Retrorsine

Details

• 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

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

Synonyms

• 480-54-6
• beta-Longilobine
• Retrorsin
• CCRIS 4338
• HSDB 3530
• UNII-XJ86XWL8IY
• XJ86XWL8IY
• 12,18-Dihydroxysenecionan-11,16-dione
• NSC 107659
• cis-Retronecic acid ester of retronecine
• 12,18-Dihydroxy-senecionan-11,16-dione
• CHEBI:8822
• Senecionan-11,16-dione, 12,18-dihydroxy-
• trans-15-Ethylidene-12beta-hydroxy-12alpha-hydroxymethyl-13beta-methylsenec-1-enine
• (15Z)-12,18-dihydroxysenecionan-11,16-dione
• 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
• C18H25NO6
• Retrorcine
• NSC-107659
• (1,6)Dioxacyclododecino(2,3,4-gh)pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-(hydroxymethyl)-5-methyl-, (3Z,5R,6S,14aR,14bR)-
• [1,6]Dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-(hydroxymethyl)-5-methyl-, (3Z,5R,6S,14aR,14bR)-
• Prestwick_562
• RETRORSINE [MI]
• Prestwick2_000637
• Prestwick3_000637
• RETRORSINE [HSDB]
• RETRORSINE [IARC]
• BSPBio_000634
• MLS002153926
• SCHEMBL133058
• BPBio1_000698
• CHEMBL496894
• DTXSID6021242
• Retrorsine, >=90% (HPLC)
• BCJMNZRQJAVDLD-CQRYIUNCSA-N
• HMS1545M22
• HMS1569P16
• HMS2096P16
• HMS2231J18
• HY-N6638
• Retrorsine 100 microg/mL in Water
• AKOS024282552
• CCG-208491
• NCGC00142486-03
• MS-25432
• SMR001233270
• LS-143482
• CS-0062871
• SR-01000841220
• SR-01000841220-3
• BRD-K42142750-001-01-5
• BRD-K42142750-001-04-9
• Q27108154
• (Z)-ethylidene-hydroxy-(hydroxymethyl)-methyl-[?]dione
• (1R,4Z,6R,7S,17R)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0??,??]heptadec-11-ene-3,8-dione
• (5R,6S,9a1R,14aR,Z)-3-ethylidene-6-hydroxy-6-(hydroxymethyl)-5-methyl-3,4,5,6,9,9a1,11,13,14,14a-decahydro-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

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

• Crotalaria spartioides
• Crotalaria trichotoma
• Jacobaea maritima subsp. maritima
• Jacobaea vulgaris
• Osyris alba
• Packera candidissima
• Packera coahuilensis
• Senecio brasiliensis
• Senecio cisplatinus
• Senecio covasii
• Senecio deferens
• Senecio flaccidus var. douglasii
• Senecio gilliesianus
• Senecio grisebachii
• Senecio inaequidens
• Senecio isatideus
• Senecio latifolius
• Senecio nevadensis subsp. malacitanus
• Senecio oxyphyllus
• Senecio prionopterus
• Senecio retrorsus
• Senecio riddellii
• Senecio scandens
• Senecio selloi
• Senecio subulatus
• Senecio triangularis
• Senecio vernalis
• Senecio vulgaris
• Werneria nubigena

Cross-Links

• PubChem: 5281743
• NPASS: NPC106791
• ChEMBL: CHEMBL496894
• LOTUS: LTS0226203
• wikiData: Q27108154