4beta,8beta-dihydroxy-6alpha-(4-hydroxy-3-methoxybenzoyl)-dauc-9-ene - Compound Card

4beta,8beta-dihydroxy-6alpha-(4-hydroxy-3-methoxybenzoyl)-dauc-9-ene

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4beta,8beta-dihydroxy-6alpha-(4-hydroxy-3-methoxybenzoyl)-dauc-9-ene

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Daucane Sesquiterpenoid Ester
Canonical Smiles COc1cc(ccc1O)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/C23H32O6/c1-14(2)23(27)11-9-21(3)8-10-22(4,26)13-18(19(21)23)29-20(25)15-6-7-16(24)17(12-15)28-5/h6-8,10,12,14,18-19,24,26-27H,9,11,13H2,1-5H3/t18-,19+,21-,22+,23+/m0/s1
InChIKey VSBPKNDASTZGIN-RNJSZURPSA-N
Formula C23H32O6
HBA 6
HBD 3
MW 404.5
Rotatable Bonds 4
TPSA 96.22
LogP 3.44
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.61
Exact Mass 404.22
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: 14466072

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 404.5 g/mol

Structure

SMILES: C1CCC(C12)CCCC=C2

Level: 0

Mol. Weight: 404.5 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 404.5 g/mol

Radical scavenging

Absorption

Caco-2 (logPapp)
-4.55
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.680
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.03

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.740
Plasma Protein Binding
78.02
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
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
11.580
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.240
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.230
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.060
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
-11.120
Rat (Acute)
2.850
Rat (Chronic Oral)
2.390
Fathead Minnow
4.030
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
405.520
Hydration Free Energy
-6.570
Log(D) at pH=7.4
2.990
Log(P)
3.44
Log S
-4.21
Log(Vapor Pressure)
-7.48
Melting Point
180.58
pKa Acid
7.11
pKa Basic
5.18
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8751
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8751
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8524
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8524
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7940
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7940
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7928
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7928
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7670
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7670
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7658
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7658
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7353
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7353
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7306
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7306
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7260
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7260
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.7258
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.7258
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7238
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7238
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7176
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7176
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 4 0.7081
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 4 0.7081
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7066
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7066
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7053
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7053
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7010
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7010

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