(+)sesamin - Compound Card

(+)sesamin

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(+)sesamin

Structure
Zoomed Structure
  • Family: Plantae - Rutaceae
  • Kingdom: Plantae
  • Class: Lignan
Canonical Smiles Oc1ccc(cc1O)[C@H]1OC[C@H]2[C@@H]1CO[C@@H]2c1ccc(c(c1)O)O
InChI InChI=1S/C18H18O6/c19-13-3-1-9(5-15(13)21)17-11-7-24-18(12(11)8-23-17)10-2-4-14(20)16(22)6-10/h1-6,11-12,17-22H,7-8H2/t11-,12-,17+,18+/m0/s1
InChIKey OQSOTSIYXPYTRE-YDOWWZDFSA-N
Formula C18H18O6
HBA 6
HBD 4
MW 330.34
Rotatable Bonds 2
TPSA 99.38
LogP 2.58
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.33
Exact Mass 330.11
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Zanthoxylum usambarense Rutaceae Plantae 2562172

Showing of synonyms

  • He W, De Kimpe N. (2000). Study of biological active principles from Kenyan medicinal plants. PhD Thesis, University of Ghent, Belgium, 2000-2001. [View]
Pubchem: 46881231
Chebi: 136543
Nmrshiftdb2: 60070055
Metabolights: MTBLC136543
CPRiL: 428838
Structure

SMILES: c1ccccc1C(OC2)C(C23)COC3c4ccccc4

Level: 2

Mol. Weight: 330.34 g/mol

Structure

SMILES: C1OCC(C12)COC2c3ccccc3

Level: 1

Mol. Weight: 330.34 g/mol

Structure

SMILES: C1OCC(C12)COC2

Level: 0

Mol. Weight: 330.34 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 330.34 g/mol

Antifungal
Insecticidal

Absorption

Caco-2 (logPapp)
-5.37
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.910
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.26

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.700
Plasma Protein Binding
78.04
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
12.700
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.520
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.950
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
4.790
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
1.050
Rat (Acute)
2.140
Rat (Chronic Oral)
2.750
Fathead Minnow
4.030
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
453.160
Hydration Free Energy
-8.700
Log(D) at pH=7.4
1.690
Log(P)
1.63
Log S
-3.41
Log(Vapor Pressure)
-9.34
Melting Point
255.35
pKa Acid
7.88
pKa Basic
6.58
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.9123
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.9123
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9043
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9043
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.8900
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.8900
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8821
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8821
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8796
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8796
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8657
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8657
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8584
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8584
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8578
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8578
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8445
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8445
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.8422
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.8422
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8397
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8397
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8364
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8364
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8363
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8363
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8356
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8356
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 4 0.8351
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 4 0.8351
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8328
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8328
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8328
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8328
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8323
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8323
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8312
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8312
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8303
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8303
cAMP-dependent protein kinase catalytic subunit alpha P05132 KAPCA_MOUSE Mus musculus 5 0.8203
cAMP-dependent protein kinase catalytic subunit alpha P05132 KAPCA_MOUSE Mus musculus 5 0.8203
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8179
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8179
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8175
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8175
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.8120
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.8120
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8023
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8023
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7852
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7852
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7850
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7850
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 4 0.7845
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 4 0.7845
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7822
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7822
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7799
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7799
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7783
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7783
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7764
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7764
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7702
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7702
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7687
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7687
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7685
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7685
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7685
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7685
Putative FAD-dependent oxygenase EncM Q9KHK2 Q9KHK2_9ACTN Streptomyces maritimus 3 0.7659
Putative FAD-dependent oxygenase EncM Q9KHK2 Q9KHK2_9ACTN Streptomyces maritimus 3 0.7659
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7653
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7653
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7617
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7617
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.7605
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.7605
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7579
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7579
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7576
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7576
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7550
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7550
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7497
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7497
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7485
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7485
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7472
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7472
Beta-lactamase Q79MP6 Q79MP6_PSEAI Pseudomonas aeruginosa 2 0.7469
Beta-lactamase Q79MP6 Q79MP6_PSEAI Pseudomonas aeruginosa 2 0.7469
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7434
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7434
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7424
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7424
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7394
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7394
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7383
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7383
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7379
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7379
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7344
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7344
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7341
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7341
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7315
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7315
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7306
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7306
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7303
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7303
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7298
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7298
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7268
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7268
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7241
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7241
ATP-dependent protease subunit HslV P0A7B8 HSLV_ECOLI Escherichia coli 3 0.7222
ATP-dependent protease subunit HslV P0A7B8 HSLV_ECOLI Escherichia coli 3 0.7222
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7205
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7205
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7200
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7200
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7168
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7168
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7163
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7163
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7145
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7145
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7132
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7132
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7128
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7128
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7112
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7112
Aminopeptidase N P04825 AMPN_ECOLI Escherichia coli 3 0.7107
Aminopeptidase N P04825 AMPN_ECOLI Escherichia coli 3 0.7107
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7076
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7076
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7067
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7067
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7064
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7064
Glycogen phosphorylase, liver form P06737 PYGL_HUMAN Homo sapiens 3 0.7056
Glycogen phosphorylase, liver form P06737 PYGL_HUMAN Homo sapiens 3 0.7056
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7053
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7053
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7050
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7050
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7031
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7031
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7026
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7026
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7018
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7018
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7015
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7015
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7007
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7007
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7007
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7007

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