Megalocarpoidolide B - Compound Card

Megalocarpoidolide B

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Megalocarpoidolide B

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles COC(=O)C1=CCC[C@H]2[C@]31CC[C@H]([C@]2(C(=O)OC3)CCc1cocc1)C
InChI InChI=1S/C21H26O5/c1-14-6-9-20-13-26-19(23)21(14,10-7-15-8-11-25-12-15)17(20)5-3-4-16(20)18(22)24-2/h4,8,11-12,14,17H,3,5-7,9-10,13H2,1-2H3/t14-,17+,20-,21-/m1/s1
InChIKey AILLWNBJJGMCGQ-GYPMPWGGSA-N
Formula C21H26O5
HBA 5
HBD 0
MW 358.43
Rotatable Bonds 4
TPSA 65.74
LogP 3.68
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.62
Exact Mass 358.18
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: c1occc1CCC(C(=O)OC2)(CCC3)C(C234)CCC=C4

Level: 1

Mol. Weight: 358.43 g/mol

Structure

SMILES: C1CCC(C(=O)OC2)C(C123)CCC=C3

Level: 0

Mol. Weight: 358.43 g/mol

Structure

SMILES: c1ccoc1

Level: 0

Mol. Weight: 358.43 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.77
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.960
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.98

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.450
Plasma Protein Binding
59.17
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.320
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.460
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.870
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.640
Micronucleos
Safe
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
-6.270
Rat (Acute)
3.230
Rat (Chronic Oral)
2.320
Fathead Minnow
3.920
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
415.720
Hydration Free Energy
-5.130
Log(D) at pH=7.4
3.630
Log(P)
3.5
Log S
-5.03
Log(Vapor Pressure)
-7.07
Melting Point
144.4
pKa Acid
8.85
pKa Basic
5.99
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8031
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8031
Ferrichrome outer membrane transporter/phage receptor P06971 FHUA_ECOLI Escherichia coli 3 0.7698
Ferrichrome outer membrane transporter/phage receptor P06971 FHUA_ECOLI Escherichia coli 3 0.7698
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7657
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7657
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7634
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7634
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
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7593
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7593
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7505
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7505
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7270
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7270
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7165
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7165
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7128
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7128
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 2 0.7108
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 2 0.7108
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7104
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7104
Polymerase basic protein 2 P31345 PB2_I75A3 Influenza A virus 2 0.7080
Polymerase basic protein 2 P31345 PB2_I75A3 Influenza A virus 2 0.7080
Retinoic acid receptor RXR Q8T5C6 RXR_BIOGL Biomphalaria glabrata 3 0.7057
Retinoic acid receptor RXR Q8T5C6 RXR_BIOGL Biomphalaria glabrata 3 0.7057
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7023
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7023
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7016
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7016
Alanine racemase Q180W0 Q180W0_CLOD6 Clostridioides difficile 2 0.7006
Alanine racemase Q180W0 Q180W0_CLOD6 Clostridioides difficile 2 0.7006
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7005
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7005

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