(1R,2R,3R ,6R,7R)-1,2,3,6,7-pentahydroxy-2- acetoxy-bisabol-10(11)-ene - Compound Card

(1R,2R,3R ,6R,7R)-1,2,3,6,7-pentahydroxy-2- acetoxy-bisabol-10(11)-ene

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(1R,2R,3R ,6R,7R)-1,2,3,6,7-pentahydroxy-2- acetoxy-bisabol-10(11)-ene

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sequiterpene Lactone
Canonical Smiles CC(=CCC[C@]([C@@]1(O)CC[C@@]([C@@H]([C@H]1O)OC(=O)C)(C)O)(O)C)C
InChI InChI=1S/C17H30O6/c1-11(2)7-6-8-16(5,21)17(22)10-9-15(4,20)14(13(17)19)23-12(3)18/h7,13-14,19-22H,6,8-10H2,1-5H3/t13-,14-,15-,16-,17-/m1/s1
InChIKey HUHFSXQUPUXLLB-WRQOLXDDSA-N
Formula C17H30O6
HBA 6
HBD 4
MW 330.42
Rotatable Bonds 5
TPSA 107.22
LogP 1.05
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.82
Exact Mass 330.2
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Matricaria aurea Asteraceae Plantae 1824872

Showing of synonyms

  • Ahmed AA, Elela MAA (1999). Highly oxygenated bisabolenes and an acetylene from Matricaria aurea. Phytochemistry,1999,51,551-554. [View] [PubMed]
Pubchem: 15477699
Nmrshiftdb2: 70105824

No compound-protein relationship available.

Structure

SMILES: C1CCCCC1

Level: 0

Mol. Weight: 330.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.96
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.75
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.92

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.21
Plasma Protein Binding
60.79
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
3.42
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.44
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.63
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.35
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
-2.9
Rat (Acute)
1.99
Rat (Chronic Oral)
2.52
Fathead Minnow
3.96
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
355.43
Hydration Free Energy
-13.49
Log(D) at pH=7.4
0.71
Log(P)
1.78
Log S
-2.27
Log(Vapor Pressure)
-7.72
Melting Point
124.07
pKa Acid
7.33
pKa Basic
6.44
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8727
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8727
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8012
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8012
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7976
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7976
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7860
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7860
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7832
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7832
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7811
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7811
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7650
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7650
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7623
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7623
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7512
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7512
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7437
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7437
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7243
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7243
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7140
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7140
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7026
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7026
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7007
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7007

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