(Z)-(1R,2S)-1-acetoxy-1-(4-methoxybenzo[d][1,3]dioxol-6-yl)propan-2-yl 2-methylbut-2-enoate - Compound Card

(Z)-(1R,2S)-1-acetoxy-1-(4-methoxybenzo[d][1,3]dioxol-6-yl)propan-2-yl 2-methylbut-2-enoate

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(Z)-(1R,2S)-1-acetoxy-1-(4-methoxybenzo[d][1,3]dioxol-6-yl)propan-2-yl 2-methylbut-2-enoate

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Phenylpropanoid
Canonical Smiles C/C=C(\C(=O)O[C@H]([C@@H](c1cc(OC)c2c(c1)OCO2)OC(=O)C)C)/C
InChI InChI=1S/C18H22O7/c1-6-10(2)18(20)24-11(3)16(25-12(4)19)13-7-14(21-5)17-15(8-13)22-9-23-17/h6-8,11,16H,9H2,1-5H3/b10-6-/t11-,16-/m0/s1
InChIKey RRPAUYJABCIHOM-YIMXGHOLSA-N
Formula C18H22O7
HBA 7
HBD 0
MW 350.37
Rotatable Bonds 6
TPSA 80.29
LogP 2.93
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.44
Exact Mass 350.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Thapsia transtagana Apiaceae Plantae 512634

Showing of synonyms

  • Saouf A, Guerra FM, et al. (2006). Phenylpropanoids from Thapsia transtagana. Phytochemistry,2006,67(8),800-804. [View] [PubMed]
Pubchem: 163000659
Nmrshiftdb2: 70096245

No compound-protein relationship available.

Structure

SMILES: O1COc(c12)cccc2

Level: 0

Mol. Weight: 350.37 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.59
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.48
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.81

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.51
Plasma Protein Binding
64.99
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
5.01
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.14
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.38
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.73
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
-2.99
Rat (Acute)
2.37
Rat (Chronic Oral)
1.7
Fathead Minnow
4.69
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
357.19
Hydration Free Energy
-6.11
Log(D) at pH=7.4
2.9
Log(P)
3.72
Log S
-3.53
Log(Vapor Pressure)
-6.13
Melting Point
59.46
pKa Acid
9.7
pKa Basic
0.05
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9365
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9365
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.9051
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.9051
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.9010
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.9010
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8748
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8748
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8560
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8560
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8321
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8321
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8291
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8291
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8142
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8142
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8128
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8128
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.8108
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.8108
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7840
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7840
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7824
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7824
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7796
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7796
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7796
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7796
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7795
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7795
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7788
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7788
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7747
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7747
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7713
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7713
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7669
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7669
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7602
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7602
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7570
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7570
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7532
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7532
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7453
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7453
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7446
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7446
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7439
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7439
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7396
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7396
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7325
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7325
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7283
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7283
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7236
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7236
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7229
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7229
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7225
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7225
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7213
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7213
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7191
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7191
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7161
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7161
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7147
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7147
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7090
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7090
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7081
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7081
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7059
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7059
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7039
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7039

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