Transtaganolide C - Compound Card

Transtaganolide C

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Transtaganolide C

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@@]42[C@@H](C(=O)O1)[C@](C)(C=C)CC[C@H]4C3(C)C
InChI InChI=1S/C20H24O5/c1-6-19(4)8-7-13-18(2,3)12-9-11-10-14(23-5)24-17(22)15(19)20(11,13)25-16(12)21/h6,9-10,12-13,15H,1,7-8H2,2-5H3/t12-,13-,15-,19+,20+/m0/s1
InChIKey WEROHVUUBZUWOZ-MQEXTWSESA-N
Formula C20H24O5
HBA 5
HBD 0
MW 344.41
Rotatable Bonds 2
TPSA 61.83
LogP 3.13
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.6
Exact Mass 344.16
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]

No compound-protein relationship available.

Structure

SMILES: C123C4=CC(C(=O)O3)CC1CCCC2C(=O)OC=C4

Level: 0

Mol. Weight: 344.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.65
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.830
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.26

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.130
Plasma Protein Binding
49.58
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
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
8.480
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.570
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.180
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.950
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
-1.460
Rat (Acute)
3.130
Rat (Chronic Oral)
1.900
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
388.500
Hydration Free Energy
-4.700
Log(D) at pH=7.4
2.620
Log(P)
2.81
Log S
-4.76
Log(Vapor Pressure)
-6.74
Melting Point
181.76
pKa Acid
5.9
pKa Basic
4.69
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8326
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8326

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