4,20-dideoxy(4lpha)phorbol-12-benzoate-13-isobutyrate - Compound Card

4,20-dideoxy(4lpha)phorbol-12-benzoate-13-isobutyrate

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4,20-dideoxy(4lpha)phorbol-12-benzoate-13-isobutyrate

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles CC1=C[C@@H]2[C@]([C@H]3[C@@H](C1)C(=O)C(=C3)C)(C)[C@H](C)[C@H]([C@@]1([C@@]2(C)C1(C)C)OC(=O)C(C)C)OC(=O)c1ccccc1
InChI InChI=1S/C33H42O5/c1-18(2)28(35)38-33-27(37-29(36)22-13-11-10-12-14-22)21(5)31(8)24-17-20(4)26(34)23(24)15-19(3)16-25(31)32(33,9)30(33,6)7/h10-14,16-18,21,23-25,27H,15H2,1-9H3/t21-,23-,24-,25-,27-,31-,32-,33-/m1/s1
InChIKey YQTZYDOJRMSXRA-MIOUUXTKSA-N
Formula C33H42O5
HBA 5
HBD 0
MW 518.69
Rotatable Bonds 4
TPSA 69.67
LogP 6.58
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 38
Formal Charge 0
Fraction CSP3 0.61
Exact Mass 518.3
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Euphorbia bupleuroides Euphorbiaceae Plantae 1532838

Showing of synonyms

  • Aichour S, Haba H, et al. (2014). Terpenoids and other constituents from Euphorbia bupleuroides. Phytochemistry,2014,10,198-203. [View]
Pubchem: 162817216
Nmrshiftdb2: 60061540

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)OC(C(C23)C2)CC4C5C(C(=O)C=C5)CC=CC34

Level: 1

Mol. Weight: 518.69 g/mol

Structure

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

Level: 0

Mol. Weight: 518.69 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 518.69 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.78
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.68
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.94

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.75
Plasma Protein Binding
114.22
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
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
9.65
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.46
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.77
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.82
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
-1060.27
Rat (Acute)
2.76
Rat (Chronic Oral)
2.22
Fathead Minnow
6.41
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
469.93
Hydration Free Energy
-2.8
Log(D) at pH=7.4
5.73
Log(P)
7.39
Log S
-6.33
Log(Vapor Pressure)
-7.67
Melting Point
179.47
pKa Acid
9.09
pKa Basic
2.93
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7576
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7576
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 2 0.7228
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 2 0.7228
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 2 0.7175
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 2 0.7175
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7159
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7159
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7121
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7121
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7108
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7108
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7105
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7105
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7103
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7103
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7021
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7021
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7020
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7020

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