4beta,8beta,9alpha-trihydroxy-6alpha-p-hydroxybenzoyloxydaucane - Compound Card

4beta,8beta,9alpha-trihydroxy-6alpha-p-hydroxybenzoyloxydaucane

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4beta,8beta,9alpha-trihydroxy-6alpha-p-hydroxybenzoyloxydaucane

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles O[C@H]1CC(=C)[C@H](C[C@@]2([C@@H]1[C@@](O)(CC2)C(C)C)C)O
InChI InChI=1S/C15H26O3/c1-9(2)15(18)6-5-14(4)8-12(17)10(3)7-11(16)13(14)15/h9,11-13,16-18H,3,5-8H2,1-2,4H3/t11-,12-,13+,14+,15+/m0/s1
InChIKey BTXJIKSSLQOYHS-VQJWOFKYSA-N
Formula C15H26O3
HBA 3
HBD 3
MW 254.37
Rotatable Bonds 1
TPSA 60.69
LogP 1.86
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.87
Exact Mass 254.19
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ferula sinaica Apiaceae Plantae 1514050
2 Ferula sinaica Apiaceae Plantae 1514050

Showing of synonyms

  • Ahmed AA (1991). Daucanes and other constituents from Ferula sinaica. Phytochemistry,1991,30(4),1207-1210. [View]
  • Ahmed AA (1990). New Sesquiterpenes from Ferula sinaica. Journal of Natural Products,1990,53(2),483-486. [View] [PubMed]
Pubchem: 14681670

No compound-protein relationship available.

Structure

SMILES: C1CC(=C)CCC(C12)CCC2

Level: 0

Mol. Weight: 254.37 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.86
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.26
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.72

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.37
Plasma Protein Binding
48.25
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
Non-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
8.55
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.47
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.46
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
3.38
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
-2.69
Rat (Acute)
3.28
Rat (Chronic Oral)
1.85
Fathead Minnow
3.61
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
325.04
Hydration Free Energy
-9.64
Log(D) at pH=7.4
0.78
Log(P)
1.93
Log S
-1.88
Log(Vapor Pressure)
-5.96
Melting Point
142.02
pKa Acid
8.59
pKa Basic
6.75
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.9033
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.9033
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8866
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8866
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8850
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8850
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.8522
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.8522
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8521
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8521
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8354
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8354
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.8045
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.8045
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.8005
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.8005
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.7818
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.7818
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7704
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7704
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7684
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7684
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7664
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7664
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7627
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7627
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7564
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7564
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7506
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7506
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7484
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7484
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7473
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7473
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7389
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7389
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7348
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7348
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7182
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7182
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 3 0.7143
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 3 0.7143
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7102
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7102
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7079
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7079
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7066
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7066
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7045
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7045
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7045
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7045
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7014
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7014
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7013
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7013

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