Jacozine

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	58c2ba3e-608b-4929-87d2-a74cf741d4a6
Taxonomy	Alkaloids and derivatives
IUPAC Name	(1R,3'S,4S,7R,17R)-7-hydroxy-3',7-dimethyl-6-methylidenespiro[2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-4,2'-oxirane]-3,8-dione
SMILES (Canonical)	CC1C2(O1)CC(=C)C(C(=O)OCC3=CCN4C3C(CC4)OC2=O)(C)O
SMILES (Isomeric)	C[C@H]1[C@@]2(O1)CC(=C)[C@@](C(=O)OCC3=CCN4[C@H]3[C@@H](CC4)OC2=O)(C)O
InChI	InChI=1S/C18H23NO6/c1-10-8-18(11(2)25-18)16(21)24-13-5-7-19-6-4-12(14(13)19)9-23-15(20)17(10,3)22/h4,11,13-14,22H,1,5-9H2,2-3H3/t11-,13+,14+,17+,18-/m0/s1
InChI Key	XCEPKQNOWNOSFH-CGPXFRKCSA-N
Popularity	0 references in papers

Physical and Chemical Properties

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Molecular Formula	C₁₈H₂₃NO₆
Molecular Weight	349.40 g/mol
Exact Mass	349.15253745 g/mol
Topological Polar Surface Area (TPSA)	88.60 Å²
XlogP	-0.20
Atomic LogP (AlogP)	0.32
H-Bond Acceptor	7
H-Bond Donor	1
Rotatable Bonds	0

Synonyms

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5532-23-0

73KAJ7W3HA

12-hydroxy-13,19-didehydro-15,20-dihydro-15,20-epoxysenecionan-11,16-dione

(2S,3S,6'R,9a1'R,14a'R)-6'-hydroxy-3,6'-dimethyl-5'-methylene-5',6',9',9a1',11',13',14',14a'-octahydro-2'H-spiro[oxirane-2,3'-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine]-2',7'(4'H)-dione

Senecionan-11,16-dione, 13,19-didehydro-15,20-epoxy-15,20-dihydro-12-hydroxy-, (15alpha,20S)-

Spiro((1,6)dioxacyclododecino(2,3,4-gh)pyrrolizine-3(2H),2'-oxirane)-2,7(4H)-dione, 5,6,9,11,13,14,14a,14b-octahydro-6-hydroxy-3',6-dimethyl-5-methylene-, (3S,3'S,6R,14aR,14bR)-

13,19-didehydrojacobine

UNII-73KAJ7W3HA

DTXSID00970653

CHEBI:136458

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9004	90.04%
Caco-2	+	0.5166	51.66%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5924	59.24%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9304	93.04%
OATP1B3 inhibitior	+	0.9353	93.53%
MATE1 inhibitior	-	0.9409	94.09%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.8314	83.14%
P-glycoprotein inhibitior	-	0.8436	84.36%
P-glycoprotein substrate	-	0.5508	55.08%
CYP3A4 substrate	+	0.6385	63.85%
CYP2C9 substrate	-	0.8057	80.57%
CYP2D6 substrate	-	0.7055	70.55%
CYP3A4 inhibition	-	0.8805	88.05%
CYP2C9 inhibition	-	0.8881	88.81%
CYP2C19 inhibition	-	0.8851	88.51%
CYP2D6 inhibition	-	0.9176	91.76%
CYP1A2 inhibition	-	0.8517	85.17%
CYP2C8 inhibition	-	0.9030	90.30%
CYP inhibitory promiscuity	-	0.9880	98.80%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Danger	0.7198	71.98%
Eye corrosion	-	0.9787	97.87%
Eye irritation	-	0.9649	96.49%
Skin irritation	-	0.7270	72.70%
Skin corrosion	-	0.9017	90.17%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6039	60.39%
Micronuclear	+	0.6700	67.00%
Hepatotoxicity	+	0.9875	98.75%
skin sensitisation	-	0.8132	81.32%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	+	0.8504	85.04%
Acute Oral Toxicity (c)	II	0.5836	58.36%
Estrogen receptor binding	-	0.4897	48.97%
Androgen receptor binding	+	0.6392	63.92%
Thyroid receptor binding	-	0.5371	53.71%
Glucocorticoid receptor binding	+	0.7127	71.27%
Aromatase binding	+	0.6112	61.12%
PPAR gamma	-	0.5866	58.66%
Honey bee toxicity	-	0.8340	83.40%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.8285	82.85%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.72%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.15%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.70%	96.09%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	88.40%	93.40%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.25%	100.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	87.32%	93.04%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.30%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.22%	99.23%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.10%	97.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.87%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.26%	86.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.27%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.23%	89.00%
CHEMBL5805	Q9NR97	Toll-like receptor 8	83.90%	96.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.79%	95.89%
CHEMBL2581	P07339	Cathepsin D	81.76%	98.95%
CHEMBL4208	P20618	Proteasome component C5	80.97%	90.00%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Jacobaea aquatica

Jacobaea vulgaris

Senecio albopurpureus

Senecio integerrimus var. ochroleucus

Senecio vulgaris