5alpha-hydroxy-4alpha,15-dihydrocostic acid - Compound Card

5alpha-hydroxy-4alpha,15-dihydrocostic acid

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5alpha-hydroxy-4alpha,15-dihydrocostic acid

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles OC(=O)C(=C)[C@@H]1CC[C@@]2([C@](C1)(O)[C@@H](C)CCC2)C
InChI InChI=1S/C15H24O3/c1-10-5-4-7-14(3)8-6-12(9-15(10,14)18)11(2)13(16)17/h10,12,18H,2,4-9H2,1,3H3,(H,16,17)/t10-,12+,14+,15+/m0/s1
InChIKey ITEOVFZKXCDRFX-QMGNLALYSA-N
Formula C15H24O3
HBA 2
HBD 2
MW 252.35
Rotatable Bonds 2
TPSA 57.53
LogP 2.98
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.8
Exact Mass 252.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Chiliadenus montanus Asteraceae Plantae 1458965

Showing of synonyms

  • Hegazy MEF, Matsuda H, et al. (2014). Chemical constituents and their antibacterial and antifungal activity from the Egyptian herbal medicine Chiliadenus montanus. Phytochemistry,2014,103,154-161. [View] [PubMed]
Pubchem: 101589316
Nmrshiftdb2: 60079071

No compound-protein relationship available.

Structure

SMILES: C1CCCC(C12)CCCC2

Level: 0

Mol. Weight: 252.35 g/mol

Antimicrobial

Absorption

Caco-2 (logPapp)
-4.71
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.54
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.01

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.48
Plasma Protein Binding
57.17
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
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
4.65
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.44
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.32
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.19
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
-0.12
Rat (Acute)
2.04
Rat (Chronic Oral)
2.16
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
329.46
Hydration Free Energy
-7.34
Log(D) at pH=7.4
0.31
Log(P)
2.85
Log S
-2.8
Log(Vapor Pressure)
-5.86
Melting Point
141.48
pKa Acid
4.02
pKa Basic
9.51
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.9373
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.9373
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.9021
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.9021
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8693
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8693
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8613
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8613
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8586
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8586
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8417
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8417
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8401
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8401
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8373
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8373
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8363
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8363
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8282
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8282
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8200
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8200
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8084
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8084
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7705
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7705
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7625
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7625
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7600
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7600
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7549
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7549
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7515
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7515
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7435
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7435
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7346
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7346
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7286
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7286
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7212
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7212
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7163
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7163
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7155
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7155
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7122
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7122
Glucocorticoid receptor P04150 GCR_HUMAN Homo sapiens 3 0.7104
Glucocorticoid receptor P04150 GCR_HUMAN Homo sapiens 3 0.7104
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7101
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7101
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7065
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7065
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7056
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7056
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7015
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7015

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