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

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

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

Structure
Zoomed Structure
  • Family: Apiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles O[C@H]1C[C@](C)(O)[C@@H](C[C@@]2([C@@H]1[C@@](O)(CC2)C(C)C)C)OC(=O)c1ccc(cc1)O
InChI InChI=1S/C22H32O6/c1-13(2)22(27)10-9-20(3)12-17(21(4,26)11-16(24)18(20)22)28-19(25)14-5-7-15(23)8-6-14/h5-8,13,16-18,23-24,26-27H,9-12H2,1-4H3/t16-,17+,18+,20+,21-,22+/m0/s1
InChIKey PZBYTOJJGAKJAK-NDDOAYCYSA-N
Formula C22H32O6
HBA 6
HBD 4
MW 392.49
Rotatable Bonds 3
TPSA 107.22
LogP 2.63
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.68
Exact Mass 392.22
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 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]
Pubchem: 162885722

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)OC(C2)CCCC(C23)CCC3

Level: 1

Mol. Weight: 258.36 g/mol

Structure

SMILES: C1CCC(C12)CCCCC2

Level: 0

Mol. Weight: 138.25 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.97
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.81
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.1

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.56
Plasma Protein Binding
80.76
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
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.41
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.72
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.14
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.84
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
Safe
T. Pyriformis
-6.35
Rat (Acute)
3.53
Rat (Chronic Oral)
2.41
Fathead Minnow
4.04
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
416.66
Hydration Free Energy
-8.71
Log(D) at pH=7.4
2.36
Log(P)
3.43
Log S
-3.3
Log(Vapor Pressure)
-8.0
Melting Point
194.5
pKa Acid
6.5
pKa Basic
5.9
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9136
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9136
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8744
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8744
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8712
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8712
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8689
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8689
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8518
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8518
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8016
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8016
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7890
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7890
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7888
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7888
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7826
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7826
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7687
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7687
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7639
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7639
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7606
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7606
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7512
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7512
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7491
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7491
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7472
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7472
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 4 0.7424
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 4 0.7424
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7365
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7365
Japanin M1MR49 M1MR49_RHIAP Rhipicephalus appendiculatus 3 0.7334
Japanin M1MR49 M1MR49_RHIAP Rhipicephalus appendiculatus 3 0.7334
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7114
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7114
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7072
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7072
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7071
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7071
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7038
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7038
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7025
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7025
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 2 0.7016
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 2 0.7016
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7001
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7001

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