10alpha-hydroxy-2-epi-16-deoxysarcophine - Compound Card

10alpha-hydroxy-2-epi-16-deoxysarcophine

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10alpha-hydroxy-2-epi-16-deoxysarcophine

Structure
Zoomed Structure
  • Family: Animalia - Alcyoniidae
  • Kingdom: Animalia
  • Class: Terpenoid
    • Subclass: Cembranoid Diterpene
Canonical Smiles C/C/1=C\[C@@H](O)C[C@]2(C)O[C@H]2CC/C(=C/[C@@H]2C(=C(C)CO2)CC1)/C
InChI InChI=1S/C20H30O3/c1-13-5-7-17-15(3)12-22-18(17)10-14(2)6-8-19-20(4,23-19)11-16(21)9-13/h9-10,16,18-19,21H,5-8,11-12H2,1-4H3/b13-9+,14-10+/t16-,18-,19+,20+/m1/s1
InChIKey LZVSZONHJCIUBX-ZETDYKMVSA-N
Formula C20H30O3
HBA 3
HBD 1
MW 318.46
Rotatable Bonds 0
TPSA 41.99
LogP 4.08
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.7
Exact Mass 318.22
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Sarcophyton glaucum Alcyoniidae Animalia 70919

Showing of synonyms

  • Sawant SS, Youssef DTA, et al. (2006). Biocatalytic and antimetastatic studies of the marine cembranoids sarcophine and 2-epi-16-deoxysarcophine. Journal of Natural Products,2006,69(7),1010-1013. [View] [PubMed]
Pubchem: 11844358

No compound-protein relationship available.

Structure

SMILES: C12C(O2)CCC=CCCC=3C(OCC3)C=CCC1

Level: 0

Mol. Weight: 318.46 g/mol

Antimetastatic

Absorption

Caco-2 (logPapp)
-5.0
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.23
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.25

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.35
Plasma Protein Binding
28.34
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
16.57
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.74
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.3
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.14
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
-1.6
Rat (Acute)
1.92
Rat (Chronic Oral)
1.66
Fathead Minnow
4.65
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
386.59
Hydration Free Energy
-5.16
Log(D) at pH=7.4
2.78
Log(P)
4.09
Log S
-4.01
Log(Vapor Pressure)
-5.15
Melting Point
93.75
pKa Acid
8.05
pKa Basic
4.59
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 0.8857
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8857
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.8503
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.8503
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8257
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8257
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8040
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8040
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7908
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7908
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7870
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7870
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7642
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7642
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7618
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7618
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7599
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7599
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7597
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7597
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7588
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7588
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7583
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7583
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7410
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7410
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7355
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7355
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7338
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7338
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.7337
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.7337
Cholesterol oxidase P22637 CHOD_BREST Brevibacterium sterolicum 3 0.7336
Cholesterol oxidase P22637 CHOD_BREST Brevibacterium sterolicum 3 0.7336
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7294
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7294
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7290
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7290
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7289
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7289
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7255
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7255
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7252
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7252
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7249
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7249
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7194
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7194
Ferric enterobactin-binding periplasmic protein FepB P0AEL6 FEPB_ECOLI Escherichia coli 3 0.7152
Ferric enterobactin-binding periplasmic protein FepB P0AEL6 FEPB_ECOLI Escherichia coli 3 0.7152
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7129
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7129
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7117
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7117
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7086
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7086
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7041
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7041
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 2 0.7027
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 2 0.7027
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7020
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7020
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7017
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7017

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