12alpha-acetoxy-13beta,18beta-cyclobutan-20,24-dimethyl-24-oxoscalar-16-en-25beta-ol - Compound Card

12alpha-acetoxy-13beta,18beta-cyclobutan-20,24-dimethyl-24-oxoscalar-16-en-25beta-ol

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12alpha-acetoxy-13beta,18beta-cyclobutan-20,24-dimethyl-24-oxoscalar-16-en-25beta-ol

Structure
Zoomed Structure
  • Family: Animalia - Thorectidae
  • Kingdom: Animalia
  • Class: Terpenoid
    • Subclass: Scalarane-Type Sesterterpene
Canonical Smiles CC[C@@]1(C)CCC[C@]2([C@@H]1CC[C@@]1([C@H]2C[C@@H]([C@]23[C@H]1CC=C([C@@H]3[C@@H](C2)O)C(=O)C)OC(=O)C)C)C
InChI InChI=1S/C29H44O4/c1-7-26(4)12-8-13-27(5)21(26)11-14-28(6)22-10-9-19(17(2)30)25-20(32)16-29(22,25)24(15-23(27)28)33-18(3)31/h9,20-25,32H,7-8,10-16H2,1-6H3/t20-,21-,22+,23+,24+,25-,26+,27+,28+,29-/m1/s1
InChIKey CAMNRSFPFNRTLQ-HRJGVYIJSA-N
Formula C29H44O4
HBA 4
HBD 1
MW 456.67
Rotatable Bonds 3
TPSA 63.6
LogP 5.86
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 33
Formal Charge 0
Fraction CSP3 0.86
Exact Mass 456.32
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: 163036948
Nmrshiftdb2: 70060469

No compound-protein relationship available.

Structure

SMILES: C1CC(C123)C=CCC2C4C(CC3)C5C(CC4)CCCC5

Level: 0

Mol. Weight: 456.67 g/mol

Antibacterial
Cytotoxic

Absorption

Caco-2 (logPapp)
-4.8
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.55
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)
1.51
Plasma Protein Binding
86.9
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
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
10.22
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.67
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.8
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.53
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
-87.83
Rat (Acute)
2.22
Rat (Chronic Oral)
1.78
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
484.2
Hydration Free Energy
-2.59
Log(D) at pH=7.4
4.93
Log(P)
5.03
Log S
-5.65
Log(Vapor Pressure)
-8.36
Melting Point
198.43
pKa Acid
9.88
pKa Basic
5.22
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7105
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7105
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7068
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7068

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