Lup-20(29)-ene-2,3-diol - Compound Card

Lup-20(29)-ene-2,3-diol

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Lup-20(29)-ene-2,3-diol

Structure
Zoomed Structure
  • Family: Plantae - Caesalpinioideae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Pentacyclic Triterpenoid
Canonical Smiles CC(=C)[C@@H]1CC[C@]2(C1C1CCC3[C@@]([C@]1(C)CC2)(C)CCC1[C@]3(C)C[C@H](O)[C@@H](C1(C)C)O)C
InChI InChI=1S/C30H50O2/c1-18(2)19-11-13-27(5)15-16-29(7)20(24(19)27)9-10-23-28(6)17-21(31)25(32)26(3,4)22(28)12-14-30(23,29)8/h19-25,31-32H,1,9-17H2,2-8H3/t19-,20?,21-,22?,23?,24?,25-,27+,28-,29+,30+/m0/s1
InChIKey OESLKRXCBRUCJZ-FOHPDTPUSA-N
Formula C30H50O2
HBA 2
HBD 2
MW 442.73
Rotatable Bonds 1
TPSA 40.46
LogP 7.0
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.93
Exact Mass 442.38
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Gilbertiodendron dewevrei Caesalpinioideae Plantae 162777

Showing of synonyms

  • Stephanie DM, Stéphane FFY, et al. (2022). Dewerin and gilbertionol two new secondary metabolites from the stem bark of Gilbertiodendron dewevrei (De Wild) J. Leonard.. Natural product research,2022, 36(1), 214-222. [View] [PubMed]
Pubchem: 15127233
Chebi: 67954
Nmrshiftdb2: 60030718
Metabolights: MTBLC67954

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2CCC4C3CCC5C4CCCC5

Level: 0

Mol. Weight: 442.73 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.83
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.46
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.84

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.47
Plasma Protein Binding
78.01
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
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
Non-Inhibitor

Excretion

Clearance
10.8
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.36
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.76
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
5.29
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
Safe
T. Pyriformis
-61.0
Rat (Acute)
2.51
Rat (Chronic Oral)
1.72
Fathead Minnow
4.05
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
406.59
Hydration Free Energy
-2.98
Log(D) at pH=7.4
6.92
Log(P)
7.44
Log S
-6.52
Log(Vapor Pressure)
-8.52
Melting Point
234.43
pKa Acid
11.9
pKa Basic
7.98
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8353
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7660
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7653
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7544
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.7446
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7374
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7257
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7166
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7063

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