Clerodin

Details

• Internal ID: 1a1bfcf5-4540-4704-b3d5-dbb50cbd8e0e
• Taxonomy: Organoheterocyclic compounds > Furofurans
• IUPAC Name: [(4R,4aR,5S,7R,8S,8aR)-8-[(3aS,5S,6aS)-3a,4,5,6a-tetrahydrofuro[2,3-b]furan-5-yl]-5-acetyloxy-7,8-dimethylspiro[2,3,5,6,7,8a-hexahydro-1H-naphthalene-4,2'-oxirane]-4a-yl]methyl acetate
• SMILES (Canonical): CC1CC(C2(C(C1(C)C3CC4C=COC4O3)CCCC25CO5)COC(=O)C)OC(=O)C
• SMILES (Isomeric): C[C@@H]1C[C@@H]([C@@]2([C@@H]([C@@]1(C)[C@@H]3C[C@H]4C=CO[C@H]4O3)CCC[C@]25CO5)COC(=O)C)OC(=O)C
• InChI: InChI=1S/C24H34O7/c1-14-10-20(30-16(3)26)24(13-28-15(2)25)18(6-5-8-23(24)12-29-23)22(14,4)19-11-17-7-9-27-21(17)31-19/h7,9,14,17-21H,5-6,8,10-13H2,1-4H3/t14-,17-,18-,19+,20+,21+,22+,23+,24+/m1/s1
• InChI Key: CNIWQELMLPUFOS-NVSXQWMQSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₄O₇
• Molecular Weight: 434.50 g/mol
• Exact Mass: 434.23045342 g/mol
• Topological Polar Surface Area (TPSA): 83.60 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.36
• H-Bond Acceptor: 7
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

• CHEBI:67461
• 464-71-1
• C24H34O7
• CHEMBL2269422
• SCHEMBL21646206
• DTXSID40963564
• Clerodin, >=90% (LC/MS-ELSD)
• NCGC00347625-02
• [(4R,4aR,5S,7R,8S,8aR)-8-[(3aS,5S,6aS)-3a,4,5,6a-tetrahydrofuro[2,3-b]furan-5-yl]-5-acetyloxy-7,8-dimethylspiro[2,3,5,6,7,8a-hexahydro-1H-naphthalene-4,2'-oxirane]-4a-yl]methyl acetate
• C09075
• Q27104944
• [8-(Acetyloxy)-5,6-dimethyl-5-(2,3,3a,6a-tetrahydrofuro[2,3-b]furan-2-yl)octahydro-8aH-spiro[naphthalene-1,2'-oxiran]-8a-yl]methyl acetate
• {(1R,4aR,5S,6R,8S,8aR)-8-(acetyloxy)-5,6-dimethyl-5-[(2S,3aS,6aS)-2,3,3a,6a-tetrahydrofuro[2,3-b]furan-2-yl]octahydro-8aH-spiro[naphthalene-1,2'-oxiran]-8a-yl}methyl acetate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9851	98.51%
Caco-2	-	0.6106	61.06%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7866	78.66%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8477	84.77%
OATP1B3 inhibitior	+	0.9172	91.72%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	+	0.6278	62.78%
P-glycoprotein inhibitior	+	0.5820	58.20%
P-glycoprotein substrate	-	0.6120	61.20%
CYP3A4 substrate	+	0.6931	69.31%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8640	86.40%
CYP3A4 inhibition	-	0.7839	78.39%
CYP2C9 inhibition	-	0.8112	81.12%
CYP2C19 inhibition	-	0.7886	78.86%
CYP2D6 inhibition	-	0.9442	94.42%
CYP1A2 inhibition	-	0.8948	89.48%
CYP2C8 inhibition	+	0.6608	66.08%
CYP inhibitory promiscuity	-	0.7937	79.37%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5404	54.04%
Eye corrosion	-	0.9842	98.42%
Eye irritation	-	0.9139	91.39%
Skin irritation	-	0.6811	68.11%
Skin corrosion	-	0.9184	91.84%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7156	71.56%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	-	0.6476	64.76%
skin sensitisation	-	0.8669	86.69%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.5441	54.41%
Acute Oral Toxicity (c)	III	0.3706	37.06%
Estrogen receptor binding	+	0.9040	90.40%
Androgen receptor binding	+	0.6419	64.19%
Thyroid receptor binding	+	0.5849	58.49%
Glucocorticoid receptor binding	+	0.7256	72.56%
Aromatase binding	+	0.7385	73.85%
PPAR gamma	+	0.7126	71.26%
Honey bee toxicity	-	0.7636	76.36%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5213	52.13%
Fish aquatic toxicity	+	0.9935	99.35%

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	98.38%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.65%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.52%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.92%	91.11%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	91.19%	89.05%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.04%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.30%	97.25%
CHEMBL340	P08684	Cytochrome P450 3A4	89.64%	91.19%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	89.52%	82.69%
CHEMBL2581	P07339	Cathepsin D	88.53%	98.95%
CHEMBL5255	O00206	Toll-like receptor 4	86.67%	92.50%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.32%	95.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.24%	94.33%
CHEMBL221	P23219	Cyclooxygenase-1	83.81%	90.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.24%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.09%	92.94%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.95%	92.62%
CHEMBL5028	O14672	ADAM10	82.94%	97.50%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.06%	96.95%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.10%	100.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.79%	97.28%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.73%	93.04%

Plants that contains it

• Ajuga integrifolia
• Clerodendrum brachyanthum
• Clerodendrum infortunatum
• Scutellaria albida
• Scutellaria discolor
• Scutellaria violacea

Cross-Links

• PubChem: 442014
• NPASS: NPC12297
• LOTUS: LTS0235438
• wikiData: Q27104944