4,8-dihydroxy sesamin - Compound Card

4,8-dihydroxy sesamin

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4,8-dihydroxy sesamin

Structure
Zoomed Structure
  • Family: Plantae - Lamiaceae
  • Kingdom: Plantae
  • Class: Lignan
Canonical Smiles OC1OC(C2(C1C(OC2)c1ccc2c(c1)OCO2)O)c1ccc2c(c1)OCO2
InChI InChI=1S/C20H18O8/c21-19-16-17(10-1-3-12-14(5-10)26-8-24-12)23-7-20(16,22)18(28-19)11-2-4-13-15(6-11)27-9-25-13/h1-6,16-19,21-22H,7-9H2
InChIKey KCQXLVHWDSFFDF-UHFFFAOYSA-N
Formula C20H18O8
HBA 8
HBD 2
MW 386.36
Rotatable Bonds 2
TPSA 95.84
LogP 1.65
Number Rings 6
Number Aromatic Rings 2
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.4
Exact Mass 386.1
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Premna odorata Lamiaceae Plantae 1037421

Showing of synonyms

  • Elmaidomy A.H, Mohammed R, et al. (2019). Metabolomic Profiling and Cytotoxic Tetrahydrofurofuran Lignans Investigations from Premna odorata Blanco. Metabolites, 2019, 9(10), 223. [View] [PubMed]
Pubchem: 73830444

No compound-protein relationship available.

Structure

SMILES: O1COc(c12)ccc(c2)C3OCC(C34)C(OC4)c(c5)ccc(c56)OCO6

Level: 2

Mol. Weight: 386.36 g/mol

Structure

SMILES: O1COc(c12)ccc(c2)C3OCC(C34)COC4

Level: 1

Mol. Weight: 386.36 g/mol

Structure

SMILES: O1COc(c12)cccc2

Level: 0

Mol. Weight: 386.36 g/mol

Structure

SMILES: C1OCC(C12)COC2

Level: 0

Mol. Weight: 386.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.95
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.36
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.02

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.12
Plasma Protein Binding
30.04
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
Non-Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
13.85
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.87
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.43
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.27
Micronucleos
Toxic
NR-AhR
Toxic
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
Toxic
T. Pyriformis
-34.45
Rat (Acute)
2.25
Rat (Chronic Oral)
1.56
Fathead Minnow
4.77
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
440.1
Hydration Free Energy
-4.6
Log(D) at pH=7.4
2.28
Log(P)
2.34
Log S
-3.5
Log(Vapor Pressure)
-9.86
Melting Point
156.92
pKa Acid
8.8
pKa Basic
-0.65
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.9385
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8914
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.8691
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8627
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8442
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8327
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.8248
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8199
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8165
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8151
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 4 0.8005
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7854
Pol protein Q000H7 Q000H7_9HIV1 Human immunodeficiency virus 1 3 0.7769
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7728
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7655
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7600
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7547
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7526
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7509
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7457
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7454
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7448
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7413
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7371
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7358
Prothrombin P00734 THRB_HUMAN Homo sapiens 4 0.7348
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7325
Genome polyprotein C0LMU0 C0LMU0_9FLAV dengue virus type 3 3 0.7316
Microcin C7 self-immunity protein MccF Q47511 MCCF_ECOLX Escherichia coli 4 0.7312
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7300
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7243
[LysW]-aminoadipate kinase O50147 LYSZ_THET2 Thermus thermophilus 3 0.7242
Geranyl diphosphate 2-C-methyltransferase D3KYU3 GPPMT_STRLS Streptomyces lasalocidi 3 0.7227
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7227
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7216
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7212
Bifunctional protein GlmU P43889 GLMU_HAEIN Haemophilus influenzae 4 0.7209
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7202
Orf1ab polyprotein Q6T1E9 Q6T1E9_CVHSA SARS coronavirus CUHK-L2 3 0.7195
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7167
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.7167
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 2 0.7137
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7107
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7094
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7079
Interstitial collagenase P03956 MMP1_HUMAN Homo sapiens 3 0.7045
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7029
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 2 0.7026
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7024
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7020

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