3-O-acetyl-28-hydroxylupeolic acid - Compound Card

3-O-acetyl-28-hydroxylupeolic acid

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3-O-acetyl-28-hydroxylupeolic acid

Structure
Zoomed Structure
  • Family: Plantae - Burseraceae
  • Kingdom: Plantae
  • Class: Terpene
    • Subclass: Triterpene
Canonical Smiles OC[C@@]12CC[C@H]([C@@H]2[C@@H]2[C@](CC1)(C)[C@]1(C)CC[C@@H]3[C@]([C@H]1CC2)(C)CC[C@H]([C@]3(C)C(=O)O)OC(=O)C)C(=C)C
InChI InChI=1S/C32H50O5/c1-19(2)21-10-15-32(18-33)17-16-29(5)22(26(21)32)8-9-23-28(4)13-12-25(37-20(3)34)31(7,27(35)36)24(28)11-14-30(23,29)6/h21-26,33H,1,8-18H2,2-7H3,(H,35,36)/t21-,22+,23+,24+,25+,26+,28+,29+,30+,31+,32+/m0/s1
InChIKey IOOOTJXCAVXHMX-BRSKACALSA-N
Formula C32H50O5
HBA 4
HBD 2
MW 514.75
Rotatable Bonds 4
TPSA 83.83
LogP 6.63
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 37
Formal Charge 0
Fraction CSP3 0.88
Exact Mass 514.37
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Boswellia dalzielii Burseraceae Plantae 2303552

Showing of synonyms

  • Tegasne C, Kapche GDWF, et al. (2021). Bioguided chemical study of Boswellia dalzielii Hutch. (Burseraceae) for antibacterial agents and a new glucopyranoxylmethoxybenzyle.. Natural product research,2021, 35(23), 5199-5208. [View] [PubMed]
Pubchem: 102341095

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2CCC4C3CCC5C4CCCC5

Level: 0

Mol. Weight: 514.75 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.45
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.88
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.07

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.88
Plasma Protein Binding
96.21
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-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
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
2.12
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.13
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.14
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
4.97
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-709.47
Rat (Acute)
2.3
Rat (Chronic Oral)
2.11
Fathead Minnow
3.59
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
500.21
Hydration Free Energy
-3.01
Log(D) at pH=7.4
4.13
Log(P)
6.0
Log S
-6.44
Log(Vapor Pressure)
-10.55
Melting Point
253.64
pKa Acid
5.43
pKa Basic
6.86
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7137

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