3-acetylsesterstatin 1 - Compound Card

3-acetylsesterstatin 1

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3-acetylsesterstatin 1

Structure
Zoomed Structure
  • Family: Animalia - Thorectidae
  • Kingdom: Animalia
  • Class: Terpenoid
    • Subclass: Scalarane-Type Sesterterpene
Canonical Smiles CC(=O)O[C@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2C[C@@H](O)[C@]2([C@H]1CCC1=C2C(=O)OC1)C)C)C
InChI InChI=1S/C27H40O5/c1-15(28)32-21-10-12-25(4)17(24(21,2)3)9-11-26(5)18-8-7-16-14-31-23(30)22(16)27(18,6)20(29)13-19(25)26/h17-21,29H,7-14H2,1-6H3/t17-,18-,19+,20+,21-,25-,26-,27+/m0/s1
InChIKey GRIVEGVPDUNMNE-JNBLGKNQSA-N
Formula C27H40O5
HBA 5
HBD 1
MW 444.61
Rotatable Bonds 1
TPSA 72.83
LogP 4.81
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.85
Exact Mass 444.29
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Hyrtios erecta Thorectidae Animalia 279628

Showing of synonyms

  • Youssef DT, Shaala LA, et al. (2005). Antimycobacterial scalarane-based sesterterpenes from the Red Sea sponge Hyrtios erecta. Journal of Natural Products,2005,68(12),1782-1784. [View] [PubMed]
Pubchem: 21629517
Nmrshiftdb2: 70034816

No compound-protein relationship available.

Structure

SMILES: O=C1OCC(=C12)CCC3C2CCC4C3CCC5C4CCCC5

Level: 0

Mol. Weight: 444.61 g/mol

Antimycobacterial

Absorption

Caco-2 (logPapp)
-4.78
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.93
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.7

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.33
Plasma Protein Binding
72.02
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
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
9.19
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.23
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.21
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.9
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
-73.06
Rat (Acute)
2.1
Rat (Chronic Oral)
1.6
Fathead Minnow
3.92
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
479.98
Hydration Free Energy
-2.72
Log(D) at pH=7.4
3.99
Log(P)
4.0
Log S
-5.5
Log(Vapor Pressure)
-8.36
Melting Point
216.23
pKa Acid
9.45
pKa Basic
6.45
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 0.7073
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7073

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