Santonin

Details

• Internal ID: 2fbb2c9b-cbaa-4a06-b192-b64a58eb5848
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3S,3aS,5aS,9bS)-3,5a,9-trimethyl-3a,4,5,9b-tetrahydro-3H-benzo[g][1]benzofuran-2,8-dione
• SMILES (Canonical): CC1C2CCC3(C=CC(=O)C(=C3C2OC1=O)C)C
• SMILES (Isomeric): C[C@H]1[C@@H]2CC[C@]3(C=CC(=O)C(=C3[C@H]2OC1=O)C)C
• InChI: InChI=1S/C15H18O3/c1-8-10-4-6-15(3)7-5-11(16)9(2)12(15)13(10)18-14(8)17/h5,7-8,10,13H,4,6H2,1-3H3/t8-,10-,13-,15-/m0/s1
• InChI Key: XJHDMGJURBVLLE-BOCCBSBMSA-N
• Popularity: 1,340 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₃
• Molecular Weight: 246.30 g/mol
• Exact Mass: 246.125594432 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.42
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• alpha-Santonin
• 481-06-1
• (-)-alpha-Santonin
• Semenen
• Santoninum
• Santoninic anhydride
• L-alpha-Santonin
• (-)-Santonine
• (-)-Santonin
• a-Santonin
• Santonin [JAN]
• Santonin [JAN:NF]
• NSC4900
• NSC-4900
• UNII-1VL8J38ERO
• 1VL8J38ERO
• DTXSID7045312
• CHEBI:16363
• .alpha.-Santonin
• EINECS 207-560-7
• NSC 41311
• (3S,3aS,5aS,9bS)-3,5a,9-trimethyl-3a,4,5,9b-tetrahydro-3H-benzo[g][1]benzofuran-2,8-dione
• (3S,3aS,5aS,9bS)-3,5a,9-trimethyl-3a,5,5a,9b-tetrahydronaphtho[1,2-b]furan-2,8(3H,4H)-dione
• AI3-19471
• DTXCID5025312
• NSC 4900
• l-.alpha.-Santonin
• 11-Epiisoeusantona-1,4-dienic acid, 6alpha-hydroxy-3-oxo-, gamma-lactone
• (3S)-2,3,3a,4,5,5a,8,9bbeta-Octahydro-3,5abeta,9-trimethylnaphtho(1,2-b)furan-2,8-dion
• (3S,3aS,5aS,9bS)-3,5a,9-trimethyl-3a,4,5,9b-tetrahydro-3H-benzo[g]benzofuran-2,8-dione
• Eudesma-1,4-dien-12-oic acid, 6-alpha-hydroxy-3-oxo-, gamma-lactone, (11S)-(-)-
• Naphtho(1,2-b)puran-2,8(3H,4H)-dione, 3a,5,5a,9b-tetrahydro-3,5a,9-trimethyl-
• naphtho[1,2-b]furan-2,8(3H,4H)-dione, 3a,5,5a,9b-tetrahydro-3,5a,9-trimethyl-, (3S,3aS,5aS,9bS)-
• (-)-.alpha.-Santonin
• SR-01000635568
• -santonin
• NCGC00016461-01
• Santonin (TN)
• (3S,3aS,5aS,9bS)-2,3,3a,4,5,5a,8,9b-Octahydro-3,5a,9-trimethylnaphtho(1,2-b)furan-2,8-dione
• (3S,3aS,5aS,9bS)-2,3,3a,4,5,5a,8,9b-octahydro-3,5a,9-trimethylnaphtho[1,2-b]furan-2,8-dione
• (3S,3AS,5AS,9BS)-3A,5,5A,9B-TETRAHYDRO-3,5A,9-TRIMETHYLNAPHTHO(1,2-B)FURAN-2,8(3H,4H)-DIONE
• (3S,3aS,5aS,9bS)-3a,5,5a,9b-Tetrahydro-3,5a,9-trimethylnaphtho[1,2-b]furan-2,8(3H,4H)-dione
• CAS-481-06-1
• Naphtho(1,2-b)furan-2,8(3H,4H)-dione, 3a,5,5a,9b-tetrahydro-3,5a,9-trimethyl-, (3S,3aS,5aS,9bS)-
• Naphtho(1,2-b)furan-2,8(3H,4H)-dione, 3a,5,5a,9b-tetrahydro-3,5a,9-trimethyl-, (3S-(3alpha,3aalpha,5abeta,9bbeta))-
• ()-alpha-Santonin
• MFCD00135865
• SANTONINE
• Santonin (JP17)
• Spectrum_000790
• SpecPlus_000318
• (-)- alpha -Santonin
• Prestwick0_001070
• Prestwick1_001070
• Prestwick2_001070
• Prestwick3_001070
• Spectrum2_000699
• Spectrum3_001245
• Spectrum4_001476
• Spectrum5_000151
• SANTONINUM [HPUS]
• SANTONIN [MART.]
• SANTONIN [WHO-DD]
• UPCMLD-DP084
• (3S,5aS,9bS)-3a,5,5a,9b-Tetrahydro-3,5a,9-trimethylnaphtho[1,2-b]furan-2,8(3H,4H)dione
• BSPBio_001060
• BSPBio_002750
• KBioGR_002051
• KBioSS_001270
• SPECTRUM300542
• MLS002154141
• DivK1c_006414
• SPBio_000857
• SPBio_002970
• alpha-Santonin; (-)-Santonin
• BPBio1_001166
• CHEMBL259254
• MEGxp0_001636
• SCHEMBL1133565
• .ALPHA.-SANTONIN [MI]
• UPCMLD-DP084:001
• GTPL12448
• KBio1_001358
• KBio2_001270
• KBio2_003838
• KBio2_006406
• KBio3_002250
• (-)-alpha-Santonin, >=99%
• Eudesma-1,4-dien-12-oic acid, 6-alpha-hydroxy-3-oxo-, gamma-lactone, (11S)-
• HMS1571E22
• HMS2098E22
• HMS2268H12
• HY-B1761
• Tox21_110445
• CCG-40021
• s3999
• AKOS015895177
• Tox21_110445_1
• LMPR0103190001
• SDCCGMLS-0066491.P001
• (-)-alpha-Santonin, analytical standard
• NCGC00161640-01
• NCGC00161640-02
• NCGC00161640-03
• NCGC00263447-01
• SMR000112520
• AB00376930
• CS-0013789
• S0521
• EN300-34530
• C02206
• D00154
• WLN: T B566 COV LV IHTT&J E1 I1 M1
• A827469
• Q413166
• SR-01000635568-1
• SR-01000635568-4
• SR-01000635568-5
• BRD-K58787433-001-05-4
• BRD-K58787433-001-08-8
• BRD-K58787433-001-12-0
• Santonin, European Pharmacopoeia (EP) Reference Standard
• Z359371114
• 11-Epiisoeusantona-1, 6.alpha.-hydroxy-3-oxo-, .gamma.-lactone
• 3-(6-NITRO-2-OXO-1,3-BENZOXAZOL-3(2H)-YL)PROPANOICACID
• Eudesma-1, 6.alpha.-hydroxy-3-oxo-, .gamma.-lactone, (11S)-
• (11S)-6alpha-hydroxy-3-oxoeudesma-1,4-dien-12-oic acid gamma-lactone
• 6alpha-hydroxy-3-oxo-11-epiisoeusantona-1,4-dienic acid gamma-lactone
• Eudesma-1, 6.alpha.-hydroxy-3-oxo-, .gamma.-lactone, (11S)-(-)-
• Naphtho[1,8(3H,4H)-dione, 3a,5,5a,9b-tetrahydro-3,5a,9-trimethyl-
• 3a,5,5a,9b-Tetrahydro-3,5a,9-trimethyl-naphtho[1,2-b]puran-2,8(3H,4H)-dione
• (3S,3AS,5AS)-3,5A,9-TRIMETHYL-3A,4,5,5A-TETRAHYDRONAPHTHO(1,2-B)FURAN-2,8(3H,9BH)-DIONE
• (3S,3aS,5aS,9bS)-3,5a,9-trimethyl-2H,3H,3aH,4H,5H,5aH,8H,9bH-naphtho[1,2-b]furan-2,8-dione
• (3S,3aS,5aS,9bS)-3,5a,9-trimethyl-3a,4,5,5a-tetrahydronaphtho[1,2-b]furan-2,8(3H,9bH)-dione
• [3S-(3alpha,3aalpha,5abeta,9bbeta)]-3a,5,5a,9b-Tetrahydro-3,5a,9-trimethylnaphtho[1,2-b]furan-2,8(3H,4H)-dione
• 1,2,3,4,4a,7-hexahydro-1-hydroxy-alpha,4a,8-trimethyl-7-oxo-2-naphthaleneacetic acid gamma-lactone
• 1,3,4,4a,7-Hexahydro-1-hydroxy-.alpha., 4a,8-trimethyl-7-oxo-2-naphthaleneacetic acid .gamma.-lactone
• InChI=1/C15H18O3/c1-8-10-4-6-15(3)7-5-11(16)9(2)12(15)13(10)18-14(8)17/h5,7-8,10,13H,4,6H2,1-3H3/t8-,10-,13-,15-/m0/s
• Naphtho[1,8(3H,4H)-dione, 3a,5,5a,9b-tetrahydro-3,5a,9-trimethyl-, [3S-(3.alpha.,3a.alpha.,5a.beta.,9b.beta.)]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9972	99.72%
Caco-2	+	0.7449	74.49%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.8000	80.00%
Subcellular localzation	Mitochondria	0.6498	64.98%
OATP2B1 inhibitior	-	0.8568	85.68%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9651	96.51%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	-	0.8050	80.50%
P-glycoprotein inhibitior	-	0.8747	87.47%
P-glycoprotein substrate	-	0.8370	83.70%
CYP3A4 substrate	+	0.5944	59.44%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9062	90.62%
CYP3A4 inhibition	-	0.8016	80.16%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9230	92.30%
CYP1A2 inhibition	+	0.9106	91.06%
CYP2C8 inhibition	-	0.9050	90.50%
CYP inhibitory promiscuity	-	0.6579	65.79%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4133	41.33%
Eye corrosion	-	0.9840	98.40%
Eye irritation	-	0.9011	90.11%
Skin irritation	+	0.5926	59.26%
Skin corrosion	-	0.7839	78.39%
Ames mutagenesis	-	0.7270	72.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4563	45.63%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	+	0.9375	93.75%
skin sensitisation	-	0.5349	53.49%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.6035	60.35%
Acute Oral Toxicity (c)	III	0.7190	71.90%
Estrogen receptor binding	-	0.6013	60.13%
Androgen receptor binding	+	0.5657	56.57%
Thyroid receptor binding	-	0.6114	61.14%
Glucocorticoid receptor binding	-	0.6097	60.97%
Aromatase binding	-	0.8397	83.97%
PPAR gamma	-	0.6201	62.01%
Honey bee toxicity	-	0.8841	88.41%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9906	99.06%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.48%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.13%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.30%	99.23%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	86.30%	94.80%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	86.10%	93.40%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.62%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.37%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.20%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.35%	97.14%
CHEMBL1937	Q92769	Histone deacetylase 2	81.71%	94.75%
CHEMBL2581	P07339	Cathepsin D	81.43%	98.95%

Plants that contains it

• Anacyclus monanthos
• Artemisia campestris subsp. campestris
• Artemisia halophila
• Artemisia monosperma
• Artemisia pallens
• Artemisia sericea
• Fossombronia pusilla
• Nidema boothii
• Seriphidium diffusum
• Seriphidium fragrans
• Seriphidium herba-alba
• Seriphidium ifranensis
• Seriphidium saissanicum
• Seriphidium schrenkianum
• Seriphidium spicigerum
• Seriphidium subchrysolepis
• Seriphidium tenuisectum

Cross-Links

• PubChem: 221071
• NPASS: NPC177932
• ChEMBL: CHEMBL259254
• LOTUS: LTS0184841
• wikiData: Q413166