12-O-acetylphorbol-13-decanoate - Compound Card

12-O-acetylphorbol-13-decanoate

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12-O-acetylphorbol-13-decanoate

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Phorbol Diterpenoid
Canonical Smiles CCCCCCCCCC(=O)O[C@@]12[C@H](OC(=O)C)[C@@H](C)[C@]3([C@H]([C@@H]1C2(C)C)C=C(CO)C[C@]1([C@H]3C=C(C1=O)C)O)O
InChI InChI=1S/C32H48O8/c1-7-8-9-10-11-12-13-14-25(35)40-32-26(29(32,5)6)23-16-22(18-33)17-30(37)24(15-19(2)27(30)36)31(23,38)20(3)28(32)39-21(4)34/h15-16,20,23-24,26,28,33,37-38H,7-14,17-18H2,1-6H3/t20-,23+,24-,26-,28-,30-,31-,32-/m1/s1
InChIKey CSJWNHJJHIAAIG-SVOQZPEWSA-N
Formula C32H48O8
HBA 8
HBD 3
MW 560.73
Rotatable Bonds 11
TPSA 130.36
LogP 4.19
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 40
Formal Charge 0
Fraction CSP3 0.78
Exact Mass 560.33
Number of Lipinski Rule Violations 1
# 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: 124027
Nmrshiftdb2: 70035280

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 560.73 g/mol

Antiviral

Absorption

Caco-2 (logPapp)
-5.03
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.68
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.9

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.9
Plasma Protein Binding
97.46
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
Non-Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
7.41
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.84
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.6
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.41
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
-2280.01
Rat (Acute)
3.66
Rat (Chronic Oral)
2.49
Fathead Minnow
8.17
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
416.28
Hydration Free Energy
-2.91
Log(D) at pH=7.4
3.52
Log(P)
5.58
Log S
-4.14
Log(Vapor Pressure)
-9.09
Melting Point
144.93
pKa Acid
6.11
pKa Basic
2.89
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7640
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7640
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7590
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7590
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7298
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7298
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7290
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7290
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7278
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7278
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7171
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7171
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7054
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7054
Ferric enterobactin-binding periplasmic protein FepB P0AEL6 FEPB_ECOLI Escherichia coli 3 0.7052
Ferric enterobactin-binding periplasmic protein FepB P0AEL6 FEPB_ECOLI Escherichia coli 3 0.7052
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7023
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7023

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