Helenalin

Details

• Internal ID: f0849e58-7872-42d4-bd80-4cb515b1e718
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones
• IUPAC Name: (3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylidene-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-dione
• SMILES (Canonical): CC1CC2C(C(C3(C1C=CC3=O)C)O)C(=C)C(=O)O2
• SMILES (Isomeric): C[C@@H]1C[C@@H]2[C@H]([C@@H]([C@]3([C@H]1C=CC3=O)C)O)C(=C)C(=O)O2
• InChI: InChI=1S/C15H18O4/c1-7-6-10-12(8(2)14(18)19-10)13(17)15(3)9(7)4-5-11(15)16/h4-5,7,9-10,12-13,17H,2,6H2,1,3H3/t7-,9+,10-,12-,13+,15+/m1/s1
• InChI Key: ZVLOPMNVFLSSAA-XEPQRQSNSA-N
• Popularity: 402 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₄
• Molecular Weight: 262.30 g/mol
• Exact Mass: 262.12050905 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.25
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 6754-13-8
• PF 56
• Helenalin A
• HSDB 3490
• NSC85236
• NSC 85236
• BRN 0028081
• UNII-4GUY9L896T
• MLS000728512
• 4GUY9L896T
• CHEBI:5635
• 6alpha,8beta-Dihydroxy-4-oxoambrosa-2,11(13)-dien-12-oic acid 12,8-lactone
• NSC-85236
• Ambrosa-2,11(13)-dien-12-oic acid, 6-alpha,8-beta-dihydroxy-4-oxo-, 12,8-lactone
• (3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylidene-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-dione
• SMR000445626
• Ambrosa-2,11(13)-dien-12-oic acid, 6alpha,8beta-dihydroxy-4-oxo-, 12,8-lactone
• (3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylene-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-dione
• (3aS)-3,3aalpha,4alpha,4a,7aalpha,8,9,9aalpha-Octahydro-4-hydroxy-4abeta,8 alpha-dimethyl-3-methyleneazuleno(6,5-b)-furan-2,5-dione
• 4-18-00-01434 (Beilstein Handbook Reference)
• Azuleno(6,5-b)furan-2,5-dione, 3,3a,4,4a,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-3-methylene-, (3aS-(3aalpha,4alpha,4abeta,7aalpha,8alpha,9aalpha))-
• C15H18O4
• Ambrosa-2,11(13)-dien-12-oic acid, 6.alpha.,8.beta.-dihydroxy-4-oxo-, 12,8-lactone
• (3aR,5R,5aR,8aR,9S,9aS)-9-Hydroxy-5,8a-dimethyl-1-methylidene-3a,4,5,5a,9,9a-hexahydroazuleno[7,6-d]furan-2,8-dione
• Azuleno[6,5-b]furan-2,5-dione, 3,3a,4,4a,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-3-methylene-, [3aS-(3a.alpha.,4.alpha.,4a.beta.,7a.alpha.,8.alpha.,9a.alpha.)]-
• MLS002701927
• NF-kappaB inhibitor
• HELENALIN [MI]
• HELENALIN [HSDB]
• (-)-HELENALIN
• D0Q6YP
• BSPBio_001312
• cid_23205
• SCHEMBL161593
• CHEMBL338474
• BDBM43484
• DTXSID50217868
• HMS1791B14
• HMS1989B14
• HMS2236C04
• HB3927
• AKOS040741831
• NCGC00163416-01
• NCGC00163416-02
• LS-16550
• MS-23694
• NCI60_041870
• HY-119970
• CS-0078850
• C09473
• Q387505
• WLN: T C575 DYVO MV KUTJ A1 BQ DU1 I1
• BRD-K26302255-001-02-3
• Ambrosa-2, 6.alpha.,8.beta.-dihydroxy-4-oxo-, 12,8-lactone
• 6-alpha,8-beta-dihydroxy-4-oxoambrosa-2,11(13)-dien-12-oic acid 12,8-lactone
• 6.ALPHA.,8.BETA.-DIHYDROXY-4-OXOAMBROSA-2,11(13)-DIEN-12-OIC ACID 12,8-LACTONE
• (3aR,5R,5aR,8aR,9S,9aS)-5,8a-dimethyl-1-methylidene-9-oxidanyl-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-dione
• (3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylene-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-quinone
• (3aS)-3,3aalpha,4alpha,4a,7aalpha,8,9,9aalpha-octahydro-4-hydroxy-4abeta,8alpha-dimethyl-3-methyleneazuleno(6,5-b)-furan-2,5-dione
• (3aS,4S,4aR,7aR,8R,9aR)-4-hydroxy-4a,8-dimethyl-3-methylene-3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione
• (3aS,4S,4aR,7aR,8R,9aR)-4-hydroxy-4a,8-dimethyl-3-methylidene-3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione
• (3AS-(3A.ALPHA.,4.ALPHA.,4A.BETA.,7A.ALPHA.,8.ALPHA.,9A.ALPHA.))-3,3A,4,4A,7A,8,9,9A-OCTAHYDRO-4-HYDROXY-4A,8-DIMETHYL-3-METHYLENEAZULENO(6,5-B)FURAN-2,5-DIONE
• 4-Hydroxy-4a,8-dimethyl-3-methylene-3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione
• Azuleno[6,5-dione, 3,3a,4,4a,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-3-methylene-, [3aS-(3a.alpha.,4.alpha.,4a.beta.,7a.alpha.,8.alpha.,9a.alpha.)]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9628	96.28%
Caco-2	-	0.5295	52.95%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5459	54.59%
OATP2B1 inhibitior	-	0.8575	85.75%
OATP1B1 inhibitior	+	0.9049	90.49%
OATP1B3 inhibitior	+	0.9253	92.53%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9565	95.65%
P-glycoprotein inhibitior	-	0.8961	89.61%
P-glycoprotein substrate	-	0.8355	83.55%
CYP3A4 substrate	+	0.5771	57.71%
CYP2C9 substrate	-	0.8284	82.84%
CYP2D6 substrate	-	0.9011	90.11%
CYP3A4 inhibition	-	0.7867	78.67%
CYP2C9 inhibition	-	0.8755	87.55%
CYP2C19 inhibition	-	0.8915	89.15%
CYP2D6 inhibition	-	0.9572	95.72%
CYP1A2 inhibition	-	0.7171	71.71%
CYP2C8 inhibition	-	0.8730	87.30%
CYP inhibitory promiscuity	-	0.9320	93.20%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9243	92.43%
Carcinogenicity (trinary)	Non-required	0.4424	44.24%
Eye corrosion	-	0.9605	96.05%
Eye irritation	-	0.9406	94.06%
Skin irritation	-	0.5214	52.14%
Skin corrosion	-	0.7805	78.05%
Ames mutagenesis	-	0.8600	86.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6801	68.01%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	+	0.9000	90.00%
skin sensitisation	-	0.6233	62.33%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.5775	57.75%
Acute Oral Toxicity (c)	II	0.7110	71.10%
Estrogen receptor binding	+	0.5380	53.80%
Androgen receptor binding	-	0.5719	57.19%
Thyroid receptor binding	-	0.6067	60.67%
Glucocorticoid receptor binding	-	0.6412	64.12%
Aromatase binding	-	0.6386	63.86%
PPAR gamma	-	0.6575	65.75%
Honey bee toxicity	-	0.8121	81.21%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9532	95.32%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	25118.9 nM	Potency	via CMAUP
CHEMBL2524	P06280	Alpha-galactosidase A	39810.7 nM	Potency	via CMAUP
CHEMBL1075322	Q9Y2T6	G-protein coupled receptor 55	2642.28 nM	IC50	via CMAUP
CHEMBL5514	P42858	Huntingtin	2238.7 nM	Potency	via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	31622.8 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	3981.1 nM; 12589.3 nM; 3548.1 nM; 8912.5 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL1293277	O15118	Niemann-Pick C1 protein	794.3 nM; 794.3 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL5023	Q00987	p53-binding protein Mdm-2	420 nM; 420 nM	EC50; EC50	via Super-PRED; via CMAUP
CHEMBL1293294	P51151	Ras-related protein Rab-9A	1000 nM	Potency	via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	5.6 nM; 5.6 nM	Potency; Potency	via Super-PRED; via CMAUP
CHEMBL2916	O14746	Telomerase reverse transcriptase	4000 nM; 4000 nM	IC50; IC50	DOI: 10.1039/C0MD00241K; DOI: 10.1039/C0MD00241K
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	11220.2 nM	Potency	via CMAUP
CHEMBL1741176	P17861	X-box-binding protein 1	2430 nM	IC50	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.11%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.92%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.25%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	88.06%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.49%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.63%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.01%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.17%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.84%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.74%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.59%	100.00%

Plants that contains it

• Arnica acaulis
• Arnica longifolia
• Arnica montana
• Asteraceae
• Centipeda minima
• Gaillardia megapotamica
• Helenium amarum
• Helenium aromaticum
• Helenium autumnale
• Helenium donianum
• Helenium elegans
• Helenium mexicanum
• Helenium microcephalum
• Helenium puberulum
• Helenium quadridentatum
• Loxothysanus sinuatus
• Psilostrophe cooperi
• Psychotria asiatica

Cross-Links

• PubChem: 23205
• NPASS: NPC275960
• ChEMBL: CHEMBL338474
• LOTUS: LTS0155034
• wikiData: Q387505