Hyrtiosenolide A - Compound Card

Hyrtiosenolide A

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Hyrtiosenolide A

Structure
Zoomed Structure
  • Family: Animalia - Thorectidae
  • Kingdom: Animalia
  • Class: Terpenoid
    • Subclass: Sesquiterpene Gamma-Methoxybutenolide
Canonical Smiles CO[C@]12OC(=O)C=C1CC[C@@]1(C[C@@H]2CC(=C)[C@@]1(C)O)C
InChI InChI=1S/C16H22O4/c1-10-7-12-9-14(2,15(10,3)18)6-5-11-8-13(17)20-16(11,12)19-4/h8,12,18H,1,5-7,9H2,2-4H3/t12-,14+,15+,16-/m0/s1
InChIKey CSUAKCSONPLSER-XZDPQHSOSA-N
Formula C16H22O4
HBA 4
HBD 1
MW 278.35
Rotatable Bonds 1
TPSA 55.76
LogP 2.33
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.69
Exact Mass 278.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Hyrtios species Thorectidae Animalia 279627

Showing of synonyms

  • Youssef DT, Singab AN, et al. (2004). Hyrtiosenolides A and B, two new sesquiterpene gamma-methoxybutenolides and a new sterol from a Red Sea sponge Hyrtios species. Journal of Natural Products,2004,67(10),1736-1739. [View] [PubMed]
Pubchem: 101357704
Nmrshiftdb2: 80012036

No compound-protein relationship available.

Structure

SMILES: C1CC(C2)CC(=C)CC2C(C1=3)OC(=O)C3

Level: 0

Mol. Weight: 278.35 g/mol

Antibacterial

Absorption

Caco-2 (logPapp)
-4.59
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
-2.34

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.55
Plasma Protein Binding
39.93
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
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.64
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.2
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.47
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.65
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
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
-0.4
Rat (Acute)
2.51
Rat (Chronic Oral)
1.19
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
327.74
Hydration Free Energy
-5.68
Log(D) at pH=7.4
1.96
Log(P)
1.73
Log S
-2.75
Log(Vapor Pressure)
-5.3
Melting Point
147.52
pKa Acid
8.12
pKa Basic
6.1
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7750
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7750
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7716
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7716
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7438
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7438
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7345
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7345

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