Megalocarpoidolide E - Compound Card

Megalocarpoidolide E

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Megalocarpoidolide E

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles COC(=O)[C@]12CC=C([C@@]3([C@H]2CCC(=O)[C@H]1C(=O)OC)C[C@H](OC3=O)c1cocc1)C
InChI InChI=1S/C22H24O8/c1-12-6-8-21(19(25)28-3)16(5-4-14(23)17(21)18(24)27-2)22(12)10-15(30-20(22)26)13-7-9-29-11-13/h6-7,9,11,15-17H,4-5,8,10H2,1-3H3/t15-,16-,17-,21-,22+/m0/s1
InChIKey RRUOBQIYOREMKW-IDRUFVAWSA-N
Formula C22H24O8
HBA 8
HBD 0
MW 416.43
Rotatable Bonds 3
TPSA 109.11
LogP 2.53
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.55
Exact Mass 416.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Croton megalocarpoides Euphorbiaceae Plantae 1704624

Showing of synonyms

  • Ndunda B, Langat MK, et al. (2016). New ent-Clerodane and Abietane Diterpenoids from the Roots of Kenyan Croton megalocarpoides Friis and M. G. Gilbert.. Planta Med,2016,82(11-12),1079-1086. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1occc1C(C2)OC(=O)C23C4C(CC=C3)CC(=O)CC4

Level: 1

Mol. Weight: 416.43 g/mol

Structure

SMILES: C1COC(=O)C12C3C(CC=C2)CC(=O)CC3

Level: 0

Mol. Weight: 416.43 g/mol

Structure

SMILES: c1ccoc1

Level: 0

Mol. Weight: 416.43 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.87
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.830
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.36

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.830
Plasma Protein Binding
53.71
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
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
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.820
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.020
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.260
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.480
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
-43.360
Rat (Acute)
4.230
Rat (Chronic Oral)
2.640
Fathead Minnow
4.070
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
444.340
Hydration Free Energy
-3.410
Log(D) at pH=7.4
1.910
Log(P)
2.44
Log S
-4.36
Log(Vapor Pressure)
-8.42
Melting Point
214.1
pKa Acid
6.9
pKa Basic
4.14
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8870
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8870
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8691
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8691
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8611
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8611
Probable esterase KAI2 Q9SZU7 KAI2_ARATH Arabidopsis thaliana 3 0.8508
Probable esterase KAI2 Q9SZU7 KAI2_ARATH Arabidopsis thaliana 3 0.8508
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8284
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8284
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8210
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8210
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7988
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7988
17-beta-hydroxysteroid dehydrogenase 14 Q9BPX1 DHB14_HUMAN Homo sapiens 2 0.7813
17-beta-hydroxysteroid dehydrogenase 14 Q9BPX1 DHB14_HUMAN Homo sapiens 2 0.7813
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7763
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7763
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7748
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7748
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7696
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7696
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7608
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7608
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7591
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7591
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7580
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7580
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7539
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7539
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7515
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7515
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7501
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7501
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7483
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7483
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7449
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7449
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7368
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7368
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7350
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7350
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7338
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7338
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7330
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7330
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7322
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7322
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7296
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7296
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7289
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7289
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7276
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7276
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7252
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7252
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7246
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7246
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7243
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7243
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7234
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7234
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7185
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7185
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7174
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7174
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7172
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7172
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7163
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7163
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7160
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7160
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 2 0.7096
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7096
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7096
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 2 0.7096
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7090
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7090
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7071
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7071
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7057
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7057
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7049
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7049
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7049
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7049
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7043
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7043
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7032
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7032
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7029
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7029

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