12alpha-acetoxy-20,24-dimethyl-25-norscalar-16-en-24-one - Compound Card

12alpha-acetoxy-20,24-dimethyl-25-norscalar-16-en-24-one

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12alpha-acetoxy-20,24-dimethyl-25-norscalar-16-en-24-one

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@]2([C@H]1CC=C(C2)C(=O)C)C)OC(=O)C)C)C
InChI InChI=1S/C28H44O3/c1-8-25(4)13-9-14-26(5)21(25)12-15-27(6)22-11-10-20(18(2)29)17-28(22,7)24(16-23(26)27)31-19(3)30/h10,21-24H,8-9,11-17H2,1-7H3/t21-,22+,23+,24+,25+,26+,27+,28-/m1/s1
InChIKey YZYZCVQQKYLXMA-PJMBMELKSA-N
Formula C28H44O3
HBA 3
HBD 0
MW 428.66
Rotatable Bonds 3
TPSA 43.37
LogP 6.89
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.86
Exact Mass 428.33
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: 162942143
Nmrshiftdb2: 70060471

No compound-protein relationship available.

Structure

SMILES: C1C=CCC2C1CCC(C23)C4C(CC3)CCCC4

Level: 0

Mol. Weight: 428.66 g/mol

Antibacterial
Cytotoxic

Absorption

Caco-2 (logPapp)
-4.81
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.61
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.21

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.69
Plasma Protein Binding
88.04
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
11.23
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.35
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.81
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.28
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
-30.26
Rat (Acute)
1.86
Rat (Chronic Oral)
1.61
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
462.7
Hydration Free Energy
-3.91
Log(D) at pH=7.4
5.73
Log(P)
5.97
Log S
-6.17
Log(Vapor Pressure)
-7.41
Melting Point
152.58
pKa Acid
11.38
pKa Basic
5.64
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7826
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7826
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7762
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7762
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7524
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7524
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7463
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7463
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7312
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7312
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7196
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7196
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7139
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7139
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7076
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7076
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7038
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7038

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