4-[[(3R,3aR,4S,6aR,8S,9aR,9bS)-4,8-dihydroxy-6,9-dimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-3-yl]methylamino]butanoic acid

Details

• Internal ID: 5556fa2d-36c6-4557-88be-17af3b660f4b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: 4-[[(3R,3aR,4S,6aR,8S,9aR,9bS)-4,8-dihydroxy-6,9-dimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-3-yl]methylamino]butanoic acid
• InChI: InChI=1S/C19H27NO6/c1-9-6-14(22)17-12(8-20-5-3-4-15(23)24)19(25)26-18(17)16-10(2)13(21)7-11(9)16/h11-14,16-18,20-22H,1-8H2,(H,23,24)/t11-,12-,13-,14-,16-,17+,18-/m0/s1
• InChI Key: YEJKKCAGDPUPJK-ZYSTXFPBSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₇NO₆
• Molecular Weight: 365.40 g/mol
• Exact Mass: 365.18383758 g/mol
• Topological Polar Surface Area (TPSA): 116.00 Ų
• XlogP: -2.40
• Atomic LogP (AlogP): 0.47
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8966	89.66%
Caco-2	-	0.8016	80.16%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5394	53.94%
OATP2B1 inhibitior	-	0.8596	85.96%
OATP1B1 inhibitior	+	0.8234	82.34%
OATP1B3 inhibitior	+	0.9492	94.92%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.8397	83.97%
P-glycoprotein inhibitior	-	0.8370	83.70%
P-glycoprotein substrate	+	0.6302	63.02%
CYP3A4 substrate	+	0.6167	61.67%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7247	72.47%
CYP3A4 inhibition	-	0.9178	91.78%
CYP2C9 inhibition	-	0.9126	91.26%
CYP2C19 inhibition	-	0.8720	87.20%
CYP2D6 inhibition	-	0.9058	90.58%
CYP1A2 inhibition	-	0.7112	71.12%
CYP2C8 inhibition	-	0.7847	78.47%
CYP inhibitory promiscuity	-	0.9756	97.56%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5759	57.59%
Eye corrosion	-	0.9733	97.33%
Eye irritation	-	0.9542	95.42%
Skin irritation	-	0.7232	72.32%
Skin corrosion	-	0.9141	91.41%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7921	79.21%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	+	0.6361	63.61%
skin sensitisation	-	0.8430	84.30%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.5931	59.31%
Acute Oral Toxicity (c)	III	0.5204	52.04%
Estrogen receptor binding	+	0.6538	65.38%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	-	0.5393	53.93%
Glucocorticoid receptor binding	-	0.4914	49.14%
Aromatase binding	-	0.5315	53.15%
PPAR gamma	-	0.5611	56.11%
Honey bee toxicity	-	0.8342	83.42%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	-	0.3623	36.23%

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	96.96%	91.11%
CHEMBL2581	P07339	Cathepsin D	90.16%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.86%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.38%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	88.02%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.32%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.07%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.61%	99.23%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	81.23%	89.34%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.04%	94.33%
CHEMBL217	P14416	Dopamine D2 receptor	80.94%	95.62%

Plants that contains it

• Saussurea pulchella

Cross-Links

• PubChem: 162961619
• LOTUS: LTS0030999
• wikiData: Q105347276