8alpha-hydroxy-13-epi-pimar-16-en-6,18-olide - Compound Card

8alpha-hydroxy-13-epi-pimar-16-en-6,18-olide

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8alpha-hydroxy-13-epi-pimar-16-en-6,18-olide

Structure
Zoomed Structure
  • Family: Plantae - Cupressaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles C=C[C@@]1(C)CC[C@H]2[C@](C1)(O)C[C@H]1C3[C@]2(C)CCC[C@]3(C(=O)O1)C
InChI InChI=1S/C20H30O3/c1-5-17(2)10-7-14-18(3)8-6-9-19(4)15(18)13(23-16(19)21)11-20(14,22)12-17/h5,13-15,22H,1,6-12H2,2-4H3/t13-,14+,15?,17-,18+,19+,20-/m0/s1
InChIKey ROWAYMVYPPFJTI-CTIHTUHDSA-N
Formula C20H30O3
HBA 3
HBD 1
MW 318.46
Rotatable Bonds 1
TPSA 46.53
LogP 3.85
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.85
Exact Mass 318.22
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Tetraclinis articulata Cupressaceae Plantae 13717

Showing of synonyms

  • Barrero AF, Quılez del Moral JF, et al. (2003). Diterpenoids from Tetraclinis articulata that inhibit various human leukocyte functions. Journal of Natural Products,2003,66(6),844-850. [View] [PubMed]
Pubchem: 11130956

No compound-protein relationship available.

Structure

SMILES: O=C1OC(C2C13)CC4C(C2CCC3)CCCC4

Level: 0

Mol. Weight: 318.46 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.53
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.5
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.31

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.82
Plasma Protein Binding
63.15
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
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
14.29
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
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.97
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.18
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
-3.8
Rat (Acute)
1.77
Rat (Chronic Oral)
1.88
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
379.06
Hydration Free Energy
-4.11
Log(D) at pH=7.4
3.62
Log(P)
4.05
Log S
-4.65
Log(Vapor Pressure)
-5.99
Melting Point
153.17
pKa Acid
9.66
pKa Basic
6.88
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.9052
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.9052
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
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8875
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8875
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8798
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8798
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8796
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8796
Alpha/beta hydrolase fold protein D2J2T6 D2J2T6_9RHIZ Ochrobactrum sp. T63 3 0.8582
Alpha/beta hydrolase fold protein D2J2T6 D2J2T6_9RHIZ Ochrobactrum sp. T63 3 0.8582
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8361
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8361
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7791
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7791
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7588
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7588
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7452
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7452
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7436
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7436
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7413
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7413
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7408
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7408
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7402
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7402
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7400
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7400
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7368
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7368
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7359
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7359
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7359
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7359
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7270
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7270
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7228
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7228
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 2 0.7210
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 2 0.7210
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7202
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7202
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7142
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7142
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7141
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7141
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7138
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7138
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7131
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7131
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7046
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7046
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7018
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7018

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