4beta-hydroxy-6alpha-(4-hydroxy-3-methoxybenzoyl)-7-daucen-9-one - Compound Card

4beta-hydroxy-6alpha-(4-hydroxy-3-methoxybenzoyl)-7-daucen-9-one

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4beta-hydroxy-6alpha-(4-hydroxy-3-methoxybenzoyl)-7-daucen-9-one

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)C(=O)C[C@@]2([C@@H]1[C@@](O)(CC2)C(C)C)C
InChI InChI=1S/C23H30O6/c1-13(2)23(27)9-8-22(4)12-17(25)14(3)10-19(20(22)23)29-21(26)15-6-7-16(24)18(11-15)28-5/h6-7,10-11,13,19-20,24,27H,8-9,12H2,1-5H3/t19-,20+,22+,23+/m0/s1
InChIKey OZMABICMIHKNMC-KKSHJYNMSA-N
Formula C23H30O6
HBA 6
HBD 2
MW 402.49
Rotatable Bonds 4
TPSA 93.06
LogP 3.65
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.57
Exact Mass 402.2
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: 13992124
Nmrshiftdb2: 70099996

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)OC2C=CC(=O)CC(C23)CCC3

Level: 1

Mol. Weight: 402.49 g/mol

Structure

SMILES: C1CCC(C12)CC=CC(=O)C2

Level: 0

Mol. Weight: 402.49 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 402.49 g/mol

Radical scavenging

Absorption

Caco-2 (logPapp)
-4.49
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.650
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.27

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.800
Plasma Protein Binding
84.43
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.740
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.150
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.240
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.700
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
-9.940
Rat (Acute)
2.880
Rat (Chronic Oral)
2.320
Fathead Minnow
4.010
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
418.760
Hydration Free Energy
-5.700
Log(D) at pH=7.4
2.890
Log(P)
3.62
Log S
-4.75
Log(Vapor Pressure)
-7.43
Melting Point
180.07
pKa Acid
6.91
pKa Basic
4.34
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8869
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8869
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8752
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8752
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8492
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8492
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8277
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8277
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8244
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8244
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8051
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8051
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7966
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7966
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7854
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7854
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7752
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7752
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7746
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7746
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7501
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7501
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7491
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7491
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7317
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7317
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7236
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7236
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7179
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7179
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7140
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7140
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7020
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7020
Histone-lysine N-methyltransferase EHMT2 Q96KQ7 EHMT2_HUMAN Homo sapiens 3 0.7000
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 4 0.7000
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 4 0.7000
Histone-lysine N-methyltransferase EHMT2 Q96KQ7 EHMT2_HUMAN Homo sapiens 3 0.7000

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