Select a section from the left sidebar
Delta-sesamin
- Family: Plantae - Thymelaeaceae
- Kingdom: Plantae
-
Class: Lignan
- Subclass: Epoxylignan
| Canonical Smiles | C[C@@]12CO[C@H]([C@@]2(C)CO[C@H]1c1ccc2c(c1)OCO2)c1ccc2c(c1)OCO2 |
|---|---|
| InChI | InChI=1S/C22H22O6/c1-21-9-23-20(14-4-6-16-18(8-14)28-12-26-16)22(21,2)10-24-19(21)13-3-5-15-17(7-13)27-11-25-15/h3-8,19-20H,9-12H2,1-2H3/t19-,20-,21+,22+/m0/s1 |
| InChIKey | VRMHCMWQHAXTOR-FNAHDJPLSA-N |
| Formula | C22H22O6 |
| HBA | 6 |
| HBD | 0 |
| MW | 382.41 |
| Rotatable Bonds | 2 |
| TPSA | 55.38 |
| LogP | 4.0 |
| Number Rings | 6 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 28 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.45 |
| Exact Mass | 382.14 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Thymelaea lythroides | Thymelaeaceae | Plantae | 224054 |
Showing of synonyms
Delta-sesamin
- Kabbaj FZ, Lai D, et al. (2013). Chemical constituents from aerial parts of Thymelaea lythroides. Biochemical Systematics and Ecology,2013,51,153-155. [View]
No compound-protein relationship available.
SMILES: O1COc(c12)ccc(c2)C3OCC(C34)C(OC4)c(c5)ccc(c56)OCO6
Level: 2
Mol. Weight: 382.41 g/mol
SMILES: O1COc(c12)ccc(c2)C3OCC(C34)COC4
Level: 1
Mol. Weight: 382.41 g/mol
SMILES: O1COc(c12)cccc2
Level: 0
Mol. Weight: 382.41 g/mol
SMILES: C1OCC(C12)COC2
Level: 0
Mol. Weight: 382.41 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.02
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.44
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.25
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.25
- Plasma Protein Binding
- 81.85
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 14.43
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.76
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.7
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.75
- Micronucleos
- Toxic
- NR-AhR
- Toxic
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Toxic
- T. Pyriformis
- -33.74
- Rat (Acute)
- 2.11
- Rat (Chronic Oral)
- 1.24
- Fathead Minnow
- 4.39
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 462.33
- Hydration Free Energy
- -4.57
- Log(D) at pH=7.4
- 3.46
- Log(P)
- 4.34
- Log S
- -5.7
- Log(Vapor Pressure)
- -8.67
- Melting Point
- 131.66
- pKa Acid
- 10.01
- pKa Basic
- 2.79
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.9467 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.9467 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.9306 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.9306 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 3 | 0.9003 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 3 | 0.9003 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 3 | 0.8941 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 3 | 0.8941 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8940 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8940 |
| Urokinase-type plasminogen activator | P00749 | UROK_HUMAN | Homo sapiens | 3 | 0.8788 |
| Urokinase-type plasminogen activator | P00749 | UROK_HUMAN | Homo sapiens | 3 | 0.8788 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.8757 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.8757 |
| Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial | Q33862 | Q33862_ASCSU | Ascaris suum | 3 | 0.8652 |
| Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial | Q33862 | Q33862_ASCSU | Ascaris suum | 3 | 0.8652 |
| Gag-Pol polyprotein | P04584 | POL_HV2RO | Human immunodeficiency virus type 2 subtype A | 4 | 0.8400 |
| Gag-Pol polyprotein | P04584 | POL_HV2RO | Human immunodeficiency virus type 2 subtype A | 4 | 0.8400 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.8323 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.8323 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8321 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8321 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9QYJ6 | PDE10_RAT | Rattus norvegicus | 3 | 0.8183 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9QYJ6 | PDE10_RAT | Rattus norvegicus | 3 | 0.8183 |
| Cytochrome P450 2B4 | P00178 | CP2B4_RABIT | Oryctolagus cuniculus | 4 | 0.8036 |
| Cytochrome P450 2B4 | P00178 | CP2B4_RABIT | Oryctolagus cuniculus | 4 | 0.8036 |
| Lethal(3)malignant brain tumor-like protein 1 | Q9Y468 | LMBL1_HUMAN | Homo sapiens | 3 | 0.7977 |
| Lethal(3)malignant brain tumor-like protein 1 | Q9Y468 | LMBL1_HUMAN | Homo sapiens | 3 | 0.7977 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7947 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7947 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7895 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7895 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7895 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7895 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7858 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7858 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7849 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7849 |
| Histone deacetylase 8 | Q9BY41 | HDAC8_HUMAN | Homo sapiens | 3 | 0.7791 |
| Histone deacetylase 8 | Q9BY41 | HDAC8_HUMAN | Homo sapiens | 3 | 0.7791 |
| cGMP-specific 3',5'-cyclic phosphodiesterase | O76074 | PDE5A_HUMAN | Homo sapiens | 3 | 0.7787 |
| cGMP-specific 3',5'-cyclic phosphodiesterase | O76074 | PDE5A_HUMAN | Homo sapiens | 3 | 0.7787 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7757 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7757 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 3 | 0.7714 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 3 | 0.7714 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7631 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7631 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7627 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7627 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7561 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7561 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 2 | 0.7548 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 2 | 0.7548 |
| Diamine oxidase [copper-containing] | P19801 | AOC1_HUMAN | Homo sapiens | 3 | 0.7547 |
| Diamine oxidase [copper-containing] | P19801 | AOC1_HUMAN | Homo sapiens | 3 | 0.7547 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7533 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7533 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7509 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7509 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7448 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7448 |
| Nuclear receptor ROR-gamma | P51449 | RORG_HUMAN | Homo sapiens | 2 | 0.7403 |
| Nuclear receptor ROR-gamma | P51449 | RORG_HUMAN | Homo sapiens | 2 | 0.7403 |
| Succinate dehydrogenase flavoprotein subunit | P0AC41 | SDHA_ECOLI | Escherichia coli | 3 | 0.7397 |
| Succinate dehydrogenase flavoprotein subunit | P0AC41 | SDHA_ECOLI | Escherichia coli | 3 | 0.7397 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7327 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7327 |
| Urokinase-type plasminogen activator | P00749 | UROK_HUMAN | Homo sapiens | 3 | 0.7317 |
| Urokinase-type plasminogen activator | P00749 | UROK_HUMAN | Homo sapiens | 3 | 0.7317 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7314 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7314 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 2 | 0.7301 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 2 | 0.7301 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7282 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7282 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7262 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7262 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.7185 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.7185 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.7152 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.7152 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 2 | 0.7135 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 2 | 0.7135 |
| Seminal ribonuclease | P00669 | RNS_BOVIN | Bos taurus | 3 | 0.7133 |
| Seminal ribonuclease | P00669 | RNS_BOVIN | Bos taurus | 3 | 0.7133 |
| Urokinase-type plasminogen activator | P00749 | UROK_HUMAN | Homo sapiens | 2 | 0.7128 |
| Urokinase-type plasminogen activator | P00749 | UROK_HUMAN | Homo sapiens | 2 | 0.7128 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7119 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7119 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7119 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7119 |
| Phytohormone-binding protein | G7J032 | PHBP_MEDTR | Medicago truncatula | 4 | 0.7118 |
| Phytohormone-binding protein | G7J032 | PHBP_MEDTR | Medicago truncatula | 4 | 0.7118 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7109 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7109 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.7086 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.7086 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7080 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7080 |
| Gag-Pol polyprotein | P03367 | POL_HV1BR | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7078 |
| Gag-Pol polyprotein | P03367 | POL_HV1BR | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7078 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7067 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7067 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7027 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7027 |
| 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 |
| Rhodopsin kinase GRK1 | P28327 | GRK1_BOVIN | Bos taurus | 3 | 0.7006 |
| Rhodopsin kinase GRK1 | P28327 | GRK1_BOVIN | Bos taurus | 3 | 0.7006 |