(1R,2E,4S,6E,8R,11R,12R)-2,6-cembradiene-4,8,11,12-tetrol - Compound Card

(1R,2E,4S,6E,8R,11R,12R)-2,6-cembradiene-4,8,11,12-tetrol

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(1R,2E,4S,6E,8R,11R,12R)-2,6-cembradiene-4,8,11,12-tetrol

Structure
Zoomed Structure
  • Family: Animalia - Alcyoniidae
  • Kingdom: Animalia
  • Class: Terpenoid
    • Subclass: Cembranoid Diterpene
Canonical Smiles CC([C@H]1CC[C@@](C)(O)[C@H](O)CC[C@@](/C=C/C[C@](/C=C/1)(C)O)(C)O)C
InChI InChI=1S/C20H36O4/c1-15(2)16-7-12-18(3,22)10-6-11-19(4,23)13-9-17(21)20(5,24)14-8-16/h6-7,11-12,15-17,21-24H,8-10,13-14H2,1-5H3/b11-6+,12-7+/t16-,17-,18+,19+,20-/m1/s1
InChIKey IKYKEAJCCSJHEP-ANSXYVTGSA-N
Formula C20H36O4
HBA 4
HBD 4
MW 340.5
Rotatable Bonds 1
TPSA 80.92
LogP 2.95
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.8
Exact Mass 340.26
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Sarcophyton auritum Alcyoniidae Animalia 859400

Showing of synonyms

  • 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: 101891014
Nmrshiftdb2: 70100910

No compound-protein relationship available.

Structure

SMILES: C1=CCCCCCCCCC=CCC1

Level: 0

Mol. Weight: 340.5 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.91
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.36
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.41

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.74
Plasma Protein Binding
50.32
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-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
3.48
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.02
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.62
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.02
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
-4.2
Rat (Acute)
2.12
Rat (Chronic Oral)
1.9
Fathead Minnow
3.92
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
391.81
Hydration Free Energy
-12.57
Log(D) at pH=7.4
2.25
Log(P)
2.77
Log S
-2.76
Log(Vapor Pressure)
-6.43
Melting Point
150.58
pKa Acid
9.37
pKa Basic
7.1
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.9365
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.9365
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9003
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9003
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8765
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8765
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7981
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7981
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7640
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7640
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7489
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7489
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7475
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7475
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7470
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7470
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7436
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7436
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7180
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7180
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7166
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7166
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7162
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7162
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7155
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7155
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 4 0.7123
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 4 0.7123
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7083
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7083
Corticosteroid-binding globulin P31211 CBG_RAT Rattus norvegicus 3 0.7072
Corticosteroid-binding globulin P31211 CBG_RAT Rattus norvegicus 3 0.7072
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7060
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7060

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