14beta-hydroxy-2-epi-16-deoxysarcophine - Compound Card

14beta-hydroxy-2-epi-16-deoxysarcophine

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14beta-hydroxy-2-epi-16-deoxysarcophine

Structure
Zoomed Structure
  • Family: Animalia - Alcyoniidae
  • Kingdom: Animalia
  • Class: Terpenoid
    • Subclass: Cembranoid Diterpene
Canonical Smiles C/C/1=C\CC[C@]2(C)O[C@H]2CC/C(=C/[C@@H]2C(=C(C)CO2)[C@H](C1)O)/C
InChI InChI=1S/C20H30O3/c1-13-6-5-9-20(4)18(23-20)8-7-14(2)11-17-19(16(21)10-13)15(3)12-22-17/h6,11,16-18,21H,5,7-10,12H2,1-4H3/b13-6+,14-11+/t16-,17+,18-,20-/m0/s1
InChIKey ZLZPIHHAJYNCAU-NZBKKJSSSA-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: 11844490
Nmrshiftdb2: 60070611

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)
-5.03
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.32
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.24

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.32
Plasma Protein Binding
28.48
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
16.14
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.66
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.04
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.26
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
-1.87
Rat (Acute)
1.96
Rat (Chronic Oral)
1.56
Fathead Minnow
4.67
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
381.97
Hydration Free Energy
-5.55
Log(D) at pH=7.4
2.75
Log(P)
3.76
Log S
-3.95
Log(Vapor Pressure)
-5.16
Melting Point
83.34
pKa Acid
8.1
pKa Basic
4.35
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9616
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9616
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.8574
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.8574
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8542
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8542
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8182
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8182
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8126
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8126
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.8120
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.8120
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7838
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7838
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7696
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7696
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7629
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7629
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7597
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7597
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7588
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7588
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7488
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7488
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7486
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7486
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7374
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7374
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 3 0.7366
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 3 0.7366
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7354
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7354
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7260
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7260
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7247
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7247
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7187
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7187
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7122
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7122
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7110
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7110
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7020
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7020

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