Megalocarpoidolide D - Compound Card

Megalocarpoidolide D

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Megalocarpoidolide D

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles COC(=O)[C@]12CC[C@H]([C@@]3(C2=CC(=O)C=C1C(=O)OC)C[C@H](OC3=O)c1cocc1)C
InChI InChI=1S/C22H22O8/c1-12-4-6-21(19(25)28-3)15(18(24)27-2)8-14(23)9-17(21)22(12)10-16(30-20(22)26)13-5-7-29-11-13/h5,7-9,11-12,16H,4,6,10H2,1-3H3/t12-,16+,21-,22-/m1/s1
InChIKey LUAAKOQKNDIVEF-SQRPBOIWSA-N
Formula C22H22O8
HBA 8
HBD 0
MW 414.41
Rotatable Bonds 3
TPSA 109.11
LogP 2.45
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.45
Exact Mass 414.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Croton megalocarpoides Euphorbiaceae Plantae 1704624
2 Croton oligandrus Euphorbiaceae Plantae 3170015

Showing of synonyms

  • Guetchueng ST, Nahar L, et al. (2018). Ent-Clerodane Diterpenes from the Bark of Croton oligandrus Pierre ex Hutch. and Assessment of Their Cytotoxicity against Human Cancer Cell Lines. Molecules. 2018, 23(2), 410. [View] [PubMed]
  • 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)C23C=4C(CCC3)C=CC(=O)C4

Level: 1

Mol. Weight: 414.41 g/mol

Structure

SMILES: C1COC(=O)C12C=3C(CCC2)C=CC(=O)C3

Level: 0

Mol. Weight: 414.41 g/mol

Structure

SMILES: c1ccoc1

Level: 0

Mol. Weight: 414.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.81
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.810
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.7

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.720
Plasma Protein Binding
60.15
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
8.570
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.320
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.080
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.360
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
-42.230
Rat (Acute)
3.770
Rat (Chronic Oral)
2.860
Fathead Minnow
4.380
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
443.680
Hydration Free Energy
-3.640
Log(D) at pH=7.4
2.700
Log(P)
2.27
Log S
-4.64
Log(Vapor Pressure)
-8.08
Melting Point
225.2
pKa Acid
6.85
pKa Basic
4.02
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8257
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8257
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8189
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8189
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8037
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8037
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7914
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7914
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7747
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7747
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7688
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7688
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7679
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7679
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7639
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7639
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7601
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7601
NAD(P) transhydrogenase subunit alpha part 1 Q2RSB2 PNTAA_RHORT Rhodospirillum rubrum 3 0.7558
NAD(P) transhydrogenase subunit alpha part 1 Q2RSB2 PNTAA_RHORT Rhodospirillum rubrum 3 0.7558
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7455
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7455
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7424
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7424
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7389
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7389
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7379
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7379
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7342
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7342
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7341
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7341
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7236
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7236
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
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7132
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7132
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7105
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7105
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 2 0.7039
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 2 0.7039
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7029
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7029
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7014
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7014
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7001
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7001

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