4beta,8beta-dihydroxy-6alpha-p-hydroxybenzoyl-dauc-9-ene - Compound Card

4beta,8beta-dihydroxy-6alpha-p-hydroxybenzoyl-dauc-9-ene

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4beta,8beta-dihydroxy-6alpha-p-hydroxybenzoyl-dauc-9-ene

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Daucane Sesquiterpenoid Ester
Canonical Smiles Oc1ccc(cc1)C(=O)O[C@H]1C[C@](C)(O)C=C[C@@]2([C@@H]1[C@@](O)(CC2)C(C)C)C
InChI InChI=1S/C22H30O5/c1-14(2)22(26)12-10-20(3)9-11-21(4,25)13-17(18(20)22)27-19(24)15-5-7-16(23)8-6-15/h5-9,11,14,17-18,23,25-26H,10,12-13H2,1-4H3/t17-,18+,20-,21+,22+/m0/s1
InChIKey MQNDIFGHQSDIOB-ZQONDGBOSA-N
Formula C22H30O5
HBA 5
HBD 3
MW 374.48
Rotatable Bonds 3
TPSA 86.99
LogP 3.43
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.59
Exact Mass 374.21
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ferula hermonis Apiaceae Plantae 662815

Showing of synonyms

  • Ibraheim ZZ, Abdel-Mageed WM, et al. (2012). Antimicrobial antioxidant daucane sesquiterpenes from Ferula hermonis Boiss. Phytotherapy Research,2012,26,579-586. [View] [PubMed]
Pubchem: 13875698

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)OC(C(C23)CCC2)CCC=C3

Level: 1

Mol. Weight: 374.48 g/mol

Structure

SMILES: C1CCC(C12)CCCC=C2

Level: 0

Mol. Weight: 374.48 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 374.48 g/mol

Radical scavenging

Absorption

Caco-2 (logPapp)
-4.61
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.550
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.28

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.600
Plasma Protein Binding
77.19
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
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
9.450
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.470
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.330
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.230
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-5.470
Rat (Acute)
2.930
Rat (Chronic Oral)
2.290
Fathead Minnow
4.000
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
391.440
Hydration Free Energy
-7.860
Log(D) at pH=7.4
3.260
Log(P)
3.74
Log S
-4.23
Log(Vapor Pressure)
-7.41
Melting Point
189.2
pKa Acid
6.97
pKa Basic
5.59
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8153
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8153
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7640
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7640
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.7577
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.7577
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7560
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7560
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7286
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7286
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7179
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7179
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 4 0.7050
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 4 0.7050

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