7-keto-8alpha-hydroxy-deepoxysarcophine - Compound Card

7-keto-8alpha-hydroxy-deepoxysarcophine

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7-keto-8alpha-hydroxy-deepoxysarcophine

Structure
Zoomed Structure
  • Family: Animalia - Alcyoniidae
  • Kingdom: Animalia
  • Class: Terpenoid
    • Subclass: Cembranoid Diterpene
Canonical Smiles C/C/1=C\CC[C@@](C)(O)C(=O)CC/C(=C/[C@@H]2C(=C(C)C(=O)O2)CC1)/C
InChI InChI=1S/C20H28O4/c1-13-6-5-11-20(4,23)18(21)10-8-14(2)12-17-16(9-7-13)15(3)19(22)24-17/h6,12,17,23H,5,7-11H2,1-4H3/b13-6+,14-12+/t17-,20-/m1/s1
InChIKey WFFGMWPCPCUPGU-WLAAPCTLSA-N
Formula C20H28O4
HBA 4
HBD 1
MW 332.44
Rotatable Bonds 0
TPSA 63.6
LogP 3.8
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.6
Exact Mass 332.2
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Sarcophyton ehrenbergi Alcyoniidae Animalia 358800

Showing of synonyms

  • Elkhateeb A, El-Beih AA, et al. (2014). New terpenes from the Egyptian soft coral Sarcophyton ehrenbergi. Marine Drugs,2014,12,1977-1986. [View] [PubMed]
Pubchem: 162817610
Nmrshiftdb2: 70048046

No compound-protein relationship available.

Structure

SMILES: C1C(=O)OC(C=12)C=CCCC(=O)CCCC=CCC2

Level: 0

Mol. Weight: 332.44 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.69
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.56
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.72

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.68
Plasma Protein Binding
66.12
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
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
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.08
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
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.56
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.66
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-1.16
Rat (Acute)
2.13
Rat (Chronic Oral)
1.76
Fathead Minnow
4.7
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
384.68
Hydration Free Energy
-6.81
Log(D) at pH=7.4
3.22
Log(P)
3.58
Log S
-4.13
Log(Vapor Pressure)
-6.38
Melting Point
132.73
pKa Acid
9.56
pKa Basic
4.21
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8977
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8977
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.8729
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.8729
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8495
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8495
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8410
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8410
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8410
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8410
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8208
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8208
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8179
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8179
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8083
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8083
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7990
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7990
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7745
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7745
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7739
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7739
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7587
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7587
Angiotensin-converting enzyme Q10714 ACE_DROME Drosophila melanogaster 3 0.7492
Angiotensin-converting enzyme Q10714 ACE_DROME Drosophila melanogaster 3 0.7492
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7443
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7443
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7383
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7383
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7365
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7365
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7321
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7321
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7165
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7165
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7099
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7099

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