Laserine oxide - Compound Card

Laserine oxide

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Laserine oxide

Structure
Zoomed Structure
  • Family: Plantae - Umbelliferae
  • Kingdom: Plantae
  • Class: Lignan
Canonical Smiles C/C=C(\C(=O)O[C@H](c1cc(OC)c2c(c1)OCO2)[C@H](OC(=O)C1(C)OC1C)C)/C
InChI InChI=1S/C21H26O8/c1-7-11(2)19(22)28-17(12(3)27-20(23)21(5)13(4)29-21)14-8-15(24-6)18-16(9-14)25-10-26-18/h7-9,12-13,17H,10H2,1-6H3/b11-7-/t12-,13?,17+,21?/m1/s1
InChIKey AVJNVKMXZXWBFC-FCRATTDPSA-N
Formula C21H26O8
HBA 8
HBD 0
MW 406.43
Rotatable Bonds 7
TPSA 92.82
LogP 3.08
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.52
Exact Mass 406.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Daucus virgatus Umbelliferae Plantae 1869349

Showing of synonyms

  • Snene A, Sirignano C, et al. (2017). Antiproliferative metabolites from the Northern African endemic plant Daucus virgatus (Apiaceae). Phytochemistry,2017,143,194-198. [View] [PubMed]
Pubchem: 102028268

No compound-protein relationship available.

Structure

SMILES: O1CC1C(=O)OCCc(c2)ccc(c23)OCO3

Level: 1

Mol. Weight: 406.43 g/mol

Structure

SMILES: O1COc(c12)cccc2

Level: 0

Mol. Weight: 406.43 g/mol

Structure

SMILES: C1CO1

Level: 0

Mol. Weight: 406.43 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.94
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.55
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.13

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.62
Plasma Protein Binding
40.46
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
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
12.79
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.38
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.26
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.46
Micronucleos
Toxic
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
-16.38
Rat (Acute)
3.25
Rat (Chronic Oral)
1.4
Fathead Minnow
4.91
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
388.01
Hydration Free Energy
-6.33
Log(D) at pH=7.4
3.16
Log(P)
3.98
Log S
-4.27
Log(Vapor Pressure)
-6.26
Melting Point
28.68
pKa Acid
7.19
pKa Basic
-1.07
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9865
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9194
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8470
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8181
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8122
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8120
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.8066
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.7897
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7727
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7706
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7665
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7658
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7647
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7618
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7576
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7504
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7447
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7412
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7400
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7309
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7248
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7229
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7226
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7221
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7199
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7192
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7186
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7167
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7123
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7095
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7083
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7076
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7017
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7015

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