Monocrotalin

Details

• Internal ID: 83f46a1b-a3ad-485c-84d7-f0f28b2d3fb9
• Taxonomy: Organoheterocyclic compounds > Pyrrolizines
• IUPAC Name: 5,6-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.013,16]hexadec-10-ene-3,7-dione
• SMILES (Canonical): CC1C(=O)OC2CCN3C2C(=CC3)COC(=O)C(C1(C)O)(C)O
• SMILES (Isomeric): CC1C(=O)OC2CCN3C2C(=CC3)COC(=O)C(C1(C)O)(C)O
• InChI: InChI=1S/C16H23NO6/c1-9-13(18)23-11-5-7-17-6-4-10(12(11)17)8-22-14(19)16(3,21)15(9,2)20/h4,9,11-12,20-21H,5-8H2,1-3H3
• InChI Key: QVCMHGGNRFRMAD-UHFFFAOYSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₃NO₆
• Molecular Weight: 325.36 g/mol
• Exact Mass: 325.15253745 g/mol
• Topological Polar Surface Area (TPSA): 96.30 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -0.39
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• MLS002639247
• 20-Norcrotalanan-11,15-dione, 14,19-dihydro-12,13-dihydroxy-, (13.alpha.,14.alpha.)-
• NCI-C56462
• NSC 28693
• A 6080
• Oprea1_734543
• CHEMBL2134902
• DTXSID20859330
• CHEBI:125403
• QVCMHGGNRFRMAD-UHFFFAOYSA-N
• (2,3,4-gh)pyrrolizine-2,6(3H)-dione, (4,5,8,10,12,13,13a,13b)-octahydro-4,5-dihydroxy-3,4,5-trimethyl-2H-(1,6)dioxacycloundecino-
• BCP04181
• LSM-36888
• 4,5-Dihydroxy-3,4,5-trimethyl-4,5,8,10,12,13,13a,13b-octahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione
• LS-14523
• SMR001548694
• A856086
• A 6080;A-6080;A6080
• Q27215982
• (6-CHLORO-IMIDAZO[1,2-A]PYRIDIN-2-YL)-ACETICACID
• 14,19-Dihydro-12,13-dihydroxy-20-norcrotalanan-11,15-dione, 9CI
• (13-.alpha.,14-.alpha.)-14,19-Dihydro-12,13-dihydroxy-20-norcrotalanan-11,15-dione
• 12.beta.,13.beta.-Dihydroxy-12.alpha.,13.alpha.,14.alpha.-trimethylcrotal-1-enine
• 14,19-Dihydro-12,13-dihydroxy(13.alpha.,14.alpha.)-20-norcrotalanan-11,15-dione
• 2H-[1,6]Dioxacycloundecino[2,3,4-gh]pyrrolizine, 20-norcrotalanan-11,15-dione deriv.
• (2,3,4-gh)pyrrolizine-2,6(3H)-dione,(4,5,8,10,12,13,13a,13b-octahydro-4,5-dihydroxy-3,4,5-trimethyl-2H-(1,6)dioxacycloundecino-
• 4,5-Dihydroxy-3,4,5-trimethyl-4,5,8,10,12,13,13a,13b-octahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione #

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6382	63.82%
Caco-2	+	0.7001	70.01%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.6808	68.08%
OATP2B1 inhibitior	-	0.8599	85.99%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6823	68.23%
P-glycoprotein inhibitior	-	0.9166	91.66%
P-glycoprotein substrate	-	0.5349	53.49%
CYP3A4 substrate	+	0.5939	59.39%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7540	75.40%
CYP3A4 inhibition	-	0.9024	90.24%
CYP2C9 inhibition	-	0.9173	91.73%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9232	92.32%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.9346	93.46%
CYP inhibitory promiscuity	-	0.9874	98.74%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Danger	0.7983	79.83%
Eye corrosion	-	0.9804	98.04%
Eye irritation	-	0.9878	98.78%
Skin irritation	-	0.7282	72.82%
Skin corrosion	-	0.9108	91.08%
Ames mutagenesis	-	0.8200	82.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5950	59.50%
Micronuclear	+	0.7100	71.00%
Hepatotoxicity	+	1.0000	100.00%
skin sensitisation	-	0.8279	82.79%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.6844	68.44%
Acute Oral Toxicity (c)	II	0.7186	71.86%
Estrogen receptor binding	-	0.5797	57.97%
Androgen receptor binding	+	0.6385	63.85%
Thyroid receptor binding	-	0.5676	56.76%
Glucocorticoid receptor binding	+	0.6545	65.45%
Aromatase binding	-	0.5613	56.13%
PPAR gamma	-	0.8546	85.46%
Honey bee toxicity	-	0.8832	88.32%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	-	0.4404	44.04%

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	91.44%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.36%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.29%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.93%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.47%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.94%	94.45%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.29%	92.94%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.80%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.31%	97.25%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	83.03%	93.40%
CHEMBL1871	P10275	Androgen Receptor	82.58%	96.43%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.98%	99.23%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.14%	97.14%

Plants that contains it

• Crotalaria crispata

Cross-Links

• PubChem: 4246
• LOTUS: LTS0262380
• wikiData: Q27215982