8-methoxyingol-7,12-diacetate-3-phenylacetate - Compound Card

8-methoxyingol-7,12-diacetate-3-phenylacetate

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8-methoxyingol-7,12-diacetate-3-phenylacetate

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Ingol Diterpene
Canonical Smiles CO[C@@H]1[C@H](OC(=O)C)/C(=C/[C@]23O[C@]3(C(=O)[C@@H]([C@@H]([C@@H]3[C@H]1C3(C)C)OC(=O)C)C)C[C@@H]([C@@H]2OC(=O)Cc1ccccc1)C)/C
InChI InChI=1S/C33H42O9/c1-17-15-33-30(41-23(36)14-22-12-10-9-11-13-22)18(2)16-32(33,42-33)29(37)19(3)27(40-21(5)35)24-25(31(24,6)7)28(38-8)26(17)39-20(4)34/h9-13,15,18-19,24-28,30H,14,16H2,1-8H3/b17-15+/t18-,19+,24-,25+,26+,27-,28-,30-,32-,33-/m0/s1
InChIKey LBLNFSHPVYQCBI-BMHMEUBHSA-N
Formula C33H42O9
HBA 9
HBD 0
MW 582.69
Rotatable Bonds 6
TPSA 117.73
LogP 4.0
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 42
Formal Charge 0
Fraction CSP3 0.64
Exact Mass 582.28
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Euphorbia officinarum Euphorbiaceae Plantae 1130835

Showing of synonyms

  • Daoubi M, Marquez N, et al. (2007). Isolation of new phenylacetylingol derivatives that reactivate HIV-1 latency and a novel spirotriterpenoid from Euphorbia officinarum latex. Bioorganic and Medicinal Chemistry,2007,15,4577-4584. [View] [PubMed]
Pubchem: 162817203

No compound-protein relationship available.

Structure

SMILES: c1ccccc1CC(=O)OC2CCC(C234)(O4)C(=O)CCC5C(C5)CCC=C3

Level: 1

Mol. Weight: 582.69 g/mol

Structure

SMILES: C1CCC(C123)(O3)C=CCCC4C(C4)CCC2=O

Level: 0

Mol. Weight: 582.69 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 582.69 g/mol

Anti-hiv
Antileukemia

Absorption

Caco-2 (logPapp)
-4.89
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.570
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
2.63

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.600
Plasma Protein Binding
71.9
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
Non-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
Non-Inhibitor

Excretion

Clearance
13.690
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.390
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.690
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
8.370
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
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
-9739.310
Rat (Acute)
4.990
Rat (Chronic Oral)
2.480
Fathead Minnow
27.790
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
320.130
Hydration Free Energy
-2.920
Log(D) at pH=7.4
3.360
Log(P)
4.6
Log S
-5.61
Log(Vapor Pressure)
-12.92
Melting Point
129.28
pKa Acid
6.05
pKa Basic
1.33
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.9185
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.9185
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8461
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8461
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8301
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8301
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8205
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8205
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8199
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8199
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8186
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8186
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.8174
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.8174
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7955
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7955
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7942
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7942
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7869
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7869
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7839
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7839
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7773
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7773
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7715
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7715
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7539
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7539
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7521
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7521
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7502
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7502
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7495
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7495
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7479
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7479
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7452
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7452
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7436
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7436
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7379
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7379
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7376
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7376
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7351
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7351
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7348
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7348
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7343
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7343
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7339
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7339
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7289
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7289
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7261
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7261
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7247
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7247
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7233
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7233
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7232
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7232
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7231
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7231
Chitinase Q54276 Q54276_SERMA Serratia marcescens 2 0.7223
Chitinase Q54276 Q54276_SERMA Serratia marcescens 2 0.7223
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7203
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7203
Acetyl-CoA carboxylase 2 O00763 ACACB_HUMAN Homo sapiens 3 0.7198
Acetyl-CoA carboxylase 2 O00763 ACACB_HUMAN Homo sapiens 3 0.7198
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7182
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7182
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7167
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7167
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7152
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7152
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7146
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7146
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7132
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7132
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7123
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7123
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 2 0.7111
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 2 0.7111
Acidic phospholipase A2 3 P60045 PA2A3_NAJSG Naja sagittifera 2 0.7096
Acidic phospholipase A2 3 P60045 PA2A3_NAJSG Naja sagittifera 2 0.7096
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7083
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7083
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7069
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7069
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7054
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7054
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7019
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7019

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