Transtaganolide A - Compound Card

Transtaganolide A

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Transtaganolide A

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Compound With Unusual 7-Methoxy-4,5-Dihydro-3H-Oxepin-2-One Ring
Canonical Smiles COC1=CC2=C[C@@H]3C(=O)O[C@@H]4O[C@@]52[C@@H](C(=O)O1)[C@@](C)(C=C)CC[C@H]5[C@]34C
InChI InChI=1S/C20H22O6/c1-5-18(2)7-6-12-19(3)11-8-10-9-13(23-4)24-16(22)14(18)20(10,12)26-17(19)25-15(11)21/h5,8-9,11-12,14,17H,1,6-7H2,2-4H3/t11-,12+,14+,17-,18+,19+,20-/m1/s1
InChIKey ITYKFAWLXGZZMN-GCROAMGXSA-N
Formula C20H22O6
HBA 6
HBD 0
MW 358.39
Rotatable Bonds 2
TPSA 71.06
LogP 2.46
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.6
Exact Mass 358.14
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. (2005). Transtaganolides A-D: novel metabolites from Thapsia transtagana. Organic Letters,2005,7(5),881-884. [View] [PubMed]
Pubchem: 102210128
Nmrshiftdb2: 70106327

No compound-protein relationship available.

Structure

SMILES: O1C2OC(=O)C(C2C3C145)C=C4C=COC(=O)C5CCC3

Level: 0

Mol. Weight: 358.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.79
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.810
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.42

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.860
Plasma Protein Binding
49.48
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-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
7.490
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.240
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.160
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.990
Micronucleos
Toxic
NR-AhR
Safe
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
Safe
T. Pyriformis
-5.330
Rat (Acute)
3.870
Rat (Chronic Oral)
2.130
Fathead Minnow
3.920
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
401.170
Hydration Free Energy
-5.340
Log(D) at pH=7.4
2.180
Log(P)
2.41
Log S
-4.51
Log(Vapor Pressure)
-7.49
Melting Point
205.88
pKa Acid
5.7
pKa Basic
4.34
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7383
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7383
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7076
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7076

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