Lup-20(29)-en-3beta-O-(3′-beta-hydroxy) palmitate - Compound Card

Lup-20(29)-en-3beta-O-(3′-beta-hydroxy) palmitate

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Lup-20(29)-en-3beta-O-(3′-beta-hydroxy) palmitate

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpene Ester
Canonical Smiles CCCCCCCCCCCCC[C@H](CC(=O)O[C@H]1CC[C@]2(C(C1(C)C)CC[C@@]1([C@@H]2CC[C@H]2[C@@]1(C)CC[C@@]1([C@@H]2[C@@H](CC1)C(=C)C)C)C)C)O
InChI InChI=1S/C46H80O3/c1-10-11-12-13-14-15-16-17-18-19-20-21-34(47)32-40(48)49-39-26-28-44(7)37(42(39,4)5)25-29-46(9)38(44)23-22-36-41-35(33(2)3)24-27-43(41,6)30-31-45(36,46)8/h34-39,41,47H,2,10-32H2,1,3-9H3/t34-,35+,36-,37?,38-,39+,41-,43-,44+,45-,46-/m1/s1
InChIKey WBNRJAJHDJRUDM-NRBFSFIRSA-N
Formula C46H80O3
HBA 3
HBD 1
MW 681.14
Rotatable Bonds 16
TPSA 46.53
LogP 13.03
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 49
Formal Charge 0
Fraction CSP3 0.93
Exact Mass 680.61
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Acokanthera oppositifolia Apocynaceae Plantae 141525

Showing of synonyms

  • El Sayed AM, Ezzat SM, et al. (2016). A new antibacterial lupane ester from the seeds of Acokanthera oppositifolia Lam. Nat Prod Res, 2016, 30(24), 2813-2818.. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2CCC4C3CCC5C4CCCC5

Level: 0

Mol. Weight: 681.14 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.74
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-3.97
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
115.43

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
2.25
Plasma Protein Binding
108.5
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
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
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
2.71
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.7
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.25
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
6.95
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
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
-215102.07
Rat (Acute)
2.97
Rat (Chronic Oral)
2.2
Fathead Minnow
283.09
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
22753.95
Hydration Free Energy
-2.92
Log(D) at pH=7.4
9.85
Log(P)
14.22
Log S
-7.88
Log(Vapor Pressure)
-676.64
Melting Point
145.44
pKa Acid
11.04
pKa Basic
5.53
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 0.9329
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8884
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8837
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8017
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8000
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7928
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7777
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7719
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7591
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7444
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7416
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7385
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7288
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7225
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7058
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7047
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.7038
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7032

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