28-norlup-20(29)-en-3beta-hydroxy-17beta-hydroperoxide - Compound Card

28-norlup-20(29)-en-3beta-hydroxy-17beta-hydroperoxide

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28-norlup-20(29)-en-3beta-hydroxy-17beta-hydroperoxide

Structure
Zoomed Structure
  • Family: Plantae - Myrtaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpene
Canonical Smiles CC(=C)[C@@H]1CC[C@@]2([C@H]1[C@H]1CC[C@H]3[C@@]([C@]1(C)CC2)(C)CC[C@@H]1[C@]3(C)CC[C@@H](C1(C)C)O)C(=O)O
InChI InChI=1S/C30H48O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,23-,24+,27-,28+,29+,30+/m0/s1
InChIKey QGJZLNKBHJESQX-FUKRSKRZSA-N
Formula C30H48O3
HBA 2
HBD 2
MW 456.71
Rotatable Bonds 2
TPSA 57.53
LogP 7.09
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 33
Formal Charge 0
Fraction CSP3 0.9
Exact Mass 456.36
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Melaleuca ericifolia Myrtaceae Plantae 73757

Showing of synonyms

  • Abdel Bar FM, Zaghloul AM, et al. (2008). Antiproliferative triterpenes from Melaleuca ericifolia. Journal of Natural Products,2008,71(10),1787-1790. [View] [PubMed]
Pubchem: 26975211
Nmrshiftdb2: 70128788

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2CCC4C3CCC5C4CCCC5

Level: 0

Mol. Weight: 456.71 g/mol

Antiproliferative

Absorption

Caco-2 (logPapp)
-5.44
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.67
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.92

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
2.02
Plasma Protein Binding
94.1
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
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
2.92
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.81
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.94
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
3.7
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-111.23
Rat (Acute)
2.48
Rat (Chronic Oral)
2.12
Fathead Minnow
3.86
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
462.63
Hydration Free Energy
-2.54
Log(D) at pH=7.4
5.22
Log(P)
6.69
Log S
-6.44
Log(Vapor Pressure)
-9.49
Melting Point
261.82
pKa Acid
5.98
pKa Basic
8.4
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8746
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8746
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8725
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8725
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8542
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8542
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7367
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7367
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7010
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7010
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7008
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7008

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