Lancerodiol p-hydroxybenzoate - Compound Card

Lancerodiol p-hydroxybenzoate

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Lancerodiol p-hydroxybenzoate

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles Oc1ccc(cc1)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/C22H28O5/c1-13(2)22(26)10-9-21(4)12-17(24)14(3)11-18(19(21)22)27-20(25)15-5-7-16(23)8-6-15/h5-8,11,13,18-19,23,26H,9-10,12H2,1-4H3/t18-,19+,21+,22+/m0/s1
InChIKey IUZVQQNKQMFGQK-YVNJGZBMSA-N
Formula C22H28O5
HBA 5
HBD 2
MW 372.46
Rotatable Bonds 3
TPSA 83.83
LogP 3.64
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.55
Exact Mass 372.19
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ferula sinaica Apiaceae Plantae 1514050
2 Ferula sinaica Apiaceae Plantae 1514050
3 Ferula sinaica Apiaceae Plantae 1514050
4 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]
  • El-Razek MHA, Hegazy MEF, et al. (2010). Crystal and molecular structure of lancerodiol-p-hydroxybenzoate. Pharmacognosy Research,2010,2(2),69-71. [View] [PubMed]
  • Ahmed AA (1991). Daucanes and other constituents from Ferula sinaica. Phytochemistry,1991,30(4),1207-1210. [View]
  • Ahmed AA, Hegazy MEF, et al. (2007). Ferulsinaic acid, a sesquiterpene coumarin with a rare carbon skeleton from Ferula species. Phytochemistry,2007,68(5),680-686. [View]
Pubchem: 13992119
Nmrshiftdb2: 70084653

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 372.46 g/mol

Structure

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

Level: 0

Mol. Weight: 372.46 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 372.46 g/mol

Radical scavenging

Absorption

Caco-2 (logPapp)
-4.63
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.590
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.74

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.760
Plasma Protein Binding
85.31
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
Non-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
9.270
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.140
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.300
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.600
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-3.220
Rat (Acute)
3.240
Rat (Chronic Oral)
2.220
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
403.010
Hydration Free Energy
-7.150
Log(D) at pH=7.4
3.000
Log(P)
3.91
Log S
-4.6
Log(Vapor Pressure)
-7.31
Melting Point
193.02
pKa Acid
6.92
pKa Basic
3.82
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7733
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7733
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7730
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7730
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7655
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7655
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7292
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7292
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7165
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7165
Isoleucine--tRNA ligase P56690 SYI_THET8 Thermus thermophilus 3 0.7125
Isoleucine--tRNA ligase P56690 SYI_THET8 Thermus thermophilus 3 0.7125
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7102
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7102

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