3alpha,12alpha-dihydroxy-ent-8(14),15-isopimaradien-18-al - Compound Card

3alpha,12alpha-dihydroxy-ent-8(14),15-isopimaradien-18-al

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3alpha,12alpha-dihydroxy-ent-8(14),15-isopimaradien-18-al

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpene
Canonical Smiles C=C[C@]1(C)C=C2CC[C@@H]3[C@]([C@H]2C[C@H]1O)(C)CC[C@@H]([C@@]3(C)C=O)O
InChI InChI=1S/C20H30O3/c1-5-18(2)11-13-6-7-15-19(3,14(13)10-17(18)23)9-8-16(22)20(15,4)12-21/h5,11-12,14-17,22-23H,1,6-10H2,2-4H3/t14-,15+,16-,17+,18+,19+,20-/m0/s1
InChIKey FLRZSIWHIJTYQM-BEZVJNGGSA-N
Formula C20H30O3
HBA 3
HBD 2
MW 318.46
Rotatable Bonds 2
TPSA 57.53
LogP 3.26
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.75
Exact Mass 318.22
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Euphorbia quinquecostata Euphorbiaceae Plantae 3990

Showing of synonyms

  • Su BN, Park EJ, et al. (2002). New chemical constituents of Euphorbia quinquecostata and absolute configuration assignment by a convenient Mosher ester procedure carried out in NMR tubes.. Journal of Natural Products,2002,65(9),1278-1282. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C1CCCC(C=12)C3C(CC2)CCCC3

Level: 0

Mol. Weight: 318.46 g/mol

Quinone reductase-inducing

Absorption

Caco-2 (logPapp)
-4.67
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.27
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.51

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.62
Plasma Protein Binding
53.78
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
Substrate
CYP 2C9 Inhibitor
Non-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
12.96
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.21
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.04
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.68
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
Toxic
T. Pyriformis
-1.74
Rat (Acute)
3.66
Rat (Chronic Oral)
1.49
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
379.4
Hydration Free Energy
-7.55
Log(D) at pH=7.4
2.79
Log(P)
3.26
Log S
-4.05
Log(Vapor Pressure)
-7.11
Melting Point
149.19
pKa Acid
8.87
pKa Basic
6.6
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.9241
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.9241
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8502
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8502
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8088
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8088
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8041
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8041
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.8029
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.8029
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8019
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8019
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7960
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7960
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7955
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7955
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7803
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7803
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7799
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7799
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7731
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7731
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7721
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7721
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7699
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7699
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7560
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7560
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7498
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7498
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7327
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7327
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7282
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7282
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7224
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7224
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7196
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7196
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7190
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7190
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7181
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7181
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7106
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7106
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7048
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7048

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