12(S)-hydroperoxylsarcoph-10-ene - Compound Card

12(S)-hydroperoxylsarcoph-10-ene

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12(S)-hydroperoxylsarcoph-10-ene

Structure
Zoomed Structure
  • Family: Animalia - Alcyoniidae
  • Kingdom: Animalia
  • Class: Terpenoid
    • Subclass: Peroxide Cembranoid Diterpene
Canonical Smiles OO[C@]1(C)/C=C/C[C@@]2(C)O[C@@H]2CC/C(=C/[C@@H]2C(=C(C)C(=O)O2)CC1)/C
InChI InChI=1S/C20H28O5/c1-13-6-7-17-20(4,24-17)10-5-9-19(3,25-22)11-8-15-14(2)18(21)23-16(15)12-13/h5,9,12,16-17,22H,6-8,10-11H2,1-4H3/b9-5+,13-12+/t16-,17-,19-,20-/m1/s1
InChIKey PTKZNZZJRAMCOQ-LNDOVTFYSA-N
Formula C20H28O5
HBA 5
HBD 1
MW 348.44
Rotatable Bonds 1
TPSA 68.29
LogP 4.1
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.65
Exact Mass 348.19
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Sarcophyton glaucum Alcyoniidae Animalia 70919

Showing of synonyms

  • Hegazy M-EF, Eldeen AMG, et al. (2012). Bioactive hydroperoxyl cembranoids from the Red Sea soft coral Sarcophyton glaucum. Marine Drugs,2012,10,209-222. [View] [PubMed]
Pubchem: 162880616
Nmrshiftdb2: 70037292

No compound-protein relationship available.

Structure

SMILES: C12C(O2)CCC=CC3C(=CC(=O)O3)CCCC=CC1

Level: 0

Mol. Weight: 348.44 g/mol

Chemo-preventive
Tumor anti-initiating

Absorption

Caco-2 (logPapp)
-5.03
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.490
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.13

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.360
Plasma Protein Binding
34.64
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
Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
13.730
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.720
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.060
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.670
Micronucleos
Toxic
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
-3.780
Rat (Acute)
2.760
Rat (Chronic Oral)
1.690
Fathead Minnow
4.510
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Toxic
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
387.440
Hydration Free Energy
-6.400
Log(D) at pH=7.4
2.590
Log(P)
2.67
Log S
-4.04
Log(Vapor Pressure)
-5.75
Melting Point
113.68
pKa Acid
7.24
pKa Basic
3.59
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8873
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8873
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8334
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8334
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.8021
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.8021
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7826
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7826
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7675
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7675
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7579
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7579
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7483
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7483
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7326
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7326
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7324
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7324
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7310
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7310
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7301
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7301
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.7242
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.7242
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7119
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7119

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