13-O-acetylphorbol-20-linoleate - Compound Card

13-O-acetylphorbol-20-linoleate

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13-O-acetylphorbol-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]3[C@@](C3(C)C)(OC(=O)C)[C@@H]([C@H]([C@@]2([C@H]2[C@@](C1)(O)C(=O)C(=C2)C)O)C)O
InChI InChI=1S/C40H60O8/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-33(42)47-26-30-24-31-34-37(5,6)40(34,48-29(4)41)36(44)28(3)39(31,46)32-23-27(2)35(43)38(32,45)25-30/h11-12,14-15,23-24,28,31-32,34,36,44-46H,7-10,13,16-22,25-26H2,1-6H3/b12-11-,15-14-/t28-,31+,32-,34-,36-,38-,39-,40-/m1/s1
InChIKey YSXDURFMHDUCMP-BQXPDDNPSA-N
Formula C40H60O8
HBA 8
HBD 3
MW 668.91
Rotatable Bonds 17
TPSA 130.36
LogP 6.87
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 48
Formal Charge 0
Fraction CSP3 0.72
Exact Mass 668.43
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: 6451043
Nmrshiftdb2: 70035292

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 668.91 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.77
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.63
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
57.74

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.41
Plasma Protein Binding
109.83
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
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
5.59
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.05
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.06
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
7.17
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
-109670.24
Rat (Acute)
3.43
Rat (Chronic Oral)
2.85
Fathead Minnow
152.64
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
8792.46
Hydration Free Energy
-2.92
Log(D) at pH=7.4
4.92
Log(P)
7.83
Log S
-5.31
Log(Vapor Pressure)
-267.32
Melting Point
87.85
pKa Acid
6.57
pKa Basic
4.26
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 0.7828
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7828
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7765
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7765
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7582
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7582
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7458
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7458
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7388
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7388
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7367
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7367
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7290
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7290
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7261
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7261

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