13-O-tigloylphorbol-20-linoleate - Compound Card

13-O-tigloylphorbol-20-linoleate

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13-O-tigloylphorbol-20-linoleate

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Phorbol Diterpenoid
Canonical Smiles CCCCC/C=C\C/C=C\CCCCCCCC(=O)OCC1=C[C@H]2[C@@H]3C([C@]3(OC(=O)/C(=C/C)/C)[C@@H]([C@H]([C@@]2([C@H]2[C@@](C1)(O)C(=O)C(=C2)C)O)C)O)(C)C
InChI InChI=1S/C43H64O8/c1-8-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-35(44)50-28-32-26-33-36-40(6,7)43(36,51-39(47)29(3)9-2)38(46)31(5)42(33,49)34-25-30(4)37(45)41(34,48)27-32/h9,13-14,16-17,25-26,31,33-34,36,38,46,48-49H,8,10-12,15,18-24,27-28H2,1-7H3/b14-13-,17-16-,29-9+/t31-,33+,34-,36-,38-,41-,42-,43-/m1/s1
InChIKey XVWMMWFBGOHQFS-OSFSTWJBSA-N
Formula C43H64O8
HBA 8
HBD 3
MW 708.98
Rotatable Bonds 18
TPSA 130.36
LogP 7.81
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 51
Formal Charge 0
Fraction CSP3 0.7
Exact Mass 708.46
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Croton tiglium Euphorbiaceae Plantae 497687

Showing of synonyms

  • El-Mekkawy S, Meselhy MR, et al. (2000). Anti-HIV-1 phorbol esters from the seeds of Croton tiglium. Phytochemistry,2000,53,457-464. [View] [PubMed]
Pubchem: 6451044
Nmrshiftdb2: 70039046

No compound-protein relationship available.

Structure

SMILES: C12C(C1)CCC3C4C(C(=O)C=C4)CC=CC23

Level: 0

Mol. Weight: 708.98 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.84
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-3.14
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
255.81

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.22
Plasma Protein Binding
111.46
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
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
8.57
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.58
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.34
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.53
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
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
-469658.44
Rat (Acute)
3.76
Rat (Chronic Oral)
2.94
Fathead Minnow
604.96
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
49585.58
Hydration Free Energy
-2.92
Log(D) at pH=7.4
5.8
Log(P)
9.58
Log S
-5.55
Log(Vapor Pressure)
-1584.91
Melting Point
86.04
pKa Acid
5.27
pKa Basic
2.4
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.9048
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.9048
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.8895
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.8895
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.8206
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.8206
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8113
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8113
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7764
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7764
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7182
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7182

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