Guineensine

Details

• Internal ID: 7f1e1b5e-159f-4181-9177-7bb0601bb9c4
• Taxonomy: Organoheterocyclic compounds > Benzodioxoles
• IUPAC Name: (2E,4E,12E)-13-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)trideca-2,4,12-trienamide
• SMILES (Canonical): CC(C)CNC(=O)C=CC=CCCCCCCC=CC1=CC2=C(C=C1)OCO2
• SMILES (Isomeric): CC(C)CNC(=O)/C=C/C=C/CCCCCC/C=C/C1=CC2=C(C=C1)OCO2
• InChI: InChI=1S/C24H33NO3/c1-20(2)18-25-24(26)14-12-10-8-6-4-3-5-7-9-11-13-21-15-16-22-23(17-21)28-19-27-22/h8,10-17,20H,3-7,9,18-19H2,1-2H3,(H,25,26)/b10-8+,13-11+,14-12+
• InChI Key: FPMPOFBEYSSYDQ-AUVZEZIHSA-N
• Popularity: 23 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₃NO₃
• Molecular Weight: 383.50 g/mol
• Exact Mass: 383.24604391 g/mol
• Topological Polar Surface Area (TPSA): 47.60 Ų
• XlogP: 6.80
• Atomic LogP (AlogP): 5.65
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 12

Synonyms

• Guineesine
• 55038-30-7
• Pipyahyine
• (2E,4E,12E)-13-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)trideca-2,4,12-trienamide
• (E,E,E)-Guineensine
• 7DK8DMU9JX
• 2,4,12-Tridecatrienamide, 13-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)-, (2E,4E,12E)-
• 2,4,12-Tridecatrienamide, 13-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)-, (E,E,E)-
• UNII-7DK8DMU9JX
• MLS002473215
• CHEMBL404184
• SCHEMBL11309623
• CHEBI:181825
• FPMPOFBEYSSYDQ-AUVZEZIHSA-N
• DTXSID801336042
• HMS2268L12
• BDBM50479142
• AKOS040745833
• (2E,4E,12E)-13-(benzo[d][1,3]dioxol-5-yl)-N-isobutyltrideca-2,4,12-trienamide
• NCGC00247500-01
• SMR001397303
• (2E,4E,12E)-13-(1,3-benzodioxol-5-yl)-N-isobutyl-trideca-2,4,12-trienamide
• 153012-58-9
• NCGC00247500-02!(2E,4E,12E)-13-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)trideca-2,4,12-trienamide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9961	99.61%
Caco-2	-	0.5668	56.68%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6891	68.91%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9057	90.57%
OATP1B3 inhibitior	+	0.9421	94.21%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.9010	90.10%
P-glycoprotein inhibitior	+	0.8039	80.39%
P-glycoprotein substrate	-	0.6982	69.82%
CYP3A4 substrate	+	0.5220	52.20%
CYP2C9 substrate	-	0.6355	63.55%
CYP2D6 substrate	-	0.8841	88.41%
CYP3A4 inhibition	-	0.6544	65.44%
CYP2C9 inhibition	-	0.5235	52.35%
CYP2C19 inhibition	+	0.6193	61.93%
CYP2D6 inhibition	+	0.5117	51.17%
CYP1A2 inhibition	+	0.6872	68.72%
CYP2C8 inhibition	-	0.7606	76.06%
CYP inhibitory promiscuity	+	0.7623	76.23%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7700	77.00%
Carcinogenicity (trinary)	Non-required	0.5911	59.11%
Eye corrosion	-	0.9829	98.29%
Eye irritation	-	0.9522	95.22%
Skin irritation	-	0.7418	74.18%
Skin corrosion	-	0.9036	90.36%
Ames mutagenesis	-	0.7191	71.91%
Human Ether-a-go-go-Related Gene inhibition	+	0.9153	91.53%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	-	0.5967	59.67%
skin sensitisation	-	0.7379	73.79%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.8792	87.92%
Acute Oral Toxicity (c)	III	0.6716	67.16%
Estrogen receptor binding	+	0.6497	64.97%
Androgen receptor binding	+	0.8900	89.00%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6477	64.77%
Aromatase binding	+	0.6328	63.28%
PPAR gamma	-	0.5320	53.20%
Honey bee toxicity	-	0.9263	92.63%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5137	51.37%
Fish aquatic toxicity	+	0.9430	94.30%

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	99.14%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.07%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.92%	94.45%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	96.10%	94.80%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.83%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.05%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.68%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	94.16%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.06%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.89%	95.56%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	89.66%	80.96%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.79%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.30%	89.00%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	88.12%	85.30%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.36%	96.77%
CHEMBL4208	P20618	Proteasome component C5	86.38%	90.00%
CHEMBL5261	Q7L7X3	Serine/threonine-protein kinase TAO1	82.75%	89.33%
CHEMBL3975	P09467	Fructose-1,6-bisphosphatase	80.93%	92.95%

Plants that contains it

• Acanthosyris paulo-alvinii
• Aglaia perviridis
• Ardisia japonica
• Bellardia viscosa
• Betula alnoides
• Brickellia longifolia
• Bupleurum rigidum
• Carpesium longifolium
• Cochlearia officinalis
• Coelogyne nitida
• Crocus corsicus
• Dichotomanthes tristaniicarpa
• Dracontium spruceanum
• Dryopteris arguta
• Euphorbia micractina
• Frullania brasiliensis
• Heptapleurum venulosum
• Hippocrepis emerus
• Homalium laurifolium
• Kopsia lapidilecta
• Lychnis coronata
• Matsumurella chinensis
• Palisota barteri
• Phoebe grandis
• Pinus aristata
• Piper longum
• Piper nigrum
• Piper retrofractum
• Piper sarmentosum
• Plenckia populnea
• Retrophyllum minus
• Rubus pileatus
• Verbesina virginica

Cross-Links

• PubChem: 6442405
• NPASS: NPC291449
• ChEMBL: CHEMBL404184