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

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

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

Structure
Zoomed Structure
  • Family: Asteraceae-Compositae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sequiterpene Lactone
Canonical Smiles CC(=CCC[C@]([C@@]1(O)CC[C@@]([C@@H]([C@H]1O)O)(C)O)(O)C)C
InChI InChI=1S/C15H28O5/c1-10(2)6-5-7-14(4,19)15(20)9-8-13(3,18)11(16)12(15)17/h6,11-12,16-20H,5,7-9H2,1-4H3/t11-,12-,13-,14-,15-/m1/s1
InChIKey NHBJWMZRJYBAPG-KJWHEZOQSA-N
Formula C15H28O5
HBA 5
HBD 5
MW 288.38
Rotatable Bonds 4
TPSA 101.15
LogP 0.48
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.87
Exact Mass 288.19
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Matricaria aurea Asteraceae-Compositae 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: 10613353
Nmrshiftdb2: 70105825

No compound-protein relationship available.

Structure

SMILES: C1CCCCC1

Level: 0

Mol. Weight: 84.16 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.19
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.42
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.45

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.5
Plasma Protein Binding
61.26
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
0.58
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.69
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.24
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
3.35
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
-2.93
Rat (Acute)
1.6
Rat (Chronic Oral)
2.72
Fathead Minnow
2.88
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
402.9
Hydration Free Energy
-19.08
Log(D) at pH=7.4
0.73
Log(P)
1.1
Log S
-2.19
Log(Vapor Pressure)
-10.35
Melting Point
141.0
pKa Acid
7.71
pKa Basic
7.61
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.9239
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.9239
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8984
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8984
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8496
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8496
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8485
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8485
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7892
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7892
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7891
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7891
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7890
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7890
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7877
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7877
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7754
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7754
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7720
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7720
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
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7610
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7610
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7602
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7602
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7567
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7567
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7444
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7444
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7405
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7405
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7398
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7398
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.7376
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.7376
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7360
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7360
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7316
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7316
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7279
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7279
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7247
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7247
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7193
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7193
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7157
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7157
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7124
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7124
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7086
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7086
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7076
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7076
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7057
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7057

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