Phyllospongin A - Compound Card

Phyllospongin A

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Phyllospongin A

Structure
Zoomed Structure
  • Family: Animalia - Thorectidae
  • Kingdom: Animalia
  • Class: Terpenoid
    • Subclass: Scalarane-Type Sesterterpene
Canonical Smiles CC(=O)O[C@H]1C[C@@H]2[C@@]([C@H]3[C@@]1(C)C=C(C(=O)C)[C@@H](C3)OC(=O)C)(C)CC[C@H]1[C@]2(C)CCCC1(C)C
InChI InChI=1S/C29H44O5/c1-17(30)20-16-29(8)23(14-21(20)33-18(2)31)28(7)13-10-22-26(4,5)11-9-12-27(22,6)24(28)15-25(29)34-19(3)32/h16,21-25H,9-15H2,1-8H3/t21-,22-,23+,24+,25+,27+,28+,29-/m1/s1
InChIKey KXMLXMWJHMVIFC-XGEDQLNESA-N
Formula C29H44O5
HBA 5
HBD 0
MW 472.67
Rotatable Bonds 3
TPSA 69.67
LogP 6.04
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.83
Exact Mass 472.32
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Phyllospongia lamellosa Thorectidae Animalia 1162757

Showing of synonyms

  • Hassan MHA, Rateb ME, et al. (2015). Scalarane sesterterpenes from the Egyptian Red Sea sponge Phyllospongia lamellosa. Tetrahedron,2015,71,(4),577-583. [View]
Pubchem: 163084275
Nmrshiftdb2: 70060470

No compound-protein relationship available.

Structure

SMILES: C1=CCCC(C12)C3C(CC2)C4C(CC3)CCCC4

Level: 0

Mol. Weight: 472.67 g/mol

Antibacterial
Cytotoxic

Absorption

Caco-2 (logPapp)
-4.69
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.68
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.16

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.44
Plasma Protein Binding
86.37
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
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
10.5
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.4
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.56
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.27
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
-92.06
Rat (Acute)
1.93
Rat (Chronic Oral)
1.71
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
474.6
Hydration Free Energy
-2.5
Log(D) at pH=7.4
4.67
Log(P)
5.14
Log S
-6.03
Log(Vapor Pressure)
-7.71
Melting Point
174.81
pKa Acid
10.67
pKa Basic
4.89
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 0.8055
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8055
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7707
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7707
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7359
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7359
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7031
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7031

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