Thapsitranstagin - Compound Card

Thapsitranstagin

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Thapsitranstagin

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Meroterpenoid
Canonical Smiles CCC(C(=O)O[C@@H]1C[C@@](C)(OC(=O)C)[C@H]2C(=C([C@H]([C@@H]2OC(=O)CC(C)C)OC(=O)/C(=C\C)/C)C)[C@@H]2[C@]1(O)[C@@](C)(O)C(=O)O2)C
InChI InChI=1S/C32H46O12/c1-11-16(5)27(35)40-20-14-30(9,44-19(8)33)23-22(26-32(20,39)31(10,38)29(37)43-26)18(7)24(42-28(36)17(6)12-2)25(23)41-21(34)13-15(3)4/h12,15-16,20,23-26,38-39H,11,13-14H2,1-10H3/b17-12-/t16?,20-,23+,24-,25-,26-,30-,31+,32+/m1/s1
InChIKey XHFQVCZACDPUSC-OWKZXDOKSA-N
Formula C32H46O12
HBA 12
HBD 2
MW 622.71
Rotatable Bonds 9
TPSA 171.96
LogP 2.86
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 44
Formal Charge 0
Fraction CSP3 0.72
Exact Mass 622.3
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Thapsia transtagana Apiaceae Plantae 512634

Showing of synonyms

  • Rubala JJ, Moreno-Dorado FJ, et al. (2007). A pyran-2-one and four meroterpenoids from Thapsia transtagana and their implication in the biosynthesis of transtaganolides. Phytochemistry,2007,68(19),2480-2486. [View]
Pubchem: 5458630
Nmrshiftdb2: 60050299
CPRiL: 27441
Structure

SMILES: O=C(O1)CC(C1C=23)CCCC3CCC2

Level: 0

Mol. Weight: 622.71 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.15
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.64
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
0.87

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.49
Plasma Protein Binding
92.63
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-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
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
8.99
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.26
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.09
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
8.68
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
-7305.7
Rat (Acute)
4.0
Rat (Chronic Oral)
2.8
Fathead Minnow
20.26
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
339.02
Hydration Free Energy
-2.92
Log(D) at pH=7.4
2.62
Log(P)
4.74
Log S
-4.61
Log(Vapor Pressure)
-11.33
Melting Point
161.98
pKa Acid
7.22
pKa Basic
1.3
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7516
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7516

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