[(3aS,4R,10aS)-2-amino-5,10,10-trihydroxy-6-imino-3a,4,8,9-tetrahydro-1H-pyrrolo[1,2-c]purin-4-yl]methyl carbamate

Details

• Internal ID: 1c441f39-a473-48d4-be69-b466fc58c286
• Taxonomy: Phenylpropanoids and polyketides > Saxitoxins, gonyautoxins, and derivatives
• IUPAC Name: [(3aS,4R,10aS)-2,6-diamino-10,10-dihydroxy-5-oxido-3a,4,8,9-tetrahydro-1H-pyrrolo[1,2-c]purin-5-ium-4-yl]methyl carbamate
• SMILES (Canonical): C1CN2C(=[N+](C(C3C2(C1(O)O)NC(=N3)N)COC(=O)N)[O-])N
• SMILES (Isomeric): C1CN2C(=[N+]([C@H]([C@H]3[C@]2(C1(O)O)NC(=N3)N)COC(=O)N)[O-])N
• InChI: InChI=1S/C10H17N7O5/c11-6-14-5-4(3-22-8(13)18)17(21)7(12)16-2-1-9(19,20)10(5,16)15-6/h4-5,19-20H,1-3,12H2,(H2,13,18)(H3,11,14,15)/t4-,5-,10-/m0/s1
• InChI Key: BBWULCNJOJRQBM-HGRQIUPRSA-N
• Popularity: 78 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₇N₇O₅
• Molecular Weight: 315.29 g/mol
• Exact Mass: 315.12911667 g/mol
• Topological Polar Surface Area (TPSA): 201.00 Ų
• XlogP: -5.80
• Atomic LogP (AlogP): -4.34
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 2

Synonyms

• [(3aS,4R,10aS)-2-amino-5,10,10-trihydroxy-6-imino-3a,4,8,9-tetrahydro-1H-pyrrolo[1,2-c]purin-4-yl]methyl carbamate
• [(3aS,4R,10aS)-2,6-diamino-10,10-dihydroxy-5-oxido-3a,4,8,9-tetrahydro-1H-pyrrolo[1,2-c]purin-5-ium-4-yl]methyl carbamate
• SCHEMBL21803819
• SCHEMBL22320000
• CHEBI:181363
• SMP2_000311
• C17208
• [(R,7aS,7bS)-2-amino-7,7-trihydroxy--imino-H,H,H,1H,5H,6H,7H,7bH-pyrrolo[1,2-c]purin--yl]methyl carbamate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5000	50.00%
Caco-2	-	0.8385	83.85%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Lysosomes	0.4690	46.90%
OATP2B1 inhibitior	-	0.8558	85.58%
OATP1B1 inhibitior	+	0.9368	93.68%
OATP1B3 inhibitior	+	0.9392	93.92%
MATE1 inhibitior	-	0.6200	62.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.8708	87.08%
P-glycoprotein inhibitior	-	0.8861	88.61%
P-glycoprotein substrate	-	0.5215	52.15%
CYP3A4 substrate	+	0.5855	58.55%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8061	80.61%
CYP3A4 inhibition	-	0.9487	94.87%
CYP2C9 inhibition	-	0.8413	84.13%
CYP2C19 inhibition	-	0.8004	80.04%
CYP2D6 inhibition	-	0.8797	87.97%
CYP1A2 inhibition	-	0.7802	78.02%
CYP2C8 inhibition	-	0.8214	82.14%
CYP inhibitory promiscuity	-	0.9837	98.37%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.5064	50.64%
Eye corrosion	-	0.9791	97.91%
Eye irritation	-	0.9899	98.99%
Skin irritation	-	0.7470	74.70%
Skin corrosion	-	0.9166	91.66%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6651	66.51%
Micronuclear	+	0.8900	89.00%
Hepatotoxicity	-	0.5565	55.65%
skin sensitisation	-	0.8135	81.35%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.7708	77.08%
Acute Oral Toxicity (c)	III	0.4251	42.51%
Estrogen receptor binding	+	0.8214	82.14%
Androgen receptor binding	+	0.6739	67.39%
Thyroid receptor binding	+	0.6890	68.90%
Glucocorticoid receptor binding	+	0.7363	73.63%
Aromatase binding	+	0.6096	60.96%
PPAR gamma	+	0.7144	71.44%
Honey bee toxicity	-	0.8594	85.94%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	-	0.8276	82.76%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.81%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.62%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.62%	97.09%
CHEMBL4040	P28482	MAP kinase ERK2	90.76%	83.82%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	90.23%	96.90%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	89.13%	95.50%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	84.32%	92.32%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	84.14%	92.86%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.30%	97.28%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.86%	99.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.23%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.73%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.56%	95.89%
CHEMBL204	P00734	Thrombin	80.00%	96.01%

Plants that contains it

• Salvia prionitis

Cross-Links

• PubChem: 135562690
• LOTUS: LTS0049020
• wikiData: Q105025831