2R,7R,8R-dihydroxydeepoxysarcophine - Compound Card

2R,7R,8R-dihydroxydeepoxysarcophine

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2R,7R,8R-dihydroxydeepoxysarcophine

Structure
Zoomed Structure
  • Family: Animalia - Alcyoniidae
  • Kingdom: Animalia
  • Class: Terpenoid
    • Subclass: Cembranoid Diterpene
Canonical Smiles C/C/1=C\CC[C@](C)(O)[C@@H](O)CC/C(=C/[C@@H]2C(=C(C)C(=O)O2)CC1)/C
InChI InChI=1S/C20H30O4/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/h6,12,17-18,21,23H,5,7-11H2,1-4H3/b13-6+,14-12+/t17-,18+,20+/m1/s1
InChIKey KISXSEZMRISOQB-JWSMNLEESA-N
Formula C20H30O4
HBA 4
HBD 2
MW 334.46
Rotatable Bonds 0
TPSA 66.76
LogP 3.59
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.65
Exact Mass 334.21
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Sarcophyton glaucum Alcyoniidae Animalia 70919

Showing of synonyms

  • Hegazy M-EF, El-Beih AA, et al. (2011). Cytotoxic cembranoids from the Red Sea soft coral Sarcophyton glaucum. Natural Product Communications,2011,6(12),1809-1812. [View] [PubMed]
Pubchem: 162988935
Nmrshiftdb2: 70081524

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 334.46 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.73
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.4
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)
0.6
Plasma Protein Binding
56.32
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
4.09
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.43
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.06
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.97
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
-0.8
Rat (Acute)
2.21
Rat (Chronic Oral)
1.95
Fathead Minnow
4.45
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
388.07
Hydration Free Energy
-7.93
Log(D) at pH=7.4
3.05
Log(P)
3.5
Log S
-4.04
Log(Vapor Pressure)
-6.74
Melting Point
152.32
pKa Acid
9.49
pKa Basic
5.97
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 0.8999
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8999
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8970
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8970
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8863
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8863
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8791
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8791
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8609
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8609
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8557
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8557
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8400
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8400
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8271
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8271
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8266
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8266
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8183
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8183
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8179
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8179
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8045
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8045
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8040
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8040
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7944
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7944
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7903
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7903
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7833
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7833
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7807
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7807
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7778
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7778
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7448
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7448
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7425
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7425
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7387
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7387
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7333
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7333
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7296
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7296
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7264
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7264
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7218
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7218
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7187
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7187
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7116
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7116
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7096
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7096
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7087
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7087
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7073
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7073
Lanosterol 14-alpha demethylase CYP51 P10614 CP51_YEAST Saccharomyces cerevisiae 3 0.7039
Lanosterol 14-alpha demethylase CYP51 P10614 CP51_YEAST Saccharomyces cerevisiae 3 0.7039
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7016
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7016
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7002
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7002

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