Jacobine

Details

• Internal ID: 094cc517-9d71-4f09-8b3e-9d6b8b75446e
• Taxonomy: Alkaloids and derivatives
• IUPAC Name: (1R,3'S,4S,6R,7R,17R)-7-hydroxy-3',6,7-trimethylspiro[2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-4,2'-oxirane]-3,8-dione
• SMILES (Canonical): CC1CC2(C(O2)C)C(=O)OC3CCN4C3C(=CC4)COC(=O)C1(C)O
• SMILES (Isomeric): C[C@@H]1C[C@]2([C@@H](O2)C)C(=O)O[C@@H]3CCN4[C@@H]3C(=CC4)COC(=O)[C@]1(C)O
• InChI: InChI=1S/C18H25NO6/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/h4,10-11,13-14,22H,5-9H2,1-3H3/t10-,11+,13-,14-,17-,18+/m1/s1
• InChI Key: IAPHXJRHXBQDQJ-WKMWQDDRSA-N
• Popularity: 27 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₅NO₆
• Molecular Weight: 351.40 g/mol
• Exact Mass: 351.16818752 g/mol
• Topological Polar Surface Area (TPSA): 88.60 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): 0.40
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 6870-67-3
• CCRIS 5777
• HSDB 3500
• NSC 89936
• BRN 0054580
• GM32U80H1R
• 4-27-00-06827 (Beilstein Handbook Reference)
• Jacobine.
• 471-14-7
• 15,20-Epoxy-15,20-dihydro-12-hydroxysenecionan-11,16-dione
• NSC-89936
• (15alpha,20R)15,20-Epoxy-15,20-dihydro-12-hydroxysenecionan-11,16-dione
• 12beta-Hydroxy-12alpha,13beta-dimethylsenec-1-enine-15S-spiro-2'-(3'R-methyloxiran)
• Senecionan-11,16-dione, 15,20-epoxy-15,20-dihydro-12-hydroxy-, (15-alpha,20S)-
• Senecionan-11,16-dione, 15,20-epoxy-15,20-dihydro-12-hydroxy-, (15alpha,20R)-
• JACOBINE [IARC]
• UNII-GM32U80H1R
• CHEBI:6080
• (15alpha,20R)15,20-Epoxy-15,20-dihydro-12-hydroxy-senecionan-11,16-dione
• Senecionan-11,16-dione, 15,20-epoxy-15,20-dihydro-12-hydroxy-, (15.alpha.,20R)-
• DTXSID501020078
• HY-124058
• CS-0084068
• Q27107031
• (2S,3S,5'R,6'R,9a1'R,14a'R)-6'-hydroxy-3,5',6'-trimethyl-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, 15,20-EPOXY-15,20-DIHYDRO-12-HYDROXY-, (15.ALPHA.,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',5,6-TRIMETHYL-, (2'S,3'S,5R,6R,14AR,14BR)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9070	90.70%
Caco-2	+	0.6573	65.73%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5648	56.48%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9427	94.27%
OATP1B3 inhibitior	+	0.9313	93.13%
MATE1 inhibitior	-	0.9609	96.09%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.7256	72.56%
P-glycoprotein inhibitior	-	0.8624	86.24%
P-glycoprotein substrate	-	0.5055	50.55%
CYP3A4 substrate	+	0.6172	61.72%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7145	71.45%
CYP3A4 inhibition	-	0.8736	87.36%
CYP2C9 inhibition	-	0.9047	90.47%
CYP2C19 inhibition	-	0.8915	89.15%
CYP2D6 inhibition	-	0.9148	91.48%
CYP1A2 inhibition	-	0.8414	84.14%
CYP2C8 inhibition	-	0.9190	91.90%
CYP inhibitory promiscuity	-	0.9856	98.56%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Danger	0.7723	77.23%
Eye corrosion	-	0.9807	98.07%
Eye irritation	-	0.9856	98.56%
Skin irritation	-	0.7244	72.44%
Skin corrosion	-	0.9105	91.05%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5735	57.35%
Micronuclear	+	0.6400	64.00%
Hepatotoxicity	+	0.9875	98.75%
skin sensitisation	-	0.8273	82.73%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	+	0.7994	79.94%
Acute Oral Toxicity (c)	II	0.5801	58.01%
Estrogen receptor binding	+	0.6950	69.50%
Androgen receptor binding	+	0.5824	58.24%
Thyroid receptor binding	-	0.5467	54.67%
Glucocorticoid receptor binding	+	0.7141	71.41%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	-	0.6252	62.52%
Honey bee toxicity	-	0.8402	84.02%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.8120	81.20%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5697	Q9GZT9	Egl nine homolog 1	93.94%	93.40%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.81%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.57%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.98%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.94%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.88%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.00%	99.23%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.85%	97.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.48%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.47%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.27%	86.33%
CHEMBL4208	P20618	Proteasome component C5	84.07%	90.00%
CHEMBL1871	P10275	Androgen Receptor	83.16%	96.43%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.04%	92.94%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.22%	97.09%

Plants that contains it

• Crassocephalum crepidioides
• Crotalaria micans
• Jacobaea aquatica
• Jacobaea maritima subsp. maritima
• Jacobaea vulgaris
• Senecio albopurpureus
• Senecio brasiliensis
• Senecio integerrimus var. ochroleucus
• Senecio scandens
• Senecio vulgaris

Cross-Links

• PubChem: 442741
• NPASS: NPC286109
• LOTUS: LTS0126233
• wikiData: Q27107031