14-hydroxy-eudesm-4,11(13)-dien-12-oic acid - Compound Card

14-hydroxy-eudesm-4,11(13)-dien-12-oic acid

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14-hydroxy-eudesm-4,11(13)-dien-12-oic acid

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles OO[C@@]12CC[C@H]([C@@H]2CC2[C@@H](CC1=C)OC(=O)C2=C)O
InChI InChI=1S/C14H18O5/c1-7-5-12-9(8(2)13(16)18-12)6-10-11(15)3-4-14(7,10)19-17/h9-12,15,17H,1-6H2/t9?,10-,11+,12+,14-/m0/s1
InChIKey ZKGFAIXNJVVISV-KJAYNUCNSA-N
Formula C14H18O5
HBA 5
HBD 2
MW 266.29
Rotatable Bonds 1
TPSA 75.99
LogP 1.43
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.64
Exact Mass 266.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pluchea dioscoridis Asteraceae Plantae —

Showing of synonyms

  • Mahmoud AA (1997). 7-Epi-eudesmanes, eudesmanoic acids, eudesmanolides and other sesquiterpenenes from Pluchea dioscoridis. Phytochemistry,1997,45(8),1633-1638. [View]
Pubchem: 162816858
Nmrshiftdb2: 60045972

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(C12)CC(=C)C3C(C2)CCC3

Level: 0

Mol. Weight: 266.29 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.74
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.510
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.46

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.390
Plasma Protein Binding
43.48
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
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
8.910
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.340
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.850
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.240
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-1.260
Rat (Acute)
3.310
Rat (Chronic Oral)
2.020
Fathead Minnow
3.920
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
328.630
Hydration Free Energy
-11.350
Log(D) at pH=7.4
0.250
Log(P)
0.28
Log S
-1.78
Log(Vapor Pressure)
-6.77
Melting Point
145.71
pKa Acid
7.77
pKa Basic
5.36
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.9137
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.9137
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.9029
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.9029
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8997
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8997
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8831
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8831
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8770
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8770
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.8713
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.8713
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8697
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8697
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.8606
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.8606
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8581
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8581
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8565
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8565
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8270
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8270
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8192
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8192
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8162
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8162
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8009
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8009
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7985
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7985
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7938
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7938
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7930
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7930
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7625
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7625
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7551
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7551
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7449
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7449
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7387
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7387
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7180
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7180
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7157
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7157
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7061
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7061
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7059
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7059
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7049
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7049
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7001
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7001

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