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Alpha-santonin
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | C[C@@H]1C(=O)O[C@H]2[C@H]1CC[C@@]1(C2=C(C)C(=O)C=C1)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 |
| InChIKey | XJHDMGJURBVLLE-BOCCBSBMSA-N |
| Formula | C15H18O3 |
| HBA | 3 |
| HBD | 0 |
| MW | 246.31 |
| Rotatable Bonds | 0 |
| TPSA | 43.37 |
| LogP | 2.42 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 18 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.6 |
| Exact Mass | 246.13 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Artemisia herba-alba | Asteraceae | Plantae | 72329 |
| 2 | Artemisia hugueti | Asteraceae | Plantae | 4219 |
| 3 | Artemisia ifranensis | Asteraceae | Plantae | 1903206 |
Showing of synonyms
Alpha-santonin
Santonin
Semenen
(-)-alpha-Santonin
Santoninum
Santoninic anhydride
L-alpha-Santonin
(-)-Santonine
UNII-1VL8J38ERO
NSC 4900
NSC-4900
1VL8J38ERO
DTXSID7045312
CHEBI:16363
EINECS 207-560-7
NSC 41311
AI3-19471
DTXCID5025312
(3S,3aS,5aS,9bS)-3,5a,9-trimethyl-3a,5,5a,9b-tetrahydronaphtho[1,2-b]furan-2,8(3H,4H)-dione
SANTONIN (MART.)
SANTONIN [MART.]
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
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-
6alpha-hydroxy-3-oxo-11-epiisoeusantona-1,4-dienic acid gamma-lactone
(11S)-6alpha-hydroxy-3-oxoeudesma-1,4-dien-12-oic acid gamma-lactone
Eudesma-1,4-dien-12-oic acid, 6-alpha-hydroxy-3-oxo-, gamma-lactone, (11S)-
(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)-3A,5,5A,9B-TETRAHYDRO-3,5A,9-TRIMETHYLNAPHTHO(1,2-B)FURAN-2,8(3H,4H)-DIONE
Santonins
(3S,3aS,5aS,9bS)-3,5a,9-trimethyl-3a,5,5a,9b-tetrahydronaphtho(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
Naphtho(1,2-b)furan-2,8(3H,4H)-dione, 3a,5,5a,9b-tetrahydro-3,5a,9-trimethyl-, (3S-(3alpha,3aalpha,5abeta,9bbeta))-
CHEBI:26604
207-560-7
481-06-1
(-)-Santonin
NSC4900
MFCD00135865
(3S,3aS,5aS,9bS)-3,5a,9-trimethyl-3a,4,5,9b-tetrahydro-3H-benzo[g][1]benzofuran-2,8-dione
.alpha.-Santonin
C15H14O3
(3S,5aS,9bS)-3a,5,5a,9b-Tetrahydro-3,5a,9-trimethylnaphtho[1,2-b]furan-2,8(3H,4H)dione
L-.alpha.-Santonin
(3S,3aS,5aS,9bS)-3,5a,9-trimethyl-3a,4,5,9b-tetrahydro-3H-benzo[g]benzofuran-2,8-dione
Santonin [JAN]
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
Santonin [JAN:NF]
SR-01000635568
Santonin-a
NCGC00016461-01
Santonin (TN)
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)-
()-alpha-Santonin
Santonin (Standard)
SANTONINE
Santonin (JP18)
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 [WHO-DD]
UPCMLD-DP084
BSPBio_001060
BSPBio_002750
KBioGR_002051
KBioSS_001270
SPECTRUM300542
MLS002154141
DivK1c_006414
SPBio_000857
SPBio_002970
BPBio1_001166
CHEMBL259254
MEGxp0_001636
SCHEMBL1133565
.ALPHA.-SANTONIN [MI]
UPCMLD-DP084:001
GTPL12448
HY-B1761R
KBio1_001358
KBio2_001270
KBio2_003838
KBio2_006406
KBio3_002250
(-)-alpha-Santonin, >=99%
XJHDMGJURBVLLE-BOCCBSBMSA-N
HMS1571E22
HMS2098E22
HMS2268H12
HY-B1761
Tox21_110445
CCG-40021
S3999
AKOS015895177
Tox21_110445_1
FS65157
LMPR0103190001
SDCCGMLS-0066491.P001
(-)-alpha-Santonin, analytical standard
NCGC00161640-01
NCGC00161640-02
NCGC00161640-03
NCGC00263447-01
SMR000112520
AB00376930
CS-0013789
NS00022216
S0521
EN300-34530
C02206
D00154
WLN: T B566 COV LV IHTT&J E1 I1 M1
A827469
AC-907/21098009
AJ-738/21061005
AK-861/20800026
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
Eudesma-1, 6.alpha.-hydroxy-3-oxo-, .gamma.-lactone, (11S)-
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,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)-3,5a,9-trimethyl-2H,3H,3aH,4H,5H,5aH,8H,9bH-naphtho[1,2-b]furan-2,8-dione
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.)]-
Pubchem:
221071
Cas:
481-06-1
Gnps:
CCMSLIB00006568325
Zinc:
ZINC000003881689
Kegg Ligand:
C02206
Chebi:
16363
Nmrshiftdb2:
20028247
Metabolights:
MTBLC16363
Chembl:
CHEMBL259254
Comptox:
DTXSID7045312
CPRiL:
118128
SMILES: C1C(=O)OC(C12)C=3C(CC2)C=CC(=O)C3
Level: 0
Mol. Weight: 246.31 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.71
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.36
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.32
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.61
- Plasma Protein Binding
- 51.21
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 7.91
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.6
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.22
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 4.74
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -1.17
- Rat (Acute)
- 2.38
- Rat (Chronic Oral)
- 1.89
- Fathead Minnow
- 3.91
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 334.05
- Hydration Free Energy
- -5.64
- Log(D) at pH=7.4
- 1.66
- Log(P)
- 1.34
- Log S
- -2.83
- Log(Vapor Pressure)
- -4.56
- Melting Point
- 151.34
- pKa Acid
- 9.53
- pKa Basic
- 5.99
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7499 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7499 |
| Aromatase | P11511 | CP19A_HUMAN | Homo sapiens | 2 | 0.7422 |
| Aromatase | P11511 | CP19A_HUMAN | Homo sapiens | 2 | 0.7422 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7378 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7378 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7366 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7366 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 2 | 0.7265 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 2 | 0.7265 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7207 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7207 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7139 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7139 |
| 3-ketosteroid dehydrogenase | Q9RA02 | Q9RA02_RHOER | Rhodococcus erythropolis | 2 | 0.7121 |
| 3-ketosteroid dehydrogenase | Q9RA02 | Q9RA02_RHOER | Rhodococcus erythropolis | 2 | 0.7121 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7071 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7071 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7021 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7021 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 2 | 0.7009 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 2 | 0.7009 |