Retrorsine

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	dd82f984-c113-4339-aa49-030fde550c0d
Taxonomy	Phenylpropanoids and polyketides > Macrolides and analogues
IUPAC Name	(1R,4Z,6R,7S,17R)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione
SMILES (Canonical)	CC=C1CC(C(C(=O)OCC2=CCN3C2C(CC3)OC1=O)(CO)O)C
SMILES (Isomeric)	C/C=C\1/C[C@H]([C@@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(CO)O)C
InChI	InChI=1S/C18H25NO6/c1-3-12-8-11(2)18(23,10-20)17(22)24-9-13-4-6-19-7-5-14(15(13)19)25-16(12)21/h3-4,11,14-15,20,23H,5-10H2,1-2H3/b12-3-/t11-,14-,15-,18-/m1/s1
InChI Key	BCJMNZRQJAVDLD-CQRYIUNCSA-N
Popularity	509 references in papers

Physical and Chemical Properties

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Molecular Formula	C₁₈H₂₅NO₆
Molecular Weight	351.40 g/mol
Exact Mass	351.16818752 g/mol
Topological Polar Surface Area (TPSA)	96.30 Å²
XlogP	0.60

Synonyms

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480-54-6

beta-Longilobine

XJ86XWL8IY

cis-Retronecic acid ester of retronecine

12,18-Dihydroxy-senecionan-11,16-dione

Senecionan-11,16-dione, 12,18-dihydroxy-

DTXSID6021242

trans-15-Ethylidene-12beta-hydroxy-12alpha-hydroxymethyl-13beta-methylsenec-1-enine

NSC-107659

3-Ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-hydroxymethyl-5-methyl(1,6)dioxacyclododeca(2,3,4-gh)pyrrolizidine-2,7-dione

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 (%)
No predicted properties yet!

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	22387.2 nM 39810.7 nM	Potency Potency	via CMAUP via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.13%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.64%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.51%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.89%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.68%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.90%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.47%	85.14%
CHEMBL2581	P07339	Cathepsin D	86.41%	98.95%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	83.52%	93.40%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.29%	95.83%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.94%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.88%	99.23%
CHEMBL4588	P22894	Matrix metalloproteinase 8	81.82%	94.66%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.16%	97.14%

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.

Crotalaria spartioides

Crotalaria trichotoma

Jacobaea maritima subsp. maritima

Senecio flaccidus var. douglasii