24-methylenecycloartanyl-2′E,4′Z-tetradecadienoate - Compound Card

24-methylenecycloartanyl-2′E,4′Z-tetradecadienoate

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24-methylenecycloartanyl-2′E,4′Z-tetradecadienoate

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Tetracyclic Triterpene
Canonical Smiles CCCCCCCCC/C=C\C=C\C(=O)O[C@H]1CC[C@]23C(C1(C)C)CCC1[C@@]3(C2)CC[C@]2([C@@]1(C)CC[C@@H]2[C@@H](CCC(=C)C(C)C)C)C
InChI InChI=1S/C45H74O2/c1-10-11-12-13-14-15-16-17-18-19-20-21-40(46)47-39-27-29-44-32-45(44)31-30-42(8)36(35(5)23-22-34(4)33(2)3)26-28-43(42,9)38(45)25-24-37(44)41(39,6)7/h18-21,33,35-39H,4,10-17,22-32H2,1-3,5-9H3/b19-18-,21-20+/t35-,36-,37?,38?,39+,42-,43+,44-,45+/m1/s1
InChIKey QTGKGYNMHAANGT-ZPVPRBEJSA-N
Formula C45H74O2
HBA 2
HBD 0
MW 647.09
Rotatable Bonds 16
TPSA 26.3
LogP 13.22
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 47
Formal Charge 0
Fraction CSP3 0.84
Exact Mass 646.57
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Euphorbia pterococca Euphorbiaceae Plantae 1087778

Showing of synonyms

  • Benabdelaziz I, Gómez-Ruiz S, et al. (2018). New cycloartane-type ester triterpenes from Euphorbia pterococca and biological evaluation. Fitoterapia, 2018, 127, 271-278. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C1CCCC(C1(C234)C2)CCC3C5C(CC4)CCC5

Level: 0

Mol. Weight: 647.09 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.71
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.33
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
57.33

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
2.77
Plasma Protein Binding
108.75
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
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
Inhibitor

Excretion

Clearance
1.33
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.68
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.31
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
7.41
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
Toxic
T. Pyriformis
-110508.89
Rat (Acute)
2.79
Rat (Chronic Oral)
2.47
Fathead Minnow
152.92
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
10534.62
Hydration Free Energy
-2.92
Log(D) at pH=7.4
9.94
Log(P)
14.63
Log S
-7.51
Log(Vapor Pressure)
-311.83
Melting Point
115.62
pKa Acid
12.88
pKa Basic
5.29
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8785
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8707
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8620
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8573
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8556
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8521
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8398
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8316
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.8274
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 4 0.8149
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8066
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7925
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7849
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7848
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7758
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7665
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7637
Japanin M1MR49 M1MR49_RHIAP Rhipicephalus appendiculatus 5 0.7560
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7480
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7447
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7417
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7375
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7344
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7342
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7296
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7270
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.7214
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7145
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7120
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7109
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7075
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7062
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 5 0.7022

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