Lactucin

Details

• Internal ID: d6666fa2-b352-408a-8024-966470ab1f60
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (3aR,4S,9aS,9bR)-4-hydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2,7-dione
• SMILES (Canonical): CC1=C2C(C3C(C(C1)O)C(=C)C(=O)O3)C(=CC2=O)CO
• SMILES (Isomeric): CC1=C2[C@@H]([C@@H]3[C@@H]([C@H](C1)O)C(=C)C(=O)O3)C(=CC2=O)CO
• InChI: InChI=1S/C15H16O5/c1-6-3-9(17)12-7(2)15(19)20-14(12)13-8(5-16)4-10(18)11(6)13/h4,9,12-14,16-17H,2-3,5H2,1H3/t9-,12+,13-,14-/m0/s1
• InChI Key: VJQAFLAZRVKAKM-VZLIPTOUSA-N
• Popularity: 12 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆O₅
• Molecular Weight: 276.28 g/mol
• Exact Mass: 276.09977361 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): 0.28
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• Lactucine
• 1891-29-8
• VJQAFLAZRVKAKM-VZLIPTOUSA-
• UNII-R6E2918904
• R6E2918904
• (3aR,4S,9aS,9bR)-4-Hydroxy-9-(hydroxymethyl)-6-methyl-3-methylene-3,3a,4,5-tetrahydroazuleno[4,5-b]furan-2,7(9aH,9bH)-dione
• AC1L9CIQ
• LACTUCIN [MI]
• CHEBI:6358
• SCHEMBL14215975
• DTXSID70894751
• Azuleno[4,5-b]furan-2,7-dione, 3,3a,4,5,9a,9b-hexahydro-4-hydroxy-9-(hydroxymethyl)-6-methyl-3-methylene-, [3aR-(3a.alpha.,4.alpha.,9a.alpha.,9b.beta.)]-
• HY-N9438
• AKOS040763768
• (3aR,4S,9aS,9bR)-4-hydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2,7-dione
• CS-0169537
• C09489
• (3AR,4S,9AS,9BR)-3,3A,4,5,9A,9B-HEXAHYDRO-4-HYDROXY-9-(HYDROXYMETHYL)-6-METHYL-3-METHYLENEAZULENO(4,5-B)FURAN-2,7-DIONE
• (3aR,4S,9aS,9bR)-4-hydroxy-9-(hydroxymethyl)-6-methyl-3-methylene-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2,7-dione
• (3aR,4S,9aS,9bR)-4-hydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione
• Azuleno(4,5-b)furan-2,7-dione, 3,3a,4,5,9a,9b-hexahydro-4-hydroxy-9-(hydroxymethyl)-6-methyl-3-methylene-, (3aR-(3aalpha,4beta,9aalpha,9bbeta))-
• InChI=1/C15H16O5/c1-6-3-9(17)12-7(2)15(19)20-14(12)13-8(5-16)4-10(18)11(6)13/h4,9,12-14,16-17H,2-3,5H2,1H3/t9-,12+,13-,14-/m0/s1

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9858	98.58%
Caco-2	-	0.6264	62.64%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5590	55.90%
OATP2B1 inhibitior	-	0.8583	85.83%
OATP1B1 inhibitior	+	0.9028	90.28%
OATP1B3 inhibitior	+	0.9537	95.37%
MATE1 inhibitior	-	0.8812	88.12%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9603	96.03%
P-glycoprotein inhibitior	-	0.9054	90.54%
P-glycoprotein substrate	-	0.7611	76.11%
CYP3A4 substrate	+	0.5260	52.60%
CYP2C9 substrate	-	0.8071	80.71%
CYP2D6 substrate	-	0.8968	89.68%
CYP3A4 inhibition	-	0.8986	89.86%
CYP2C9 inhibition	-	0.8618	86.18%
CYP2C19 inhibition	-	0.8679	86.79%
CYP2D6 inhibition	-	0.9258	92.58%
CYP1A2 inhibition	-	0.7602	76.02%
CYP2C8 inhibition	-	0.9171	91.71%
CYP inhibitory promiscuity	-	0.9338	93.38%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5611	56.11%
Eye corrosion	-	0.9539	95.39%
Eye irritation	-	0.7007	70.07%
Skin irritation	-	0.6187	61.87%
Skin corrosion	-	0.8811	88.11%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7855	78.55%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	+	0.6870	68.70%
skin sensitisation	-	0.7993	79.93%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.7309	73.09%
Acute Oral Toxicity (c)	III	0.4665	46.65%
Estrogen receptor binding	-	0.6980	69.80%
Androgen receptor binding	+	0.6111	61.11%
Thyroid receptor binding	-	0.5979	59.79%
Glucocorticoid receptor binding	+	0.6648	66.48%
Aromatase binding	-	0.8042	80.42%
PPAR gamma	-	0.7407	74.07%
Honey bee toxicity	-	0.8707	87.07%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.8651	86.51%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.78%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.79%	91.11%
CHEMBL2581	P07339	Cathepsin D	90.47%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.50%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.49%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	84.98%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.58%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.09%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.96%	95.89%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.52%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.43%	89.00%

Plants that contains it

• Agathosma scaberula
• Balanophora harlandii
• Callitris drummondii
• Capuronianthus mahafalensis
• Cardiospermum grandiflorum
• Cichorium endivia
• Cichorium intybus
• Cichorium pumilum
• Crepidiastrum denticulatum subsp. denticulatum
• Euphorbia nicaeensis
• Ixeris chinensis
• Lactuca quercina
• Lactuca saligna
• Lactuca sativa
• Lactuca serriola
• Lactuca tatarica
• Lactuca virosa
• Launaea mucronata
• Lupinus cosentinii
• Picris hieracioides
• Polemonium caeruleum
• Solanum villosum
• Strychnos ledermannii
• Viburnum davidii

Cross-Links

• PubChem: 442266
• NPASS: NPC96128
• LOTUS: LTS0045302
• wikiData: Q6469057