7beta-hydroxy-4(13),8-coloratadien-11,12-olide - Compound Card

7beta-hydroxy-4(13),8-coloratadien-11,12-olide

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7beta-hydroxy-4(13),8-coloratadien-11,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Canellaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles C=C1[C@@H](C)CC[C@]2([C@H]1C[C@H](O)C1=C2C(=O)OC1)C
InChI InChI=1S/C15H20O3/c1-8-4-5-15(3)11(9(8)2)6-12(16)10-7-18-14(17)13(10)15/h8,11-12,16H,2,4-7H2,1,3H3/t8-,11-,12-,15-/m0/s1
InChIKey YIADAXTULGQCOZ-REXDEQPNSA-N
Formula C15H20O3
HBA 3
HBD 1
MW 248.32
Rotatable Bonds 0
TPSA 46.53
LogP 2.21
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 248.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Warburgia ugandensis Canellaceae Plantae 549619

Showing of synonyms

  • Wube AA, Bucar F, et al. (2005). Sesquiterpenes from Warburgia ugandensis and their antimycobacterial activity. Phytochemistry,2005,66(19),2309-2315. [View] [PubMed]
Pubchem: 11521635
Nmrshiftdb2: 70009988

No compound-protein relationship available.

Structure

SMILES: C=C1CCCC2C1CCC(=C23)COC3=O

Level: 0

Mol. Weight: 248.32 g/mol

Antimycobacterial

Absorption

Caco-2 (logPapp)
-4.72
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.6
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.93

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.88
Plasma Protein Binding
43.05
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.75
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
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.89
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.61
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
-0.94
Rat (Acute)
2.96
Rat (Chronic Oral)
1.64
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
337.14
Hydration Free Energy
-5.86
Log(D) at pH=7.4
1.73
Log(P)
2.19
Log S
-3.29
Log(Vapor Pressure)
-5.48
Melting Point
135.02
pKa Acid
8.46
pKa Basic
6.01
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8725
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8725
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8094
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8094
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8008
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8008
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7289
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7289

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