0.9073	90.73%
CYP2C8 inhibition	-	0.6176	61.76%
CYP inhibitory promiscuity	-	0.9317	93.17%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7343	73.43%
Eye corrosion	-	0.9924	99.24%
Eye irritation	-	0.8915	89.15%
Skin irritation	+	0.4913	49.13%
Skin corrosion	-	0.9557	95.57%
Ames mutagenesis	-	0.7654	76.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.3701	37.01%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.7476	74.76%
skin sensitisation	-	0.8686	86.86%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.6780	67.80%
Acute Oral Toxicity (c)	III	0.6946	69.46%
Estrogen receptor binding	+	0.5421	54.21%
Androgen receptor binding	+	0.5875	58.75%
Thyroid receptor binding	+	0.6573	65.73%
Glucocorticoid receptor binding	+	0.6620	66.20%
Aromatase binding	+	0.7018	70.18%
PPAR gamma	-	0.5086	50.86%
Honey bee toxicity	-	0.8560	85.60%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.9945	99.45%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	94.22%	83.82%
CHEMBL221	P23219	Cyclooxygenase-1	91.53%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.91%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.22%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.37%	95.56%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.35%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.25%	95.89%
CHEMBL5028	O14672	ADAM10	80.14%	97.50%

Plants that contains it

• Andrographis paniculata

Cross-Links

• PubChem: 162873187
• LOTUS: LTS0190775
• wikiData: Q105115612