Isocromadurine

Details

• Internal ID: 985297e8-a9c4-4d86-8bae-afbf000f9f79
• Taxonomy: Organoheterocyclic compounds > Pyrrolizines
• IUPAC Name: (1R,4R,5S,6S,16R)-5-hydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.013,16]hexadec-10-ene-3,7-dione
• SMILES (Canonical): CC1C(=O)OCC2=CCN3C2C(CC3)OC(=O)C(C1(C)O)C
• SMILES (Isomeric): C[C@@H]1C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC(=O)[C@@H]([C@@]1(C)O)C
• InChI: InChI=1S/C16H23NO5/c1-9-14(18)21-8-11-4-6-17-7-5-12(13(11)17)22-15(19)10(2)16(9,3)20/h4,9-10,12-13,20H,5-8H2,1-3H3/t9-,10+,12-,13-,16+/m1/s1
• InChI Key: PSUFRPOAICRSTC-ZLGRWFNRSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₃NO₅
• Molecular Weight: 309.36 g/mol
• Exact Mass: 309.15762283 g/mol
• Topological Polar Surface Area (TPSA): 76.10 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 0.49
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• Isocromadurine
• 6029-87-4
• UNII-8FS62J40NX
• Crispatine
• 8FS62J40NX
• 57495-69-9
• C10304
• (1R,4R,5S,6S,16R)-5-hydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.013,16]hexadec-10-ene-3,7-dione
• AC1L9DAT
• CHEBI:5187
• 20-Norcrotalanan-11,15-dione, 14,19-dihydro-13-hydroxy-, (13.alpha.,14.alpha.)-
• 16-H13-N-O5
• HY-133589
• CS-0128288
• Q27106682
• 20-Norcrotalanan-11,15-dione, 14,19-dihydro-13-hydroxy-, (12.xi.,13.xi.)-
• 2H-(1,6)Dioxacycloundecino(2,3,4-gh)pyrrolizine-2,6(3H)-dione, 4,5,8,10,12,13,13a,13b-octahydro-4-hydroxy-3,4,5-trimethyl-
• 2H-(1,6)DIOXACYCLOUNDECINO(2,3,4-GH)PYRROLIZINE-2,6(3H)-DIONE, 4,5,8,10,12,13,13A,13B-OCTAHYDRO-4-HYDROXY-3,4,5-TRIMETHYL-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9035	90.35%
Caco-2	+	0.7685	76.85%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6487	64.87%
OATP2B1 inhibitior	-	0.8576	85.76%
OATP1B1 inhibitior	+	0.9406	94.06%
OATP1B3 inhibitior	+	0.9428	94.28%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.7195	71.95%
P-glycoprotein inhibitior	-	0.8721	87.21%
P-glycoprotein substrate	-	0.5537	55.37%
CYP3A4 substrate	+	0.5926	59.26%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7291	72.91%
CYP3A4 inhibition	-	0.7924	79.24%
CYP2C9 inhibition	-	0.9446	94.46%
CYP2C19 inhibition	-	0.9073	90.73%
CYP2D6 inhibition	-	0.9165	91.65%
CYP1A2 inhibition	-	0.8671	86.71%
CYP2C8 inhibition	-	0.9621	96.21%
CYP inhibitory promiscuity	-	0.9854	98.54%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Danger	0.7048	70.48%
Eye corrosion	-	0.9772	97.72%
Eye irritation	-	0.9877	98.77%
Skin irritation	-	0.7386	73.86%
Skin corrosion	-	0.8990	89.90%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5158	51.58%
Micronuclear	+	0.6100	61.00%
Hepatotoxicity	+	0.9750	97.50%
skin sensitisation	-	0.8168	81.68%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.7525	75.25%
Acute Oral Toxicity (c)	II	0.5592	55.92%
Estrogen receptor binding	-	0.6939	69.39%
Androgen receptor binding	+	0.6453	64.53%
Thyroid receptor binding	-	0.5981	59.81%
Glucocorticoid receptor binding	+	0.6157	61.57%
Aromatase binding	-	0.6030	60.30%
PPAR gamma	-	0.7731	77.31%
Honey bee toxicity	-	0.8624	86.24%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	-	0.4738	47.38%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.35%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.27%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.20%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.40%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.32%	97.25%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	89.07%	93.40%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.59%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.63%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.37%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.85%	94.45%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	83.51%	86.00%
CHEMBL1871	P10275	Androgen Receptor	80.89%	96.43%

Plants that contains it

• Crotalaria berteroana
• Crotalaria crispata
• Crotalaria madurensis
• Crotalaria paniculata

Cross-Links

• PubChem: 442726
• NPASS: NPC308013
• LOTUS: LTS0035655
• wikiData: Q27106682