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

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

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7beta-hydroxy-4(13),7-coloratadiene-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@](C)(O)C1=C2C(=O)OC1)C
InChI InChI=1S/C16H22O3/c1-9-5-6-15(3)11(10(9)2)7-16(4,18)12-8-19-14(17)13(12)15/h9,11,18H,2,5-8H2,1,3-4H3/t9-,11-,15-,16-/m0/s1
InChIKey HJFZQTPLDCGBRQ-JIVACREVSA-N
Formula C16H22O3
HBA 3
HBD 1
MW 262.35
Rotatable Bonds 0
TPSA 46.53
LogP 2.6
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.69
Exact Mass 262.16
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. (2010). Antiprotozoal activity of drimane and coloratane sesquiterpenes towards Trypanosoma brucei rhodesiense and Plasmodium falciparum in vitro. Phytotherapy Research,2010,24(10),1468-1472. [View] [PubMed]

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 262.35 g/mol

Anti-plasmodial
Antitrypanosomal

Absorption

Caco-2 (logPapp)
-4.67
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.65
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.65

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.85
Plasma Protein Binding
46.89
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
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.01
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.66
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.51
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.45
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
-1.03
Rat (Acute)
2.86
Rat (Chronic Oral)
1.51
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
335.94
Hydration Free Energy
-4.66
Log(D) at pH=7.4
2.2
Log(P)
2.61
Log S
-3.69
Log(Vapor Pressure)
-5.23
Melting Point
138.71
pKa Acid
8.31
pKa Basic
6.01
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7737
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7737
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7547
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7547
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7385
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7385
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7384
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7384
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7169
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7169
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7132
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7132

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