(+)-7alpha,8beta-dihydroxydeepoxysarcophine - Compound Card

(+)-7alpha,8beta-dihydroxydeepoxysarcophine

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(+)-7alpha,8beta-dihydroxydeepoxysarcophine

Structure
Zoomed Structure
  • Family: Animalia - Alcyoniidae
  • Kingdom: Animalia
  • Class: Terpenoid
    • Subclass: Cembranoid Diterpene
Canonical Smiles C/C/1=C\CCC(C)(O)[C@H](O)CC/C(=C/[C@@]2(C(=C(C)C(=O)O2)CC1)C)/C
InChI InChI=1S/C21H32O4/c1-14-7-6-12-20(4,24)18(22)11-9-15(2)13-21(5)17(10-8-14)16(3)19(23)25-21/h7,13,18,22,24H,6,8-12H2,1-5H3/b14-7+,15-13+/t18-,20?,21-/m1/s1
InChIKey QROGSFBTQTXFEX-PEVVGAQFSA-N
Formula C21H32O4
HBA 4
HBD 2
MW 348.48
Rotatable Bonds 0
TPSA 66.76
LogP 3.98
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 348.23
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Sarcophyton glaucum Alcyoniidae Animalia 70919
2 Sarcophyton auritum Alcyoniidae Animalia 859400

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]
  • Eltahawy NA, Ibrahim AK, et al. (2014). Cytotoxic cembranoids from the Red Sea soft coral, Sarcophyton auritum. Tetrahedron Letters,2014,55,3984-3988. [View]
Pubchem: 162983731
Nmrshiftdb2: 70081751

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 348.48 g/mol

Antitumor
Cytotoxic

Absorption

Caco-2 (logPapp)
-4.72
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.43
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.84

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.57
Plasma Protein Binding
63.25
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-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
4.42
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.18
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.05
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.84
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
-1.58
Rat (Acute)
2.17
Rat (Chronic Oral)
1.86
Fathead Minnow
4.55
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
383.66
Hydration Free Energy
-7.56
Log(D) at pH=7.4
3.14
Log(P)
3.86
Log S
-4.23
Log(Vapor Pressure)
-6.49
Melting Point
136.36
pKa Acid
9.44
pKa Basic
5.82
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.9182
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.9182
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8892
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8892
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8534
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8534
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8463
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8463
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8247
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8247
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7959
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7959
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7935
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7935
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7667
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7667
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7646
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7646
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7594
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7594
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7315
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7315
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7306
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7306
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7218
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7218
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7120
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7120
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7060
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7060
FKBP-type peptidyl-prolyl cis-trans isomerase FkpA P45523 FKBA_ECOLI Escherichia coli 4 0.7058
FKBP-type peptidyl-prolyl cis-trans isomerase FkpA P45523 FKBA_ECOLI Escherichia coli 4 0.7058
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7051
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7051
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7036
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7036
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7023
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7023

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