(1S,2E,4R,6E,8S,11R,12S)-8,11-epoxy-4,12-epoxy-2,6-cembradiene - Compound Card

(1S,2E,4R,6E,8S,11R,12S)-8,11-epoxy-4,12-epoxy-2,6-cembradiene

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(1S,2E,4R,6E,8S,11R,12S)-8,11-epoxy-4,12-epoxy-2,6-cembradiene

Structure
Zoomed Structure
  • Family: Animalia - Alcyoniidae
  • Kingdom: Animalia
  • Class: Terpenoid
    • Subclass: Cembranoid Diterpene
Canonical Smiles CC([C@H]1C=C[C@@]2(C)C/C=C/[C@]3(O[C@@H]([C@](CC1)(O2)C)CC3)C)C
InChI InChI=1S/C20H32O2/c1-15(2)16-7-12-19(4)11-6-10-18(3)13-9-17(21-18)20(5,22-19)14-8-16/h6-7,10,12,15-17H,8-9,11,13-14H2,1-5H3/b10-6+,12-7?/t16-,17+,18+,19+,20-/m0/s1
InChIKey NZXAHQRVZURVSS-FEZVGTHSSA-N
Formula C20H32O2
HBA 2
HBD 0
MW 304.47
Rotatable Bonds 1
TPSA 18.46
LogP 5.04
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.8
Exact Mass 304.24
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Sarcophyton glaucum Alcyoniidae Animalia 70919

Showing of synonyms

  • El-Ezz RFA, Ahmed SA, et al. (2012). Bioactive cembranoids from the Red Sea soft coral Sarcophyton glaucum. Tetrahedron Letters,2012,54,989-992. [View]
Pubchem: 162930313

No compound-protein relationship available.

Structure

SMILES: C12C3CCCC=CC(O3)CC=CC(O2)CC1

Level: 0

Mol. Weight: 304.47 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.56
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.41
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.23

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.86
Plasma Protein Binding
52.81
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
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
14.25
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.18
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.17
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.83
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
-2.04
Rat (Acute)
2.2
Rat (Chronic Oral)
0.93
Fathead Minnow
3.94
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
322.59
Hydration Free Energy
-1.32
Log(D) at pH=7.4
4.39
Log(P)
5.79
Log S
-5.02
Log(Vapor Pressure)
-3.37
Melting Point
65.42
pKa Acid
12.6
pKa Basic
7.51
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8157
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8157
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7935
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7935
Thyroid hormone receptor alpha P04625 THA_CHICK Gallus gallus 3 0.7589
Thyroid hormone receptor alpha P04625 THA_CHICK Gallus gallus 3 0.7589
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 3 0.7417
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 3 0.7417
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.7020
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.7020

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