Aeroplysinin I

Details

• Internal ID: 7fcf9efe-87fd-4807-a009-e12a14b1c586
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Alcohols and polyols > Tertiary alcohols
• IUPAC Name: 2-[(1S,6R)-3,5-dibromo-1,6-dihydroxy-4-methoxycyclohexa-2,4-dien-1-yl]acetonitrile
• SMILES (Canonical): COC1=C(C(C(C=C1Br)(CC#N)O)O)Br
• SMILES (Isomeric): COC1=C([C@@H]([C@@](C=C1Br)(CC#N)O)O)Br
• InChI: InChI=1S/C9H9Br2NO3/c1-15-7-5(10)4-9(14,2-3-12)8(13)6(7)11/h4,8,13-14H,2H2,1H3/t8-,9-/m0/s1
• InChI Key: BGYNLOSBKBOJJD-IUCAKERBSA-N
• Popularity: 25 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₉Br₂NO₃
• Molecular Weight: 338.98 g/mol
• Exact Mass: 338.89287 g/mol
• Topological Polar Surface Area (TPSA): 73.50 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 1.54
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• Aeroplysinin 1
• 28656-91-9
• (+)-Aeroplysinin-1
• aeroplysinin
• AEROPLYSININ-1
• CHEBI:80925
• 2-[(1S,6R)-3,5-dibromo-1,6-dihydroxy-4-methoxycyclohexa-2,4-dien-1-yl]acetonitrile
• 2,4-Cyclohexadiene-1-acetonitrile, 3,5-dibromo-1,6-dihydroxy-4-methoxy-, (1S,6R)-
• 2-((1S,6R)-3,5-Dibromo-1,6-dihydroxy-4-methoxycyclohexa-2,4-dien-1-yl)acetonitrile
• 55057-73-3
• AEROPLYSININ-I (RACEMIC)
• (+)-Aeroplysinin I
• (+)--Aeroplysinin-1
• Aeroplysinin I, (+)-
• (.+-.)-Aeroplysinin I
• Aeroplysinin,aplysina aerophoba
• CHEMBL462153
• SCHEMBL14267425
• DTXSID60951322
• GLXC-19142
• HSCI1_000046
• NSC170364
• NSC286160
• NSC-170364
• NSC-286160
• 34140-52-8
• HY-19827
• 2, 3,5-dibromo-1,6-dihydroxy-4-methoxy-
• CS-0016895
• C17099
• F82085
• J-017181
• Q27151425
• 2, 3,5-dibromo-1,6-dihydroxy-4-methoxy-, (1S-trans)-
• 2, 3,5-dibromo-1,6-dihydroxy-4-methoxy-, trans-(+)-
• (3,5-dibromo-1,6-dihydroxy-4-methoxycyclohexa-2,4-dien-1-yl)acetonitrile
• 2,4-Cyclohexadiene-1-acetonitrile, 3,5-dibromo-1,6-dihydroxy-4-methoxy-
• (1S-trans)-3,5-Dibromo-1,6-dihydroxy-4-methoxy-2,4-cyclohexadiene-1- acetonitrile
• 2-((1S,6R)-3,5-dibromo-1,6-dihydroxy-4-methoxycyclohexa-2,4-dienyl)acetonitrile

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9754	97.54%
Caco-2	-	0.7890	78.90%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7517	75.17%
OATP2B1 inhibitior	-	0.8573	85.73%
OATP1B1 inhibitior	+	0.9138	91.38%
OATP1B3 inhibitior	+	0.9546	95.46%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.7924	79.24%
P-glycoprotein inhibitior	-	0.9743	97.43%
P-glycoprotein substrate	-	0.8715	87.15%
CYP3A4 substrate	+	0.5199	51.99%
CYP2C9 substrate	-	0.8071	80.71%
CYP2D6 substrate	-	0.7728	77.28%
CYP3A4 inhibition	-	0.8084	80.84%
CYP2C9 inhibition	-	0.6632	66.32%
CYP2C19 inhibition	-	0.6987	69.87%
CYP2D6 inhibition	-	0.8927	89.27%
CYP1A2 inhibition	-	0.7150	71.50%
CYP2C8 inhibition	-	0.7580	75.80%
CYP inhibitory promiscuity	-	0.7197	71.97%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.7751	77.51%
Carcinogenicity (trinary)	Non-required	0.5007	50.07%
Eye corrosion	-	0.9662	96.62%
Eye irritation	+	0.7091	70.91%
Skin irritation	-	0.7151	71.51%
Skin corrosion	-	0.9164	91.64%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6270	62.70%
Micronuclear	-	0.5209	52.09%
Hepatotoxicity	+	0.5747	57.47%
skin sensitisation	-	0.6893	68.93%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.6285	62.85%
Acute Oral Toxicity (c)	III	0.5990	59.90%
Estrogen receptor binding	-	0.7269	72.69%
Androgen receptor binding	-	0.7673	76.73%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.4906	49.06%
Aromatase binding	-	0.9073	90.73%
PPAR gamma	-	0.5240	52.40%
Honey bee toxicity	-	0.7815	78.15%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	-	0.5702	57.02%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	97.53%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.96%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.20%	96.09%
CHEMBL1871	P10275	Androgen Receptor	93.22%	96.43%
CHEMBL226	P30542	Adenosine A1 receptor	84.29%	95.93%
CHEMBL2581	P07339	Cathepsin D	83.12%	98.95%
CHEMBL2535	P11166	Glucose transporter	82.49%	98.75%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.80%	92.94%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.54%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.22%	86.33%

Plants that contains it

• Brassica rapa
• Lepidium draba
• Sonchus micranthus

Cross-Links

• PubChem: 100308
• NPASS: NPC159547
• ChEMBL: CHEMBL462153
• LOTUS: LTS0198927
• wikiData: Q27151425