Select a section from the left sidebar
Ingenol
- Family: Plantae - Euphorbiaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Diterpenoid
| Canonical Smiles | OCC1=C[C@H]2[C@H]3[C@H](C3(C)C)C[C@H]([C@]3([C@@]([C@@H]1O)(O)[C@@H](O)C(=C3)C)C2=O)C |
|---|---|
| InChI | InChI=1S/C20H28O5/c1-9-7-19-10(2)5-13-14(18(13,3)4)12(17(19)24)6-11(8-21)16(23)20(19,25)15(9)22/h6-7,10,12-16,21-23,25H,5,8H2,1-4H3/t10-,12+,13-,14+,15+,16-,19+,20-/m1/s1 |
| InChIKey | VEBVPUXQAPLADL-POYOOMFHSA-N |
| Formula | C20H28O5 |
| HBA | 5 |
| HBD | 4 |
| MW | 348.44 |
| Rotatable Bonds | 1 |
| TPSA | 97.99 |
| LogP | 0.82 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 25 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.75 |
| Exact Mass | 348.19 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Euphorbia peplus | Euphorbiaceae | Plantae | 38846 |
Showing of synonyms
Ingenol
30220-46-3
(+)-Ingenol
(1aR,2S,5R,5aR,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one
UNII-IC77UZI9G8
IC77UZI9G8
CHEBI:5922
INGENOL [MI]
INGENOL [WHO-DD]
INGENOL, (+)-
(1S,4S,5R,6R,9S,10R,12R,14R)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dien-15-one
1aalpha,2alpha,5beta,5abeta,6beta,beta,9 alpha, 10,10aalpha-Octahydro-5,5a,6-trihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-1H-2,8aalpha-methano cyclopenta(a)cyclopropa(e)cyclodecen-11-one
1H-2,8A-METHANOCYCLOPENTA(A)CYCLOPROPA(E)CYCLODECEN-11-ONE, 1A,2,5,5A,6,9,10,10A-OCTAHYDRO-5,5A,6-TRIHYDROXY-4-(HYDROXYMETHYL)-1,1,7,9-TETRAMETHYL-, (1AR,2S,5R,5AR,6S,8AS,9R,10AR)-
1H-2,8A-METHANOCYCLOPENTA(A)CYCLOPROPA(E)CYCLODECEN-11-ONE, 1A,2,5,5A,6,9,10,10A-OCTAHYDRO-5,5A,6-TRIHYDROXY-4-(HYDROXYMETHYL)-1,1,7,9-TETRAMETHYL-, (1AR-(1A.ALPHA.,2.BETA.,5.BETA.,5A.BETA.,6.BETA.,8A.ALPHA.,9.ALPHA.,10A.ALPHA.))-
(1aR,2S,5R,5aR,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta(a)cyclopropa(e)(10)annulen-11-one
(1S,4S,5R,6R,9S,10R,12R,14R)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo(7.5.1.01,5.010,12)pentadeca-2,7-dien-15-one
1H-2,8a-Methanocyclopenta[a]cyclopropa[e]cyclodecen-11-one, 1a,2,5,5a,6,9,10,10a-octahydro-5,5a,6-trihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-, (1aR,2S,5R,5aR,6S,8aS,9R,10aR)-
1a alpha,2 alpha,5 beta,5a beta,6 beta,beta,9 alpha, 10,10a alpha-octahydro-5,5a,6-trihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-1H-2,8a alpha-methano cyclopenta(a)cyclopropa(e)cyclodecen-11-one
1H-2,8A-METHANOCYCLOPENTA(A)CYCLOPROPA(E)CYCLODECEN-11-ONE, 1A,2,5,5A,6,9,10,10A-OCTAHYDRO-5,5A,6-TRIHYDROXY-4-(HYDROXYMETHYL)-1,1,7,9-TETRAMETHYL-, (1AR-(1AALPHA,2BETA,5BETA,5ABETA,6BETA,8AALPHA,9ALPHA,10AALPHA))-
636-889-2
1H-2,8a-Methanocyclopenta[a]cyclopropa[e]cyclodecen-11-one,1a,2,5,5a,6,9,10,10a-octahydro-5,5a,6-trihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-, (1aR,2S,5R,5aR,6S,8aS,9R,10aR)-
SCHEMBL317087
CHEMBL2165402
SCHEMBL17691258
BCBcMAP01_000158
S9101
CCG-268016
FI73952
SMP1_000044
AS-75318
I1112
NS00093855
C09112
Q27106930
(1S,4S,5R,6R,9S,10R,12R,14R)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.0(1),?.0(1)?,(1)(2)]pentadeca-2,7-dien-15-one
- Rizk AM, Hammouda FM, et al. (1985). Biologically active diterpene esters from Euphorbia peplus. Phytochemistry,1985,24(7),1605-1606. [View]
Pubchem:
442042
Cas:
30220-46-3
Zinc:
ZINC000027652832
Kegg Ligand:
C09112
Chebi:
5922
Nmrshiftdb2:
70045373
Chembl:
CHEMBL2165402
CPRiL:
40225
SMILES: C1CC(C2)C2C(C3=O)C=CCC(C134)CC=C4
Level: 0
Mol. Weight: 348.44 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.64
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.84
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.59
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.81
- Plasma Protein Binding
- 66.54
- 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
- Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 1.28
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -2.08
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.92
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 4.25
- 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
- -3.9
- Rat (Acute)
- 3.06
- Rat (Chronic Oral)
- 2.91
- Fathead Minnow
- 3.91
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 416.31
- Hydration Free Energy
- -11.35
- Log(D) at pH=7.4
- 1.7
- Log(P)
- 1.05
- Log S
- -2.62
- Log(Vapor Pressure)
- -10.15
- Melting Point
- 191.44
- pKa Acid
- 4.79
- pKa Basic
- 5.62
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7069 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7069 |
| Laminarinase | Q9WXN1 | Q9WXN1_THEMA | Thermotoga maritima | 3 | 0.7068 |
| Laminarinase | Q9WXN1 | Q9WXN1_THEMA | Thermotoga maritima | 3 | 0.7068 |